WO2018178555A1 - Method for the production and purification of 2,3,3,3-tetrafluoro-1-propene - Google Patents

Method for the production and purification of 2,3,3,3-tetrafluoro-1-propene Download PDF

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Publication number
WO2018178555A1
WO2018178555A1 PCT/FR2018/050735 FR2018050735W WO2018178555A1 WO 2018178555 A1 WO2018178555 A1 WO 2018178555A1 FR 2018050735 W FR2018050735 W FR 2018050735W WO 2018178555 A1 WO2018178555 A1 WO 2018178555A1
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Prior art keywords
propene
tetrafluoro
stream
trans
equal
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PCT/FR2018/050735
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French (fr)
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Dominique Deur-Bert
Laurent Wendlinger
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Arkema France
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C07C17/386—Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation

Definitions

  • the invention relates to a process for purifying 2,3,3,3-tetrafluoro-1-propene.
  • the invention also relates to a process for producing and purifying 2,3,3,3-tetrafluoro-1-propene.
  • Hydrofluorocarbons such as 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf)
  • HFOs hydrofluoroolefins
  • HFO-1234yf 2,3,3,3-tetrafluoro-1-propene
  • hydrofluoroolefin manufacturing processes involve a fluorination and / or dehydrohalogenation reaction. This type of reaction is carried out in the gas phase and generates impurities which must therefore be eliminated in order to obtain the desired compound in a degree of purity sufficient for the intended applications.
  • WO 03/068716 discloses a process for recovering pentafluoroethane from a mixture comprising pentafluoroethane and chloropentafluoroethane by distillation in the presence of hexafluoropropene.
  • WO 98/19982 also discloses a process for purifying 1,1-difluoroethane by extractive distillation.
  • the method comprises contacting an extractant with a mixture of 1,1-difluoroethane and vinyl chloride.
  • the extraction agent is chosen from hydrocarbons, alcohols and chlorocarbons having a boiling point of between 10 ° C. and 120 ° C.
  • the selection of the extraction agent can be complex depending on the products to be separated.
  • the present invention allows the purification of 2,3,3,3-tetrafluoro-1-propene.
  • the present invention makes it possible in particular to obtain a stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane having a low trans-1 content.
  • the present invention thus allows the production of 2,3,3,3-tetrafluoro-1-propene with improved purity.
  • the present invention provides a process for purifying 2,3,3,3-tetrafluoro-1-propene (1234yf) from a first composition comprising 2,3,3,3-tetrafluoro-1 propene, 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), said process comprising the steps of:
  • step a) recovering and separating said third composition to form a stream comprising said organic extractant and a stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E); preferably the stream comprising said organic extraction agent is recycled in step a);
  • the first composition is obtained from a mixture C comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and HF, said mixture being subjected to the following steps:
  • the method also comprises the steps of: iv ') neutralizing said stream C1 obtained in stage iii') with an aqueous alkaline solution to form a neutralized stream C3, and
  • the aqueous hydrofluoric acid solution used in step i ') is at a temperature of between 0 and 30 ° C. before being brought into contact with the said mixture C.
  • the liquid phase resulting from the mixing of said liquid phase of said second diphasic current and said C2 stream is distilled to form a stream D, preferably at the top of the distillation column, comprising hydrofluoric acid containing less 500 ppm of water and a stream E, preferably at the bottom of the distillation column, comprising hydrofluoric acid in the form of an aqueous solution with a concentration of less than 50% by weight.
  • the ratio between the flow rate of the aqueous flow supplying the absorption column in step iii ') and the amount of hydrofluoric acid in said mixture C expressed in kg / h is between 0.05 and 1.22, preferably between 0.33 and 0.54.
  • the process also comprises a step of recovering said stream ii) comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb) obtained in step b), and of distillation thereof to form a stream A comprising 2,3,3,3-tetrafluoro-1-propene and a stream B comprising 1,1,1,2,2-pentafluoropropane (245cb).
  • said first composition also comprises at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E) cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf).
  • PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene
  • s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene (1234
  • P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E);
  • the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0.
  • said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula
  • PI represents the saturated vapor pressure of 1,1,1,2,2-pentafluoropropane (245cb)
  • Y2 represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze) E) in said organic extraction agent with infinite dilution
  • P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E); advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0.
  • said organic extraction agent is selected from the group consisting of ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2- propanediamine, n-butylacetate, 2-methoxy-1-propanol, hexanal.
  • said organic extractant is selected from the group consisting of ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy- 1-propanol, hexanal.
  • the present invention provides a method for producing and purifying 2,3,3,3-tetrafluoro-1-propene comprising the steps of:
  • Figure 1 schematically shows a device implementing a process for producing 2,3,3,3-tetrafluoro-1-propene according to a particular embodiment of the present invention.
  • Figures 2a-d schematically represent a device implementing a method for purifying 2,3,3,3-tetrafluoro-1-propene according to a particular embodiment of the present invention.
  • hydrocarbon refers to linear or branched compounds of C1-C20 alkane, C3-C20 cycloalkane, C2-C20 alkene, C3-C20 cycloalkene, C6-C18 arene.
  • alkane refers to compounds of formula C n H 2n + 2 wherein n is from 1 to 20.
  • C 1 -C 20 alkane includes, for example, pentane, hexane, heptane, octane, nonane, decane or isomers thereof.
  • C2-C20 alkene refers to hydrocarbon compounds comprising one or more carbon-carbon double bonds and comprising from 2 to 20 carbon atoms.
  • C3-C20 cycloalkane refers to a saturated hydrocarbon ring having 3 to 20 carbon atoms.
  • C 6 -C 18 aryl refers to cyclic and aromatic hydrocarbon compounds having from 6 to 18 carbon atoms.
  • C3-C20 cycloalkene refers to cyclic hydrocarbon compounds comprising from 3 to 20 carbon atoms and comprising one or more carbon-carbon double bonds.
  • alkyl denotes a monovalent radical derived from a linear or branched alkane comprising from 1 to 20 carbon atoms.
  • cycloalkyl refers to a monovalent radical derived from a cycloalkane comprising from 3 to 20 carbon atoms.
  • aryl denotes a monovalent radical derived from an arene comprising from 6 to 18 carbon atoms.
  • alkenyl refers to a monovalent radical of 2 to 20 carbon atoms and at least one carbon-carbon double bond.
  • alkynyl refers to a monovalent radical of 2 to 20 carbon atoms and at least one carbon-carbon triple bond.
  • halogen refers to a group -F, -Cl, -Br or -I.
  • cycloalkenyl refers to a monovalent radical derived from a cycloalkene having 3 to 20 carbon atoms.
  • C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 cycloalkenyl, C6-C18 aryl substituents may or may not be substituted by one or more -OH substituents, halogen, -N a C (O) b , -C (O) NR a R b , -CN, -NO 2 , -NR a R b , -OR a , -SR a , -COR 2 R a , -OC (0) OR a , -OC (O) R a , -C (O) H, -C (O) R a wherein R a and R b are independently of one another hydrogen, alkyl Unsubstituted C1-C20, unsubstituted C2-C20 alkenyl, unsubstituted C2-C20 alky
  • substituents -NR a R b , -NR a C (O) R b , -C (O) NR a R b , R a and R b may form with the nitrogen atom or with the functional group to which they are attached a saturated or unsaturated heterocycle, aromatic or not, comprising from 4 to 10 members.
  • hydrohalocarbons refers to compounds of the formula R a X wherein R a is selected from C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-cycloalkenyl.
  • R a is selected from C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-cycloalkenyl.
  • C20, C6-C18 aryl and X represents a chlorine, fluorine, bromine or iodine atom.
  • the substituents C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl and C 6 -C 18 aryl may or may not be substituted by one or more -OH substituents, halogen, -NR a C (O) R b , -C (O) NR a R b -CN, -NO 2 , -NR a R b , -OR a , -SR a , -COR 2 R a , -OC (O) OR a , -OC (O) R a , -C (O) H, -C (O) R a wherein R a and R b are as defined above.
  • alcohol refers to hydrocarbons or hydrohalocarbons as defined above in which at least one hydrogen atom is replaced by a hydroxyl group -OH.
  • ketone refers to hydrocarbons comprising at least one or more carbonyl functional groups R c -C (O) -R d in which R c and R d are independently of one another a C 1 -C 4 alkyl.
  • C20 alkenyl, C2-C20 alkynyl, C2-C20, C3-C20 cycloalkenyl, C3-C20, C6-C18 may be substituted or not by one or more -OH, halogen, -NR a C (0) R b , -C (O) NR a R b -CN, -NO 2 , -NR a R b , -OR a , -SR a , -COR 2 R a , -OC (O) OR a , -OC (O) R a -C (O) H, -C (O) R a wherein R a and R b are as defined above, R c and R d being bonded together to form with the carbonyl group to which they are attached a cyclic ketone comprising from 4 to 10 members, preferably from 4 to 7 members.
  • the cyclic ketone may also comprise one or more carbon-carbon double bonds.
  • amine refers to hydrocarbons comprising at least one or more amine functional groups -NR c R d in which R c and R d are as defined above, R c and R d being able to be linked together for form with the nitrogen atom to which they are attached an aromatic or non-aromatic heterocycle comprising from 4 to 10 members.
  • esters refers to compounds of formula c -C (0) -0- d wherein R c and R d are as defined above, R c and R d may be linked together to form with the ester group a ring comprising from 4 to 20 carbon atoms.
  • ether refers to compounds of the formula R c -O-R d wherein R c and R d are as defined above, where R c and R d may be linked together to form with the atom oxygen to which they are attached a heterocycle comprising from 4 to 20 carbon atoms.
  • aldehyde refers to compounds comprising at least one or more -C (O) -H functional groups.
  • nitrile refers to compounds comprising at least one or more functional groups -CN.
  • carbonate refers to compounds of the formula R c -O-C (O) -O-R d wherein R c and R d are as defined above.
  • thioalkyl relates to compounds of formula R c SR d wherein R c and R d are as defined above.
  • amide relates to compounds of formula R c C (O) NR e R d in which R c and
  • R d are as defined above, wherein R e is selected from the same substituents as those defining R c , where R c and R d may be bonded together to form with the amide group - C (O) N- at which they are attached a cyclic amide comprising from 4 to 10 members, preferably from 4 to 7 members.
  • the cyclic amide may also include one or more carbon-carbon double bonds.
  • the cyclic amide may also be substituted or unsubstituted by one or more substituents as defined above.
  • heterocycle refers to a 4- to 10-membered carbon ring of which at least one of the linkages is a heteroatom selected from the group consisting of O, S, P and N.
  • the heterocycle may comprise one or more carbon-carbon double bonds. carbon or one or more carbon-heteroatom double bonds or one or more heteroatom-heteroatom double bonds.
  • the heterocycle may comprise 1, 2, 3, 4 or 5 heteroatoms as defined above.
  • the heterocycle may comprise 1, 2 or 3 heteroatoms selected from oxygen, nitrogen or sulfur.
  • the heterocycle may be a 4- to 6-membered carbon ring of which 1, 2 or 3 members are heteroatoms selected from O or N.
  • the heterocycle may or may not be substituted by one or more substituents selected from -OH , halogen, -NR a C (O) R b , -C (O) NR a R b -CN, -NO 2 , -NR a R b , -OR a , -SR a , -CO 2 R a , - OC (O) OR a , -OC (O) R a , -C (O) H, -C (O) R a in which R a and R b are as defined above.
  • organic extractant refers to a compound having at least one carbon atom.
  • the invention relates to a process for purifying 2,3,3,3-tetrafluoro-1-propene (1234yf).
  • the purification process is carried out from a first composition comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3 3,3-tetrafluoro-1-propene (1234ze-E).
  • said method comprises the steps of:
  • the first composition is obtained from a mixture C comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3 , 3,3-tetrafluoro-1-propene (1234ze-E) and HF, said mixture being subjected to the following steps:
  • aqueous solution of hydrofluoric acid used in step i ') is of concentration greater than 40% by weight.
  • the hydrofluoric acid aqueous solution is of concentration greater than 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52% 53% 54% 55% 56% 57% 58% 59% 60% 61% 62% 63% 64% 65% 66% 67% 68% 69 % 70% 71% 72% 73% 74% 75% 76% 77% 78% 79% 80% 81% 82% 83% 84% 85% 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% or 95% by weight. More particularly, the aqueous solution of hydrofluoric acid is of concentration greater than or equal to 50% by weight, or greater than or equal to 60% by weight or greater than or equal to 70% by weight.
  • the aqueous solution of hydrofluoric acid may be between any of the values mentioned above.
  • the hydrofluoric acid aqueous solution may be between 45% and 95% by weight, between 50% and 90% by weight, between 55% and 85% by weight, between 60% by weight and 80% by weight or between 65% by weight and 75% by weight.
  • Step i ') of the present process allows formation of said second two-phase stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and HF.
  • Said two-phase current consists of a gaseous phase and a liquid phase.
  • the gaseous phase may comprise 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene ( 1234ze-E).
  • the gas phase may comprise hydrofluoric acid.
  • the content thereof is generally low, preferably less than 5% by weight based on the total weight of said gaseous phase, in particular less than 2% by weight based on total weight of said gaseous phase, more particularly less than 1% by weight based on the total weight of said gaseous phase.
  • the liquid phase of said two-phase stream may comprise hydrofluoric acid.
  • Said liquid phase may optionally comprise a small amount of 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) or trans-1,3,3,3-tetrafluoro propylene (1234ze-E), preferably said liquid phase may comprise a content of 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) or trans -l, 3,3,3-tetrafluoro-1-propene (1234ze-E) less than 5% by weight based on the total weight of said liquid phase, in particular less than 1% by weight based on the total weight of said liquid phase, plus particularly lower than 5000 ppm by weight based on the total weight of said liquid phase, preferably less than 1000 ppm by weight based on the total weight of said liquid phase, more preferably less than 500 ppm by
  • Said liquid phase may comprise a total content of 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoropropane.
  • 1-propene (1234ze-E) less than 5% by weight based on the total weight of said liquid phase, in particular less than 1% by weight based on the total weight of said liquid phase, more particularly less than 5000 ppm by weight on the basis of the total weight of said liquid phase, preferably less than 1000 ppm by weight based on the total weight of said liquid phase, more preferably less than 500 ppm by weight, particularly preferably less than 100 ppm based on the total weight of said liquid phase.
  • the hydrofluoric acid concentration in said liquid phase of said second diphasic stream is greater than the concentration of said hydrofluoric acid aqueous solution used in step i ').
  • Said liquid phase of said second two-phase current may have a hydrofluoric acid concentration greater than 41% by weight based on the total weight of said liquid phase of said second two-phase current.
  • said liquid phase of said second two-phase current may have a hydrofluoric acid concentration greater than 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%.
  • said liquid phase of said second two-phase stream may have a hydrofluoric acid concentration of between 45% and 95% by weight, between 50% and 90% by weight, between 55% and 85% by weight, and between 60% by weight. weight and 80% by weight or between 65% by weight and 75% by weight while being greater than the concentration of said aqueous hydrofluoric acid solution used in stage i ').
  • the aqueous hydrofluoric acid solution used in step i ') is at a temperature of between -20 ° C. and 80 ° C. before being brought into contact with the said mixture C, advantageously between -15 ° C. and 70 ° C. C., preferably between -10 ° C. and 60 ° C., more preferably between -5 ° C. and 50 ° C., in particular between -5 ° C. and 40 ° C., more particularly between 0 ° C. and 30 ° C.
  • the temperature of the aqueous hydrofluoric acid solution used in step i '), before it comes into contact with said mixture C can be 0 ° C, 1 ° C, 2 ° C, 3 ° C, 4 ° C, 5 ° C, 6 ° C, 7 ° C, 8 ° C, 9 ° C, 10 ° C 11 ° C, 12 ° C, 13 ° C, 14 ° C, 15 ° C, 16 ° C, 17 ° C, 18 ° C, 19 ° C, 20 ° C, 21 ° C, 22 ° C, 23 ° C, 24 ° C, 25 ° C, 26 ° C, 27 ° C, 28 ° C, 29 ° C or 30 ° C.
  • the implementation of said aqueous hydrofluoric acid solution at the temperatures mentioned above is intended to control the exothermicity occurring when it is brought into contact with said mixture C.
  • step ii ') of the method according to the present invention implements the storage of said second two-phase current in a buffer tank, said second two-phase current consisting of said liquid phase and said gas phase as described. above.
  • step iii ') of the process according to the present invention implements the passage of said gaseous phase of said second diphasic current in an absorption column supplied countercurrently with an aqueous stream to form a C1 stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234 E) and a stream C2 comprising HF.
  • the flow rate of the aqueous stream used in step iii ') is determined as a function of the amount of hydrofluoric acid contained in said mixture C.
  • the ratio between the flow rate of the aqueous flow expressed in kg / h feeding the absorption column in step iii ') and the amount of hydrofluoric acid in said mixture C expressed in kg / h is between 0.05 and 1.22.
  • the ratio between the flow rate of the aqueous flow supplying the absorption column in step (iii) and the amount of hydrofluoric acid in said mixture C expressed in kg / h may be between 0.11 and 1.00.
  • the ratio between the flow rate of the aqueous flow supplying the absorption column in step (iii) and the quantity of hydrofluoric acid in said mixture C expressed in kg / h may be 0.25, 0.26, 0.
  • An additional aqueous stream corresponding to the vaporized water fraction at the top of said absorption column may also supply said column.
  • the aqueous stream as described above is different from said additional aqueous stream linked to the vaporized water fraction at the top of the column and does not include it.
  • said absorption column implemented in step iii ') comprises at least one absorption stage.
  • said absorption column implemented in step iii ') comprises at least two absorption stages.
  • said absorption column implemented in step iii ') comprises at least three absorption stages.
  • Said absorption column implemented in step iii ') may thus comprise two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen or fifteen absorption stages.
  • said stream C1 comprises less than 1000 ppm of hydrofluoric acid by weight based on the total weight of said third stream, preferably less than 900 ppm of hydrofluoric acid, more preferably less than 800 ppm of hydrofluoric acid, in particular less 700 ppm of hydrofluoric acid, more particularly less than 600 ppm of hydrofluoric acid, preferably less than 500 ppm of hydrofluoric acid, even more preferred less than 400 ppm of hydrofluoric acid, preferably less favored 300 ppm of hydrofluoric acid, particularly preferably less than 200 ppm of hydrofluoric acid, more particularly preferred less than 100 ppm of hydrofluoric acid.
  • said third stream may have a hydrofluoric acid content of between 1 and 200 ppm, between 5 and 190 ppm, between 10 and 180 ppm, between 15 and 170 ppm, between 20 and 160 ppm, between 25 and 150 ppm or between 30 and 140 ppm by weight based on the total weight of said stream C1.
  • At least 80% by weight of the hydrofluoric acid optionally present in said gas phase of said second two-phase current is absorbed by the first absorption stage of said absorption column, in particular at least 85% by weight of the hydrofluoric acid optionally present in said gas phase of said second two-phase current is absorbed by the first absorption stage of said absorption column, more particularly at least 90% by weight of the hydrofluoric acid possibly present in said gaseous phase of said second two-phase current is absorbed by the first absorption stage of said absorption column.
  • said aqueous stream can be introduced at least at the head of the absorption column.
  • said stream C1 can be said first composition according to the present invention.
  • said stream C2 is in the form of an aqueous solution of hydrofluoric acid.
  • said stream C2 is an acid solution fluorhydric concentration of less than 30% by weight based on the total weight of said fourth stream.
  • said stream C2 is a hydrofluoric acid solution of concentration less than 25% by weight based on the total weight of said stream C2.
  • said stream C2 is a hydrofluoric acid solution with a concentration of between 5 and 25% by weight based on the total weight of said C2 stream, more particularly between 10 and 20% by weight based on the total weight of said C2 stream.
  • said stream C2 is recycled in step ii '). The current C2 can thus be mixed with said liquid phase of said second two-phase current.
  • said method also comprises the steps of: iv ') neutralizing said stream C1 obtained in stage iii') by an aqueous alkaline solution to form a neutralized stream C3, and
  • said aqueous alkaline solution may be an aqueous solution of hydroxide of an alkali metal or alkaline earth metal.
  • the aqueous alkaline solution may be an aqueous solution of sodium hydroxide, potassium hydroxide, calcium hydroxide or magnesium hydroxide or a mixture thereof.
  • said aqueous alkaline solution has a concentration of between 5 and 50% by weight based on the total weight of said alkaline aqueous solution.
  • said alkaline aqueous solution has a concentration of at least 5%, at least 6%, at least 7%, at least 8%, at least 9%, at least 10%.
  • Said neutralized stream C3 formed in stage iv ') preferably comprises 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3, 3,3-tetrafluoro-1-propene (1234ze-E).
  • the hydrofluoric acid content in said neutralized stream C3 is lower than the hydrofluoric acid content of said Cl, before its neutralization.
  • Said neutralized stream C3 formed in step iv ') may also contain water. Said neutralized stream C3 formed in step iv ') can thus be dried in step v') of the present process.
  • said neutralized stream C3 formed in step iv ') is dried on a molecular sieve.
  • said neutralized stream C3 formed in step iv ') is dried on 3A molecular sieve, such as siliporite.
  • Step v ') of the present process allows the formation of a neutralized and dried C4 stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E).
  • Said C4 stream can then be compressed and liquefied at a pressure of at most 8 bara to form a compressed C5 stream in which 2,3,3,3-tetrafluoro-1-propene, 1,1, 1,2,2- pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) are in liquid form.
  • the current C4 or the current C5 may be said first composition according to the present invention.
  • the liquid phase resulting from mixing said liquid phase of said second two-phase current with said stream C2 is recycled in step i ').
  • the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 may have a hydrofluoric acid concentration of greater than 41% by weight based on the total weight of said liquid phase resulting from the mixing of said liquid phase of said second stream two-phase with said current C2.
  • the liquid phase resulting from the mixing of said liquid phase of said second diphasic current with said stream C2 can have a hydrofluoric acid concentration of greater than 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65 66% 67% 68% 69% 70% 71% 72% 73% 74% 75% 76% 77% 78% 79% 80% 81% 82 %, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% or 95% by weight based on the total weight of said phase liquid resulting from the mixing of said liquid phase of said second two-phase current with said stream C2.
  • the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 may have a hydrofluoric acid concentration of between 45% and 95% by weight, between 50% and 90% by weight, and between 55% and 55% by weight. and 85% by weight, between 60% by weight and 80% by weight or between 65% by weight and 75% by weight based on the total weight of said liquid phase resulting from the mixing of said liquid phase of said second diphasic current with said current C2.
  • the liquid phase resulting from mixing said liquid phase of said second two-phase current with said stream C2 is distilled to form a stream D, preferably at the top of the distillation column.
  • said stream D comprises hydrofluoric acid containing less than 3000 ppm of water, preferably less than 2000 ppm of water, more preferably less than 1000 ppm of water, in particular less than 500 ppm of water, more particularly less than 200 ppm water, preferably less than 100 ppm water, more preferably less than 50 ppm water based on the total weight of current D.
  • Said current D may also include less than 50 ppm of hydrochloric acid, advantageously less than 45 ppm of hydrochloric acid, preferably less than 40 ppm of hydrochloric acid, more preferably less than 35 ppm of hydrochloric acid, in particular less than 30 ppm of hydrochloric acid, more particularly less than 20 ppm of hydrochloric acid based on the total weight of the current D
  • Said current D may also comprise less than 50 ppm of organic compounds, advantageously less than 45 ppm of organic compounds, preferably less than 40 ppm pm of organic compounds, more preferably less than 35 ppm of organic compounds, in particular less than 30 ppm of organic compounds, more particularly less than 20 ppm of organic compounds based on the total weight of the current D.
  • An organic compound is a compound comprising at least one carbon atom.
  • the distillation of said liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 forms a stream E, preferably at the bottom of the distillation column, comprising hydrofluoric acid in the form of a solution. aqueous concentration of less than 50% by weight.
  • said stream E comprises hydrofluoric acid in the form of an aqueous solution with a concentration of less than 50% by weight, 49% by weight, 48% by weight, 47% by weight, 46% by weight, 45% by weight. weight, 44% by weight, 43% by weight, 42% by weight based on the total weight of said stream E.
  • said stream E comprising hydrofluoric acid in the form of an aqueous solution with a concentration greater than 20% by weight based on the total weight of said stream E.
  • said stream E comprising hydrofluoric acid in the form of an aqueous solution of higher concentration 21% by weight, 22% by weight, 23% by weight, 24% by weight, 25% by weight, 26% by weight, 27% by weight, 28% by weight, 29% by weight, 30% by weight, 31% by weight, 32% by weight, 33% by weight, 34% by weight, 35% by weight based on the total weight of said stream E.
  • Said aqueous solution obtained in the stream E can be marketed or destroyed by neutralization.
  • the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 can thus be either distilled or recycled in step i ').
  • a part of the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 is distilled while the other part of the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said current C2 is recycled in step i ').
  • second diphasic current with said stream C2 is recycled to step i '); and less than 50%, preferably less than 40%, more preferably less than 30%, especially less than 20%, more preferably less than 10% by weight is distilled.
  • the stream comprising said organic extraction agent is recycled in step a).
  • the stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) is purified or destroyed by incineration.
  • said process also comprises a step of recovering said stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1,1,1,2,2-pentafluoropropane (245cb) obtained from step b), and distillation thereof to form a stream A comprising 2,3,3,3-tetrafluoro-1-propene and a stream B comprising 1,1,1,2,2-pentafluoropropane (245cb).
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise 2,3,3,3-tetrafluoro-1-propene, 1, 1, 1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and at least one of the compounds selected from the group consisting of chloromethane (40), 1, 1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2, 3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf).
  • chloromethane 40
  • 1, 1-difluoroethane 152a
  • said first composition, mixture C, stream C1, stream C3 and / or stream C4 may comprise at least two, at least three, at least four, at least five, at least six or all of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3 3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf).
  • chloromethane 40
  • 1,1-difluoroethane 152a
  • 1,1,1,2-tetrafluoroethane 134a
  • chloropentafluoroethane 115
  • trans-1,2,3 3,3-pentafluoropropene (1225ye-E
  • the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 contain at least one of the compounds selected from the group consisting of chloromethane (40), 1.1 difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis- 1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), this or these are contained in said second and third compositions.
  • chloromethane 40
  • 1.1 difluoroethane 152a
  • 1,1,1,2-tetrafluoroethane 134a
  • chloropentafluoroethane 115
  • trans-1,2,3,3,3-pentafluoropropene (1225ye-E
  • Step c) of the present process may thus consist of the recovery of said third composition and the separation between, on the one hand, said organic extraction agent and, on the other hand, trans-1,3,3,3-tetrafluoroethylene.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 can comprise between 50 and 99% by weight of 2,3,3,3-tetrafluoro-1.
  • propene on the basis of the total weight of the first composition advantageously between 50 and 95% by weight, preferably between 55 and 90% and in particular between 60 and 80% by weight of 2,3,3,3-tetrafluoro-1; -propene on the basis of the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise between 0.1 and 50% by weight of 1,1,2,2,2-pentafluoropropane (245cb) based on the total weight of the first composition, advantageously between 0.1 and 49.9% by weight, preferably between 1 and 45% by weight, more preferably between 2 and 40% and in particular between 5 and 40% by weight. % by weight of 1,1,2,2,2-pentafluoropropane (245cb) based on the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise between 0.1 and 50% by weight of trans-1,3,3,3-tetrafluoro 1-propene (1234ze-E) based on the total weight of the first composition, advantageously between 0.1 and 49.9% by weight, preferably between 0.5 and 40% by weight, more preferably between 1 and 30% and in particular between 5 and 25% by weight of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) based on the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 1% by weight of chloromethane (40) based on the total weight of the first composition preferably between 1 and 5000 ppm by weight, preferably between 5 and 2000 ppm and in particular between 10 and 1000 ppm by weight of chloromethane (40) based on the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of 1,1-difluoroethane (152a) based on the total weight of the first composition, advantageously between 1 and 1000 ppm weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of 1,1-difluoroethane (152a) based on the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of chloropentafluoroethane (115) based on the total weight of the first composition preferably between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of chloropentafluoroethane (115) based on the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of 1,1,1,2-tetrafluoroethane (134a) on based on the total weight of the first composition, advantageously between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of 1,1,1,2-tetrafluoroethane (134a) on the basis of the weight total of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of trans-1,2,3,3,3-pentafluoropropene (1225ye-E) based on the total weight of the first composition, advantageously between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of trans-1, 2,3,3, 3-pentafluoropropene (1225ye-E) based on the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of cis-1,2,3,3,3-pentafluoropropene (1225ye-Z) based on the total weight of the first composition, advantageously between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of cis-1, 2,3,3, 3-pentafluoropropene (1225ye-Z) based on the total weight of the first composition.
  • Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 1% by weight of 3,3,3-trifluoropropene (1243zf) based on the total weight of the first composition, advantageously between 1 and 5000 ppm by weight, preferably between 5 and 2000 ppm and in particular between 10 and 1500 ppm by weight of 3,3,3-trifluoropropene (1243zf) on the basis of the total weight of the first composition.
  • said organic extraction agent may be a solvent chosen from the group consisting of hydrohalocarbon, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, thioalkyl, amide, heterocycle; or the organic extractant is triethylfluorosilane.
  • the organic extractant is selected from the group consisting of amine, ether, ester, aldehyde, ketone, alcohol and heterocycle.
  • the hydrohalocarbons are selected from the group consisting of bromofluoromethane, 1-bromo-1,2-difluoroethylene, 1,1,1-trifluoro-2-bromoethane, 2-chloropropane, bromoethane, iodomethane, 2-chloro-2- methylpropane, 2-bromopropane, chlorobromomethane, 3-bromopropene, 1-bromopropane, iodoethane, 2-bromo-2-methylpropane, 1-chloro-3-fluoropropane, 2-chloro-2-methylbutane, 1,2-dichloroethane, 2- iodopropane, dichlorobromomethane, 2-bromobutane, 1,2-dichloropropane, trichloroacetaldehyde, 1-chloro-4-fluorobutane, 1-bromo-3-fluoropropane, 1-bromo
  • the alcohols are selected from the group consisting of methanol, 2,2,2-trifluoroethanol, 1,1,1-trifluoro-2-propanol, ethanol, 2-propanol, tert-butanol, 2,2-difluoroethanol, propanol, 2-allyloxyethanol, 2-butanol, 2-methyl-2-butanol, isobutanol, 2,2,3,3-tetraflouro-1-propanol, 2,2-dimethyl-1-propanol, 3-pentanol, butanol, 1-methoxy-2-propanol, 1- (dimethylamino) -2-propanol, 3-methyl-3-pentanol, 1-chloro-2-methyl-2-propanol, 4,4,4-trifluorobutanol, 3-fluoropropanol, 2-chloroethanol, 2-methoxyl-propanol, 1-ethoxy-2-propanol, 4-methyl-2-pentano
  • the ketones are selected from the group consisting of 1,1,1-trifluoro-2-propanone, propanone, butanone, 3-pentanone, 2-pentanone, 3,3-dimethyl-2-butanone, 4-methyl- 2-pentanone, 2-hexanone, 5-hexen-2-one, 4-methyl-2-hexanone.
  • the amines are selected from the group consisting of ethylamine, isopropylamine, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, diethylamine, 2-butanamine, n-methylpropylamine, 1-butylamine, diisopropylamine, 3- methyl-2-butanamine, 3-pentylamine, n-methylbutylamine, 1-methoxy-2- propanamine, 2-methoxyethanamine, 2-methoxy-1propanamine, n-pentylamine, n-methylhydroxylamine, dipropylamine, 2-ethoxyethanamine, n-methyl-1,2-ethanediamine, pyridine, 1,2-diaminoethane, 1,2-propanediamine, 2-ethylbutylamine, n-ethylethylenediamine,
  • the esters are selected from the group consisting of methylformate, methylacetate, isopropylformate, ethylacetate, n-propylformate, isopropylacetate, tertbutylacetate, ethylpropionate, sec-butylacetate, diethylcarbonate, n-butylacetate, bromoaceticacidmethylester, methylhexanoate.
  • the ethers are selected from the group consisting of 2,2,2-trifluoroethylmethylether, 2-methoxy-1-propene, diethylether, ethoxyethene, dimethoxymethane, methylcyclopropylether, 2-ethoxy-propane, methyl-t-butylether, chloromethoxymethane, diisopropyl ether, 2-ethoxy-2-methyl-propane, 2-ethoxy-butane, 1-methoxy-2-methyl-butane, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane, diethoxymethane, di-n-propylether, 1-ethoxybutane, 1-methoxy-pentane,
  • 1,2-dimethoxypropane isopropyl-isobutyl-ether, 1,1-diethoxyethane, trimethoxymethane, 2,2-diethoxypropane, isobutyl-tert-butylether, sec-butyl-tert-butylether, 1,1-diethoxypropane, 2-methoxyethanol, 2- chloro-1,1-dimethoxyethane, methoxycyclohexane, ethoxyethanol, di-n-butylether, 1-ethoxy-hexane, 1,1,1-triethoxyethane, 1-methoxy-2-acetoxypropane.
  • the aldehydes are selected from the group consisting of acetaldehyde, ethanedial, isobutanal, methylglyoxal, 2-methylbutanal, 2,6-dimethyl-5-heptenal, hexanal.
  • the nitriles are selected from the group consisting of acetonitrile, propionitrile, butyronitrile, valeronitrile, (methyleneamino) acetonitrile.
  • the carbonate is diethylcaarbonate.
  • the amide is ethanethioamide.
  • the thioalkyls are selected from the group consisting of ethanethiol, dimethylsulfide, 2-propanethiol, 4-methoxy-2-methyl-2-butanethiol, tert-butylthiol, 1-propanethiol, 2-butanethiol, 2-methyl-1- propanethiol, diethylsulfide, butanethiol, 3-mercapto-1,2-propanediol, tetrahydrothiophene, 1-pentanethiol.
  • the heterocycles are selected from the group consisting of tetrahydrofuran, 1,4-dioxane, 1,3-dioxane, 1,3,5-trioxane, n-methylmorpholine, 2-methylpyrazine, n-ethyl-morpholine, 1- methylpiperazine, 1,2-epoxypropane, piperidine, 3-furfural, 2,6-dimethylmorpholine.
  • Said organic extraction agent may be ethylamine, bromofluoromethane, 1-bromo-1,2-difluoroethylene, acetaldehyde, 1,1,1-trifluoro-2-propanone, 1,1,1-trifluoro-2-bromoethane, 2, 2,2-trifluoroethylmethylether, isopropylamine, methylformate, 2-methoxy-1-propene, diethylether, 1,2-epoxypropane, ethanethiol, ethoxyethene, ethylmethylamine, dimethylsulfide, 2-chloropropane, bromoethane, dimethoxymethane, iodomethane, 2-amino- 2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, ethanedial, 2-chloro-2-methylpropane, 2-propanethiol, 2-eth
  • said organic extraction agent may be ethylamine, bromofluoromethane, acetaldehyde, isopropylamine, methylformate, 2-methoxy-1-propene, diethyl ether, 1,2-epoxypropane, ethanethiol, ethoxy-ethene, ethylmethylamine, dimethylsulfide, bromoethane, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-propanethiol, 2-ethoxypropane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-bromopropane, 2-butanamine, n-methylpropylamine, tert-butylthiol, isobutanal, tetra
  • said organic extraction agent may be ethylamine, acetaldehyde, isopropylamine, methylformate, diethylether, 1,2-epoxypropane, ethylmethylamine, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-ethoxy propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, isopropylformate, diisopropylether, 2-ethoxy-2-methyl -propane, 1-butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy-butane, 1-methoxy-2-methyl-butane
  • said organic extraction agent may be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate , 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane, 3-methyl-2 -butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine
  • the organic extraction agent to be used may be selected depending on the compounds present in said first composition.
  • the organic extractant can be selected depending on the separation factor and the absorption capacity established for a particular composition.
  • the choice of the organic extraction agent may optionally be based on other commercial or environmental criteria, such as, for example, the cost of the organic extraction agent, its availability on the market, its toxic or flammable properties.
  • the boiling point of the organic extractant may be from 0 ° C to 200 ° C, preferably from 10 ° C to 190 ° C, preferably from 10 ° C to 180 ° C, in particular 10 ° C C at 170 ° C, more preferably from 10 ° C to 160 ° C, and preferably from 10 ° C to 150 ° C.
  • PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene (1234yf)
  • s represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze-E) in said organic infinite dilution extractant
  • P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
  • PI represents the saturated vapor pressure of 1,1,2,2-pentafluoropropane (245cb)
  • Y2 represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze) E) in said organic extraction agent with infinite dilution
  • P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
  • said organic extraction agent has:
  • PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene (1234yf)
  • s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene (1234
  • P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene
  • PI represents the saturated vapor pressure of 1,1,2,2-pentafluoropropane (245cb)
  • Y2 represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze) -
  • the separation factor Si, 2 may be greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to 2.0.
  • the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.
  • said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.1, advantageously greater than or equal to 1.2, preferably greater than or equal to 1.4, plus preferably greater than or equal to 1.6, in particular greater than or equal to 1.8 and more particularly greater than or equal to 2.0; and an absorption capacity C2, s greater than or equal to 0.20, advantageously greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 0.80, equal to 1.0.
  • the separation factor and the said absorption capacity can be calculated for the particular binary pair consisting of 2 , 3,3,3-tetrafluoro-1-propene and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and / or 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E).
  • the separation factor Si, 2 makes it possible to determine the capacity of an organic extraction agent to separate two or more compounds.
  • the absorption capacity C2, s makes it possible to determine the amount of solvent to be used to obtain the separation between the compounds under consideration.
  • said organic extraction agent may be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate , 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane, 3-methyl-2 -butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethan
  • said organic extraction agent can be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, diethylamine, 2-butanamine, n-methylpropylamine, 1 -butylamine, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2 propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, 1,2-dimethoxypropane, dioxane, 1-diethoxyethane, 2-methoxy-1propanamine, trimeth
  • said organic extraction agent may be ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1 , 4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate 2-methoxy-1-propanol, hexanal.
  • said organic extractant may be ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy-1-propanol, hexanal .
  • said third composition comprising said organic extraction agent and trans-1,1,3,3-tetrafluoro-1-propene (1234ze-E); preferably the third composition comprising said organic extractant and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane ( 40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis 1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf); may be subjected to distillation to separate the organic extractant and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E); preferably, to separate,
  • the stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E) cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) may be subjected to one or more subsequent purification steps or may be destroyed by incineration.
  • the present process thus makes it possible to purify 2,3,3,3-tetrafluoro-1-propene (1234yf).
  • the content of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) in the stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1.1 , 1,2,2-pentafluoropropane (245cb) and obtained in step b) of the present purification process is less than the content thereof in said first composition.
  • the content of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and / or at least one of the compounds selected from the group consisting of chloromethane (40), 1,1- difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3, 3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) in the stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1,1,1,2 , 2-pentafluoropropane (245cb) and obtained in step b) of the present purification process is less than the content thereof in said first composition.
  • trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) or any of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3 , 3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) can be reduced by 50%, advantageously by 75%, preferably by 90%, in particular by 95%, more particularly by 98%.
  • the content of at least two, at least three, at least four, at least five, at least six or all of said compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a) , 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3- pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) can be reduced by 50%, advantageously by 75%, preferably by 90%, in particular by 95%, more particularly by 98%.
  • the content of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) can be reduced by 50%, advantageously by 75%, preferably by 90%, in particular by 95%, more particularly 98%.
  • the stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane obtained in step b) of the present purification process may be devoid of trans- 1,3,3,3-tetrafluoro-1-propene (1234ze-E).
  • the current comprising the 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane obtained in step b) of the present purification process may be devoid of trans-1,3,3,3 -tetrafluoro-1-propene (1234ze-E) and / or optionally at least one, at least two, at least three, at least four, at least five, at least six or all of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2 , 3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) when the latter or those ci are present in said first
  • free means that the stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) comprises less than 50 ppm, preferably less than 20 ppm, preferably less than 10 ppm of the compound under consideration. total weight of the current. The contents are expressed by weight.
  • said mixture C implemented in stage i ') of the present process can be previously purified before being used. Indeed, if said mixture C comprises impurities having a boiling point below the boiling point of 2,3,3,3-tetrafluoro-1-propene and optionally heavy impurities, the present process can comprise beforehand 'step i') the steps:
  • compositions comprising 2,3,3,3-tetrafluoro-1-propene, impurities having a boiling point below the boiling point of 2,3,3,3- tetrafluoro-1-propene, HF, 1,1,1,2,2-pentafluoropropane (245cb), and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), optionally optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3 , 3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), and optionally or not heavy impurities; ii-) distill
  • 1-propene (1234ze-E) optionally optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3- trifluoropropene (1243zf), and optionally or not heavy impurities recovered at the bottom of the distillation column;
  • step iii-) optionally or not, distillation of said first stream recovered at the bottom of the distillation column in step ii-) to recover at the top of the column a second stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane
  • said first stream recovered in step ii-) or said second stream recovered in step iii-) correspond to said mixture C implemented in step i ').
  • the present invention provides a process for producing 2,3,3,3-tetrafluoro-1-propene.
  • this process may include its purification.
  • the present invention provides a process for producing 2,3,3,3-tetrafluoro-1-propene comprising the steps of:
  • a carbon-carbon double bond may be present to complete the valence of carbon atoms of compounds of formula CH ( n + 2) (X) m-CHp (X) (n + 1) -CX (3 + p- m) ).
  • the current recovered in step B) corresponds to said mixture C according to the present invention.
  • the stream comprising said organic extractant can be recycled in step a).
  • the stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1- difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3, 3,3-Pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) can be purified or destroyed by incineration.
  • the stream recovered in stage B) from the process for producing 2,3,3,3-tetrafluoro-1-propene may comprise impurities having a boiling point below the boiling point 2,3,3,3-tetrafluoro-1-propene.
  • the stream recovered in stage B) can be subjected to a preliminary distillation ⁇ ) to eliminate at the top of the distillation column said impurities having a boiling point below the boiling point 2,3,3,3-tetrafluoro-1-propene and forming a first stream comprising 2,3,3,3-tetrafluoro-1-propene, HF, 1,1,1,2,2-pentafluoropropane, trans- 1,1,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1 , 1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye),
  • the stream recovered in stage B) of the process for producing 2,3,3,3-tetrafluoro-1-propene may comprise heavy impurities.
  • the stream recovered in stage B) prior to step C), may be subjected to preliminary distillation B2 '), which may or may not be subsequent to stage ⁇ ), in order to eliminate the said impurities at the bottom of the distillation column.
  • the stream recovered in stage B) of the process for producing 2,3,3,3-tetrafluoro-1-propene may also comprise HCl.
  • Hydrochloric acid can be recovered by distillation before or after step ⁇ independently of the other steps of the process.
  • step A) is carried out from 1,1,2,3-tetrachloropropene, 2,3,3,3, -tetrachloropropene, 1,1,1,2,3-pentachloropropane, 2-chloroacetylene, 3,3,3-trifluoropropene, 1,2-dichloro-3,3,3-trifluoropropane, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and 1, 1,1,2,2-pentachloropropane, preferably from 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, 2-chloro 3,3,3-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,2-dichloro-3,3,3-trifluoropropane, 1,1,1,2,2-pentafluoro
  • the catalyst used in the present process for producing 2,3,3,3-tetrafluoropropene may for example be based on a metal comprising a transition metal oxide or a derivative or a halide or an oxyhalide of such a metal.
  • a metal comprising a transition metal oxide or a derivative or a halide or an oxyhalide of such a metal.
  • FeCU chromium oxyfluoride
  • chromium oxides possibly subjected to fluorination treatments
  • chromium fluorides and mixtures thereof may be mentioned.
  • Other possible catalysts are carbon-supported catalysts, antimony catalysts, aluminum catalysts (eg AlF 3 and Al 2 O 3, alumina oxyfluoride and alumina fluoride).
  • a chromium oxyfluoride a fluoride or an aluminum oxyfluoride, or a supported or non-supported catalyst containing a metal such as Cr, Ni, Fe, Zn, Ti, V, Zr, Mo, Ge or Sn. Pb, Mg, Sb.
  • the catalyst is more preferably based on chromium and it is more particularly a mixed catalyst comprising chromium.
  • a mixed catalyst comprising chromium and nickel is used.
  • the molar ratio Cr / Ni (based on the metal element) is generally 0.5 to 5, for example 0.7 to 2, for example about 1.
  • the catalyst may contain from 0.5 to 20% by weight of nickel.
  • the metal may be present in metallic form or in the form of a derivative, for example an oxide, halide or oxyhalide. These derivatives are preferably obtained by activation of the catalytic metal.
  • the support is preferably made of aluminum, for example alumina, activated alumina or aluminum derivatives, such as aluminum halides and aluminum oxyhalides, for example described in US Pat. US 4,902,838, or obtained by the activation method described above.
  • aluminum for example alumina, activated alumina or aluminum derivatives, such as aluminum halides and aluminum oxyhalides, for example described in US Pat. US 4,902,838, or obtained by the activation method described above.
  • the catalyst may comprise chromium and nickel in an activated or non-activated form, on a support which has been subjected to activation or not.
  • Another preferred embodiment is based on a chromium-containing mixed catalyst and at least one element selected from Mg and Zn.
  • the atomic ratio of Mg or Zn / Cr is preferably from 0.01 to 5.
  • the catalyst Prior to use, the catalyst is preferably activated with air, oxygen or chlorine and / or with HF.
  • the catalyst is preferably subjected to activation with air or oxygen and HF at a temperature of 100 to 500 ° C, preferably 250 to 500 ° C and more preferably 300 to 400 ° C. ° C.
  • the activation time is preferably from 1 to 200 hours and more particularly from 1 to 50 hours.
  • This activation may be followed by a final fluorination activation step in the presence of an oxidizing agent, HF and organic compounds.
  • the molar ratio of HF / organic compounds is preferably from 2 to 40 and the molar ratio of oxidation agent / organic compounds is preferably from 0.04 to 25.
  • the temperature of the final activation is preferably from 300 to 400 ° C. C and its duration preferably from 6 to 100 h.
  • the fluorination reaction in the gas phase can be carried out: with an HF / compound of formula (I) and / or (II) molar ratio of from 3: 1 to 150: 1, preferably from 4: 1 to 125: 1 and more particularly preferably from 5: 1 to 100 : 1;
  • contact time 3 to 100 seconds, preferably 4 to 75 seconds and more particularly 5 to 50 seconds (volume of catalyst divided by the total incoming flow, adjusted to the temperature and to the operating pressure);
  • a temperature (temperature of the catalyst bed) of 200 to 450 ° C., preferably of 250 to 400 ° C., and more particularly of 280 to 380 ° C.
  • the duration of the reaction step is typically from 10 to 8000 hours, preferably from 50 to 5000 hours and more preferably from 70 to 1000 hours.
  • An oxidizing agent preferably oxygen
  • oxygen may optionally be added during the fluorination reaction.
  • the oxygen / organic compounds molar ratio may be from 0.005 to 2, preferably from 0.01 to 1.5.
  • the oxygen can be introduced pure or in the form of air or oxygen / nitrogen mixture. Oxygen can also be replaced by chlorine.
  • Fig. 1 schematically illustrates a device implementing a process for producing 2,3,3,3-tetrafluoropropene according to a particular embodiment of the present invention.
  • Hydrofluoric acid 1 is brought into contact with 1,1,1,2,3-pentachloropropane (240db) 2 in a reactor 3.
  • the reactor 3 can also be fed with the stream comprising 1,1,1,2 , 2-pentafluoropropane (245cb) and from the recycling of the process for purifying 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb).
  • the resulting mixture comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), HF, trans-1, 3,3,3-tetrafluoro-1- propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115) trans-1, 2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), It is recovered at the outlet of the reactor and conveyed to a distillation column 5 via line 4.
  • the mixture may also comprise HCl and impurities which are heavy or have a boiling point lower than that of 2,3,3,3-tetrafluoroethylene. l-propene.
  • the stream obtained at the bottom of the distillation column comprises a part of the HF and possibly heavy impurities conveyed to the purification device 7 via the pipe 6 to purify HF which will be optionally recycled into 3.
  • the mixture supplied via line 8 to a purifying device 9 comprises 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), HF, trans-1,33 , 3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane ( 134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3.3, 3-trifluoropropene (1243zf); and corresponds to said mixture C according to the present invention.
  • FIG. 2a represents a simplified diagram of a part of the device 9 implementing a process for purifying 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane according to a particular embodiment of the invention.
  • FIG. 2a schematically represents the steps for recovering hydrofluoric acid as described in steps i ') to v') according to the present invention.
  • the mixture C comes from the pipe 8 described in FIG. 1.
  • the mixture C feeds a device 12 in which it is brought into contact with a solution of hydrofluoric acid 11 'or a solution of hydrofluoric acid from the device 14 via the pipe having a concentration ranging from 65 to 75% by weight.
  • the device 12 may for example be a hydrolaver.
  • the storage device 14 separates the two-phase current into a gas phase and a liquid phase.
  • the gaseous phase of said two-phase current is fed via line 24 to the absorption column 13 comprising three absorption stages 31a, 31b and 31c.
  • the absorption column 13 is also fed with an aqueous stream 17.
  • the aqueous stream 17 feeds the absorption column 13 at the top of the absorption column 17, that is to say above above the three absorption stages 31a-31c.
  • the aqueous stream 17 can feed the absorption column 13 above each of the absorption stages 31a-31c.
  • a gas stream C1 as described in the present application can be extracted at the top of the absorption column 17 via line 26 to feed a neutralization device 15.
  • an aqueous solution of Hydrofluoric acid corresponding to said stream C2 is recycled to the storage device 14 via the line 25.
  • the stream C1 is neutralized in the neutralization device 15 with an alkaline solution of 20% NaOH.
  • the alkaline solution 18 feeds the neutralization device 15 through line 29.
  • the neutralized stream is discharged through line 27 and recovered at 20 to be dried on molecular sieve. of 3A.
  • the neutralized and dried stream corresponds to the C4 stream according to the present process. This can therefore be compressed and liquefied at a pressure of at most 8 bara (current C5 according to the present method).
  • a spent alkaline solution 19 may be removed from the neutralization device 15 to be either recycled via lines 28 and 29 or discharged via line 28 for further processing.
  • the liquid phase resulting from the mixing of the liquid phase of the two-phase current with the current C2 stored in the storage device 14 is conveyed to a distillation column 16 via the pump 32 and the pipe 33 to form the stream D recovered at the top of the column 21 and the stream E recovered at the bottom of the distillation column 22.
  • the pump 32 also feeds the liquid phase resulting from the mixing of the liquid phase of the two-phase current with the stream C2 stored in the storage device 14 to the device 12 via
  • the pump 32 is thus configured to allow supply of the distillation column 16 and the device 12 alternately or simultaneously, preferably simultaneously.
  • Mixture C can be purified prior to use according to the present method. This is described in Figures 2b and 2c according to particular embodiments.
  • a mixture comprising 2,3,3,3-tetrafluoro-1-propene, HF, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene ( 1234ze-E) and impurities having a boiling point below the boiling point of 2,3,3,3-tetrafluoro-1-propene are provided at 41.
  • the mixture is transferred to a distillation column 42 by conduit 43.
  • the impurities having a boiling point below the boiling point of 2,3,3,3-tetrafluoro-1-propene are recovered at the top of distillation column 42 and conveyed via line 45 to an incinerator or a purification device 50.
  • the mixture C is obtained at the bottom of the distillation column and is conveyed to the device 12 described in FIG. 2a via the pipe 44.
  • the mixture also comprises heavy impurities.
  • a distillation can be performed from the stream obtained at the bottom of the distillation column 42. The latter is thus conveyed via line 44 to the distillation column 46.
  • the heavy impurities are recovered at the bottom of the distillation column 47.
  • the stream recovered at the top of the distillation column 46 corresponds to said mixture C. This stream is transferred via the conduit 48 to the device 12 to be treated as explained above in connection with FIG. 2a.
  • the stream C1, C3, C4 or C5 corresponds to said first composition according to the present invention which is treated by extractive distillation as illustrated in FIG. 2d.
  • the extractive distillation carried out in 66 to separate 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb) from the other constituents of the mixture.
  • the extractive distillation column 66 is supplied with the organic extractant 70.
  • the stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb) is recovered at the top of the distillation column 66 and conveyed to the distillation column 72 via line 67.
  • the organic extraction agent 70 and the trans-1,3,3,3-tetrafluoro-1-propene (1234ze) -E) are recovered at the bottom of the distillation column 66 to be conveyed to the distillation column 69 where they are separated.
  • the organic extraction agent is recovered at the bottom of the distillation column 69 to be recycled to the extractive distillation column 66 via line 71.
  • Trans-1,3,3,3-tetrafluoro-1-propene is recovered in the following manner: distillation column head 69 to be conveyed to an incinerator or a purification device 50.
  • the distillation column 72 allows the separation between the 2,3,3,3-tetrafluoro-1-propene recovered at the top of the distillation column. and the 1,1,1,2,2-pentafluoropropane recovered at the bottom of the distillation column 74.
  • the 1,1,1,2,2-pentafluoropropane can be recycled to the reactor 3 described in FIG. 1 above.
  • the stream C1, C3, C4 or C5 may also comprise at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf). These compounds are found in the same current as trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E).
  • PI represents the saturated vapor pressure of the first compound 1
  • Y2 represents the coefficient of activity of the second compound 2 of the binary pair in the organic extraction agent considered at infinite dilution
  • P2 represents the saturating vapor pressure of the second compound.
  • An absorption capacity is also calculated for each of the solvents studied and for a binary pair (1,2) considered.
  • Examples to purify 2,3,3,3-tetrafluoro-1-propene the binary pair 2,3,3,3-tetrafluoro-1-propene / trans-1,,3,3-tetrafluoro-1-propene (1234ze-E) is considered to select the organic extractant (see Table 1).
  • the mixture to be purified comprises 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane, and trans-1,3,3,3-tetrafluoro-1-propene (1234 E).

Abstract

The invention relates to a method for the purification of 2,3,3,3-tetrafluoro-1-propene (1234yf) using a first composition comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), said method comprising the steps of: (a) bringing the first composition into contact with at least one organic extraction agent in order to form a second composition; (b) extractively distilling the second composition in order to form a third composition comprising the organic extraction agent and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), and a stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb); and (c) recovering and separating the third composition in order to form a stream comprising the organic extraction agent and a stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E). The invention also relates to a method for producing 2,3,3,3-tetrafluoro-1-propene.

Description

Procédé de production et de purification du 2,3,3,3-tetrafluoro-l-propène  Process for producing and purifying 2,3,3,3-tetrafluoro-1-propene
Domaine technique de l'invention Technical field of the invention
L'invention se rapporte à un procédé de purification du 2,3,3,3-tetrafluoro-l-propène. En outre, l'invention se rapporte également à un procédé de production et de purification du 2,3,3,3-tetrafluoro-l-propène.  The invention relates to a process for purifying 2,3,3,3-tetrafluoro-1-propene. In addition, the invention also relates to a process for producing and purifying 2,3,3,3-tetrafluoro-1-propene.
Arrière-plan technologique de l'invention Technological background of the invention
Les hydrofluorocarbures (HFC) et en particulier les hydrofluorooléfines (HFOs), telles que le 2,3,3,3-tétrafluoro-l-propène (HFO-1234yf) sont des composés connus pour leurs propriétés de réfrigérants et fluides caloporteurs, extinctrices, propulseurs, agents moussants, agents gonflants, diélectriques gazeux, milieu de polymérisation ou monomère, fluides supports, agents pour abrasifs, agents de séchage et fluides pour unité de production d'énergie. Les HFO ont été identifiés comme des alternatives souhaitables au HCFC du fait de leurs faibles valeurs d'ODP (Ozone Depletion Potential ou potentiel d'appauvrissement de la couche d'ozone) et de GWP (Global Warming Potential ou potentiel de réchauffement climatique).  Hydrofluorocarbons (HFCs) and in particular hydrofluoroolefins (HFOs), such as 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), are compounds known for their properties as refrigerants and heat-transfer fluids, extinguishers, propellants, foaming agents, blowing agents, gaseous dielectrics, polymerization medium or monomer, carrier fluids, abrasive agents, drying agents and fluids for power generation units. HFOs have been identified as desirable alternatives to HCFCs because of their low ODP (Ozone Depletion Potential or GWP) and GWP (Global Warming Potential) values.
La plupart des procédés de fabrication des hydrofluorooléfines font appel à une réaction de fluoration et/ou déshydrohalogénation. Ce type de réaction est effectué en phase gazeuse et génère des impuretés qu'il faut par conséquent éliminer pour obtenir le composé désiré dans un degré de pureté suffisant pour les applications visées.  Most of the hydrofluoroolefin manufacturing processes involve a fluorination and / or dehydrohalogenation reaction. This type of reaction is carried out in the gas phase and generates impurities which must therefore be eliminated in order to obtain the desired compound in a degree of purity sufficient for the intended applications.
Par exemple, dans le cadre de la production de 2,3,3,3-tétrafluoro-l-propène (HFO- 1234yf), la présence d'impuretés telle que le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) est observée. Des produits secondaires tels que par exemple le 1,1,1,2,2-pentafluoropropène sont également formés. La purification de ce type de mélange réactionnel peut être effectuée par exemple par distillation. Cependant lorsque les composés à purifier ont des points d'ébullition trop proches ou lorsque ceux-ci forment des compositions azéotropes ou quasi-azéotropes, la distillation n'est pas un procédé efficace. Des procédés de distillation extractive ont ainsi été décrits.  For example, in the production of 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), the presence of impurities such as trans-1, 3,3,3-tetrafluoro-1 -propene (1234ze-E) is observed. Secondary products such as, for example, 1,1,1,2,2-pentafluoropropene are also formed. The purification of this type of reaction mixture can be carried out for example by distillation. However, when the compounds to be purified have boiling points too close or when they form azeotropic or quasi-azeotropic compositions, distillation is not an effective method. Extractive distillation processes have thus been described.
On connaît par WO 03/068716 un procédé de récupération de pentafluoroéthane à partir d'un mélange comprenant du pentafluoroéthane et du chloropentafluoroéthane par distillation en présence d'hexafluoropropène.  WO 03/068716 discloses a process for recovering pentafluoroethane from a mixture comprising pentafluoroethane and chloropentafluoroethane by distillation in the presence of hexafluoropropene.
On connaît aussi par WO 98/19982 un procédé de purification du 1,1-difluoroéthane par distillation extractive. Le procédé consiste à mettre en contact un agent d'extraction avec un mélange de 1,1-difluoroéthane et de chlorure de vinyle. L'agent d'extraction est choisi parmi les hydrocarbures, les alcools, les chlorocarbures ayant un point d'ébullition compris entre 10°C et 120°C. Comme mentionné par WO 98/19982, la sélection de l'agent d'extraction peut s'avérer complexe en fonction des produits à séparer. WO 98/19982 also discloses a process for purifying 1,1-difluoroethane by extractive distillation. The method comprises contacting an extractant with a mixture of 1,1-difluoroethane and vinyl chloride. The extraction agent is chosen from hydrocarbons, alcohols and chlorocarbons having a boiling point of between 10 ° C. and 120 ° C. As mentioned by WO 98/19982, the selection of the extraction agent can be complex depending on the products to be separated.
Résumé de l'invention Summary of the invention
La présente invention permet la purification du 2,3,3,3-tetrafluoro-l-propène. La présente invention permet en particulier l'obtention d'un courant comprenant du 2,3,3,3- tetrafluoro-l-propène et du 1,1,1,2,2-pentafluoropropane ayant une faible teneur en trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E). La présente invention permet ainsi la production de 2,3,3,3-tetrafluoro-l-propène avec une pureté améliorée.  The present invention allows the purification of 2,3,3,3-tetrafluoro-1-propene. The present invention makes it possible in particular to obtain a stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane having a low trans-1 content. 3,3,3-tetrafluoro-1-propene (1234ze-E). The present invention thus allows the production of 2,3,3,3-tetrafluoro-1-propene with improved purity.
Selon un premier aspect, la présente invention fournit un procédé de purification du 2,3,3,3-tétrafluoro-l-propène (1234yf) à partir d'une première composition comprenant du 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb) et trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E), ledit procédé comprenant les étapes de:  According to a first aspect, the present invention provides a process for purifying 2,3,3,3-tetrafluoro-1-propene (1234yf) from a first composition comprising 2,3,3,3-tetrafluoro-1 propene, 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), said process comprising the steps of:
a) mise en contact de ladite première composition avec au moins un agent d'extraction organique pour former une seconde composition ; b) distillation extractive de ladite seconde composition pour former : i) une troisième composition comprenant ledit agent d'extraction organique et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E); et ii) un courant comprenant le 2,3,3,3-tétrafluoro-l-propène (1234yf) et le 1,1,1,2,2-pentafluoropropane (245cb),  a) contacting said first composition with at least one organic extractant to form a second composition; b) extractively distilling said second composition to form: i) a third composition comprising said organic extractant and trans-1,,3,3,3-tetrafluoro-1-propene (1234ze-E); and ii) a stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1,1,1,2,2-pentafluoropropane (245cb),
c) récupération et séparation de ladite troisième composition pour former un courant comprenant ledit agent d'extraction organique et un courant comprenant le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) ; de préférence le courant comprenant ledit agent d'extraction organique est recyclé à l'étape a) ;  c) recovering and separating said third composition to form a stream comprising said organic extractant and a stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E); preferably the stream comprising said organic extraction agent is recycled in step a);
caractérisé en ce que la première composition est obtenue à partir d'un mélange C comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro- 1-propène (1234ze-E) et HF, ledit mélange étant soumis aux étapes suivantes : characterized in that the first composition is obtained from a mixture C comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and HF, said mixture being subjected to the following steps:
i') mise en contact dudit mélange C avec une solution aqueuse d'acide fluorhydrique de concentration supérieure à 40% en poids pour former un courant diphasique comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro- 1-propène (1234ze-E) et H F, i ') bringing said mixture C into contact with an aqueous solution of hydrofluoric acid with a concentration of greater than 40% by weight to form a two-phase stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,33,3-tetrafluoro-1-propene (1234ze-E) and HF,
ϋ') stockage dudit second courant diphasique dans un réservoir tampon, ledit courant diphasique étant constitué d'une phase liquide et d'une phase gazeuse,  ϋ ') storing said second diphasic current in a buffer tank, said two-phase current consisting of a liquid phase and a gaseous phase,
iii') passage de ladite phase gazeuse dudit second courant diphasique dans une colonne d'absorption alimenté à contre-courant par un flux aqueux pour former un courant Cl comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) et un courant C2 comprenant HF.  iii ') passing said gaseous phase from said second diphasic stream into an absorption column fed countercurrently with an aqueous stream to form a stream C1 comprising 2,3,3,3-tetrafluoro-1-propene, 1,1 1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and a stream C2 comprising HF.
Selon un mode de réalisation préféré, le procédé comprend également les étapes de : iv') neutralisation dudit courant Cl obtenu à l'étape iii') par une solution aqueuse alcaline pour former un courant neutralisé C3, et  According to a preferred embodiment, the method also comprises the steps of: iv ') neutralizing said stream C1 obtained in stage iii') with an aqueous alkaline solution to form a neutralized stream C3, and
v') séchage dudit courant neutralisé C3 obtenu à l'étape iv') sur tamis moléculaire pour former un courant neutralisé et séché C4 comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E).  v ') drying said neutralized stream C3 obtained in step iv') on molecular sieve to form a neutralized and dried C4 stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2, 2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
Selon un mode de réalisation préféré, la solution aqueuse d'acide fluorhydrique utilisé à l'étape i') est à une température comprise entre 0 à 30°C avant sa mise en contact avec ledit mélange C.  According to a preferred embodiment, the aqueous hydrofluoric acid solution used in step i ') is at a temperature of between 0 and 30 ° C. before being brought into contact with the said mixture C.
Selon un mode de réalisation préféré, la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique et dudit courant C2 est distillée pour former un courant D, de préférence en tête de colonne de distillation, comprenant de l'acide fluorhydrique contenant moins de 500 ppm d'eau et un courant E, de préférence en pied de colonne de distillation, comprenant de l'acide fluorhydrique sous forme d'une solution aqueuse de concentration inférieure à 50% en poids.  According to a preferred embodiment, the liquid phase resulting from the mixing of said liquid phase of said second diphasic current and said C2 stream is distilled to form a stream D, preferably at the top of the distillation column, comprising hydrofluoric acid containing less 500 ppm of water and a stream E, preferably at the bottom of the distillation column, comprising hydrofluoric acid in the form of an aqueous solution with a concentration of less than 50% by weight.
Selon un mode de réalisation préféré, le rapport entre le débit du flux aqueux alimentant la colonne d'absorption à l'étape iii') et la quantité d'acide fluorhydrique dans ledit mélange C exprimée en kg/h est compris entre 0,05 et 1,22, de préférence entre 0,33 et 0,54.  According to a preferred embodiment, the ratio between the flow rate of the aqueous flow supplying the absorption column in step iii ') and the amount of hydrofluoric acid in said mixture C expressed in kg / h is between 0.05 and 1.22, preferably between 0.33 and 0.54.
Selon un mode de réalisation préféré, le procédé comprend également une étape de récupération dudit courant ii) comprenant le 2,3,3,3-tétrafluoro-l-propène et le 1,1,1,2,2- pentafluoropropane (245cb) obtenu à l'étape b), et de distillation de celui-ci pour former un courant A comprenant 2,3,3,3-tétrafluoro-l-propène et un courant B comprenant 1,1,1,2,2- pentafluoropropane (245cb).  According to a preferred embodiment, the process also comprises a step of recovering said stream ii) comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb) obtained in step b), and of distillation thereof to form a stream A comprising 2,3,3,3-tetrafluoro-1-propene and a stream B comprising 1,1,1,2,2-pentafluoropropane (245cb).
Selon un mode de réalisation préféré, ladite première composition comprend également au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf). According to a preferred embodiment, said first composition also comprises at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E) cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf).
Selon un mode de réalisation préféré, ledit agent d'extraction organique a un facteur de séparation Si,2 supérieur ou égal à 1,1, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(Y2,s*P2) dans laquelle  According to a preferred embodiment, said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * Pl) / (Y2, s * P2) in which
Yi,s représente le coefficient d'activité du 2,3,3,3-tétrafluoro-l-propène dans ledit agent d'extraction organique à dilution infinie,  Yi, s represents the coefficient of activity of 2,3,3,3-tetrafluoro-1-propene in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 2,3,3,3-tétrafluoro-l-propène, PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene,
Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-Y2, s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene (1234
E) dans ledit agent d'extraction organique à dilution infinie, E) in said organic infinite dilution extractant,
P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) ;  P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E);
avantageusement, le facteur de séparation est supérieur ou égal à 1,2, de préférence supérieur ou égal à 1,4, plus préférentiellement supérieur ou égal à 1,6, en particulier supérieur ou égal à 1,8, plus particulièrement supérieur ou égal à 2,0.  advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0.
Selon un mode de réalisation préféré, ledit agent d'extraction organique a un facteur de séparation Si,2 supérieur ou égal à 1,1, ledit facteur de séparation étant calculé par la formule According to a preferred embodiment, said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula
Si,2 = (Yi,s*Pl)/(Y2,s*P2) dans laquelle If, 2 = (Yi, s * Pl) / (Y2, s * P2) in which
Yi,s représente le coefficient d'activité du 1,1,1,2,2-pentafluoropropane (245cb) dans ledit agent d'extraction organique à dilution infinie,  Yi, s represents the activity coefficient of 1,1,1,2,2-pentafluoropropane (245cb) in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 1,1,1,2,2-pentafluoropropane (245cb), Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze- E) dans ledit agent d'extraction organique à dilution infinie,  PI represents the saturated vapor pressure of 1,1,1,2,2-pentafluoropropane (245cb), Y2, s represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze) E) in said organic extraction agent with infinite dilution,
P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) ; avantageusement, le facteur de séparation est supérieur ou égal à 1,2, de préférence supérieur ou égal à 1,4, plus préférentiellement supérieur ou égal à 1,6, en particulier supérieur ou égal à 1,8, plus particulièrement supérieur ou égal à 2,0.  P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E); advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0.
Selon un mode de réalisation préféré, ledit agent d'extraction organique a une capacité d'absorption C2,s supérieure ou égale à 0,20, ladite capacité d'absorption étant calculé par la formule C2,s = l/(Y2,s) dans laquelle Y2,s représente le coefficient d'activité dudit au moins un des composés consistant en trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) dans ledit agent d'extraction organique à dilution infinie, de préférence Y2,s représente le coefficient d'activité dudit au moins un des composés consistant en trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E), dans ledit agent d'extraction organique à dilution infinie ; avantageusement, la capacité d'absorption C2,s est supérieure ou égale à 0,40, de préférence supérieure ou égale à 0,60, plus préférentiellement supérieure ou égale à 0,80, en particulier supérieure ou égale à 1,0. According to a preferred embodiment, said organic extraction agent has an absorption capacity C2, s greater than or equal to 0.20, said absorption capacity being calculated by the formula C2, s = 1 / (Y2, s wherein Y2, s represents the activity coefficient of said at least one of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) compounds in said infinitely diluted organic extractant , preferably Y2, s represents the activity coefficient said at least one of trans-1,3,3,3-tetrafluoro-1-propene compounds (1234ze-E) in said infinitely diluted organic extractant; advantageously, the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.
Selon un mode de réalisation préféré, ledit agent d'extraction organique est choisi parmi le groupe consistant en éthylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2- methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy-2-propanol, 1,2- propanediamine, n-butylacetate, 2-methoxy-l-propanol, hexanal. De préférence, ledit agent d'extraction organique est choisi parmi le groupe consistant en éthylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1- methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy-l-propanol, hexanal.  According to a preferred embodiment, said organic extraction agent is selected from the group consisting of ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2- propanediamine, n-butylacetate, 2-methoxy-1-propanol, hexanal. Preferably, said organic extractant is selected from the group consisting of ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy- 1-propanol, hexanal.
Selon un autre aspect, la présente invention fournit un procédé de production et de purification du 2,3,3,3-tetrafluoro-l-propène comprenant les étapes de :  In another aspect, the present invention provides a method for producing and purifying 2,3,3,3-tetrafluoro-1-propene comprising the steps of:
A) fluoration en présence d'un catalyseur d'un composé de formule CH(n+2)(X)m- CHp(X)(n+i)-CX(3+p-m) où X représente indépendamment F ou Cl ; n, m, p sont indépendamment les uns des autres 0 ou 1 avec (n+m) = 0 ou 1, (n+p) = 0 ou 1 et (m-p)A) fluorination in the presence of a catalyst of a compound of formula CH ( n + 2) (X) m-CH p (X) (n + 1) -CX (3 + pm) where X independently represents F or Cl ; n, m, p are independently of each other 0 or 1 with (n + m) = 0 or 1, (n + p) = 0 or 1 and (mp)
= 0 ou 1, au moins un X étant Cl; = 0 or 1, at least one X being Cl;
B) récupération d'un courant comprenant du 2,3,3,3-tetrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E), et optionnellement ou non au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane B) recovering a stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoropropane, 1-propene (1234ze-E), and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane
(134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) ; (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3.3 3-trifluoropropene (1243zf);
C) mise en œuvre du procédé de purification du 2,3,3,3-tetrafluoro-l-propène selon la présente invention à partir du courant récupéré à l'étape B).  C) implementation of the process for purifying 2,3,3,3-tetrafluoro-1-propene according to the present invention from the stream recovered in step B).
Brève description des figures La figure 1 représente schématiquement un dispositif mettant en œuvre un procédé de production du 2,3,3,3-tetrafluoro-l-propène selon un mode de réalisation particulier de la présente invention. Brief description of the figures Figure 1 schematically shows a device implementing a process for producing 2,3,3,3-tetrafluoro-1-propene according to a particular embodiment of the present invention.
Les figures 2a-d représentent schématiquement un dispositif mettant en œuvre un procédé de purification du 2,3,3,3-tetrafluoro-l-propène selon un mode de réalisation particulier de la présente invention.  Figures 2a-d schematically represent a device implementing a method for purifying 2,3,3,3-tetrafluoro-1-propene according to a particular embodiment of the present invention.
Description détaillée de l'invention Detailed description of the invention
Le terme « hydrocarbure » tel qu'utilisé ici se réfère à des composés linéaires ou branchés d'alcane en C1-C20, cycloalcane en C3-C20, alcène en C2-C20, cycloalcène en C3-C20, arène en C6-C18. Par exemple, le terme alcane se réfère à des composés de formule CnH2n+2 dans lequel n est compris entre 1 et 20. Le terme alcane en C1-C20 englobe par exemple le pentane, hexane, heptane, octane, nonane, décane ou des isomères de ceux-ci. Le terme alcène en C2-C20 se réfère à des composés hydrocarbonés comprenant une ou plusieurs doubles liaisons carbone-carbone et comprenant de 2 à 20 atomes de carbone. Le terme cycloalcane en C3-C20 se réfère à un cycle hydrocarboné saturé comprenant de 3 à 20 atomes de carbone. Le terme aryle en C6-C18 se réfère à des composés hydrocarbonés cycliques et aromatiques comprenant de 6 à 18 atomes de carbone. Le terme cycloalcène en C3-C20 se réfère à des composés hydrocarbonés cycliques comprenant de 3 à 20 atomes de carbone et comprenant une ou plusieurs doubles liaisons carbone-carbone. The term "hydrocarbon" as used herein refers to linear or branched compounds of C1-C20 alkane, C3-C20 cycloalkane, C2-C20 alkene, C3-C20 cycloalkene, C6-C18 arene. For example, the term alkane refers to compounds of formula C n H 2n + 2 wherein n is from 1 to 20. The term C 1 -C 20 alkane includes, for example, pentane, hexane, heptane, octane, nonane, decane or isomers thereof. The term C2-C20 alkene refers to hydrocarbon compounds comprising one or more carbon-carbon double bonds and comprising from 2 to 20 carbon atoms. The term C3-C20 cycloalkane refers to a saturated hydrocarbon ring having 3 to 20 carbon atoms. The term C 6 -C 18 aryl refers to cyclic and aromatic hydrocarbon compounds having from 6 to 18 carbon atoms. The term C3-C20 cycloalkene refers to cyclic hydrocarbon compounds comprising from 3 to 20 carbon atoms and comprising one or more carbon-carbon double bonds.
Le terme « alkyle » désigne un radical monovalent issu d'un alcane, linéaire ou branché, comprenant de 1 à 20 atomes de carbone. Le terme « cycloalkyle » désigne un radical monovalent issu d'un cycloalcane comprenant de 3 à 20 atomes de carbone. Le terme « aryle » désigne un radical monovalent issu d'un arène comprenant de 6 à 18 atomes de carbone. Le terme « alkényle » désigne un radical monovalent de 2 à 20 atomes de carbone et au moins une double liaison carbone-carbone. Le terme « alkynyle » désigne un radical monovalent de 2 à 20 atomes de carbone et au moins une triple liaison carbone-carbone. Le terme « halogène » se réfère à un groupement -F, -Cl, -Br ou -I. Le terme « cycloalkényle » se réfère à un radical monovalent issu d'un cycloalcène comprenant de 3 à 20 atomes de carbone. Les substituants alkyle en C1-C20, alkényle en C2-C20, alkynyle en C2-C20, cycloalkyle en C3-C20, cycloalkényle en C3- C20, aryle en C6-C18 peuvent être substitués ou non par un ou plusieurs substituants -OH, halogène, -N aC(0) b, -C(0)NRaRb, -CN, -N02, -NRaRb, -ORa, -SRa, -C02Ra, -OC(0)ORa, -OC(0)Ra, - C(0)H, -C(0)Ra dans lequel Ra et Rb sont indépendamment l'un de l'autre hydrogène, alkyle en C1-C20 non substitué, alkényle en C2-C20 non substitué, alkynyle en C2-C20 non substitué, cycloalkyle en C3-C20 non substitué, cycloalkényle en C3-C20 non substitué, aryle en C6-C18 non substitué. Dans les substituants -NRaRb, -NRaC(0)Rb, -C(0)NRaRb, Ra et Rb peuvent former avec l'atome d'azote ou avec le groupement fonctionnel auquel ils sont rattachés un hétérocycle saturé ou insaturé, aromatique ou non, comprenant de 4 à 10 chaînons. The term "alkyl" denotes a monovalent radical derived from a linear or branched alkane comprising from 1 to 20 carbon atoms. The term "cycloalkyl" refers to a monovalent radical derived from a cycloalkane comprising from 3 to 20 carbon atoms. The term "aryl" denotes a monovalent radical derived from an arene comprising from 6 to 18 carbon atoms. The term "alkenyl" refers to a monovalent radical of 2 to 20 carbon atoms and at least one carbon-carbon double bond. The term "alkynyl" refers to a monovalent radical of 2 to 20 carbon atoms and at least one carbon-carbon triple bond. The term "halogen" refers to a group -F, -Cl, -Br or -I. The term "cycloalkenyl" refers to a monovalent radical derived from a cycloalkene having 3 to 20 carbon atoms. C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 cycloalkenyl, C6-C18 aryl substituents may or may not be substituted by one or more -OH substituents, halogen, -N a C (O) b , -C (O) NR a R b , -CN, -NO 2 , -NR a R b , -OR a , -SR a , -COR 2 R a , -OC (0) OR a , -OC (O) R a , -C (O) H, -C (O) R a wherein R a and R b are independently of one another hydrogen, alkyl Unsubstituted C1-C20, unsubstituted C2-C20 alkenyl, unsubstituted C2-C20 alkynyl, unsubstituted C3-C20 cycloalkyl, unsubstituted C3-C20 cycloalkenyl, unsubstituted C6-C18 aryl. In the substituents -NR a R b , -NR a C (O) R b , -C (O) NR a R b , R a and R b may form with the nitrogen atom or with the functional group to which they are attached a saturated or unsaturated heterocycle, aromatic or not, comprising from 4 to 10 members.
Le terme « hydrohalocarbures » se réfère à des composés de formule RaX dans laquelle Ra est sélectionné parmi alkyle en C1-C20, alkényle en C2-C20, alkynyle en C2-C20, cycloalkyle en C3- C20, cycloalkényle en C3-C20, aryle en C6-C18 et X représente un atome de chlore, de fluor, de brome ou d'iode. Les substituants alkyle en C1-C20, alkényle en C2-C20, alkynyle en C2-C20, cycloalkyle en C3-C20, cycloalkényle en C3-C20, aryle en C6-C18 peuvent être substitués ou non par un ou plusieurs substituants -OH, halogène, -NRaC(0)Rb, -C(0)NRaRb -CN, -N02, -NRaRb, -ORa, - SRa, -C02Ra, -OC(0)ORa, -OC(0)Ra, -C(0)H, -C(0)Ra dans lequel Ra et Rb sont tels que définis ci- dessus. The term "hydrohalocarbons" refers to compounds of the formula R a X wherein R a is selected from C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-cycloalkenyl. C20, C6-C18 aryl and X represents a chlorine, fluorine, bromine or iodine atom. The substituents C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl and C 6 -C 18 aryl may or may not be substituted by one or more -OH substituents, halogen, -NR a C (O) R b , -C (O) NR a R b -CN, -NO 2 , -NR a R b , -OR a , -SR a , -COR 2 R a , -OC (O) OR a , -OC (O) R a , -C (O) H, -C (O) R a wherein R a and R b are as defined above.
Le terme « alcool » se réfère à des hydrocarbures ou hydrohalocarbures tels que définis ci-dessus dans lequel au moins un atome d'hydrogène est remplacé par un groupement hydroxyle -OH.  The term "alcohol" refers to hydrocarbons or hydrohalocarbons as defined above in which at least one hydrogen atom is replaced by a hydroxyl group -OH.
Le terme « cétone » se réfère à des hydrocarbures comprenant au moins un ou plusieurs groupements fonctionnels carbonyle Rc-C(0)-Rd dans lequel Rc et Rd sont indépendamment l'un de l'autre un alkyle en C1-C20, alkényle en C2-C20, alkynyle en C2-C20, cycloalkyle en C3-C20, cycloalkényle en C3-C20, aryle en C6-C18 peuvent être substitués ou non par un ou plusieurs substituants -OH, halogène, -NRaC(0)Rb, -C(0)NRaRb -CN, -N02, -NRaRb, -ORa, -SRa, -C02Ra, - OC(0)ORa, -OC(0)Ra, -C(0)H, -C(0)Ra dans lequel Ra et Rb sont tels que définis ci-dessus, Rc et Rd pouvant être liés entre eux pour former avec le groupement carbonyle auquel ils sont rattachés une cétone cyclique comprenant de 4 à 10 chaînons, de préférence de 4 à 7 chaînons. La cétone cyclique peut également comprendre une ou plusieurs doubles liaisons carbone-carbone. La cétone cyclique peut également être substituée ou non par un ou plusieurs substituants tels que définis ci-dessus. The term "ketone" refers to hydrocarbons comprising at least one or more carbonyl functional groups R c -C (O) -R d in which R c and R d are independently of one another a C 1 -C 4 alkyl. C20 alkenyl, C2-C20 alkynyl, C2-C20, C3-C20 cycloalkenyl, C3-C20, C6-C18 may be substituted or not by one or more -OH, halogen, -NR a C (0) R b , -C (O) NR a R b -CN, -NO 2 , -NR a R b , -OR a , -SR a , -COR 2 R a , -OC (O) OR a , -OC (O) R a -C (O) H, -C (O) R a wherein R a and R b are as defined above, R c and R d being bonded together to form with the carbonyl group to which they are attached a cyclic ketone comprising from 4 to 10 members, preferably from 4 to 7 members. The cyclic ketone may also comprise one or more carbon-carbon double bonds. The cyclic ketone may also be substituted or unsubstituted by one or more substituents as defined above.
Le terme « aminé » se réfère à des hydrocarbures comprenant au moins un ou plusieurs groupements fonctionnels aminé -NRcRd dans lequel Rc et Rd sont tels que définis ci-dessus, Rc et Rd pouvant être liés entre eux pour former avec l'atome d'azote auquel ils sont rattachés un hétérocycle aromatique ou non comprenant de 4 à 10 chaînons. Le terme « esters » se réfère à des composés de formule c-C(0)-0- d dans lequel Rc et Rd sont tels que définis ci-dessus, Rc et Rd pouvant être liés entre eux pour former avec le groupement ester un cycle comprenant de 4 à 20 atomes de carbone. The term "amine" refers to hydrocarbons comprising at least one or more amine functional groups -NR c R d in which R c and R d are as defined above, R c and R d being able to be linked together for form with the nitrogen atom to which they are attached an aromatic or non-aromatic heterocycle comprising from 4 to 10 members. The term "esters" refers to compounds of formula c -C (0) -0- d wherein R c and R d are as defined above, R c and R d may be linked together to form with the ester group a ring comprising from 4 to 20 carbon atoms.
Le terme « éther » se réfère à des composés de formule Rc-0-Rd dans lequel Rc et Rd sont tels que définis ci-dessus, Rc et Rd pouvant être liés entre eux pour former avec l'atome d'oxygène auquel ils sont rattachés un hétérocycle comprenant de 4 à 20 atomes de carbone. The term "ether" refers to compounds of the formula R c -O-R d wherein R c and R d are as defined above, where R c and R d may be linked together to form with the atom oxygen to which they are attached a heterocycle comprising from 4 to 20 carbon atoms.
Le terme « aldéhyde » se réfère à des composés comprenant au moins un ou plusieurs groupements fonctionnels -C(0)-H.  The term "aldehyde" refers to compounds comprising at least one or more -C (O) -H functional groups.
Le terme « nitrile » se réfère à des composés comprenant au moins un ou plusieurs groupements fonctionnels -CN.  The term "nitrile" refers to compounds comprising at least one or more functional groups -CN.
Le terme « carbonate » se réfère à des composés de formule Rc-0-C(0)-0-Rd dans lequel Rc et Rd sont tels que définis ci-dessus. The term "carbonate" refers to compounds of the formula R c -O-C (O) -O-R d wherein R c and R d are as defined above.
Le terme « thioalkyle » concerne des composés de formule RcSRd dans laquelle Rc et Rd sont tels que définis ci-dessus. The term "thioalkyl" relates to compounds of formula R c SR d wherein R c and R d are as defined above.
Le terme « amide » concerne des composés de formule RcC(0)NReRd dans laquelle Rc etThe term "amide" relates to compounds of formula R c C (O) NR e R d in which R c and
Rd sont tels que définis ci-dessus, Re étant choisi parmi les mêmes substituants que ceux définissant Rc, Rc et Rd pouvant être liés entre eux pour former avec le groupement amide - C(0)N- auquel ils sont rattachés une amide cyclique comprenant de 4 à 10 chaînons, de préférence de 4 à 7 chaînons. L'amide cyclique peut également comprendre une ou plusieurs doubles liaisons carbone-carbone. L'amide cyclique peut également être substituée ou non par un ou plusieurs substituants tels que définis ci-dessus. R d are as defined above, wherein R e is selected from the same substituents as those defining R c , where R c and R d may be bonded together to form with the amide group - C (O) N- at which they are attached a cyclic amide comprising from 4 to 10 members, preferably from 4 to 7 members. The cyclic amide may also include one or more carbon-carbon double bonds. The cyclic amide may also be substituted or unsubstituted by one or more substituents as defined above.
Le terme « hétérocycle » désigne un cycle carboné comprenant de 4 à 10 chaînons dont au moins un des chaînons est un hétéroatome sélectionné parmi le groupe consistant en O, S, P et N. L'hétérocycle peut comprendre un ou plusieurs double liaison carbone-carbone ou une ou plusieurs double liaison carbone-hétéroatome ou une ou plusieurs double liaison hétéroatome- hétéroatome. De préférence, l'hétérocycle peut comprendre 1, 2, 3, 4 ou 5 hétéroatomes tel que défini ci-dessus. En particulier, l'hétérocycle peut comprendre 1, 2 ou 3 hétéroatomes sélectionné parmi l'oxygène, l'azote ou le soufre. De préférence, l'hétérocycle peut être un cycle carboné comprenant de 4 à 6 chaînons dont 1, 2 ou 3 chaînons sont des hétéroatomes sélectionnés parmi O ou N. L'hétérocycle peut être ou non substitué par un ou plusieurs substituants choisi parmi -OH, halogène, -NRaC(0)Rb, -C(0)NRaRb -CN, -N02, -NRaRb, -ORa, -SRa, - C02Ra, -OC(0)ORa, -OC(0)Ra, -C(0)H, -C(0)Ra dans lequel Ra et Rb sont tels que définis ci-dessus. Le terme « agent d'extraction organique » se réfère à un composé comportant au moins un atome de carbone. The term "heterocycle" refers to a 4- to 10-membered carbon ring of which at least one of the linkages is a heteroatom selected from the group consisting of O, S, P and N. The heterocycle may comprise one or more carbon-carbon double bonds. carbon or one or more carbon-heteroatom double bonds or one or more heteroatom-heteroatom double bonds. Preferably, the heterocycle may comprise 1, 2, 3, 4 or 5 heteroatoms as defined above. In particular, the heterocycle may comprise 1, 2 or 3 heteroatoms selected from oxygen, nitrogen or sulfur. Preferably, the heterocycle may be a 4- to 6-membered carbon ring of which 1, 2 or 3 members are heteroatoms selected from O or N. The heterocycle may or may not be substituted by one or more substituents selected from -OH , halogen, -NR a C (O) R b , -C (O) NR a R b -CN, -NO 2 , -NR a R b , -OR a , -SR a , -CO 2 R a , - OC (O) OR a , -OC (O) R a , -C (O) H, -C (O) R a in which R a and R b are as defined above. The term "organic extractant" refers to a compound having at least one carbon atom.
Selon un premier aspect, l'invention se rapporte à un procédé de purification du 2,3,3,3- tetrafluoro-l-propène (1234yf). Le procédé de purification est effectué à partir d'une première composition comprenant du 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb) et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E).  According to a first aspect, the invention relates to a process for purifying 2,3,3,3-tetrafluoro-1-propene (1234yf). The purification process is carried out from a first composition comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3 3,3-tetrafluoro-1-propene (1234ze-E).
De préférence, ledit procédé comprend les étapes de :  Preferably, said method comprises the steps of:
a) mise en contact de ladite première composition avec au moins un agent d'extraction organique pour former une seconde composition ; b) distillation extractive de ladite seconde composition pour former : i) une troisième composition comprenant ledit agent d'extraction organique et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et ii) un courant comprenant le 2,3,3,3-tétrafluoro-l-propène et 1,1,1,2,2- pentafluoropropane (245cb),  a) contacting said first composition with at least one organic extractant to form a second composition; b) extractively distilling said second composition to form: i) a third composition comprising said organic extractant and trans-1,1,3,3-tetrafluoro-1-propene (1234ze-E) and ii) a stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb),
c) récupération et séparation de ladite troisième composition pour former un courant comprenant ledit agent d'extraction organique et un courant comprenant le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E).  c) recovering and separating said third composition to form a stream comprising said organic extractant and a stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
De préférence, la première composition est obtenue à partir d'un mélange C comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) et HF, ledit mélange étant soumis aux étapes suivantes :  Preferably, the first composition is obtained from a mixture C comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3 , 3,3-tetrafluoro-1-propene (1234ze-E) and HF, said mixture being subjected to the following steps:
i') mise en contact dudit mélange C avec une solution aqueuse d'acide fluorhydrique de concentration supérieure à 40% en poids pour former un courant diphasique comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro- 1-propène (1234ze-E) et HF,  i ') bringing said mixture C into contact with an aqueous solution of hydrofluoric acid with a concentration of greater than 40% by weight to form a diphasic stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1 2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and HF,
ii') stockage dudit second courant diphasique dans un réservoir tampon, ledit courant diphasique étant constitué d'une phase liquide et d'une phase gazeuse,  ii ') storing said second diphasic current in a buffer tank, said two-phase current consisting of a liquid phase and a gaseous phase,
iii') passage de ladite phase gazeuse dudit second courant diphasique dans une colonne d'absorption alimenté à contre-courant par un flux aqueux pour former un courant Cl comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) et un courant C2 comprenant HF. De préférence, la solution aqueuse d'acide fluorhydrique utilisée à l'étape i') est de concentration supérieure à 40% en poids. En particulier, la solution aqueuse d'acide fluorhydrique est de concentration supérieure à 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% ou 95% en poids. Plus particulièrement, la solution aqueuse d'acide fluorhydrique est de concentration supérieure ou égale à 50% en poids, ou supérieure ou égale 60% en poids ou supérieure ou égale à 70% en poids. iii ') passing said gaseous phase from said second diphasic stream into an absorption column fed countercurrently with an aqueous stream to form a stream C1 comprising 2,3,3,3-tetrafluoro-1-propene, 1,1 1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and a stream C2 comprising HF. Preferably, the aqueous solution of hydrofluoric acid used in step i ') is of concentration greater than 40% by weight. In particular, the hydrofluoric acid aqueous solution is of concentration greater than 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52% 53% 54% 55% 56% 57% 58% 59% 60% 61% 62% 63% 64% 65% 66% 67% 68% 69 % 70% 71% 72% 73% 74% 75% 76% 77% 78% 79% 80% 81% 82% 83% 84% 85% 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% or 95% by weight. More particularly, the aqueous solution of hydrofluoric acid is of concentration greater than or equal to 50% by weight, or greater than or equal to 60% by weight or greater than or equal to 70% by weight.
Plus particulièrement, la solution aqueuse d'acide fluorhydrique peut être comprise entre l'une quelconque des valeurs mentionnées ci-dessus. Ainsi, la solution aqueuse d'acide fluorhydrique peut être comprise entre 45% et 95% en poids, entre 50% et 90% en poids, entre 55% et 85% en poids, entre 60% en poids et 80% en poids ou entre 65% en poids et 75% en poids.  More particularly, the aqueous solution of hydrofluoric acid may be between any of the values mentioned above. Thus, the hydrofluoric acid aqueous solution may be between 45% and 95% by weight, between 50% and 90% by weight, between 55% and 85% by weight, between 60% by weight and 80% by weight or between 65% by weight and 75% by weight.
L'étape i') du présent procédé permet la formation dudit second courant diphasique comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) et HF. Ledit courant diphasique consiste en une phase gazeuse et une phase liquide. La phase gazeuse peut comprendre 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E). Optionnellement, la phase gazeuse peut comprendre de l'acide fluorhydrique. Lorsque la phase gazeuse comprend de l'acide fluorhydrique, la teneur de celui-ci est généralement faible, de préférence inférieure à 5% en poids sur base du poids total de ladite phase gazeuse, en particulier inférieure à 2% en poids sur base du poids total de ladite phase gazeuse, plus particulièrement inférieure à 1% en poids sur base du poids total de ladite phase gazeuse.  Step i ') of the present process allows formation of said second two-phase stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and HF. Said two-phase current consists of a gaseous phase and a liquid phase. The gaseous phase may comprise 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene ( 1234ze-E). Optionally, the gas phase may comprise hydrofluoric acid. When the gaseous phase comprises hydrofluoric acid, the content thereof is generally low, preferably less than 5% by weight based on the total weight of said gaseous phase, in particular less than 2% by weight based on total weight of said gaseous phase, more particularly less than 1% by weight based on the total weight of said gaseous phase.
La phase liquide dudit courant diphasique peut comprendre de l'acide fluorhydrique. Ladite phase liquide peut comprendre optionnellement une faible quantité de 2,3,3,3- tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb) ou trans-l,3,3,3-tetrafluoro-l- propène (1234ze-E), de préférence ladite phase liquide peut comprendre une teneur en 2,3,3,3- tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb) ou trans-l,3,3,3-tetrafluoro-l- propène (1234ze-E) inférieure à 5% en poids sur base du poids total de ladite phase liquide, en particulier inférieure à 1% en poids sur base du poids total de ladite phase liquide, plus particulièrement inférieure à 5000 ppm en poids sur base du poids total de ladite phase liquide, de manière privilégiée inférieure à 1000 ppm en poids sur base du poids total de ladite phase liquide, de manière plus privilégiée inférieure à 500 ppm en poids, de manière particulièrement privilégiée inférieure à 100 ppm sur base du poids total de ladite phase liquide. Ladite phase liquide peut comprendre une teneur totale en 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb) et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) inférieure à 5% en poids sur base du poids total de ladite phase liquide, en particulier inférieure à 1% en poids sur base du poids total de ladite phase liquide, plus particulièrement inférieure à 5000 ppm en poids sur base du poids total de ladite phase liquide, de manière privilégiée inférieure à 1000 ppm en poids sur base du poids total de ladite phase liquide, de manière plus privilégiée inférieure à 500 ppm en poids, de manière particulièrement privilégiée inférieure à 100 ppm sur base du poids total de ladite phase liquide. De préférence, la concentration en acide fluorhydrique dans ladite phase liquide dudit second courant diphasique est supérieure à la concentration de ladite solution aqueuse d'acide fluorhydrique utilisée à l'étape i'). Ladite phase liquide dudit second courant diphasique peut être avoir une concentration en acide fluorhydrique supérieure à 41% en poids sur base du poids total de ladite phase liquide dudit second courant diphasique. Avantageusement, ladite phase liquide dudit second courant diphasique peut être avoir une concentration en acide fluorhydrique supérieure à 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% ou 95% en poids sur base du poids total de ladite phase liquide dudit second courant diphasique. De préférence, ladite phase liquide dudit second courant diphasique peut être avoir une concentration en acide fluorhydrique comprise entre 45% et 95% en poids, entre 50% et 90% en poids, entre 55% et 85% en poids, entre 60% en poids et 80% en poids ou entre 65% en poids et 75% en poids tout en étant supérieure à la concentration de ladite solution aqueuse d'acide fluorhydrique utilisée à l'étape i'). The liquid phase of said two-phase stream may comprise hydrofluoric acid. Said liquid phase may optionally comprise a small amount of 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) or trans-1,3,3,3-tetrafluoro propylene (1234ze-E), preferably said liquid phase may comprise a content of 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) or trans -l, 3,3,3-tetrafluoro-1-propene (1234ze-E) less than 5% by weight based on the total weight of said liquid phase, in particular less than 1% by weight based on the total weight of said liquid phase, plus particularly lower than 5000 ppm by weight based on the total weight of said liquid phase, preferably less than 1000 ppm by weight based on the total weight of said liquid phase, more preferably less than 500 ppm by weight, particularly preferably preferred less than 100 ppm based on the total weight of said liquid phase. Said liquid phase may comprise a total content of 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoropropane. 1-propene (1234ze-E) less than 5% by weight based on the total weight of said liquid phase, in particular less than 1% by weight based on the total weight of said liquid phase, more particularly less than 5000 ppm by weight on the basis of the total weight of said liquid phase, preferably less than 1000 ppm by weight based on the total weight of said liquid phase, more preferably less than 500 ppm by weight, particularly preferably less than 100 ppm based on the total weight of said liquid phase. Preferably, the hydrofluoric acid concentration in said liquid phase of said second diphasic stream is greater than the concentration of said hydrofluoric acid aqueous solution used in step i '). Said liquid phase of said second two-phase current may have a hydrofluoric acid concentration greater than 41% by weight based on the total weight of said liquid phase of said second two-phase current. Advantageously, said liquid phase of said second two-phase current may have a hydrofluoric acid concentration greater than 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%. %, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85% , 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% or 95% by weight based on the total weight of said liquid phase of said second two-phase current. Preferably, said liquid phase of said second two-phase stream may have a hydrofluoric acid concentration of between 45% and 95% by weight, between 50% and 90% by weight, between 55% and 85% by weight, and between 60% by weight. weight and 80% by weight or between 65% by weight and 75% by weight while being greater than the concentration of said aqueous hydrofluoric acid solution used in stage i ').
De préférence, la solution aqueuse d'acide fluorhydrique utilisé à l'étape i') est à une température comprise entre -20°C à 80°C avant sa mise en contact avec ledit mélange C, avantageusement entre -15°C et 70°C, de préférence entre -10°C et 60°C, plus préférentiellement entre -5°C et 50°C, en particulier entre -5°C et 40°C, plus particulièrement entre 0°C et 30°C. Ainsi, dans un mode de réalisation particulièrement préféré, la température de la solution aqueuse d'acide fluorhydrique utilisé à l'étape i'), avant sa mise en contact avec ledit mélange C, peut être de 0°C, 1°C, 2°C, 3°C, 4°C, 5°C, 6°C, 7°C, 8°C, 9°C, 10°C, 11°C, 12°C, 13°C, 14°C, 15°C, 16°C, 17°C, 18°C, 19°C, 20°C, 21°C, 22°C, 23°C, 24°C, 25°C, 26°C, 27°C, 28°C, 29°C ou 30°C. La mise en œuvre de ladite solution aqueuse d'acide fluorhydrique aux températures mentionnées ci-dessus a pour but de contrôler l'exothermicité survenant lors de la mise en contact de celle-ci avec ledit mélange C. Preferably, the aqueous hydrofluoric acid solution used in step i ') is at a temperature of between -20 ° C. and 80 ° C. before being brought into contact with the said mixture C, advantageously between -15 ° C. and 70 ° C. C., preferably between -10 ° C. and 60 ° C., more preferably between -5 ° C. and 50 ° C., in particular between -5 ° C. and 40 ° C., more particularly between 0 ° C. and 30 ° C. Thus, in a particularly preferred embodiment, the temperature of the aqueous hydrofluoric acid solution used in step i '), before it comes into contact with said mixture C can be 0 ° C, 1 ° C, 2 ° C, 3 ° C, 4 ° C, 5 ° C, 6 ° C, 7 ° C, 8 ° C, 9 ° C, 10 ° C 11 ° C, 12 ° C, 13 ° C, 14 ° C, 15 ° C, 16 ° C, 17 ° C, 18 ° C, 19 ° C, 20 ° C, 21 ° C, 22 ° C, 23 ° C, 24 ° C, 25 ° C, 26 ° C, 27 ° C, 28 ° C, 29 ° C or 30 ° C. The implementation of said aqueous hydrofluoric acid solution at the temperatures mentioned above is intended to control the exothermicity occurring when it is brought into contact with said mixture C.
Comme mentionné ci-dessus, l'étape ii') du procédé selon la présente invention met en œuvre le stockage dudit second courant diphasique dans un réservoir tampon, ledit second courant diphasique étant constitué de ladite phase liquide et de ladite phase gazeuse telle que décrit ci-dessus.  As mentioned above, step ii ') of the method according to the present invention implements the storage of said second two-phase current in a buffer tank, said second two-phase current consisting of said liquid phase and said gas phase as described. above.
Comme mentionné ci-dessus, l'étape iii') du procédé selon la présente invention met en œuvre, le passage de ladite phase gazeuse dudit second courant diphasique dans une colonne d'absorption alimenté à contre-courant par un flux aqueux pour former un courant Cl comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) et un courant C2 comprenant HF.  As mentioned above, step iii ') of the process according to the present invention implements the passage of said gaseous phase of said second diphasic current in an absorption column supplied countercurrently with an aqueous stream to form a C1 stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234 E) and a stream C2 comprising HF.
De préférence, le débit du flux aqueux utilisé à l'étape iii') est déterminé en fonction de la quantité d'acide fluorhydrique contenue dans ledit mélange C. Ainsi, le rapport entre le débit du flux aqueux exprimé en kg/h alimentant la colonne d'absorption à l'étape iii') et la quantité d'acide fluorhydrique dans ledit mélange C exprimée en kg/h est compris entre 0,05 et 1,22. Avantageusement, le rapport entre le débit du flux aqueux alimentant la colonne d'absorption à l'étape (iii) et la quantité d'acide fluorhydrique dans ledit mélange C exprimée en kg/h peut être compris entre 0,11 et 1,00, de préférence entre 0,18 et 0,82, plus préférentiellement entre 0,25 et 0,67, en particulier entre 0,33 et 0,54. Ainsi le rapport entre le débit du flux aqueux alimentant la colonne d'absorption à l'étape (iii) et la quantité d'acide fluorhydrique dans ledit mélange C exprimée en kg/h peut être de 0,25, 0,26, 0,27, 0,28, 0,29, 0,30, 0,31, 0,32, 0,33, 0,34, 0,35, 0,36, 0,37, 0,38, 0,39, 0,40, 0,41, 0,42, 0,43, 0,44, 0,45, 0,46, 0,47, 0,48, 0,49, 0,50, 0,51, 0,52, 0,53, 0,54, 0,55, 0,56, 0,57, 0,58, 0,59, 0,60, 0,61, 0,62, 0,63, 0,64, 0,65, 0,66, 0,67, 0,68, 0,69 ou 0,70. Un courant aqueux supplémentaire correspondant à la fraction d'eau vaporisée en tête de ladite colonne d'absorption peut également alimenter ladite colonne. Le flux aqueux tel que décrit ci-dessus est différent dudit courant aqueux supplémentaire lié à la fraction d'eau vaporisée en tête de la colonne et ne l'englobe pas.  Preferably, the flow rate of the aqueous stream used in step iii ') is determined as a function of the amount of hydrofluoric acid contained in said mixture C. Thus, the ratio between the flow rate of the aqueous flow expressed in kg / h feeding the absorption column in step iii ') and the amount of hydrofluoric acid in said mixture C expressed in kg / h is between 0.05 and 1.22. Advantageously, the ratio between the flow rate of the aqueous flow supplying the absorption column in step (iii) and the amount of hydrofluoric acid in said mixture C expressed in kg / h may be between 0.11 and 1.00. preferably between 0.18 and 0.82, more preferably between 0.25 and 0.67, in particular between 0.33 and 0.54. Thus, the ratio between the flow rate of the aqueous flow supplying the absorption column in step (iii) and the quantity of hydrofluoric acid in said mixture C expressed in kg / h may be 0.25, 0.26, 0. , 27, 0.28, 0.29, 0.30, 0.31, 0.32, 0.33, 0.34, 0.35, 0.36, 0.37, 0.38, 0.39 , 0.40, 0.41, 0.42, 0.43, 0.44, 0.45, 0.46, 0.47, 0.48, 0.49, 0.50, 0.51, 0 , 52, 0.53, 0.54, 0.55, 0.56, 0.57, 0.58, 0.59, 0.60, 0.61, 0.62, 0.63, 0.64 , 0.65, 0.66, 0.67, 0.68, 0.69 or 0.70. An additional aqueous stream corresponding to the vaporized water fraction at the top of said absorption column may also supply said column. The aqueous stream as described above is different from said additional aqueous stream linked to the vaporized water fraction at the top of the column and does not include it.
Selon un mode de réalisation préféré, ladite colonne d'absorption mise en œuvre à l'étape iii') comprend au moins un étage d'absorption. Avantageusement, ladite colonne d'absorption mise en œuvre à l'étape iii') comprend au moins deux étages d'absorption. De préférence, ladite colonne d'absorption mise en œuvre à l'étape iii') comprend au moins trois étages d'absorption. Ladite colonne d'absorption mise en œuvre à l'étape iii') peut ainsi comprendre deux, trois, quatre, cinq, six, sept, huit, neuf, dix, onze, douze, treize, quatorze ou quinze étages d'absorption. According to a preferred embodiment, said absorption column implemented in step iii ') comprises at least one absorption stage. Advantageously, said absorption column implemented in step iii ') comprises at least two absorption stages. Of Preferably, said absorption column implemented in step iii ') comprises at least three absorption stages. Said absorption column implemented in step iii ') may thus comprise two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen or fifteen absorption stages.
La mise en œuvre d'une colonne d'absorption ayant au moins un étage d'absorption, avantageusement au moins deux étages d'absorption, de préférence au moins trois étages d'absorption, permet d'obtenir un courant Cl ayant une faible teneur en acide fluorhydrique. Avantageusement, ledit courant Cl comprend moins de 1000 ppm d'acide fluorhydrique en poids sur base du poids total dudit troisième courant, de préférence moins de 900 ppm d'acide fluorhydrique, plus préférentiellement moins de 800 ppm d'acide fluorhydrique, en particulier moins de 700 ppm d'acide fluorhydrique, plus particulièrement moins de 600 ppm d'acide fluorhydrique, de manière privilégiée moins de 500 ppm d'acide fluorhydrique, de manière encore plus privilégiée moins de 400 ppm d'acide fluorhydrique, de manière préférentiellement privilégiée moins de 300 ppm d'acide fluorhydrique, de manière particulièrement privilégiée moins de 200 ppm d'acide fluorhydrique, de manière plus particulièrement privilégiée moins de 100 ppm d'acide fluorhydrique. Ainsi, ledit troisième courant peut avoir une teneur en acide fluorhydrique comprise entre 1 et 200 ppm, entre 5 et 190 ppm, entre 10 et 180 ppm, entre 15 et 170 ppm, entre 20 et 160 ppm, entre 25 et 150 ppm ou entre 30 et 140 ppm en poids sur base du poids total dudit courant Cl.  The use of an absorption column having at least one absorption stage, advantageously at least two absorption stages, preferably at least three absorption stages, makes it possible to obtain a low-grade Cl stream. in hydrofluoric acid. Advantageously, said stream C1 comprises less than 1000 ppm of hydrofluoric acid by weight based on the total weight of said third stream, preferably less than 900 ppm of hydrofluoric acid, more preferably less than 800 ppm of hydrofluoric acid, in particular less 700 ppm of hydrofluoric acid, more particularly less than 600 ppm of hydrofluoric acid, preferably less than 500 ppm of hydrofluoric acid, even more preferred less than 400 ppm of hydrofluoric acid, preferably less favored 300 ppm of hydrofluoric acid, particularly preferably less than 200 ppm of hydrofluoric acid, more particularly preferred less than 100 ppm of hydrofluoric acid. Thus, said third stream may have a hydrofluoric acid content of between 1 and 200 ppm, between 5 and 190 ppm, between 10 and 180 ppm, between 15 and 170 ppm, between 20 and 160 ppm, between 25 and 150 ppm or between 30 and 140 ppm by weight based on the total weight of said stream C1.
De préférence, au moins 80% en poids de l'acide fluorhydrique éventuellement présent dans ladite phase gazeuse dudit second courant diphasique est absorbé par le premier étage d'absorption de ladite colonne d'absorption, en particulier au moins 85% en poids de l'acide fluorhydrique éventuellement présent dans ladite phase gazeuse dudit second courant diphasique est absorbé par le premier étage d'absorption de ladite colonne d'absorption, plus particulièrement au moins 90% en poids de l'acide fluorhydrique éventuellement présent dans ladite phase gazeuse dudit second courant diphasique est absorbé par le premier étage d'absorption de ladite colonne d'absorption.  Preferably, at least 80% by weight of the hydrofluoric acid optionally present in said gas phase of said second two-phase current is absorbed by the first absorption stage of said absorption column, in particular at least 85% by weight of the hydrofluoric acid optionally present in said gas phase of said second two-phase current is absorbed by the first absorption stage of said absorption column, more particularly at least 90% by weight of the hydrofluoric acid possibly present in said gaseous phase of said second two-phase current is absorbed by the first absorption stage of said absorption column.
De préférence, ledit flux aqueux peut être introduit au moins au niveau de la tête de la colonne d'absorption.  Preferably, said aqueous stream can be introduced at least at the head of the absorption column.
Selon un mode de réalisation particulier, ledit courant Cl peut être ladite première composition selon la présente invention.  According to a particular embodiment, said stream C1 can be said first composition according to the present invention.
Selon un mode de réalisation préféré, ledit courant C2 est sous la forme d'une solution aqueuse d'acide fluorhydrique. Avantageusement, ledit courant C2 est une solution d'acide fluorhydrique de concentration inférieure à 30% en poids sur base du poids total dudit quatrième courant. De préférence, ledit courant C2 est une solution d'acide fluorhydrique de concentration inférieure à 25% en poids sur base du poids total dudit courant C2. En particulier, ledit courant C2 est une solution d'acide fluorhydrique de concentration comprise entre 5 et 25% en poids sur base du poids total dudit courant C2, plus particulièrement, entre 10 et 20% en poids sur base du poids total dudit courant C2. Selon un mode de réalisation préféré, ledit courant C2 est recyclé à l'étape ii'). Le courant C2 peut ainsi être mélangé avec ladite phase liquide dudit second courant diphasique. According to a preferred embodiment, said stream C2 is in the form of an aqueous solution of hydrofluoric acid. Advantageously, said stream C2 is an acid solution fluorhydric concentration of less than 30% by weight based on the total weight of said fourth stream. Preferably, said stream C2 is a hydrofluoric acid solution of concentration less than 25% by weight based on the total weight of said stream C2. In particular, said stream C2 is a hydrofluoric acid solution with a concentration of between 5 and 25% by weight based on the total weight of said C2 stream, more particularly between 10 and 20% by weight based on the total weight of said C2 stream. . According to a preferred embodiment, said stream C2 is recycled in step ii '). The current C2 can thus be mixed with said liquid phase of said second two-phase current.
Selon un mode de réalisation préféré, ledit procédé comprend également les étapes de : iv') neutralisation dudit courant Cl obtenu à l'étape iii') par une solution aqueuse alcaline pour former un courant neutralisé C3, et According to a preferred embodiment, said method also comprises the steps of: iv ') neutralizing said stream C1 obtained in stage iii') by an aqueous alkaline solution to form a neutralized stream C3, and
') séchage dudit courant neutralisé C3 obtenu à l'étape iv') sur tamis moléculaire pour former un courant neutralisé et séché C4 comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E).  drying said neutralized stream C3 obtained in step iv ') on a molecular sieve to form a neutralized and dried C4 stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2 pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
Selon un mode de réalisation préféré, ladite solution aqueuse alcaline peut être une solution aqueuse d'hydroxyde d'un métal alcalin ou alcalino-terreux. La solution aqueuse alcaline peut être une solution aqueuse d'hydroxyde de sodium, d'hydroxyde de potassium, d'hydroxyde de calcium ou d'hydroxyde de magnésium ou un mélange de ceux-ci. De préférence, ladite solution aqueuse alcaline présente une concentration comprise entre 5 et 50% en poids sur base du poids total de ladite solution aqueuse alcaline. Avantageusement, ladite solution aqueuse alcaline présente une concentration d'au moins 5%, d'au moins 6%, d'au moins 7%, d'au moins 8%, d'au moins 9%, d'au moins 10%, d'au moins 11%, d'au moins 12%, d'au moins 13%, d'au moins 14%, d'au moins 15%, d'au moins 16% ou d'au moins 17% en poids sur base du poids total de ladite solution aqueuse alcaline ; et d'au plus 50%, d'au plus 48%, d'au plus 46%, d'au plus 44%, d'au plus 42%, d'au plus 40%, d'au plus 38%, d'au plus 36%, d'au plus 34%, d'au plus 32%, d'au plus 30%, d'au plus 28%, d'au plus 26%, d'au plus 24%, d'au plus 22% en poids sur base du poids total de ladite solution aqueuse alcaline.  According to a preferred embodiment, said aqueous alkaline solution may be an aqueous solution of hydroxide of an alkali metal or alkaline earth metal. The aqueous alkaline solution may be an aqueous solution of sodium hydroxide, potassium hydroxide, calcium hydroxide or magnesium hydroxide or a mixture thereof. Preferably, said aqueous alkaline solution has a concentration of between 5 and 50% by weight based on the total weight of said alkaline aqueous solution. Advantageously, said alkaline aqueous solution has a concentration of at least 5%, at least 6%, at least 7%, at least 8%, at least 9%, at least 10%. at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, at least 16% or at least weight based on the total weight of said alkaline aqueous solution; and not more than 50%, not more than 48%, not more than 46%, not more than 44%, not more than 42%, not more than 40%, not more than 38%, not more than 36%, not more than 34%, not more than 32%, not more than 30%, not more than 28%, not more than 26%, not more than 24%, at most 22% by weight based on the total weight of said alkaline aqueous solution.
Ledit courant neutralisé C3 formé à l'étape iv') comprend de préférence 2,3,3,3- tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l- propène (1234ze-E). La teneur en acide fluorhydrique dans ledit courant neutralisé C3 est inférieure à la teneur en acide fluorhydrique dudit Cl, avant sa neutralisation. Ledit courant neutralisé C3 formé à l'étape iv') peut également contenir de l'eau. Ledit courant neutralisé C3 formé à l'étape iv') peut ainsi être séché à l'étape v') du présent procédé. De préférence, ledit courant neutralisé C3 formé à l'étape iv') est séché sur tamis moléculaire. Par exemple, ledit courant neutralisé C3 formé à l'étape iv') est séché sur tamis moléculaire de 3A, tel que la siliporite. Said neutralized stream C3 formed in stage iv ') preferably comprises 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3, 3,3-tetrafluoro-1-propene (1234ze-E). The hydrofluoric acid content in said neutralized stream C3 is lower than the hydrofluoric acid content of said Cl, before its neutralization. Said neutralized stream C3 formed in step iv ') may also contain water. Said neutralized stream C3 formed in step iv ') can thus be dried in step v') of the present process. Preferably, said neutralized stream C3 formed in step iv ') is dried on a molecular sieve. For example, said neutralized stream C3 formed in step iv ') is dried on 3A molecular sieve, such as siliporite.
L'étape v') du présent procédé permet la formation d'un courant neutralisé et séché C4 comprenant 2,3,3,3-tétrafluoro-l-propène, 1, 1, 1,2,2-pentafluoropropane (245cb), trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E). Ledit courant C4 peut ensuite être comprimé et liquéfié à une pression d'au plus 8 bara pour former un courant C5 comprimé dans lequel 2,3,3,3-tétrafluoro-l-propène, 1,1, 1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro- 1-propène (1234ze-E) sont sous forme liquide.  Step v ') of the present process allows the formation of a neutralized and dried C4 stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E). Said C4 stream can then be compressed and liquefied at a pressure of at most 8 bara to form a compressed C5 stream in which 2,3,3,3-tetrafluoro-1-propene, 1,1, 1,2,2- pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) are in liquid form.
Selon un mode de réalisation particulier, le courant C4 ou le courant C5 peut être ladite première composition selon la présente invention.  According to a particular embodiment, the current C4 or the current C5 may be said first composition according to the present invention.
Selon un mode de réalisation préféré la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 est recyclée à l'étape i').  According to a preferred embodiment, the liquid phase resulting from mixing said liquid phase of said second two-phase current with said stream C2 is recycled in step i ').
La phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 peut avoir une concentration en acide fluorhydrique supérieure à 41% en poids sur base du poids total de ladite phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2. Avantageusement, la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 peut avoir une concentration en acide fluorhydrique supérieure à 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% ou 95% en poids sur base du poids total de ladite phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2. De préférence, la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 peut avoir une concentration en acide fluorhydrique comprise entre 45% et 95% en poids, entre 50% et 90% en poids, entre 55% et 85% en poids, entre 60% en poids et 80% en poids ou entre 65% en poids et 75% en poids sur base du poids total de ladite phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2.  The liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 may have a hydrofluoric acid concentration of greater than 41% by weight based on the total weight of said liquid phase resulting from the mixing of said liquid phase of said second stream two-phase with said current C2. Advantageously, the liquid phase resulting from the mixing of said liquid phase of said second diphasic current with said stream C2 can have a hydrofluoric acid concentration of greater than 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65 66% 67% 68% 69% 70% 71% 72% 73% 74% 75% 76% 77% 78% 79% 80% 81% 82 %, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94% or 95% by weight based on the total weight of said phase liquid resulting from the mixing of said liquid phase of said second two-phase current with said stream C2. Preferably, the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 may have a hydrofluoric acid concentration of between 45% and 95% by weight, between 50% and 90% by weight, and between 55% and 55% by weight. and 85% by weight, between 60% by weight and 80% by weight or between 65% by weight and 75% by weight based on the total weight of said liquid phase resulting from the mixing of said liquid phase of said second diphasic current with said current C2.
Selon un autre mode de réalisation préféré, la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 est distillée pour former un courant D, de préférence en tête de colonne de distillation. Avantageusement, ledit courant D comprend de l'acide fluorhydrique contenant moins de 3000 ppm d'eau, de préférence moins de 2000 ppm d'eau, plus préférentiellement moins de 1000 ppm d'eau, en particulier moins de 500 ppm d'eau, plus particulièrement moins de 200 ppm d'eau, de manière privilégiée moins de 100 ppm d'eau, de manière plus privilégiée moins de 50 ppm d'eau sur base du poids total du courant D. Ledit courant D peut comprendre également moins de 50 ppm d'acide chlorhydrique, avantageusement moins de 45 ppm d'acide chlorhydrique, de préférence moins de 40 ppm d'acide chlorhydrique, plus préférentiellement moins de 35 ppm d'acide chlorhydrique, en particulier moins de 30 ppm d'acide chlorhydrique, plus particulièrement moins de 20 ppm d'acide chlorhydrique sur base du poids total du courant D Ledit courant D peut comprendre également moins de 50 ppm de composés organiques, avantageusement moins de 45 ppm de composés organiques, de préférence moins de 40 ppm de composés organiques, plus préférentiellement moins de 35 ppm de composés organiques, en particulier moins de 30 ppm de composés organiques, plus particulièrement moins de 20 ppm de composés organiques sur base du poids total du courant D. Un composé organique est un composé comprenant au moins un atome de carbone. According to another preferred embodiment, the liquid phase resulting from mixing said liquid phase of said second two-phase current with said stream C2 is distilled to form a stream D, preferably at the top of the distillation column. Advantageously, said stream D comprises hydrofluoric acid containing less than 3000 ppm of water, preferably less than 2000 ppm of water, more preferably less than 1000 ppm of water, in particular less than 500 ppm of water, more particularly less than 200 ppm water, preferably less than 100 ppm water, more preferably less than 50 ppm water based on the total weight of current D. Said current D may also include less than 50 ppm of hydrochloric acid, advantageously less than 45 ppm of hydrochloric acid, preferably less than 40 ppm of hydrochloric acid, more preferably less than 35 ppm of hydrochloric acid, in particular less than 30 ppm of hydrochloric acid, more particularly less than 20 ppm of hydrochloric acid based on the total weight of the current D Said current D may also comprise less than 50 ppm of organic compounds, advantageously less than 45 ppm of organic compounds, preferably less than 40 ppm pm of organic compounds, more preferably less than 35 ppm of organic compounds, in particular less than 30 ppm of organic compounds, more particularly less than 20 ppm of organic compounds based on the total weight of the current D. An organic compound is a compound comprising at least one carbon atom.
En outre, la distillation de ladite phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 forme un courant E, de préférence en pied de colonne de distillation, comprenant de l'acide fluorhydrique sous forme d'une solution aqueuse de concentration inférieure à 50% en poids. Avantageusement, ledit courant E comprenant de l'acide fluorhydrique sous forme d'une solution aqueuse de concentration inférieure à 50% en poids, 49% en poids, 48% en poids, 47% en poids, 46% en poids, 45% en poids, 44% en poids, 43% en poids, 42% en poids sur base du poids total dudit courant E. De préférence, ledit courant E comprenant de l'acide fluorhydrique sous forme d'une solution aqueuse de concentration supérieure à 20% en poids sur base du poids total dudit courant E. En particulier, ledit courant E comprenant de l'acide fluorhydrique sous forme d'une solution aqueuse de concentration supérieure 21% en poids, 22% en poids, 23% en poids, 24% en poids, 25% en poids, 26% en poids, 27% en poids, 28% en poids, 29% en poids, 30% en poids, 31% en poids, 32% en poids, 33% en poids, 34% en poids, 35% en poids sur base du poids total dudit courant E. Ladite solution aqueuse obtenue dans le courant E peut être commercialisée ou détruite par neutralisation.  In addition, the distillation of said liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 forms a stream E, preferably at the bottom of the distillation column, comprising hydrofluoric acid in the form of a solution. aqueous concentration of less than 50% by weight. Advantageously, said stream E comprises hydrofluoric acid in the form of an aqueous solution with a concentration of less than 50% by weight, 49% by weight, 48% by weight, 47% by weight, 46% by weight, 45% by weight. weight, 44% by weight, 43% by weight, 42% by weight based on the total weight of said stream E. Preferably, said stream E comprising hydrofluoric acid in the form of an aqueous solution with a concentration greater than 20% by weight based on the total weight of said stream E. In particular, said stream E comprising hydrofluoric acid in the form of an aqueous solution of higher concentration 21% by weight, 22% by weight, 23% by weight, 24% by weight, 25% by weight, 26% by weight, 27% by weight, 28% by weight, 29% by weight, 30% by weight, 31% by weight, 32% by weight, 33% by weight, 34% by weight, 35% by weight based on the total weight of said stream E. Said aqueous solution obtained in the stream E can be marketed or destroyed by neutralization.
La phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 peut ainsi être soit distillée soit recyclée à l'étape i'). De préférence, une partie de la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 est distillée tandis que l'autre partie de la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 est recyclée à l'étape i'). De préférence, au moins 50%, plus préférentiellement au moins 60%, en particulier au moins 70%, plus particulièrement au moins 80%, de manière privilégiée au moins 90% en poids de la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique avec ledit courant C2 est recyclée à l'étape i') ; et moins de 50%, de préférence moins de 40%, plus préférentiellement moins de 30%, en particulier moins de 20%, plus particulièrement moins de 10% en poids est distillée. The liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 can thus be either distilled or recycled in step i '). Of preferably, a part of the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said stream C2 is distilled while the other part of the liquid phase resulting from the mixing of said liquid phase of said second two-phase current with said current C2 is recycled in step i '). Preferably, at least 50%, more preferably at least 60%, in particular at least 70%, more particularly at least 80%, preferably at least 90% by weight of the liquid phase resulting from the mixing of said liquid phase of said liquid phase. second diphasic current with said stream C2 is recycled to step i '); and less than 50%, preferably less than 40%, more preferably less than 30%, especially less than 20%, more preferably less than 10% by weight is distilled.
De préférence, le courant comprenant ledit agent d'extraction organique est recyclé à l'étape a). De préférence, le courant comprenant le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) est purifié ou détruit par incinération.  Preferably, the stream comprising said organic extraction agent is recycled in step a). Preferably, the stream comprising trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) is purified or destroyed by incineration.
De préférence, ledit procédé comprend également une étape de récupération dudit courant comprenant le 2,3,3,3-tetrafluoro-l-propène (1234yf) et le 1, 1,1,2,2- pentafluoropropane (245cb) obtenu à l'étape b), et distillation de celui-ci pour former un courant A comprenant 2,3,3,3-tetrafluoro-l-propène et un courant B comprenant 1, 1, 1,2,2- pentafluoropropane (245cb).  Preferably, said process also comprises a step of recovering said stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1,1,1,2,2-pentafluoropropane (245cb) obtained from step b), and distillation thereof to form a stream A comprising 2,3,3,3-tetrafluoro-1-propene and a stream B comprising 1,1,1,2,2-pentafluoropropane (245cb).
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre du 2,3,3,3-tétrafluoro-l-propène, 1, 1, 1,2,2- pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1, 1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-1,2,3,3,3- pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3- trifluoropropène (1243zf). De préférence, ladite première composition, le mélange C, le courant Cl, le courant C3 et/ou le courant C4 peu(ven)t comprendre au moins deux, au moins trois, au moins quatre, au moins cinq, au moins six ou l'ensemble des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1, 1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis- 1,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf).  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise 2,3,3,3-tetrafluoro-1-propene, 1, 1, 1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and at least one of the compounds selected from the group consisting of chloromethane (40), 1, 1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2, 3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf). Preferably, said first composition, mixture C, stream C1, stream C3 and / or stream C4 may comprise at least two, at least three, at least four, at least five, at least six or all of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3 3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf).
Lorsque Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 contien(nen)t au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1, 1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis- 1,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf), celui-ci ou ceux-ci sont contenus dans lesdites seconde et troisième compositions. When said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 contain at least one of the compounds selected from the group consisting of chloromethane (40), 1.1 difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis- 1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), this or these are contained in said second and third compositions.
L'étape c) du présent procédé peut ainsi consister en la récupération de ladite troisième composition et la séparation entre d'une part ledit agent d'extraction organique et d'autre part le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et ledit au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1, 1-difluoroéthane (152a), 1, 1,1,2- tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf).  Step c) of the present process may thus consist of the recovery of said third composition and the separation between, on the one hand, said organic extraction agent and, on the other hand, trans-1,3,3,3-tetrafluoroethylene. 1-propene (1234ze-E) and said at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane ( 115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) ).
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre entre 50 et 99 % en poids de 2,3,3,3-tétrafluoro-l- propène sur base du poids total de la première composition, avantageusement entre 50 et 95% en poids, de préférence entre 55 et 90% et en particulier entre 60 et 80% en poids de 2,3,3,3- tétrafluoro-l-propène sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 can comprise between 50 and 99% by weight of 2,3,3,3-tetrafluoro-1. propene on the basis of the total weight of the first composition, advantageously between 50 and 95% by weight, preferably between 55 and 90% and in particular between 60 and 80% by weight of 2,3,3,3-tetrafluoro-1; -propene on the basis of the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre entre 0.1 et 50 % en poids de 1, 1, 1,2,2- pentafluoropropane (245cb) sur base du poids total de la première composition, avantageusement entre 0,1 et 49,9 % en poids, de préférence entre 1 et 45% en poids, plus préférentiellement entre 2 et 40% et en particulier entre 5 et 40% en poids de 1, 1,1,2,2- pentafluoropropane (245cb) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise between 0.1 and 50% by weight of 1,1,2,2,2-pentafluoropropane (245cb) based on the total weight of the first composition, advantageously between 0.1 and 49.9% by weight, preferably between 1 and 45% by weight, more preferably between 2 and 40% and in particular between 5 and 40% by weight. % by weight of 1,1,2,2,2-pentafluoropropane (245cb) based on the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre entre 0.1 et 50 % en poids de trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E) sur base du poids total de la première composition, avantageusement entre 0,1 et 49,9 % en poids, de préférence entre 0.5 et 40% en poids, plus préférentiellement entre 1 et 30% et en particulier entre 5 et 25% en poids de trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise between 0.1 and 50% by weight of trans-1,3,3,3-tetrafluoro 1-propene (1234ze-E) based on the total weight of the first composition, advantageously between 0.1 and 49.9% by weight, preferably between 0.5 and 40% by weight, more preferably between 1 and 30% and in particular between 5 and 25% by weight of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) based on the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre moins de 1% poids de chlorométhane (40) sur base du poids total de la première composition, avantageusement entre 1 et 5000 ppm poids, de préférence entre 5 et 2000 ppm et en particulier entre 10 et 1000 ppm en poids de chlorométhane (40) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 1% by weight of chloromethane (40) based on the total weight of the first composition preferably between 1 and 5000 ppm by weight, preferably between 5 and 2000 ppm and in particular between 10 and 1000 ppm by weight of chloromethane (40) based on the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre moins de 2000 ppm poids de 1, 1-difluoroéthane (152a) sur base du poids total de la première composition, avantageusement entre 1 et 1000 ppm poids, de préférence entre 5 et 500 ppm et en particulier entre 10 et 250 ppm en poids de 1,1-difluoroéthane (152a) sur base du poids total de la première composition. Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of 1,1-difluoroethane (152a) based on the total weight of the first composition, advantageously between 1 and 1000 ppm weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of 1,1-difluoroethane (152a) based on the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre moins de 2000 ppm poids de chloropentafluoroéthane (115) sur base du poids total de la première composition, avantageusement entre 1 et 1000 ppm poids, de préférence entre 5 et 500 ppm et en particulier entre 10 et 250 ppm en poids de chloropentafluoroéthane (115) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of chloropentafluoroethane (115) based on the total weight of the first composition preferably between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of chloropentafluoroethane (115) based on the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre moins de 2000 ppm poids de 1, 1,1,2- tetrafluoroethane (134a) sur base du poids total de la première composition, avantageusement entre 1 et 1000 ppm poids, de préférence entre 5 et 500 ppm et en particulier entre 10 et 250 ppm poids de 1,1,1,2-tetrafluoroethane (134a) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of 1,1,1,2-tetrafluoroethane (134a) on based on the total weight of the first composition, advantageously between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of 1,1,1,2-tetrafluoroethane (134a) on the basis of the weight total of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre moins de 2000 ppm poids de trans-1,2,3,3,3- pentafluoropropène (1225ye-E) sur base du poids total de la première composition, avantageusement entre 1 et 1000 ppm poids, de préférence entre 5 et 500 ppm et en particulier entre 10 et 250 ppm poids de trans-l,2,3,3,3-pentafluoropropène (1225ye-E) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of trans-1,2,3,3,3-pentafluoropropene (1225ye-E) based on the total weight of the first composition, advantageously between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of trans-1, 2,3,3, 3-pentafluoropropene (1225ye-E) based on the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre moins de 2000 ppm poids de cis-1,2,3,3,3- pentafluoropropène (1225ye-Z) sur base du poids total de la première composition, avantageusement entre 1 et 1000 ppm poids, de préférence entre 5 et 500 ppm et en particulier entre 10 et 250 ppm poids de cis-l,2,3,3,3-pentafluoropropène (1225ye-Z) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 2000 ppm by weight of cis-1,2,3,3,3-pentafluoropropene (1225ye-Z) based on the total weight of the first composition, advantageously between 1 and 1000 ppm by weight, preferably between 5 and 500 ppm and in particular between 10 and 250 ppm by weight of cis-1, 2,3,3, 3-pentafluoropropene (1225ye-Z) based on the total weight of the first composition.
Ladite première composition, le mélange C, le courant Cl, le courant C3, le courant C4 et/ou le courant C5 peu(ven)t comprendre moins de 1 % en poids de 3,3,3-trifluoropropène (1243zf) sur base du poids total de la première composition, avantageusement entre 1 et 5000 ppm poids, de préférence entre 5 et 2000 ppm et en particulier entre 10 et 1500 ppm poids de 3,3,3-trifluoropropène (1243zf) sur base du poids total de la première composition.  Said first composition, the mixture C, the stream C1, the stream C3, the stream C4 and / or the stream C5 may comprise less than 1% by weight of 3,3,3-trifluoropropene (1243zf) based on the total weight of the first composition, advantageously between 1 and 5000 ppm by weight, preferably between 5 and 2000 ppm and in particular between 10 and 1500 ppm by weight of 3,3,3-trifluoropropene (1243zf) on the basis of the total weight of the first composition.
Selon un mode de réalisation particulier, ledit agent d'extraction organique peut être un solvant choisi parmi le groupe consistant en hydrohalocarbure, alcool, cétone, aminé, ester, éther, aldéhyde, nitrile, carbonate, thioalkyle, amide, hétérocycle; ou l'agent d'extraction organique est triethylfluorosilane. De préférence, l'agent d'extraction organique est choisi parmi le groupe consistant en aminé, éther, ester, aldéhyde, cétone, alcool et hétérocycle. According to one particular embodiment, said organic extraction agent may be a solvent chosen from the group consisting of hydrohalocarbon, alcohol, ketone, amine, ester, ether, aldehyde, nitrile, carbonate, thioalkyl, amide, heterocycle; or the organic extractant is triethylfluorosilane. Preferably, the organic extractant is selected from the group consisting of amine, ether, ester, aldehyde, ketone, alcohol and heterocycle.
De préférence, les hydrohalocarbures sont sélectionnés parmi le groupe consistant en bromofluoromethane, l-bromo-l,2-difluoroethylene, l,l,l-trifluoro-2-bromoethane, 2- chloropropane, bromoethane, iodomethane, 2-chloro-2-methylpropane, 2-bromopropane, chlorobromomethane, 3-bromopropène, 1-bromopropane, iodoethane, 2-bromo-2- methylpropane, l-chloro-3-fluoropropane, 2-chloro-2-methylbutane, 1,2-dichloroethane, 2- iodopropane, dichlorobromomethane, 2-bromobutane, 1,2-dichloropropane, trichloroacetaldehyde, l-chloro-4-fluorobutane, l-bromo-3-fluoropropane, 1-bromobutane, 1- iodopropane, cis-l,3-dichloropropène, bromotrichloromethane, l-bromo-2-chloroethane, 2- bromo-2-methylbutane, trans-l,3-dichloropropène, 1,1,2-trichloroethane, 2-bromopentane, 2,3-dichlorobutane, l-bromo-3-methylbutane, l,3-dichloro-trans-2-butene, 1,3- dichloropropane, 1,2-dibromo-l-fluoroethane, 1,2,2-trichloropropane, 2,3-dichloro-2- methylbutane, 1-bromopentane, l,2-dichloro-2-butene, 1-iodobutane, 1,2-dibromoethane, 1,1,2-trichloropropane, 1,3-dichlorobutane, 1,2-dibromopropane, 1,2,3-trichloropropène, 1- chloro-3-bromopropane, tribromomethane.  Preferably, the hydrohalocarbons are selected from the group consisting of bromofluoromethane, 1-bromo-1,2-difluoroethylene, 1,1,1-trifluoro-2-bromoethane, 2-chloropropane, bromoethane, iodomethane, 2-chloro-2- methylpropane, 2-bromopropane, chlorobromomethane, 3-bromopropene, 1-bromopropane, iodoethane, 2-bromo-2-methylpropane, 1-chloro-3-fluoropropane, 2-chloro-2-methylbutane, 1,2-dichloroethane, 2- iodopropane, dichlorobromomethane, 2-bromobutane, 1,2-dichloropropane, trichloroacetaldehyde, 1-chloro-4-fluorobutane, 1-bromo-3-fluoropropane, 1-bromobutane, 1-iodopropane, cis-1,3-dichloropropene, bromotrichloromethane, 1-bromo-2-chloroethane, 2-bromo-2-methylbutane, trans-1,3-dichloropropene, 1,1,2-trichloroethane, 2-bromopentane, 2,3-dichlorobutane, 1-bromo-3-methylbutane, 1,3-dichloro-trans-2-butene, 1,3-dichloropropane, 1,2-dibromo-1-fluoroethane, 1,2,2-trichloropropane, 2,3-dichloro-2-methylbutane, 1-bromopentane, 1,2-dichloro-2-butene, 1-iodobutane, 1,2-dibro moethane, 1,1,2-trichloropropane, 1,3-dichlorobutane, 1,2-dibromopropane, 1,2,3-trichloropropene, 1-chloro-3-bromopropane, tribromomethane.
De préférence, les alcools sont sélectionnés parmi le groupe consistant en méthanol, 2,2,2-trifluoroethanol, l,l,l-trifluoro-2-propanol, ethanol, 2-propanol, tert-butanol, 2,2- difluoroethanol, propanol, 2-allyloxyethanol, 2-butanol, 2-methyl-2-butanol, isobutanol, 2,2,3,3-tetraflouro-l-propanol, 2,2-dimethyl-l-propanol, 3-pentanol, 1-butanol, l-methoxy2- propanol, l-(dimethylamino)-2-propanol, 3-methyl-3-pentanol, l-chloro-2-methyl-2-propanol, 4,4,4-trifluorobutanol, 3-fluoropropanol, 2-chloroethanol, 2-methoxyl-propanol, l-ethoxy-2- propanol, 4-methyl-2-pentanol, 1,2-octanediol, 2-chloro-l-propanol, 2-(dimethylamino)- ethanol, 3-hexanol, 2-hexanol, 2-ethoxy-l-propanol, 1-pentanol, 2,3-dimethylbutanol, 2-ethyl- 1-butanol, 2-methyl-l-pentanol, 2-propoxyethanol.  Preferably, the alcohols are selected from the group consisting of methanol, 2,2,2-trifluoroethanol, 1,1,1-trifluoro-2-propanol, ethanol, 2-propanol, tert-butanol, 2,2-difluoroethanol, propanol, 2-allyloxyethanol, 2-butanol, 2-methyl-2-butanol, isobutanol, 2,2,3,3-tetraflouro-1-propanol, 2,2-dimethyl-1-propanol, 3-pentanol, butanol, 1-methoxy-2-propanol, 1- (dimethylamino) -2-propanol, 3-methyl-3-pentanol, 1-chloro-2-methyl-2-propanol, 4,4,4-trifluorobutanol, 3-fluoropropanol, 2-chloroethanol, 2-methoxyl-propanol, 1-ethoxy-2-propanol, 4-methyl-2-pentanol, 1,2-octanediol, 2-chloro-1-propanol, 2- (dimethylamino) ethanol, 3- hexanol, 2-hexanol, 2-ethoxy-1-propanol, 1-pentanol, 2,3-dimethylbutanol, 2-ethyl-1-butanol, 2-methyl-1-pentanol, 2-propoxyethanol.
De préférence, les cétones sont sélectionnées parmi le groupe consistant en 1,1,1- trifluoro-2-propanone, propanone, butanone, 3-pentanone, 2-pentanone, 3,3-dimethyl-2- butanone, 4-methyl-2-pentanone, 2-hexanone, 5-hexen-2-one, 4-methyl-2-hexanone.  Preferably, the ketones are selected from the group consisting of 1,1,1-trifluoro-2-propanone, propanone, butanone, 3-pentanone, 2-pentanone, 3,3-dimethyl-2-butanone, 4-methyl- 2-pentanone, 2-hexanone, 5-hexen-2-one, 4-methyl-2-hexanone.
De préférence, les aminés sont sélectionnées parmi le groupe consistant en Ethylamine, isopropylamine, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, diethylamine, 2-butanamine, n-methylpropylamine, 1-butylamine, diisopropylamine, 3-methyl-2-butanamine, 3-pentylamine, n-methylbutylamine, l-methoxy-2- propanamine, 2-methoxyethanamine, 2-methoxy-lpropanamine, n-pentylamine, n- methylhydroxylamine, dipropylamine, 2-ethoxyethanamine, n-methyl-l,2-ethanediamine, pyridine, 1,2-diaminoethane, 1,2-propanediamine, 2-ethylbutylamine, n-ethylethylenediamine,Preferably, the amines are selected from the group consisting of ethylamine, isopropylamine, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, diethylamine, 2-butanamine, n-methylpropylamine, 1-butylamine, diisopropylamine, 3- methyl-2-butanamine, 3-pentylamine, n-methylbutylamine, 1-methoxy-2- propanamine, 2-methoxyethanamine, 2-methoxy-1propanamine, n-pentylamine, n-methylhydroxylamine, dipropylamine, 2-ethoxyethanamine, n-methyl-1,2-ethanediamine, pyridine, 1,2-diaminoethane, 1,2-propanediamine, 2-ethylbutylamine, n-ethylethylenediamine,
1.1- diethoxy-n,n-dimethylmethanamine, 2-methylpyridine, 4-methyl-2-hexanamine, hexylamine, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, 1,3-propanediamine, 2- heptanamine, η,η-diethylethylenediamine, 2,6-dimethylpyridine, 4-methylpyridine, η,η'- diethyl-l,2-ethanediamine. 1,1-diethoxy-n, n-dimethylmethanamine, 2-methylpyridine, 4-methyl-2-hexanamine, hexylamine, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, 1,3-propanediamine, 2-heptanamine, η, η-diethylethylenediamine, 2,6-dimethylpyridine, 4-methylpyridine, η, η'-diethyl-1,2-ethanediamine.
De préférence, les esters sont sélectionnés parmi le groupe consistant Methylformate, methylacetate, isopropylformate, ethylacetate, n-propylformate, isopropylacetate, tertbutylacetate, ethylpropionate, sec-butylacetate, diethylcarbonate, n-butylacetate, bromoaceticacidmethylester, methylhexanoate.  Preferably, the esters are selected from the group consisting of methylformate, methylacetate, isopropylformate, ethylacetate, n-propylformate, isopropylacetate, tertbutylacetate, ethylpropionate, sec-butylacetate, diethylcarbonate, n-butylacetate, bromoaceticacidmethylester, methylhexanoate.
De préférence, les éthers sont sélectionnés parmi le groupe consistant en 2,2,2- trifluoroethylmethylether, 2-methoxy-l-propène, diethylether, ethoxy-ethene, dimethoxymethane, methylcyclopropylether, 2-ethoxy-propane, methyl-t-butylether, chloromethoxymethane, diisopropylether, 2-ethoxy-2-methyl-propane, 2-ethoxy-butane, 1- methoxy-2-methyl-butane, 2,2-dimethoxypropane, l-ethoxy-2-methylpropane, 1,2- dimethoxyethane, diethoxymethane, di-n-propylether, 1-ethoxybutane, 1-methoxy-pentane, Preferably, the ethers are selected from the group consisting of 2,2,2-trifluoroethylmethylether, 2-methoxy-1-propene, diethylether, ethoxyethene, dimethoxymethane, methylcyclopropylether, 2-ethoxy-propane, methyl-t-butylether, chloromethoxymethane, diisopropyl ether, 2-ethoxy-2-methyl-propane, 2-ethoxy-butane, 1-methoxy-2-methyl-butane, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane, diethoxymethane, di-n-propylether, 1-ethoxybutane, 1-methoxy-pentane,
1.2- dimethoxypropane„ isopropyl-isobutyl-ether, 1,1-diethoxyethane, trimethoxymethane, 2,2-diethoxypropane, isobutyl-tert-butylether, sec-butyl-tert-butylether, 1,1-diethoxypropane, 2-methoxyethanol, 2-chloro-l,l-dimethoxyethane, methoxycyclohexane, ethoxyethanol, di-n- butylether, 1-ethoxy-hexane, 1,1,1-triethoxyethane, l-methoxy-2-acetoxypropane. 1,2-dimethoxypropane "isopropyl-isobutyl-ether, 1,1-diethoxyethane, trimethoxymethane, 2,2-diethoxypropane, isobutyl-tert-butylether, sec-butyl-tert-butylether, 1,1-diethoxypropane, 2-methoxyethanol, 2- chloro-1,1-dimethoxyethane, methoxycyclohexane, ethoxyethanol, di-n-butylether, 1-ethoxy-hexane, 1,1,1-triethoxyethane, 1-methoxy-2-acetoxypropane.
De préférence, les aldéhydes sont sélectionnés parmi le groupe consistant en acétaldehyde, ethanedial, isobutanal, methylglyoxal, 2-methylbutanal, 2,6-dimethyl-5- heptenal, hexanal.  Preferably, the aldehydes are selected from the group consisting of acetaldehyde, ethanedial, isobutanal, methylglyoxal, 2-methylbutanal, 2,6-dimethyl-5-heptenal, hexanal.
De préférence, les nitriles sont sélectionnés parmi le groupe consistant en acétonitrile, propionitrile, butyronitrile, valeronitrile, (methyleneamino)acetonitrile.  Preferably, the nitriles are selected from the group consisting of acetonitrile, propionitrile, butyronitrile, valeronitrile, (methyleneamino) acetonitrile.
De préférence, le carbonate est le diéthylcaarbonate.  Preferably, the carbonate is diethylcaarbonate.
De préférence, l'amide est l'éthanethioamide.  Preferably, the amide is ethanethioamide.
De préférence, les thioalkyles sont sélectionnés parmi le groupe consistant en éthanethiol, dimethylsulfide, 2-propanethiol, 4-methoxy-2-methyl-2-butanethiol, tert- butylthiol, 1-propanethiol, 2-butanethiol, 2-methyl-l-propanethiol, diethylsulfide, butanethiol, 3-mercapto-l,2-propanediol, tetrahydrothiophene, 1-pentanethiol. De préférence, les hétérocycles sont choisis parmi le groupe consistant en tétrahydrofurane, 1,4-dioxane, 1,3-dioxane, 1,3,5-trioxane, n-methylmorpholine, 2- methylpyrazine, n-ethyl-morpholine, 1-methylpiperazine, 1,2-epoxypropane, piperidine, 3- furfural, 2,6-dimethylmorpholine. Preferably, the thioalkyls are selected from the group consisting of ethanethiol, dimethylsulfide, 2-propanethiol, 4-methoxy-2-methyl-2-butanethiol, tert-butylthiol, 1-propanethiol, 2-butanethiol, 2-methyl-1- propanethiol, diethylsulfide, butanethiol, 3-mercapto-1,2-propanediol, tetrahydrothiophene, 1-pentanethiol. Preferably, the heterocycles are selected from the group consisting of tetrahydrofuran, 1,4-dioxane, 1,3-dioxane, 1,3,5-trioxane, n-methylmorpholine, 2-methylpyrazine, n-ethyl-morpholine, 1- methylpiperazine, 1,2-epoxypropane, piperidine, 3-furfural, 2,6-dimethylmorpholine.
Ledit agent d'extraction organique peut être éthylamine, bromofluoromethane, 1- bromo-l,2-difluoroethylene, acetaldehyde, l,l,l-trifluoro-2-propanone, l,l,l-trifluoro-2- bromoethane, 2,2,2-trifluoroethylmethylether, isopropylamine, methylformate, 2-methoxy-l- propène, diethylether, 1,2-epoxypropane, ethanethiol, ethoxy-ethene, ethylmethylamine, dimethylsulfide, 2-chloropropane, bromoethane, dimethoxymethane, iodomethane, 2-amino- 2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, ethanedial, 2-chloro-2-methylpropane, 2-propanethiol, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2- bromopropane, chloromethoxymethane, 2-butanamine, n-methylpropylamine, tert-butylthiol, isobutanal, methanol, tétrahydrofurane, 1-propanethiol, chlorobromomethane, isopropylformate, diisopropylether, 3-bromopropène, 1-bromopropane, methylglyoxal, iodoethane, 2-ethoxy-2-methyl-propane, 2-bromo-2-methylpropane, 2,2,2-trifluoroethanol, 1- chloro-3-fluoropropane, l,l,l-trifluoro-2-propanol, 1-butylamine, ethylacetate, ethanol, butanone, n-propylformate, 2-ethoxy-butane, 2-propanol, acetonitrile, tert-butanol, 1- methoxy-2-methyl-butane, 2,2-dimethoxypropane, 2-chloro-2-methylbutane, 1,2- dichloroethane, l-ethoxy-2-methylpropane, diisopropylamine, 2-butanethiol, 1,2- dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, 2-methyl-l-propanethiol, isopropylacetate, 2-iodopropane, di-n-propylether, 3-pentylamine, n-methylbutylamine, 2- bromobutane, diethylsulfide, 1-ethoxybutane, l-methoxy-2-propanamine, 2-methylbutanal, 2- methoxyethanamine, 2,2-difluoroethanol, 1,2-dichloropropane, propanol, tert-butylacetate, propionitrile, trichloroacetaldehyde, 2-allyloxyethanol, butanethiol, 1-methoxy-pentane, ethylpropionate, 2-butanol, 1,2-dimethoxypropane, isopropyl-isobutyl-ether, l-chloro-4- fluorobutane, l-bromo-3-fluoropropane, 1,4-dioxane, 1-bromobutane, 3-pentanone, 1,1- diethoxyethane, 2-pentanone, 2-methyl-2-butanol, 1-iodopropane, 2-methoxy-lpropanamine, trimethoxymethane, cis-l,3-dichloropropène, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3- dioxane, piperidine, l-bromo-2-chloroethane, isobutanol, 2-bromo-2-methylbutane, dipropylamine, 2,2,3,3-tetraflouro-l-propanol, 2-ethoxyethanamine, triethylfluorosilane, sec- butylacetate, trans-l,3-dichloropropène, 2,2-dimethyl-l-propanol, n-methyl-1,2- ethanediamine, 2,2-diethoxypropane, 1,3,5-trioxane, pyridine, n-methylmorpholine, 3- pentanol, 4-methyl-2-pentanone, 1,2-diaminoethane, isobutyl-tert-butylether, 2- bromopentane, butyronitrile, 1-butanol, 2,3-dichlorobutane, sec-butyl-tert-butylether, 1- methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, l-bromo-3-methylbutane, l,3-dichloro-trans-2-butene, 1,3-dichloropropane, l-(dimethylamino)-2-propanol, tetrahydrothiophene, 3-methyl-3-pentanol, 1,2-dibromo-l-fluoroethane, 1,1-diethoxypropane, 1,2,2-trichloropropane, l-chloro-2-methyl-2-propanol, 2-methoxyethanol, 4,4,4- trifluorobutanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 1-pentanethiol, 2- chloro-l,l-dimethoxyethane, 2-hexanone, n-ethylethylenediamine, 3-fluoropropanol, 5-hexen-Said organic extraction agent may be ethylamine, bromofluoromethane, 1-bromo-1,2-difluoroethylene, acetaldehyde, 1,1,1-trifluoro-2-propanone, 1,1,1-trifluoro-2-bromoethane, 2, 2,2-trifluoroethylmethylether, isopropylamine, methylformate, 2-methoxy-1-propene, diethylether, 1,2-epoxypropane, ethanethiol, ethoxyethene, ethylmethylamine, dimethylsulfide, 2-chloropropane, bromoethane, dimethoxymethane, iodomethane, 2-amino- 2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, ethanedial, 2-chloro-2-methylpropane, 2-propanethiol, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2- methyl-2-butanethiol, 2-bromopropane, chloromethoxymethane, 2-butanamine, n-methylpropylamine, tert-butylthiol, isobutanal, methanol, tetrahydrofuran, 1-propanethiol, chlorobromomethane, isopropylformate, diisopropylether, 3-bromopropene, 1-bromopropane, methylglyoxal, iodoethane, 2-ethoxy-2-methylpropane, 2-bromo-2-methylpropane, 2, 2,2-trifluoroethanol, 1-chloro-3-fluoropropane, 1,1,1-trifluoro-2-propanol, 1-butylamine, ethylacetate, ethanol, butanone, n-propylformate, 2-ethoxy-butane, 2-propanol, acetonitrile, tert-butanol, 1-methoxy-2-methyl-butane, 2,2-dimethoxypropane, 2-chloro-2-methylbutane, 1,2-dichloroethane, 1-ethoxy-2-methylpropane, diisopropylamine, 2-butanethiol, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, 2-methyl-1-propanethiol, isopropylacetate, 2-iodopropane, di-n-propylether, 3-pentylamine, n-methylbutylamine, 2-bromobutane, diethylsulfide, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, 2,2-difluoroethanol, 1,2-dichloropropane, propanol, tert-butylacetate, propionitrile, trichloroacetaldehyde, 2-allyloxyethanol, butanethiol, 1- methoxy-pentane, ethylpropionate, 2-butanol, 1,2-dimethoxypropane, isopropyl-isobutyl-ether, 1-chloro-4-fluorobutane, 1-bromo-3-fluoropropane, 1,4-dioxane, 1-bromobutane, 3- pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methyl-2-butanol, 1-iodopropane, 2-methoxy-1-propanamine, trimethoxymethane, cis-1,3-dichloropropene, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, 1-bromo-2-chloroethane, isobutanol, 2-bromo-2-methylbutane, dipropylamine, 2,2,3,3-tetraflouro-1-propanol, 2-ethoxyethanamine, triethylfluorosilane, sec-butylacetate, trans-1,3- dichloropropene, 2,2-dimethyl-1-propanol, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane, 1,3,5-trioxane, pyridine, n-methylmorpholine, 3- pentanol, 4-methyl-2-pentanone, 1,2-diaminoethane, isobutyl-tert-butylether, 2-bromopentane, butyronitrile, 1-butanol, 2,3-dichlorobutane, sec-butyl-tert-butylether, 1-methoxy2- propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1-bromo-3-methylbutane, 1,3-dichloro-trans-2-butene, 1,3-dichloropropane, 1- (dimethylamino) - 2-propanol, tetrahydrothiophene, 3-methyl-3-pentanol, 1,2-dibromo-1-fluoroethane, 1,1-diethoxypropane, 1,2,2-trichloropropane, 1-chloro-2-methyl-2-propanol, 2-methoxyethanol, 4,4,4-trifluorobutanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 1-pentanethiol, 2-chloro-1,1-dimethoxyethane, 2-hexanone, n-ethylethylenediamine, 3-fluoropropanol, 5- hexen-
2- one, 2,3-dichloro-2-methylbutane, l,l-diethoxy-n,n-dimethylmethanamine, 2- methylpyridine, 1-bromopentane, 2-methoxyl-propanol, l,2-dichloro-2-butene, 1-iodobutane, hexanal, l-ethoxy-2-propanol, 1,2-dibromoethane, 4-methyl-2-pentanol, bromoaceticacidmethylester, 1,1,2-trichloropropane, 1,2-octanediol, 4-methyl-2-hexanamine, hexylamine, 2-chloro-l-propanol, methoxycyclohexane, 2-(dimethylamino)-ethanol, 1,3- dichlorobutane, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 3- hexanol, 2-hexanol, 2-methylpyrazine, 2-ethoxy-l-propanol, 1-pentanol, n-ethyl-morpholine, 1- methylpiperazine, 1,3-propanediamine, di-n-butylether, valeronitrile, (methyleneamino)acetonitrile, 1,2-dibromopropane, 1,2,3-trichloropropène, 2-heptanamine, 2,3-dimethylbutanol, 1-ethoxy-hexane, l-chloro-3-bromopropane, n,n-diethylethylenediamine,2- one, 2,3-dichloro-2-methylbutane, 1,1-diethoxy-n, n-dimethylmethanamine, 2-methylpyridine, 1-bromopentane, 2-methoxyl-propanol, 1,2-dichloro-2-butene, 1-iodobutane, hexanal, 1-ethoxy-2-propanol, 1,2-dibromoethane, 4-methyl-2-pentanol, bromoaceticacidmethylester, 1,1,2-trichloropropane, 1,2-octanediol, 4-methyl-2- hexanamine, hexylamine, 2-chloro-1-propanol, methoxycyclohexane, 2- (dimethylamino) ethanol, 1,3-dichlorobutane, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 3-hexanol, 2-hexanol, 2- methylpyrazine, 2-ethoxy-1-propanol, 1-pentanol, n-ethyl-morpholine, 1-methylpiperazine, 1,3-propanediamine, di-n-butylether, valeronitrile, (methyleneamino) acetonitrile, 1,2-dibromopropane, 1 2,3-trichloropropene, 2-heptanamine, 2,3-dimethylbutanol, 1-ethoxy-hexane, 1-chloro-3-bromopropane, n, n-diethylethylenediamine,
3- furfural, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, l-methoxy-2- acetoxypropane, 4-methylpyridine, n,n'-diethyl-l,2-ethanediamine, 2,6-dimethylmorpholine, 2- ethyl-l-butanol, 2-methyl-l-pentanol, methylhexanoate, 2-propoxyethanol, l-propoxy-2- propanol, dimethylethanolamine. 3-furfural, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-1,2-ethanediamine 2,6-dimethylmorpholine, 2-ethyl-1-butanol, 2-methyl-1-pentanol, methylhexanoate, 2-propoxyethanol, 1-propoxy-2-propanol, dimethylethanolamine.
Avantageusement, ledit agent d'extraction organique peut être éthylamine, bromofluoromethane, acetaldehyde, isopropylamine, methylformate, 2-methoxy-l-propène, diethylether, 1,2-epoxypropane, ethanethiol, ethoxy-ethene, ethylmethylamine, dimethylsulfide, bromoethane, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-propanethiol, 2-ethoxy- propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl- 2-butanethiol, 2-bromopropane, 2-butanamine, n-methylpropylamine, tert-butylthiol, isobutanal, tetrahydrofurane, 1-propanethiol, isopropylformate, diisopropylether, 1- bromopropane, methylglyoxal, 2-ethoxy-2-methyl-propane, 2-bromo-2-methylpropane, 1- butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy-butane, 2-propanol, tert- butanol, l-methoxy-2-methyl-butane, 2,2-dimethoxypropane, l-ethoxy-2-methylpropane, diisopropylamine, 2-butanethiol, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, 2-methyl-l-propanethiol, isopropylacetate, 2-iodopropane, di-n- propylether, 3-pentylamine, n-methylbutylamine, 2-bromobutane, diethylsulfide, 1- ethoxybutane, l-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, propanol, tert-butylacetate, propionitrile, 2-allyloxyethanol, butanethiol, 1-methoxy-pentane, ethylpropionate, 2-butanol, 1,2-dimethoxypropane, isopropyl-isobutyl-ether, l-bromo-3- fluoropropane, 1,4-dioxane, 1-bromobutane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methyl-2-butanol, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3- dimethyl-2-butanone, 1,3-dioxane, piperidine, isobutanol, 2-bromo-2-methylbutane, dipropylamine, 2-ethoxyethanamine, sec-butylacetate, 2,2-dimethyl-l-propanol, n-methyl-1,2- ethanediamine, 2,2-diethoxypropane, 1,3,5-trioxane, pyridine, n-methylmorpholine, 3- pentanol, 4-methyl-2-pentanone, 1,2-diaminoethane, isobutyl-tert-butylether, 2- bromopentane, butyronitrile, 1-butanol, sec-butyl-tert-butylether, l-methoxy2-propanol, 1,2- propanediamine, 2,6-dimethyl-5-heptenal, l-bromo-3-methylbutane, l-(dimethylamino)-2- propanol, tetrahydrothiophene, 3-methyl-3-pentanol, 1,1-diethoxypropane, 2-methoxyethanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 1-pentanethiol, 2-chloro-l,l- dimethoxyethane, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, l,l-diethoxy-n,n- dimethylmethanamine, 2-methylpyridine, 1-bromopentane, 2-methoxyl-propanol, hexanal, 1- ethoxy-2-propanol, 4-methyl-2-pentanol, 1,2-octanediol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2-(dimethylamino)-ethanol, cyclohexylamine, n-ethyl-2- dimethylaminoethylamine, ethoxyethanol, 3-hexanol, 2-hexanol, 2-methylpyrazine, 2-ethoxy-l- propanol, 1-pentanol, n-ethyl-morpholine, 1-methylpiperazine, 1,3-propanediamine, di-n- butylether, valeronitrile, (methyleneamino)acetonitrile, 2-heptanamine, 2,3-dimethylbutanol, 1-ethoxy-hexane, η,η-diethylethylenediamine, 3-furfural, 2,6-dimethylpyridine, 4-methyl-2- hexanone, 1,1,1-triethoxyethane, l-methoxy-2-acetoxypropane, 4-methylpyridine, n,n'-diethyl- 1,2-ethanediamine, 2,6-dimethylmorpholine, 2-ethyl-l-butanol, 2-methyl-l-pentanol, methylhexanoate, 2-propoxyethanol, l-propoxy-2-propanol, dimethylethanolamine Advantageously, said organic extraction agent may be ethylamine, bromofluoromethane, acetaldehyde, isopropylamine, methylformate, 2-methoxy-1-propene, diethyl ether, 1,2-epoxypropane, ethanethiol, ethoxy-ethene, ethylmethylamine, dimethylsulfide, bromoethane, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-propanethiol, 2-ethoxypropane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-bromopropane, 2-butanamine, n-methylpropylamine, tert-butylthiol, isobutanal, tetrahydrofuran, 1-propanethiol, isopropylformate, diisopropylether, 1-bromopropane, methylglyoxal, 2-ethoxy-2-methylpropane, 2-bromo-2- methylpropane, 1-butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy-butane, 2-propanol, tert-butanol, 1-methoxy-2-methyl-butane, 2,2-dimethoxypropane, 1-ethoxy-2- methylpropane, diisopropylamine, 2-butanethiol, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, 2-methyl-1-propanethiol, isopropylacetate, 2-iodopropane, di-n-propylether, 3-pentylamine, n-methylbutylamine, 2-bromobutane, diethylsulfide, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, propanol, tert-butylacetate, propionitrile, 2-allyloxyethanol, butanethiol, 1-methoxy-pentane, ethylpropionate, 2- butanol, 1,2-dimethoxypropane, isopropyl-isobutyl-ether, 1-bromo-3-fluoropropane, 1,4-dioxane, 1-bromobutane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methyl- 2-butanol, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, isobutanol, 2-bromo-2-methylbutane, dipropylamine, 2-ethoxyethanamine, sec-butylacetate, 2,2-dimethyl-1-propanol, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane, 1,3,5-trioxane, pyridine, n-methylmorpholine, 3-pentanol, 4- methyl-2-pentanone, 1,2-diaminoethane, isobutyl-tert-butyl ether, 2-bromopentane, butyronitrile, 1-butanol, sec-butyl-tert-butylether, 1-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1-bromo-3-methylbutane, 1- (dimethylamino) -2-propanol, tetrahydrothiophene, 3-methyl-3-pentanol, 1,1-diethoxypropane, 2-methoxyethanol, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 1-pentanethiol, 2-chloro-1, 1-dimethoxyethane, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 1,1-diethoxy-n, n-dimethylmethanamine, 2-methylpyridine, 1-bromopentane, 2-methoxyl-propanol, hexanal, 1- ethoxy-2-propanol, 4-methyl-2-pentanol, 1,2-octanediol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 3-hexanol, 2-hexanol, 2-methylpyrazine, 2-ethoxy-1-propanol, 1-pentanol, n-ethyl-morpholine, 1-methylpiperazine, 1,3-propanediamine, di-n-butylether, valeronitrile, (methyleneamino) acetonitrile, 2-heptanamine, 2,3-dimethylbutanol, 1-ethoxy-hexane, η, η-d iethylethylenediamine, 3-furfural, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, n-1,2-diethyl -ethanediamine, 2,6-dimethylmorpholine, 2-ethyl-1-butanol, 2-methyl-1-pentanol, methylhexanoate, 2-propoxyethanol, 1-propoxy-2-propanol, dimethylethanolamine
De préférence, ledit agent d'extraction organique peut être éthylamine, acetaldehyde, isopropylamine, methylformate, diethylether, 1,2-epoxypropane, ethylmethylamine, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofurane, isopropylformate, diisopropylether, 2-ethoxy-2-methyl-propane, 1- butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy-butane, l-methoxy-2- methyl-butane, 2,2-dimethoxypropane, l-ethoxy-2-methylpropane, diisopropylamine, 1,2- dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, di-n- propylether, 3-pentylamine, n-methylbutylamine, diethylsulfide, 1-ethoxybutane, l-methoxy-2- propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, propionitrile, 2- allyloxyethanol, 1-methoxy-pentane, ethylpropionate, 1,2-dimethoxypropane, isopropyl- isobutyl-ether, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy- lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, dipropylamine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2- ethanediamine, 2,2-diethoxypropane, pyridine, n-methylmorpholine, 4-methyl-2-pentanone, 1,2-diaminoethane, isobutyl-tert-butylether, butyronitrile, sec-butyl-tert-butylether, 1- methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, l-(dimethylamino)-2- propanol, 3-methyl-3-pentanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n- butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, l,l-diethoxy-n,n- dimethylmethanamine, 2-methylpyridine, 2-methoxyl-propanol, hexanal, l-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2-(dimethylamino)-ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2-methylpyrazine, 2- ethoxy-l-propanol, n-ethyl-morpholine, 1-methylpiperazine, 1,3-propanediamine, di-n- butylether, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, n,n-diethylethylenediamine, 2,6- dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, l-methoxy-2-acetoxypropane, 4-methylpyridine, n,n'-diethyl-l,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate,Preferably, said organic extraction agent may be ethylamine, acetaldehyde, isopropylamine, methylformate, diethylether, 1,2-epoxypropane, ethylmethylamine, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-ethoxy propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, isopropylformate, diisopropylether, 2-ethoxy-2-methyl -propane, 1-butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy-butane, 1-methoxy-2-methyl-butane, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, di-n-propylether, 3-pentylamine, n-methylbutylamine, diethylsulfide, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert- butylacetate, propionitrile, 2-allyloxyethanol, 1-methoxy-pentane, ethylpropionate, 1,2-dimethoxypropane, isopropylisobutylether, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2- methoxypropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, dipropylamine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2-ethanediamine, 2, 2-diethoxypropane, pyridine, n-methylmorpholine, 4-methyl-2-pentanone, 1,2-diaminoethane, isobutyl-tert-butylether, butyronitrile, sec-butyl-tert-butylether, 1-methoxy-2-propanol, 1,2- propanediamine, 2,6-dimethyl 5-heptenal, 1- (dimethylamino) -2-propanol, 3-methyl-3-pentanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen -2-one, 1,1-diethoxy-n, n-dimethylmethanamine, 2-methylpyridine, 2-methoxyl-propanol, hexanal, 1-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2 - (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2-methylpyrazine, 2-ethoxy-1-propanol, n-ethyl-morpholine, 1-methylpiperazine, 1,3-propanediamine, di-n butylether, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, n, n-diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, 1-methoxy-2-acetoxypropane 4-methylpyridine, n, N'-diethyl-1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate,
2- propoxyethanol, l-propoxy-2-propanol. 2- propoxyethanol, 1-propoxy-2-propanol.
En particulier, ledit agent d'extraction organique peut être éthylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofurane, 1- butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, l-ethoxy-2- methylpropane, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, l-methoxy-2- propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, ethylpropionate, 1,2-dimethoxypropane, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2- pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2- butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2- ethanediamine, 2,2-diethoxypropane, 4-methyl-2-pentanone, 1,2-diaminoethane, butyronitrile, l-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino)-2-propanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n- butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2- methoxyl-propanol, hexanal, l-ethoxy-2-propanol, 4-methyl-2, hexanamine, hexylamine, methoxycyclohexane, 2-(dimethylamino)-ethanol, cyclohexylamine, n-ethyl-2- dimethylaminoethylamine, 2-methylpyrazine, 2-ethoxy-l-propanol, 1-methylpiperazine, 1,3- propanediamine, di-n-butylether, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, n,n- diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, 1- methoxy-2-acetoxypropane, 4-methylpyridine, n,n'-diethyl-l,2-ethanediamine, 2,6- dimethylmorpholine, methylhexanoate, 2-propoxyethanol, l-propoxy-2-propanol. In particular, said organic extraction agent may be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate , 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane, 3-methyl-2 -butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, ethylpropionate, 1,2 -dimethoxypropane, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane , piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2- andhanediamine, 2,2-diethoxypropane, 4-methyl-2-pentanone, 1,2-diaminoethane, butyronitrile, 1-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2-propanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2-methoxyl-propanol, hexanal, 1-ethoxy-2-propanol, 4-methyl-2, hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, 2-methylpyrazine, 2-ethoxy-1- propanol, 1-methylpiperazine, 1,3-propanediamine, di-n-butylether, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, n, n-diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-Triethoxyethane, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, 1-propoxy-2 propanol.
L'agent d'extraction organique à utiliser peut être sélectionné en fonction des composés présents dans ladite première composition. Ainsi, l'agent d'extraction organique peut être sélectionné en fonction du facteur de séparation et de la capacité d'absorption établi pour une composition particulière. Outre ces deux critères, le choix de l'agent d'extraction organique peut se baser optionnellement sur d'autres critères commerciaux ou environnementaux, tels que par exemple le coût de l'agent d'extraction organique, sa disponibilité sur le marché, ses propriétés toxiques ou inflammable. De plus, selon un mode de réalisation particulier, afin d'optimiser le fonctionnement des colonnes de distillation utilisées à l'étape b) et c) du présent procédé de purification du 2,3,3,3-tetrafluoro-l-propène, le point d'ébullition de l'agent d'extraction organique peut être de 0°C à 200°C, avantageusement de 10°C à 190°C, de préférence de 10°C à 180°C, en particulier de 10°C à 170°C, plus particulièrement de 10°C à 160°C, et de manière privilégiée de 10°C à 150°C.  The organic extraction agent to be used may be selected depending on the compounds present in said first composition. Thus, the organic extractant can be selected depending on the separation factor and the absorption capacity established for a particular composition. In addition to these two criteria, the choice of the organic extraction agent may optionally be based on other commercial or environmental criteria, such as, for example, the cost of the organic extraction agent, its availability on the market, its toxic or flammable properties. In addition, according to a particular embodiment, in order to optimize the operation of the distillation columns used in step b) and c) of the present process for purifying 2,3,3,3-tetrafluoro-1-propene, the boiling point of the organic extractant may be from 0 ° C to 200 ° C, preferably from 10 ° C to 190 ° C, preferably from 10 ° C to 180 ° C, in particular 10 ° C C at 170 ° C, more preferably from 10 ° C to 160 ° C, and preferably from 10 ° C to 150 ° C.
Selon un mode de réalisation préféré, ledit agent d'extraction organique a un facteur de séparation Si,2 supérieur ou égal à 1,1, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(Y2,s*P2) dans laquelle  According to a preferred embodiment, said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * Pl) / (Y2, s * P2) in which
Yi,s représente le coefficient d'activité du 2,3,3,3-tétrafluoro-l-propène (1234yf) dans ledit agent d'extraction organique à dilution infinie,  Yi, s represents the activity coefficient of 2,3,3,3-tetrafluoro-1-propene (1234yf) in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 2,3,3,3-tétrafluoro-l-propène (1234yf),  PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene (1234yf),
Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze- E) dans ledit agent d'extraction organique à dilution infinie, P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E). Y2, s represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze-E) in said organic infinite dilution extractant, P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
Selon un mode de réalisation préféré, ledit agent d'extraction organique a un facteur de séparation Si,2 supérieur ou égal à 1, 1, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s* Pl)/(Y2,s* P2) dans laquelle According to a preferred embodiment, said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * Pl) / (Y2, s * P2) in which
Yi,s représente le coefficient d'activité du 1, 1,1,2,2-pentafluoropropane (245cb) dans ledit agent d'extraction organique à dilution infinie,  Yi, s represents the activity coefficient of 1,1,1,2,2-pentafluoropropane (245cb) in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 1,1, 1,2,2-pentafluoropropane (245cb), Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze- E) dans ledit agent d'extraction organique à dilution infinie,  PI represents the saturated vapor pressure of 1,1,2,2-pentafluoropropane (245cb), Y2, s represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze) E) in said organic extraction agent with infinite dilution,
P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E).  P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
Selon un mode de réalisation préféré, ledit agent d'extraction organique a :  According to a preferred embodiment, said organic extraction agent has:
- un facteur de séparation Si,2 supérieur ou égal à 1, 1, ledit facteur de séparation étant calculé par la formule Si,2 = (YI,S* P1)/(Y2,S* P2) dans laquelle  a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (YI, S * P1) / (Y2, S * P2) in which
Yi,s représente le coefficient d'activité du 2,3,3,3-tétrafluoro-l-propène (1234yf) dans ledit agent d'extraction organique à dilution infinie,  Yi, s represents the activity coefficient of 2,3,3,3-tetrafluoro-1-propene (1234yf) in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 2,3,3,3-tétrafluoro-l-propène (1234yf),  PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene (1234yf),
Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze- Y2, s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene (1234
E) dans ledit agent d'extraction organique à dilution infinie, E) in said organic infinite dilution extractant,
P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene
(1234ze-E) ; (1234ze-E);
et  and
- un facteur de séparation Si,2 supérieur ou égal à 1, 1, ledit facteur de séparation étant calculé par la formule Si,2 = (YI,S* P1)/(Y2,S* P2) dans laquelle  a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (YI, S * P1) / (Y2, S * P2) in which
Yi,s représente le coefficient d'activité du 1, 1, 1,2,2-pentafluoropropane (245cb) dans ledit agent d'extraction organique à dilution infinie,  Yi, s represents the activity coefficient of 1,1,2,2,2-pentafluoropropane (245cb) in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 1,1, 1,2,2-pentafluoropropane (245cb), Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze- PI represents the saturated vapor pressure of 1,1,2,2-pentafluoropropane (245cb), Y2, s represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze) -
E) dans ledit agent d'extraction organique à dilution infinie, E) in said organic infinite dilution extractant,
P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E). Avantageusement, dans les deux cas, le facteur de séparation Si,2 peut être supérieur ou égal à 1,2, de préférence supérieur ou égal à 1,4, plus préférentiellement supérieur ou égal à 1,6, en particulier supérieur ou égal à 1,8, plus particulièrement supérieur ou égal à 2,0. P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E). Advantageously, in both cases, the separation factor Si, 2 may be greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to 2.0.
Selon un mode de réalisation préféré, ledit agent d'extraction organique a une capacité d'absorption C2,s supérieure ou égale à 0,20, ladite capacité d'absorption étant calculée par la formule C2,s = l/(y2,s) dans laquelle y2,s représente le coefficient d'activité du trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E) dans ledit agent d'extraction organique à dilution infinie. Avantageusement, la capacité d'absorption C2,s est supérieure ou égale à 0,40, de préférence supérieure ou égale à 0,60, plus préférentiellement supérieure ou égale à 0,80, en particulier supérieure ou égale à 1,0.  According to a preferred embodiment, said organic extraction agent has an absorption capacity C2, s greater than or equal to 0.20, said absorption capacity being calculated by the formula C2, s = 1 / (y2, s ) wherein y2, s represents the activity coefficient of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) in said organic infinite dilution extractant. Advantageously, the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.
Selon un mode de réalisation préféré, ledit agent d'extraction organique peut avoir un facteur de séparation Si,2 supérieur ou égal à 1,1, avantageusement supérieur ou égal à 1,2, de préférence supérieur ou égal à 1,4, plus préférentiellement supérieur ou égal à 1,6, en particulier supérieur ou égal à 1,8 et plus particulièrement supérieur ou égal à 2,0 ; et une capacité d'absorption C2,s supérieure ou égale à 0,20, avantageusement supérieure ou égale à 0,40, de préférence supérieure ou égale à 0,60, plus préférentiellement supérieure ou égale à 0,80, en particulier supérieure ou égale à 1,0.  According to a preferred embodiment, said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.1, advantageously greater than or equal to 1.2, preferably greater than or equal to 1.4, plus preferably greater than or equal to 1.6, in particular greater than or equal to 1.8 and more particularly greater than or equal to 2.0; and an absorption capacity C2, s greater than or equal to 0.20, advantageously greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 0.80, equal to 1.0.
Le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) étant une des principales impuretés à éliminer, le facteur de séparation et ladite capacité d'absorption peuvent être calculés pour le couple binaire particulier consistant en 2,3,3,3-tetrafluoro-l-propène et trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E) et/ou 1,1,1,2,2-pentafluoropropane (245cb) et trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E). Le facteur de séparation Si,2 permet de déterminer la capacité d'un agent d'extraction organique à séparer deux ou plusieurs composés. La capacité d'absorption C2,s permet de déterminer la quantité de solvant à utiliser pour obtenir la séparation entre les composés considérés.  Since trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) is one of the main impurities to be removed, the separation factor and the said absorption capacity can be calculated for the particular binary pair consisting of 2 , 3,3,3-tetrafluoro-1-propene and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and / or 1,1,1,2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E). The separation factor Si, 2 makes it possible to determine the capacity of an organic extraction agent to separate two or more compounds. The absorption capacity C2, s makes it possible to determine the amount of solvent to be used to obtain the separation between the compounds under consideration.
Ledit agent d'extraction organique peut avoir un facteur de séparation Si,2 supérieur ou égal à 1,4, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(y2,s*P2) dans laquelle yi,s représente le coefficient d'activité du 2,3,3,3-tetrafluoro-l-propène par rapport audit agent d'extraction organique, PI représente la pression de vapeur saturante du 2,3,3,3- tetrafluoro-l-propène, y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l- propène dans ledit agent d'extraction organique à dilution infinie, P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène et/ou ledit agent d'extraction organique peut avoir un facteur de séparation Si,2 supérieur ou égal à 1,4, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(y2,s*P2) dans laquelle yi,s représente le coefficient d'activité du 1,1,1,2,2-pentafluoropropane (245cb) par rapport audit agent d'extraction organique, PI représente la pression de vapeur saturante du 1,1,1,2,2- pentafluoropropane (245cb), Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro- 1-propène dans ledit agent d'extraction organique à dilution infinie, P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène ; et de préférence ledit agent d'extraction organique peut avoir une capacité d'absorption C2,s supérieure ou égale à 0,60, ladite capacité d'absorption étant calculé par la formule C2,s = l/(y2,s) dans laquelle y2,s représente le coefficient d'activité de trans-l,3,3,3-tetrafluoro-l-propène dans ledit agent d'extraction organique à dilution infinie ; ledit agent d'extraction organique peut ainsi être éthylamine, acetaldehyde, isopropylamine, methylformate, diethylether, 1,2-epoxypropane, ethylmethylamine, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n- propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-butanamine, n- methylpropylamine, isobutanal, tetrahydrofurane, isopropylformate, diisopropylether, 2- ethoxy-2-methyl-propane, 1-butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy- butane, l-methoxy-2-methyl-butane, 2,2-dimethoxypropane, l-ethoxy-2-methylpropane, diisopropylamine, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, di-n-propylether, 3-pentylamine, n-methylbutylamine, diethylsulfide, 1- ethoxybutane, l-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert- butylacetate, propionitrile, 2-allyloxyethanol, 1-methoxy-pentane, ethylpropionate, 1,2- dimethoxypropane, isopropyl-isobutyl-ether, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2- pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2- butanone, 1,3-dioxane, piperidine, dipropylamine, 2-ethoxyethanamine, sec-butylacetate, n- methyl-l,2-ethanediamine, 2,2-diethoxypropane, pyridine, n-methylmorpholine, 4-methyl-2- pentanone, 1,2-diaminoethane, isobutyl-tert-butylether, butyronitrile, sec-butyl-tert- butylether, l-methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino)-2-propanol, 3-methyl-3-pentanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 1,1- diethoxy-n,n-dimethylmethanamine, 2-methylpyridine, 2-methoxyl-propanol, hexanal, 1- ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino)-ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, ethoxyethanol, 2-methylpyrazine, 2-ethoxy-l-propanol, n-ethyl-morpholine, 1- methylpiperazine, 1,3-propanediamine, di-n-butylether, valeronitrile, 2-heptanamine, 1- ethoxy-hexane, η,η-diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1- triethoxyethane, l-methoxy-2-acetoxypropane, 4-methylpyridine, n,n'-diethyl-l,2- ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, l-propoxy-2- propanol. Said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.4, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2 ) where yi, s represents the coefficient of activity of 2,3,3,3-tetrafluoro-1-propene relative to said organic extraction agent, PI represents the saturated vapor pressure of 2,3,3,3 tetrafluoro-1-propene, y 2, s represents the coefficient of activity of trans-1, 3,3,3-tetrafluoro-1-propene in said organic extraction agent with infinite dilution, P2 represents the saturation vapor pressure trans-1,1,3,3-tetrafluoro-1-propene and / or said organic extractant may have a separation factor Si, 2 greater than or equal to 1.4, said separation being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2) in which yi, s represents the activity coefficient of 1,1,1,2,2-pentafluoropropane (245cb ) with respect to said organic extraction agent, PI represents the saturated vapor pressure of 1,1,1,2,2-pentafluoropropane (245cb), Y2, s represents the activity coefficient of the trans-1, 3,3 , 3-tetrafluoro-1-propene in said infinitely diluted organic extractant, P2 is the saturated vapor pressure of trans-1,3,3,3-tetrafluoro-1-propene; and preferably said organic extractant may have an absorption capacity C2, s greater than or equal to 0.60, said absorption capacity being calculated by the formula C2, s = 1 / (y 2, s) in which y2, s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene in said organic infinite dilution extractant; said organic extraction agent can thus be ethylamine, acetaldehyde, isopropylamine, methylformate, diethylether, 1,2-epoxypropane, ethylmethylamine, dimethoxymethane, 2-amino-2-methylpropane, methylcyclopropylether, n-propylamine, isopropylmethylamine, 2-ethoxy-propane methyl-t-butylether, diethylamine, propanone, methylacetate, 4-methoxy-2-methyl-2-butanethiol, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, isopropylformate, diisopropylether, 2-ethoxy-2-methylpropane , 1-butylamine, ethylacetate, butanone, n-propylformate, 2-ethoxy-butane, 1-methoxy-2-methyl-butane, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, diisopropylamine, 1,2-dimethoxyethane , 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, di-n-propylether, 3-pentylamine, n-methylbutylamine, diethylsulfide, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert butylacetate, propionitrile, 2-allyloxyethanol, 1-methoxy-pentane, ethylpropionate, 1,2-dim ethoxypropane, isopropylisobutylether, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine, dipropylamine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane, pyridine, n-methylmorpholine, 4-methyl-2-pentanone, 1, 2-diaminoethane, isobutyl-tert-butylether, butyronitrile, sec-butyl-tert-butylether, 1-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2- propanol, 3-methyl-3-pentanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 1,1-diethoxy-n, n-dimethylmethanamine, 2-methylpyridine, 2-methoxyl-propanol, hexanal, 1-ethoxy-2-propanol, 4-methyl-2-hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl- 2-dimethylaminoethylamine, ethoxyethanol, 2-methylpyrazine, 2-ethoxy-1-propanol, n-eth yl-morpholine, 1- methylpiperazine, 1,3-propanediamine, di-n-butylether, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, η, η-diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1, 1- triethoxyethane, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, 1-propoxy-2-propanol.
Ledit agent d'extraction organique peut avoir un facteur de séparation Si,2 supérieur ou égal à 1,6, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(y2,s*P2) dans laquelle yi,s représente le coefficient d'activité du 2,3,3,3-tetrafluoro-l-propène par rapport audit agent d'extraction organique, PI représente la pression de vapeur saturante du 2,3,3,3- tetrafluoro-l-propène, y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l- propène dans ledit agent d'extraction organique à dilution infinie, P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène et/ou ledit agent d'extraction organique peut avoir un facteur de séparation Si,2 supérieur ou égal à 1,6, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(y2,s*P2) dans laquelle yi,s représente le coefficient d'activité du 1,1,1,2,2-pentafluoropropane (245cb) par rapport audit agent d'extraction organique, PI représente la pression de vapeur saturante du 1,1,1,2,2- pentafluoropropane (245cb), Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro- 1-propène dans ledit agent d'extraction organique à dilution infinie, P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène ; et de préférence ledit agent d'extraction organique peut avoir une capacité d'absorption C2,s supérieure ou égale à 0,80, ladite capacité d'absorption étant calculé par la formule C2,s = l/(y2,s) dans laquelle y2,s représente le coefficient d'activité de trans-l,3,3,3-tetrafluoro-l-propène dans ledit agent d'extraction organique à dilution infinie ; ledit agent d'extraction organique peut ainsi être éthylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n- propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofurane, 1-butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, l-ethoxy-2- methylpropane, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, l-methoxy-2- propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, ethylpropionate, 1,2-dimethoxypropane, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2- pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2- butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2- ethanediamine, 2,2-diethoxypropane, 4-methyl-2-pentanone, 1,2-diaminoethane, butyronitrile, l-methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino)-2-propanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n- butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2- methoxyl-propanol, hexanal, l-ethoxy-2-propanol, 4-methyl-2, hexanamine, hexylamine, methoxycyclohexane, 2-(dimethylamino)-ethanol, cyclohexylamine, n-ethyl-2- dimethylaminoethylamine, 2-methylpyrazine, 2-ethoxy-l-propanol, 1-methylpiperazine, 1,3- propanediamine, di-n-butylether, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, n,n- diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1,1,1-triethoxyethane, 1- methoxy-2-acetoxypropane, 4-methylpyridine, n,n'-diethyl-l,2-ethanediamine, 2,6- dimethylmorpholine, methylhexanoate, 2-propoxyethanol, l-propoxy-2-propanol. Said organic extraction agent may have a separation factor Si, 2 greater than or equal to 1.6, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2 ) where yi, s represents the coefficient of activity of 2,3,3,3-tetrafluoro-1-propene relative to said organic extraction agent, PI represents the saturated vapor pressure of 2,3,3,3 tetrafluoro-1-propene, y 2, s represents the coefficient of activity of trans-1, 3,3,3-tetrafluoro-1-propene in said organic extraction agent with infinite dilution, P2 represents the saturation vapor pressure trans-1,1,3,3-tetrafluoro-1-propene and / or said organic extractant may have a separation factor Si, 2 greater than or equal to 1.6, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2) in which yi, s represents the activity coefficient of 1,1,1,2,2-pentafluoropropane (245cb) relative to said agent organic extraction, PI reprocesses the saturated vapor pressure of 1,1,1,2,2-pentafluoropropane (245cb), Y2, s represents the activity coefficient of trans-1,3,3,3-tetrafluoro-1-propene in said agent P2 is the saturated vapor pressure of trans-1,3,3,3-tetrafluoro-1-propene; and preferably said organic extractant can have an absorption capacity C2, s greater than or equal to 0.80, said absorption capacity being calculated by the formula C2, s = 1 / (y2, s) in which y2, s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene in said organic infinite dilution extractant; said organic extraction agent can thus be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 2 -butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane, 3-methyl-2-butanamine , diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, ethylpropionate, 1,2-dimethoxypropane 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-1-propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane, piperidine , 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2- ethanediamine, 2,2-diethoxypropane, 4-methyl-2-pentanone, 1,2-diaminoethane, butyronitrile, 1-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2-propanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n-butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2-methoxyl-propanol, hexanal, 1-ethoxy-2-propanol, 4-methyl-2, hexanamine, hexylamine, methoxycyclohexane, 2- (dimethylamino) ethanol, cyclohexylamine, n-ethyl-2-dimethylaminoethylamine, 2-methylpyrazine, 2-ethoxy-1-propanol, 1-methylpiperazine, 1,3-propanediamine, di-n-butylether, valeronitrile, 2-heptanamine, 1-ethoxy-hexane, n, n-diethylethylenediamine, 2,6-dimethylpyridine, 4-methyl-2-hexanone, 1, 1,1-Triethoxyethane, 1-methoxy-2-acetoxypropane, 4-methylpyridine, n, N'-diethyl-1,2-ethanediamine, 2,6-dimethylmorpholine, methylhexanoate, 2-propoxyethanol, 1-propoxy-2-propanol .
De préférence, ledit agent d'extraction organique peut être éthylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate, 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofurane, 1- butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, l-ethoxy-2- methylpropane, 1,2-dimethoxyethane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, l-methoxy-2- propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, ethylpropionate, 1,2-dimethoxypropane, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2- pentanone, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2- butanone, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2- ethanediamine, 2,2-diethoxypropane, 4-methyl-2-pentanone, 1,2-diaminoethane, butyronitrile, l-methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino)-2-propanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n- butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2- methoxyl-propanol, hexanal. En particulier, ledit agent d'extraction organique peut être éthylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n- propylamine, isopropylmethylamine, 2-ethoxy-propane, diethylamine, 2-butanamine, n- methylpropylamine, 1-butylamine, n-propylformate, 2,2-dimethoxypropane, l-ethoxy-2- methylpropane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, l-methoxy-2-propanamine, 2-methylbutanal, 2- methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, 1,2-dimethoxypropane, 1,4- dioxane, ,1-diethoxyethane, 2-methoxy-lpropanamine, trimethoxymethane, n-pentylamine, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-l,2-ethanediamine, 2,2-diethoxypropane, 1,2-diaminoethane, butyronitrile, l-methoxy2-propanol, 1,2- propanediamine, 2,6-dimethyl-5-heptenal, l-(dimethylamino)-2-propanol, 1,1- diethoxypropane, 2-ethylbutylamine, n-butylacetate, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2-methoxyl-propanol, hexanal. Preferably, said organic extraction agent may be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, methyl-t-butylether, diethylamine, propanone, methylacetate , 2-butanamine, n-methylpropylamine, isobutanal, tetrahydrofuran, 1-butylamine, ethylacetate, butanone, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 1,2-dimethoxyethane, 3-methyl-2 -butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2-propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, ethylpropionate, 1,2 -dimethoxypropane, 1,4-dioxane, 3-pentanone, 1,1-diethoxyethane, 2-pentanone, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 3,3-dimethyl-2-butanone, 1,3-dioxane , piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane, 4-methyl-2-pentanone, 1,2-diaminoetha ne, butyronitrile, 1-methoxy2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2-propanol, 1,1-diethoxypropane, 2-ethylbutylamine, diethylcarbonate, n- butylacetate, 2-hexanone, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2-methoxyl-propanol, hexanal. In particular, said organic extraction agent can be ethylamine, isopropylamine, diethylether, ethylmethylamine, 2-amino-2-methylpropane, n-propylamine, isopropylmethylamine, 2-ethoxy-propane, diethylamine, 2-butanamine, n-methylpropylamine, 1 -butylamine, n-propylformate, 2,2-dimethoxypropane, 1-ethoxy-2-methylpropane, 3-methyl-2-butanamine, diethoxymethane, isopropylacetate, 3-pentylamine, n-methylbutylamine, 1-ethoxybutane, 1-methoxy-2 propanamine, 2-methylbutanal, 2-methoxyethanamine, tert-butylacetate, 1-methoxy-pentane, 1,2-dimethoxypropane, dioxane, 1-diethoxyethane, 2-methoxy-1propanamine, trimethoxymethane, n-pentylamine, 1,3-dioxane, piperidine, 2-ethoxyethanamine, sec-butylacetate, n-methyl-1,2-ethanediamine, 2,2-diethoxypropane 1,2-diaminoethane, butyronitrile, 1-methoxy-2-propanol, 1,2-propanediamine, 2,6-dimethyl-5-heptenal, 1- (dimethylamino) -2-propanol, 1,1-diethoxypropane, 2-ethylbutylamine , n-butylacetate, n-ethylethylenediamine, 5-hexen-2-one, 2-methylpyridine, 2-methoxyl-propanol, hexanal.
Selon un mode de réalisation préféré, ledit agent d'extraction organique peut être éthylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2- methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy-2-propanol, 1,2- propanediamine, n-butylacetate, 2-methoxy-l-propanol, hexanal. En particulier, ledit agent d'extraction organique peut être éthylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert- butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3- dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy-2-propanol, 1,2-propanediamine, n- butylacetate, 2-methoxy-l-propanol, hexanal.  According to a preferred embodiment, said organic extraction agent may be ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1 , 4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate 2-methoxy-1-propanol, hexanal. In particular, said organic extractant may be ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy-1-propanol, hexanal .
Selon un mode de réalisation préféré, ladite troisième composition comprenant ledit agent d'extraction organique et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E); de préférence la troisième composition comprenant ledit agent d'extraction organique et trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E) et optionnellement ou non au moins un des composés choisi parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2- tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) ; peut être soumise à une distillation pour séparer l'agent d'extraction organique et le trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E); de préférence pour séparer d'une part l'agent d'extraction organique et d'autre part le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et optionnellement ou non au moins un des composés choisi parmi le groupe consistant en chlorométhane (40), 1,1- difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans- 1,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3- trifluoropropène (1243zf). Ledit agent d'extraction organique est ainsi recyclé à l'étape a) du procédé de purification. Le courant comprenant le trans-l,3,3,3-tetrafluoro-l-propène (1234ze- E) et optionnellement ou non au moins un des composés choisi parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) peut être soit soumis à une ou plusieurs étapes de purification ultérieures ou peut être détruit par incinération. According to a preferred embodiment, said third composition comprising said organic extraction agent and trans-1,1,3,3-tetrafluoro-1-propene (1234ze-E); preferably the third composition comprising said organic extractant and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane ( 40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis 1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf); may be subjected to distillation to separate the organic extractant and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E); preferably, to separate, on the one hand, the organic extraction agent and, on the other hand, trans-1,1,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3- pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf). Said organic extraction agent is thus recycled to step a) of the purification process. The stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E) cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) may be subjected to one or more subsequent purification steps or may be destroyed by incineration.
Le présent procédé permet donc de purifier le 2,3,3,3-tetrafluoro-l-propène (1234yf). The present process thus makes it possible to purify 2,3,3,3-tetrafluoro-1-propene (1234yf).
Avantageusement, la teneur en trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) dans le courant comprenant du 2,3,3,3-tetrafluoro-l-propène (1234yf) et 1,1,1,2,2-pentafluoropropane (245cb) et obtenu à l'étape b) du présent procédé de purification est inférieure à la teneur de celui-ci dans ladite première composition. De préférence, la teneur en trans-l,3,3,3-tetrafluoro-l- propène (1234ze-E) et/ou en au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) dans le courant comprenant du 2,3,3,3-tetrafluoro-l-propène (1234yf) et 1,1,1,2,2-pentafluoropropane (245cb) et obtenu à l'étape b) du présent procédé de purification est inférieure à la teneur de celui-ci dans ladite première composition. Advantageously, the content of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) in the stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1.1 , 1,2,2-pentafluoropropane (245cb) and obtained in step b) of the present purification process is less than the content thereof in said first composition. Preferably, the content of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and / or at least one of the compounds selected from the group consisting of chloromethane (40), 1,1- difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3, 3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) in the stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1,1,1,2 , 2-pentafluoropropane (245cb) and obtained in step b) of the present purification process is less than the content thereof in said first composition.
Par exemple, la teneur en trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) ou en l'un quelconque des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1- difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans- 1,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3- trifluoropropène (1243zf) peut être diminuée de 50%, avantageusement de 75%, de préférence de 90%, en particulier de 95%, plus particulièrement de 98%. Avantageusement, la teneur en au moins deux, au moins trois, au moins quatre, au moins cinq, au moins six ou en l'ensemble desdits composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1- difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans- 1,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3- trifluoropropène (1243zf) peut être diminuée de 50%, avantageusement de 75%, de préférence de 90%, en particulier de 95%, plus particulièrement de 98%. De préférence, la teneur en trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) peut être diminuée de 50%, avantageusement de 75%, de préférence de 90%, en particulier de 95%, plus particulièrement de 98%.  For example, the content of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) or any of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3 , 3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) can be reduced by 50%, advantageously by 75%, preferably by 90%, in particular by 95%, more particularly by 98%. Advantageously, the content of at least two, at least three, at least four, at least five, at least six or all of said compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a) , 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3- pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) can be reduced by 50%, advantageously by 75%, preferably by 90%, in particular by 95%, more particularly by 98%. Preferably, the content of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) can be reduced by 50%, advantageously by 75%, preferably by 90%, in particular by 95%, more particularly 98%.
De préférence, le courant comprenant le 2,3,3,3-tetrafluoro-l-propène et 1,1,1,2,2- pentafluoropropane obtenu à l'étape b) du présent procédé de purification peut être dépourvu de trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E). En particulier, le courant comprenant le 2,3,3,3-tetrafluoro-l-propène et 1,1,1,2,2-pentafluoropropane obtenu à l'étape b) du présent procédé de purification peut être dépourvu de trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et/ou optionnellement d'au moins un, d'au moins deux, d'au moins trois, d'au moins quatre, d'au moins cinq, d'au moins six ou de l'ensemble des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) lorsque celui-ci ou ceux-ci sont présents dans ladite première composition. Le terme « dépourvu » signifie que le courant comprenant le 2,3,3,3-tetrafluoro-l-propène (1234yf) comprend moins de 50 ppm, avantageusement moins de 20 ppm, de préférence moins de 10 ppm du composé considéré sur base du poids total du courant. Les teneurs sont exprimées en poids. Preferably, the stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane obtained in step b) of the present purification process may be devoid of trans- 1,3,3,3-tetrafluoro-1-propene (1234ze-E). In particular, the current comprising the 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane obtained in step b) of the present purification process may be devoid of trans-1,3,3,3 -tetrafluoro-1-propene (1234ze-E) and / or optionally at least one, at least two, at least three, at least four, at least five, at least six or all of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2 , 3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) when the latter or those ci are present in said first composition. The term "free" means that the stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) comprises less than 50 ppm, preferably less than 20 ppm, preferably less than 10 ppm of the compound under consideration. total weight of the current. The contents are expressed by weight.
Selon un mode de réalisation préféré, ledit mélange C mise en œuvre à l'étape i') du présent procédé peut être préalablement purifié avant d'être utilisé. En effet, si ledit mélange C comprend des impuretés ayant un point d'ébullition inférieur au point d'ébullition du 2,3,3,3- tetrafluoro-l-propène et optionnellement des impuretés lourdes, le présent procédé peut comprendre préalablement à l'étape i') les étapes :  According to a preferred embodiment, said mixture C implemented in stage i ') of the present process can be previously purified before being used. Indeed, if said mixture C comprises impurities having a boiling point below the boiling point of 2,3,3,3-tetrafluoro-1-propene and optionally heavy impurities, the present process can comprise beforehand 'step i') the steps:
i- l') mise en œuvre d'une composition comprenant 2,3,3,3-tetrafluoro-l-propène, des impuretés ayant un point d'ébullition inférieur au point d'ébullition du 2,3,3,3- tetrafluoro-l-propène, HF, 1,1,1,2,2-pentafluoropropane (245cb), et trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E), optionnellement ou non au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans- 1,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf), et optionnellement ou non des impuretés lourdes ; ii- ) distillation de ladite composition de l'étape i-1') pour éliminer en tête de colonne des impuretés ayant un point d'ébullition inférieur au point d'ébullition du 2,3,3,3- tetrafluoro-l-propène et former un premier courant comprenant 2,3,3,3-tetrafluoro-l- propène, HF, 1,1,1,2,2-pentafluoropropane (245cb), et trans-l,3,3,3-tetrafluoro-l- propène (1234ze-E), optionnellement ou non au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2- tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-1,2,3,3,3- pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3- trifluoropropène (1243zf), et optionnellement ou non des impuretés lourdes, récupéré en bas de colonne de distillation ; the use of a composition comprising 2,3,3,3-tetrafluoro-1-propene, impurities having a boiling point below the boiling point of 2,3,3,3- tetrafluoro-1-propene, HF, 1,1,1,2,2-pentafluoropropane (245cb), and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), optionally optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3 , 3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), and optionally or not heavy impurities; ii-) distilling said composition of step i-1 ') to remove at the top of the column impurities having a boiling point below the boiling point of 2,3,3,3-tetrafluoro-1-propene and forming a first stream comprising 2,3,3,3-tetrafluoro-1-propene, HF, 1,1,1,2,2-pentafluoropropane (245cb), and trans-1,3,3,3-tetrafluoropropane. 1-propene (1234ze-E), optionally optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3- trifluoropropene (1243zf), and optionally or not heavy impurities recovered at the bottom of the distillation column;
iii- ) optionnellement ou non, distillation dudit premier courant récupéré en bas de colonne de distillation à l'étape ii- ) pour récupérer en tête de colonne un second courant comprenant du 2,3,3,3-tetrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane iii-) optionally or not, distillation of said first stream recovered at the bottom of the distillation column in step ii-) to recover at the top of the column a second stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane
(245cb), H F et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E), optionnellement ou non au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis- 1,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf), et en bas de colonne de distillation un courant comprenant les impuretés lourdes ; (245cb), HF and trans-1,33,3-tetrafluoro-1-propene (1234ze-E), optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1- difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3, 3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), and at the bottom of the distillation column a stream comprising heavy impurities;
ledit premier courant récupéré à l'étape ii- ) ou ledit second courant récupéré à l'étape iii- ) correspondent audit mélange C mise en œuvre à l'étape i').  said first stream recovered in step ii-) or said second stream recovered in step iii-) correspond to said mixture C implemented in step i ').
Selon un second aspect, la présente invention fournit un procédé de production du 2,3,3,3-tetrafluoro-l-propène. En outre, ce procédé peut inclure sa purification. Ainsi, la présente invention fournit un procédé de production de 2,3,3,3-tetrafluoro-l-propène comprenant les étapes de :  In a second aspect, the present invention provides a process for producing 2,3,3,3-tetrafluoro-1-propene. In addition, this process may include its purification. Thus, the present invention provides a process for producing 2,3,3,3-tetrafluoro-1-propene comprising the steps of:
A) fluoration en présence d'un catalyseur d'un composé de formule CH(n+2)(X)m- CHp(X)(n+i)-CX(3+p-m) où X représente indépendamment F ou Cl ; n, m, p sont indépendamment les uns des autres 0 ou 1 avec (n+m) = 0 ou 1, (n+p) = 0 ou 1 et (m-p)A) fluorination in the presence of a catalyst of a compound of formula CH ( n + 2) (X) m-CH p (X) (n + 1) -CX (3 + pm) where X independently represents F or Cl ; n, m, p are independently of each other 0 or 1 with (n + m) = 0 or 1, (n + p) = 0 or 1 and (mp)
= 0 ou 1, au moins un X étant Cl ; = 0 or 1, at least one X being Cl;
B) récupération d'un courant comprenant du 2,3,3,3-tetrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb), H F, trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E), et optionnellement ou non au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane B) recovering a stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), HF, trans-1,1,3,3- tetrafluoro-1-propene (1234ze-E), and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane
(134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) ; (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3.3 3-trifluoropropene (1243zf);
C) mise en œuvre du procédé de purification du 2,3,3,3-tetrafluoro-l-propène selon la présente invention à partir du courant récupéré à l'étape B).  C) implementation of the process for purifying 2,3,3,3-tetrafluoro-1-propene according to the present invention from the stream recovered in step B).
Une double liaison carbone-carbone peut être présente pour compléter la valence de des atomes de carbone des composés de formule CH(n+2)(X)m-CHp(X)(n+i)-CX(3+p-m). Par exemple, lorsque p et m valent 0, les composés de formule (I) sont soit CH2=CX-CX3 (n = 0) soit CH3CX2CX3 (n = l). Selon un mode de réalisation préféré, le courant récupéré à l'étape B) correspond audit mélange C selon la présente invention. A carbon-carbon double bond may be present to complete the valence of carbon atoms of compounds of formula CH ( n + 2) (X) m-CHp (X) (n + 1) -CX (3 + p- m) ). For example, when p and m are 0, the compounds of formula (I) are either CH2 = CX-CX3 (n = 0) or CH3CX2CX3 (n = 1). According to a preferred embodiment, the current recovered in step B) corresponds to said mixture C according to the present invention.
De préférence, le courant comprenant ledit agent d'extraction organique peut être recyclé à l'étape a). De préférence, le courant comprenant trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et optionnellement ou non au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) peut être purifié ou détruit par incinération.  Preferably, the stream comprising said organic extractant can be recycled in step a). Preferably, the stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1- difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3, 3,3-Pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf) can be purified or destroyed by incineration.
Selon un mode de réalisation particulier, le courant récupéré à l'étape B) du procédé de production du 2,3,3,3-tétrafluoro-l-propène peut comprendre des impuretés ayant un point d'ébullition inférieur au point d'ébullition du 2,3,3,3-tetrafluoro-l-propène. Dans ce cas, préalablement à l'étape C), le courant récupéré à l'étape B) peut subir une distillation préalable Β ) pour éliminer en tête de colonne de distillation lesdites impuretés ayant un point d'ébullition inférieur au point d'ébullition du 2,3,3,3-tetrafluoro-l-propène et former un premier courant comprenant 2,3,3,3-tetrafluoro-l-propène, HF, 1,1,1,2,2-pentafluoropropane, trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et optionnellement ou non au moins un des composés choisi parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-1,2,3,3,3- pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3- trifluoropropène (1243zf), récupéré en bas de colonne de distillation. Ce dernier courant récupéré en bas de colonne de distillation est ensuite soumis à l'étape C) du procédé de production du 2,3,3,3-tetrafluoro-l-propène, et correspond audit mélange C.  According to a particular embodiment, the stream recovered in stage B) from the process for producing 2,3,3,3-tetrafluoro-1-propene may comprise impurities having a boiling point below the boiling point 2,3,3,3-tetrafluoro-1-propene. In this case, prior to step C), the stream recovered in stage B) can be subjected to a preliminary distillation Β) to eliminate at the top of the distillation column said impurities having a boiling point below the boiling point 2,3,3,3-tetrafluoro-1-propene and forming a first stream comprising 2,3,3,3-tetrafluoro-1-propene, HF, 1,1,1,2,2-pentafluoropropane, trans- 1,1,3,3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1 , 1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye), Z), 3,3,3-trifluoropropene (1243zf), recovered at the bottom of the distillation column. This latter stream recovered at the bottom of the distillation column is then subjected to stage C) of the process for the production of 2,3,3,3-tetrafluoro-1-propene, and corresponds to said mixture C.
Selon un mode de réalisation particulier, le courant récupéré à l'étape B) du procédé de production du 2,3,3,3-tétrafluoro-l-propène peut comprendre des impuretés lourdes. Dans ce cas, préalablement à l'étape C), le courant récupéré à l'étape B) peut subir une distillation préalable B2'), subséquente ou non à l'étape Β ), pour éliminer en bas de colonne de distillation lesdites impuretés lourdes ; et former un premier courant comprenant 2,3,3,3-tetrafluoro-l- propène, 1,1,1,2,2-pentafluoropropane, HF, trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et optionnellement ou non au moins un des composés choisi parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf), récupéré en tête de colonne de distillation. Ce dernier courant récupéré en tête de colonne de distillation est ensuite soumis à l'étape C) du procédé de production du 2,3,3,3-tetrafluoro-l-propène et correspond audit mélange C. According to a particular embodiment, the stream recovered in stage B) of the process for producing 2,3,3,3-tetrafluoro-1-propene may comprise heavy impurities. In this case, prior to step C), the stream recovered in stage B) may be subjected to preliminary distillation B2 '), which may or may not be subsequent to stage Β), in order to eliminate the said impurities at the bottom of the distillation column. heavy; and forming a first stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane, HF, trans-1,33,3-tetrafluoro-1-propene ( 1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115) trans-1, 2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), recovered at the top of the column distillation. This latter stream recovered at the top of the distillation column is then subjected to stage C) of the process for producing 2,3,3,3-tetrafluoro-1-propene and corresponds to said mixture C.
Selon un mode de réalisation particulier, le courant récupéré à l'étape B) du procédé de production du 2,3,3,3-tétrafluoro-l-propène peut également comprendre HCI. L'acide chlorhydrique peut être récupéré par distillation avant ou après l'étape Β indépendamment des autres étapes du procédé.  According to a particular embodiment, the stream recovered in stage B) of the process for producing 2,3,3,3-tetrafluoro-1-propene may also comprise HCl. Hydrochloric acid can be recovered by distillation before or after step Β independently of the other steps of the process.
Plus particulièrement, l'étape A) est effectuée à partir de 1,1,2,3-tetrachloropropène, 2,3,3,3,-tetrachloropropène, 1,1,1,2,3-pentachloropropane, 2-chloro-3,3,3-trifluoropropène, l,2-dichloro-3,3,3-trifluoropropane, 2-chloro-l,l,l,2-tetrafluoropropane, 1,1,1,2,2- pentafluoropropane et 1,1,1,2,2-pentachloropropane, de préférence à partir de 1,1,1,2,3- pentachloropropane, 1,1,2,3-tetrachloropropène, 2,3,3,3-tetrachloropropène, 2-chloro-3,3,3- trifluoropropène, 2-chloro-l,l,l,2-tetrafluoropropane, l,2-dichloro-3,3,3-trifluoropropane, 1,1,1,2,2-pentafluoropropane et 1,1,1,2,2-pentachloropropane ou un mélange de ceux-ci en particulier à partir du 1,1,1,2,3-pentachloropropane (240db).  More particularly, step A) is carried out from 1,1,2,3-tetrachloropropene, 2,3,3,3, -tetrachloropropene, 1,1,1,2,3-pentachloropropane, 2-chloroacetylene, 3,3,3-trifluoropropene, 1,2-dichloro-3,3,3-trifluoropropane, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and 1, 1,1,2,2-pentachloropropane, preferably from 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, 2-chloro 3,3,3-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,2-dichloro-3,3,3-trifluoropropane, 1,1,1,2,2-pentafluoropropane and , 1,1,2,2-pentachloropropane or a mixture thereof, in particular from 1,1,1,2,3-pentachloropropane (240db).
Le catalyseur utilisé dans le présent procédé de production de 2,3,3,3- tétrafluoropropène peut être par exemple à base d'un métal comprenant un oxyde de métal de transition ou un dérivé ou un halogénure ou un oxyhalogénure d'un tel métal. On peut citer par exemple FeCU, l'oxyfluorure de chrome, les oxydes de chrome (éventuellement soumis à des traitements de fluoration), les fluorures de chrome et leurs mélanges. D'autres catalyseurs possibles sont les catalyseurs supportés sur du carbone, les catalyseurs à base d'antimoine, les catalyseurs à base d'aluminium (par exemple AIF3 et AI2O3, l'oxyfluorure d'alumine et le fluorure d'alumine).  The catalyst used in the present process for producing 2,3,3,3-tetrafluoropropene may for example be based on a metal comprising a transition metal oxide or a derivative or a halide or an oxyhalide of such a metal. . For example, FeCU, chromium oxyfluoride, chromium oxides (possibly subjected to fluorination treatments), chromium fluorides and mixtures thereof may be mentioned. Other possible catalysts are carbon-supported catalysts, antimony catalysts, aluminum catalysts (eg AlF 3 and Al 2 O 3, alumina oxyfluoride and alumina fluoride).
On peut utiliser en général un oxyfluorure de chrome, un fluorure ou un oxyfluorure d'aluminium, ou un catalyseur supporté ou non contenant un métal tel que Cr, Ni, Fe, Zn, Ti, V, Zr, Mo, Ge, Sn, Pb, Mg, Sb.  It is generally possible to use a chromium oxyfluoride, a fluoride or an aluminum oxyfluoride, or a supported or non-supported catalyst containing a metal such as Cr, Ni, Fe, Zn, Ti, V, Zr, Mo, Ge or Sn. Pb, Mg, Sb.
On peut faire référence à cet égard au document WO 2007/079431 (en p.7, 1.1-5 et 28- 32), au document EP 939071 (paragraphe [0022]), au document WO 2008/054781 (en p.9 1.22- p.10 1.34), et au document WO 2008/040969 (revendication 1), auxquels il est fait expressément référence.  Reference can be made in this regard to document WO 2007/079431 (at p.7, 1.1-5 and 28-32), EP 939071 (paragraph [0022]), WO 2008/054781 (at p.9). 1.22- p.10 1.34), and WO 2008/040969 (claim 1), to which reference is expressly made.
Le catalyseur est de manière plus particulièrement préférée à base de chrome et il s'agit plus particulièrement d'un catalyseur mixte comprenant du chrome. Selon un mode de réalisation, on utilise un catalyseur mixte comprenant du chrome et du nickel. Le rapport molaire Cr / Ni (sur la base de l'élément métallique) est généralement de 0,5 à 5, par exemple de 0,7 à 2, par exemple d'environ 1. Le catalyseur peut contenir de 0,5 à 20 % en poids de nickel. The catalyst is more preferably based on chromium and it is more particularly a mixed catalyst comprising chromium. According to one embodiment, a mixed catalyst comprising chromium and nickel is used. The molar ratio Cr / Ni (based on the metal element) is generally 0.5 to 5, for example 0.7 to 2, for example about 1. The catalyst may contain from 0.5 to 20% by weight of nickel.
Le métal peut être présent sous forme métallique ou sous forme de dérivé, par exemple un oxyde, halogénure ou oxyhalogénure. Ces dérivés sont de préférence obtenus par activation du métal catalytique.  The metal may be present in metallic form or in the form of a derivative, for example an oxide, halide or oxyhalide. These derivatives are preferably obtained by activation of the catalytic metal.
Le support est de préférence constitué avec de l'aluminium, par exemple de l'alumine, de l'alumine activée ou des dérivés d'aluminium, tels que les halogénures d'aluminium et les oxyhalogénures d'aluminium, par exemple décrits dans le document US 4,902,838, ou obtenus par le procédé d'activation décrit ci-dessus.  The support is preferably made of aluminum, for example alumina, activated alumina or aluminum derivatives, such as aluminum halides and aluminum oxyhalides, for example described in US Pat. US 4,902,838, or obtained by the activation method described above.
Le catalyseur peut comprendre du chrome et du nickel sous une forme activée ou non, sur un support qui a été soumis à une activation ou non.  The catalyst may comprise chromium and nickel in an activated or non-activated form, on a support which has been subjected to activation or not.
On peut se reporter au document WO 2009/118628 (notamment en p.4, l.30-p.7 1.16), auquel il est fait expressément référence ici.  Reference can be made to WO 2009/118628 (especially at p.4, l.30-p.7 1.16), which is expressly referred to herein.
Un autre mode de réalisation préféré repose sur un catalyseur mixte contenant du chrome et au moins un élément choisi parmi Mg et Zn. Le rapport atomique de Mg ou Zn/Cr est de préférence de 0,01 à 5.  Another preferred embodiment is based on a chromium-containing mixed catalyst and at least one element selected from Mg and Zn. The atomic ratio of Mg or Zn / Cr is preferably from 0.01 to 5.
Avant son utilisation, le catalyseur est de préférence soumis à une activation avec de l'air, de l'oxygène ou du chlore et/ou avec de l'HF.  Prior to use, the catalyst is preferably activated with air, oxygen or chlorine and / or with HF.
Par exemple, le catalyseur est de préférence soumis à une activation avec de l'air ou de l'oxygène et du HF à une température de 100 à 500°C, de préférence de 250 à 500°C et plus particulièrement de 300 à 400°C. La durée d'activation est de préférence de 1 à 200 h et plus particulièrement de 1 à 50 h.  For example, the catalyst is preferably subjected to activation with air or oxygen and HF at a temperature of 100 to 500 ° C, preferably 250 to 500 ° C and more preferably 300 to 400 ° C. ° C. The activation time is preferably from 1 to 200 hours and more particularly from 1 to 50 hours.
Cette activation peut être suivie d'une étape d'activation de fluoration finale en présence d'un agent d'oxydation, d'HF et de composés organiques.  This activation may be followed by a final fluorination activation step in the presence of an oxidizing agent, HF and organic compounds.
Le rapport molaire HF / composés organiques est de préférence de 2 à 40 et le rapport molaire agent d'oxydation / composés organiques est de préférence de 0,04 à 25. La température de l'activation finale est de préférence de 300 à 400°C et sa durée de préférence de 6 à 100 h.  The molar ratio of HF / organic compounds is preferably from 2 to 40 and the molar ratio of oxidation agent / organic compounds is preferably from 0.04 to 25. The temperature of the final activation is preferably from 300 to 400 ° C. C and its duration preferably from 6 to 100 h.
La réaction de fluoration en phase gazeuse peut être effectuée : - avec un rapport molaire HF / composé de formule (I) et/ou (II) de 3:1 à 150:1, de préférence de 4:1 à 125:1 et de manière plus particulièrement préférée de 5:1 à 100:1 ; The fluorination reaction in the gas phase can be carried out: with an HF / compound of formula (I) and / or (II) molar ratio of from 3: 1 to 150: 1, preferably from 4: 1 to 125: 1 and more particularly preferably from 5: 1 to 100 : 1;
- avec un temps de contact de 3 à 100 s, de préférence 4 à 75 s et plus particulièrement 5 à 50 s (volume de catalyseur divisé par le flux entrant total, ajusté à la température et à la pression de fonctionnement) ;  with a contact time of 3 to 100 seconds, preferably 4 to 75 seconds and more particularly 5 to 50 seconds (volume of catalyst divided by the total incoming flow, adjusted to the temperature and to the operating pressure);
- à une pression allant de la pression atmosphérique à 20 bara, de préférence de 2 à 18 bara et plus particulièrement de 3 à 15 bara;  at a pressure ranging from atmospheric pressure to 20 bara, preferably from 2 to 18 bara and more particularly from 3 to 15 bara;
- à une température (température du lit de catalyseur) de 200 à 450°C, de préférence de 250 à 400°C, et plus particulièrement de 280 à 380°C.  at a temperature (temperature of the catalyst bed) of 200 to 450 ° C., preferably of 250 to 400 ° C., and more particularly of 280 to 380 ° C.
La durée de l'étape de réaction est typiquement de 10 à 8000 heures, de préférence de 50 à 5000 heures et de manière plus particulièrement préférée de 70 à 1000 heures.  The duration of the reaction step is typically from 10 to 8000 hours, preferably from 50 to 5000 hours and more preferably from 70 to 1000 hours.
Un agent oxydant, de préférence l'oxygène, peut éventuellement être ajouté lors de la réaction de fluoration. Le rapport molaire oxygène / composés organiques peut être de 0,005 à 2, de préférence de 0,01 à 1,5. L'oxygène peut être introduit pur ou sous forme d'air ou de mélange oxygène / azote. On peut également remplacer l'oxygène par du chlore.  An oxidizing agent, preferably oxygen, may optionally be added during the fluorination reaction. The oxygen / organic compounds molar ratio may be from 0.005 to 2, preferably from 0.01 to 1.5. The oxygen can be introduced pure or in the form of air or oxygen / nitrogen mixture. Oxygen can also be replaced by chlorine.
La Fig. 1 illustre schématiquement un dispositif mettant en œuvre un procédé de production du 2,3,3,3-tetrafluoropropène selon un mode de réalisation particulier de la présente invention. L'acide fluorhydrique 1 est mis en contact avec le 1,1,1,2,3- pentachloropropane (240db) 2 dans un réacteur 3. Le réacteur 3 peut également être alimenté avec le courant 10 comprenant 1,1,1,2,2-pentafluoropropane (245cb) et provenant du recyclage du procédé de purification du 2,3,3,3-tetrafluoro-l-propène et du 1,1,1,2,2-pentafluoropropane (245cb). Le mélange obtenu et comprenant 2,3,3,3-tetrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb), HF, trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et optionnellement au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf), est récupéré en sortie de réacteur et acheminé vers une colonne de distillation 5 par le conduit 4. Le mélange peut aussi comprendre HCI et des impuretés lourdes ou ayant un point d'ébullition inférieur à celui du 2,3,3,3-tetrafluoro-l-propène. Le courant obtenu en bas de colonne de distillation comprend une partie du HF et éventuellement des impuretés lourdes acheminées vers le dispositif de purification 7 via le conduit 6 pour purifier HF qui sera recyclé éventuellement en 3. Le mélange acheminé via le conduit 8 vers un dispositif 9 de purification comprend 2,3,3,3-tetrafluoro-l- propène, 1,1,1,2,2-pentafluoropropane (245cb), HF, trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) et optionnellement au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-1,2,3,3,3- pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) ; et correspond audit mélange C selon la présente invention. Fig. 1 schematically illustrates a device implementing a process for producing 2,3,3,3-tetrafluoropropene according to a particular embodiment of the present invention. Hydrofluoric acid 1 is brought into contact with 1,1,1,2,3-pentachloropropane (240db) 2 in a reactor 3. The reactor 3 can also be fed with the stream comprising 1,1,1,2 , 2-pentafluoropropane (245cb) and from the recycling of the process for purifying 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb). The resulting mixture comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), HF, trans-1, 3,3,3-tetrafluoro-1- propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115) trans-1, 2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf), It is recovered at the outlet of the reactor and conveyed to a distillation column 5 via line 4. The mixture may also comprise HCl and impurities which are heavy or have a boiling point lower than that of 2,3,3,3-tetrafluoroethylene. l-propene. The stream obtained at the bottom of the distillation column comprises a part of the HF and possibly heavy impurities conveyed to the purification device 7 via the pipe 6 to purify HF which will be optionally recycled into 3. The mixture supplied via line 8 to a purifying device 9 comprises 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), HF, trans-1,33 , 3-tetrafluoro-1-propene (1234ze-E) and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane ( 134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3.3, 3-trifluoropropene (1243zf); and corresponds to said mixture C according to the present invention.
La figure 2a représente un schéma simplifié d'une partie du dispositif 9 mettant en œuvre un procédé de purification du 2,3,3,3-tetrafluoro-l-propène et du 1,1,1,2,2- pentafluoropropane selon un mode de réalisation particulier de l'invention. En particulier la figure 2a représente schématiquement les étapes de récupération de l'acide fluorhydrique tel que décrit aux étapes i') à v') selon la présente invention. Le mélange C provient de la conduite 8 décrit à la figure 1. Le mélange C alimente un dispositif 12 dans lequel il est mis en contact avec une solution d'acide fluorhydrique 11' ou une solution d'acide fluorhydrique issue du dispositif 14 via la conduite 30 ayant une concentration variant entre 65 et 75% en poids. Le dispositif 12 peut être par exemple un hydrolaveur. La mise en contact entre la solution d'acide fluorhydrique 11' ou une solution d'acide fluorhydrique issue du dispositif 14 via la conduite 30 et le mélange C génère la formation d'un courant diphasique qui est acheminé vers un dispositif de stockage 14 par la conduite 23. Le dispositif de stockage 14 permet de séparer le courant diphasique en une phase gazeuse et une phase liquide. La phase gazeuse dudit courant diphasique est acheminée par la conduite 24 vers la colonne d'absorption 13 comprenant 3 étages d'absorption 31a, 31b et 31c. La colonne d'absorption 13 est également alimentée par un flux aqueux 17. Dans ce mode de réalisation, le flux aqueux 17 alimente la colonne d'absorption 13 en tête de colonne d'absorption 17, c'est-à-dire au-dessus des trois étages d'absorption 31a-31c. Alternativement, le flux aqueux 17 peut alimenter la colonne d'absorption 13 au-dessus de chacun des étages d'absorption 31a-31c. Un courant gazeux Cl tel que décrit dans la présente demande peut être extrait en tête de colonne d'absorption 17 par la conduite 26 pour alimenter un dispositif de neutralisation 15. En outre, en pied de colonne d'absorption 17, une solution aqueuse d'acide fluorhydrique correspondant audit courant C2 est recyclée vers le dispositif de stockage 14 par la conduite 25. Le courant Cl est neutralisé dans le dispositif de neutralisation 15 par une solution alcaline de NaOH à 20%. La solution alcaline 18 alimente le dispositif de neutralisation 15 par l'intermédiaire de la conduite 29. Le courant neutralisé est évacué par la conduite 27 et récupéré en 20 pour être séché sur tamis moléculaire de 3A. Le courant neutralisé et séché correspond au courant C4 selon le présent procédé. Celui- ci peut donc être comprimé et liquéfié à une pression d'au plus 8 bara (courant C5 selon le présent procédé). Une solution alcaline usée 19 peut être extraite du dispositif de neutralisation 15 pour être soit recyclée via les conduites 28 et 29 ou évacuée via la conduite 28 pour traitement ultérieur. La phase liquide résultant du mélange de la phase liquide du courant diphasique et du courant C2 stockée dans le dispositif de stockage 14 est acheminée vers une colonne de distillation 16 via la pompe 32 et la conduite 33 pour former le courant D récupéré en tête de colonne de distillation 21 et le courant E récupéré en pied de colonne de distillation 22. La pompe 32 alimente également la phase liquide résultant du mélange de la phase liquide du courant diphasique et du courant C2 stockée dans le dispositif de stockage 14 vers le dispositif 12 via la conduite 30. La pompe 32 est ainsi configurée pour permettre l'alimentation de la colonne de distillation 16 et le dispositif 12 de manière alternée ou de manière simultanée, de préférence de manière simultanée. FIG. 2a represents a simplified diagram of a part of the device 9 implementing a process for purifying 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane according to a particular embodiment of the invention. In particular, FIG. 2a schematically represents the steps for recovering hydrofluoric acid as described in steps i ') to v') according to the present invention. The mixture C comes from the pipe 8 described in FIG. 1. The mixture C feeds a device 12 in which it is brought into contact with a solution of hydrofluoric acid 11 'or a solution of hydrofluoric acid from the device 14 via the pipe having a concentration ranging from 65 to 75% by weight. The device 12 may for example be a hydrolaver. Contacting the hydrofluoric acid solution 11 'or a solution of hydrofluoric acid from the device 14 via the pipe 30 and the mixture C generates the formation of a two-phase current which is conveyed to a storage device 14 by 23. The storage device 14 separates the two-phase current into a gas phase and a liquid phase. The gaseous phase of said two-phase current is fed via line 24 to the absorption column 13 comprising three absorption stages 31a, 31b and 31c. The absorption column 13 is also fed with an aqueous stream 17. In this embodiment, the aqueous stream 17 feeds the absorption column 13 at the top of the absorption column 17, that is to say above above the three absorption stages 31a-31c. Alternatively, the aqueous stream 17 can feed the absorption column 13 above each of the absorption stages 31a-31c. A gas stream C1 as described in the present application can be extracted at the top of the absorption column 17 via line 26 to feed a neutralization device 15. In addition, at the bottom of absorption column 17, an aqueous solution of Hydrofluoric acid corresponding to said stream C2 is recycled to the storage device 14 via the line 25. The stream C1 is neutralized in the neutralization device 15 with an alkaline solution of 20% NaOH. The alkaline solution 18 feeds the neutralization device 15 through line 29. The neutralized stream is discharged through line 27 and recovered at 20 to be dried on molecular sieve. of 3A. The neutralized and dried stream corresponds to the C4 stream according to the present process. This can therefore be compressed and liquefied at a pressure of at most 8 bara (current C5 according to the present method). A spent alkaline solution 19 may be removed from the neutralization device 15 to be either recycled via lines 28 and 29 or discharged via line 28 for further processing. The liquid phase resulting from the mixing of the liquid phase of the two-phase current with the current C2 stored in the storage device 14 is conveyed to a distillation column 16 via the pump 32 and the pipe 33 to form the stream D recovered at the top of the column 21 and the stream E recovered at the bottom of the distillation column 22. The pump 32 also feeds the liquid phase resulting from the mixing of the liquid phase of the two-phase current with the stream C2 stored in the storage device 14 to the device 12 via The pump 32 is thus configured to allow supply of the distillation column 16 and the device 12 alternately or simultaneously, preferably simultaneously.
Le mélange C peut être purifié avant son utilisation selon le présent procédé. Ceci est décrit aux figures 2b et 2c suivant des modes de réalisation particulier. Un mélange comprenant 2,3,3,3-tetrafluoro-l-propène, HF, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E) et des impuretés ayant un point d'ébullition inférieur au point d'ébullition du 2,3,3,3-tetrafluoro-l-propène est fourni en 41. Le mélange est transféré dans une colonne de distillation 42 par le conduit 43. Les impuretés ayant un point d'ébullition inférieur au point d'ébullition du 2,3,3,3-tetrafluoro-l-propène sont récupérées en tête de la colonne de distillation 42 et acheminées par le conduit 45 à un incinérateur ou un dispositif de purification 50. Le mélange C est obtenu en bas de colonne de distillation et est acheminé vers le dispositif 12 décrit à la figure 2a via la conduite 44. Dans un autre mode de réalisation particulier illustré à la Fig. 2c, le mélange comprend également des impuretés lourdes. Dans ce cas, une distillation peut être effectuée à partir du courant obtenu en bas de la colonne de distillation 42. Ce dernier est donc acheminé par le conduit 44 vers la colonne de distillation 46. Les impuretés lourdes sont récupérées en bas de colonne de distillation 47. Le courant récupéré en tête de la colonne de distillation 46 correspond audit mélange C. Ce courant est transféré par l'intermédiaire du conduit 48 vers le dispositif 12 pour y être traité comme expliqué ci-dessus en relation avec la Fig. 2a.  Mixture C can be purified prior to use according to the present method. This is described in Figures 2b and 2c according to particular embodiments. A mixture comprising 2,3,3,3-tetrafluoro-1-propene, HF, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene ( 1234ze-E) and impurities having a boiling point below the boiling point of 2,3,3,3-tetrafluoro-1-propene are provided at 41. The mixture is transferred to a distillation column 42 by conduit 43. The impurities having a boiling point below the boiling point of 2,3,3,3-tetrafluoro-1-propene are recovered at the top of distillation column 42 and conveyed via line 45 to an incinerator or a purification device 50. The mixture C is obtained at the bottom of the distillation column and is conveyed to the device 12 described in FIG. 2a via the pipe 44. In another particular embodiment illustrated in FIG. 2c, the mixture also comprises heavy impurities. In this case, a distillation can be performed from the stream obtained at the bottom of the distillation column 42. The latter is thus conveyed via line 44 to the distillation column 46. The heavy impurities are recovered at the bottom of the distillation column 47. The stream recovered at the top of the distillation column 46 corresponds to said mixture C. This stream is transferred via the conduit 48 to the device 12 to be treated as explained above in connection with FIG. 2a.
Suivant le mode de réalisation particulier de l'invention, le courant Cl, C3, C4 ou C5 correspond à ladite première composition selon la présente invention qui est traité par distillation extractive comme illustré à la figure 2d. La distillation extractive effectuée en 66 vise à séparer le 2,3,3,3-tetrafluoro-l-propène et le 1,1,1,2,2-pentafluoropropane (245cb) des autres constituants du mélange. La colonne de distillation extractive 66 est approvisionnée avec l'agent d'extraction organique 70. Le courant comprenant 2,3,3,3-tetrafluoro-l-propène et le 1,1,1,2,2- pentafluoropropane (245cb) est récupéré en tête de la colonne de distillation 66 et acheminé vers la colonne de distillation 72 par le conduit 67. L'agent d'extraction organique 70 et le trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) sont récupérés en bas de la colonne de distillation 66 pour être acheminés vers la colonne de distillation 69 où ceux-ci sont séparés. L'agent d'extraction organique est récupéré en bas de colonne de distillation 69 pour être recyclé vers la colonne de distillation extractive 66 par le conduit 71. Le trans-l,3,3,3-tetrafluoro-l-propène est récupéré en tête de colonne de distillation 69 pour être acheminé vers un incinérateur ou un dispositif de purification 50. La colonne de distillation 72 permet la séparation entre le 2,3,3,3-tetrafluoro-l-propène récupéré en tête de colonne de distillation 73 et le 1,1,1,2,2- pentafluoropropane récupéré en bas de colonne de distillation 74. Le 1,1,1,2,2- pentafluoropropane peut être recyclé dans le réacteur 3 décrit à la Fig. 1 ci-dessus. According to the particular embodiment of the invention, the stream C1, C3, C4 or C5 corresponds to said first composition according to the present invention which is treated by extractive distillation as illustrated in FIG. 2d. The extractive distillation carried out in 66 to separate 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb) from the other constituents of the mixture. The extractive distillation column 66 is supplied with the organic extractant 70. The stream comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1,2,2-pentafluoropropane (245cb) is recovered at the top of the distillation column 66 and conveyed to the distillation column 72 via line 67. The organic extraction agent 70 and the trans-1,3,3,3-tetrafluoro-1-propene (1234ze) -E) are recovered at the bottom of the distillation column 66 to be conveyed to the distillation column 69 where they are separated. The organic extraction agent is recovered at the bottom of the distillation column 69 to be recycled to the extractive distillation column 66 via line 71. Trans-1,3,3,3-tetrafluoro-1-propene is recovered in the following manner: distillation column head 69 to be conveyed to an incinerator or a purification device 50. The distillation column 72 allows the separation between the 2,3,3,3-tetrafluoro-1-propene recovered at the top of the distillation column. and the 1,1,1,2,2-pentafluoropropane recovered at the bottom of the distillation column 74. The 1,1,1,2,2-pentafluoropropane can be recycled to the reactor 3 described in FIG. 1 above.
Le courant Cl, C3, C4 ou C5 peut également comprendre au moins un des composés sélectionné parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-1,2,3,3,3- pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3- trifluoropropène (1243zf). Ces composés se retrouvent dans le même courant que le trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E). Ils sont donc absorbés par l'agent d'extraction organique lors de la distillation extractive 66 pour être acheminés vers la colonne de distillation 69 où ils sont récupérés en tête de colonne de distillation avec le trans-l,3,3,3-tetrafluoro-l- propène (1234ze-E) et sont incinérés ou purifiés en 50. Méthode de sélection de l'agent d'extraction organique  The stream C1, C3, C4 or C5 may also comprise at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3-trifluoropropene (1243zf). These compounds are found in the same current as trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E). They are therefore absorbed by the organic extraction agent during extractive distillation 66 to be conveyed to the distillation column 69 where they are recovered at the top of the distillation column with trans-1,3,3,3-tetrafluoro propene (1234ze-E) and are incinerated or purified at 50. Method for selecting the organic extractant
La sélection de l'agent d'extraction organique est déterminée par l'utilisation du modèle Cosmo- S implémenté dans le logiciel COSMOTHERM. Pour ce couple binaire sélectionné, un facteur de séparation est calculé pour chacun des solvants étudiés par l'équation suivante :  The selection of the organic extraction agent is determined by the use of the Cosmos model implemented in the COSMOTHERM software. For this selected binary pair, a separation factor is calculated for each of the solvents studied by the following equation:
Si,2 = (yi,s*Pl)/(Y2,s*P2) dans laquelle  If, 2 = (yi, s * Pl) / (Y2, s * P2) in which
Yi,s représente le coefficient d'activité du premier composé 1 dans l'agent d'extraction organique considéré à dilution infinie,  Yi, s represents the coefficient of activity of the first compound 1 in the organic extraction agent considered at infinite dilution,
PI représente la pression de vapeur saturante du premier composé 1, Y2,s représente le coefficient d'activité du second composé 2 du couple binaire dans l'agent d'extraction organique considéré à dilution infinie, PI represents the saturated vapor pressure of the first compound 1, Y2, s represents the coefficient of activity of the second compound 2 of the binary pair in the organic extraction agent considered at infinite dilution,
P2 représente la pression de vapeur saturante du second composé.  P2 represents the saturating vapor pressure of the second compound.
Une capacité d'absorption est également calculée pour chacun des solvants étudiés et pour un couple binaire (1,2) considéré. La capacité d'absorption est calculée par la formule C2,s = l/(Y2,s) dans laquelle y2,s représente le coefficient d'activité du second composé du couple binaire considéré dans ledit agent d'extraction organique étudié à dilution infinie.  An absorption capacity is also calculated for each of the solvents studied and for a binary pair (1,2) considered. The absorption capacity is calculated by the formula C2, s = 1 / (Y2, s) in which y2, s represents the coefficient of activity of the second compound of the binary pair considered in said organic extraction agent studied at infinite dilution .
Les calculs sont répétés pour chaque agent d'extraction organique étudié. Des valeurs minimales de facteur de séparation et de capacité d'absorption sont identifiées afin de permettre une séparation suffisante entre le premier composé et le second composé du couple binaire (1,2) considéré. La pression de vapeur saturante est considérée pour une température de 25°C. The calculations are repeated for each organic extraction agent studied. Minimum values of separation factor and absorption capacity are identified to allow sufficient separation between the first compound and the second compound of the binary pair (1,2) considered. The saturation vapor pressure is considered for a temperature of 25 ° C.
Exemples Pour purifier le 2,3,3,3-tetrafluoro-l-propène, le couple binaire 2,3,3,3-tetrafluoro-l-propène / trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) est considéré pour sélectionner l'agent d'extraction organique (voir tableau 1). Le mélange à purifier comprend 2,3,3,3-tetrafluoro-l- propène, 1,1,1,2,2-pentafluoropropane, et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E). Examples To purify 2,3,3,3-tetrafluoro-1-propene, the binary pair 2,3,3,3-tetrafluoro-1-propene / trans-1,,3,3-tetrafluoro-1-propene (1234ze-E) is considered to select the organic extractant (see Table 1). The mixture to be purified comprises 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane, and trans-1,3,3,3-tetrafluoro-1-propene (1234 E).
Tableau 1 - Capacité et Facteur de séparation de l'agent d'extraction organiqueTable 1 - Capacity and Separation Factor of the Organic Extraction Agent
Agent extraction Capacité Facteur de Facteur de organique d'absorption séparation séparation Agent Extraction Capacity Factor of Organic Absorption Factor Separation Separation
(1234zeE) (1234yf/1234zeE) (245cb/1234zeE) (1234zeE) (1234yf / 1234zeE) (245cb / 1234zeE)
Ethylamine 1,95 2,92 3,60Ethylamine 1.95 2.92 3.60
Isopropylamine 1,85 2,56 3,14 Isopropylamine 1.85 2.56 3.14
Diethylether 1,48 1,79 1,68 n-propylamine 1,86 2,61 3,14 Diethyl ether 1.48 1.79 1.68 n-propylamine 1.86 2.61 3.14
Diéthylamine 1,57 1,88 2,18Diethylamine 1.57 1.88 2.18
Diéthoxyméthane 1,41 1,86 1,63Diethyloxethane 1.41 1.86 1.63
Isopropylacétate 1,42 2,15 1,79Isopropylacetate 1.42 2.15 1.79
3-pentylamine 1,63 2,05 2,393-Pentylamine 1.63 2.05 2.39
2-methoxyethanamine 1,98 3,19 3,80 tert-butylacetate 1,37 2,10 1,632-methoxyethanamine 1.98 3.19 3.80 tert-butylacetate 1.37 2.10 1.63
1,4-dioxane 1,09 2,24 1,921,4-dioxane 1.09 2.24 1.92
1,1-diethoxyethane 1,54 1,90 1,78 trimethoxymethane 1,28 2,11 1,81 n-pentylamine 1,64 2,31 2,711,1-diethoxyethane 1.54 1.90 1.78 trimethoxymethane 1.28 2.11 1.81 n-pentylamine 1.64 2.31 2.71
1,3-dioxane 1,09 2,23 1,93 sec-butylacetate 1,45 2,12 1,791,3-dioxane 1,09 2,23 1.93 sec-butylacetate 1.45 2.12 1.79
1,2-diaminoethane 1,29 4,43 6,88 l-methoxy-2-propanol 0,87 2,31 2,151,2-diaminoethane 1,29 4,43 6,88 l-methoxy-2-propanol 0.87 2.31 2.15
1,2-propanediamine 1,50 3,54 4,92 n-butylacetate 1,35 2,14 1,861,2-propanediamine 1.50 3.54 4.92 n-butylacetate 1.35 2.14 1.86
2-methoxy-l-propanol 0,87 2,31 2,13 hexanal 1,09 1,98 1,72 2-methoxy-1-propanol 0.87 2.31 2.13 hexanal 1.09 1.98 1.72

Claims

Revendications claims
1. Procédé de purification du 2,3,3,3-tétrafluoro-l-propène (1234yf) à partir d'une première composition comprenant du 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb) et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E), ledit procédé comprenant les étapes de: A process for purifying 2,3,3,3-tetrafluoro-1-propene (1234yf) from a first composition comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1 2,2-pentafluoropropane (245cb) and trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E), said process comprising the steps of:
a) mise en contact de ladite première composition avec au moins un agent d'extraction organique pour former une seconde composition ; b) distillation extractive de ladite seconde composition pour former : i) une troisième composition comprenant ledit agent d'extraction organique et trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E); et ii) un courant comprenant le 2,3,3,3-tétrafluoro-l-propène (1234yf) et le 1,1,1,2,2-pentafluoropropane (245cb),  a) contacting said first composition with at least one organic extractant to form a second composition; b) extractively distilling said second composition to form: i) a third composition comprising said organic extractant and trans-1,,3,3,3-tetrafluoro-1-propene (1234ze-E); and ii) a stream comprising 2,3,3,3-tetrafluoro-1-propene (1234yf) and 1,1,1,2,2-pentafluoropropane (245cb),
c) récupération et séparation de ladite troisième composition pour former un courant comprenant ledit agent d'extraction organique et un courant comprenant le trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) ; de préférence le courant comprenant ledit agent d'extraction organique est recyclé à l'étape a) ;  c) recovering and separating said third composition to form a stream comprising said organic extractant and a stream comprising trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E); preferably the stream comprising said organic extraction agent is recycled in step a);
caractérisé en ce que la première composition est obtenue à partir d'un mélange C comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro- 1-propène (1234ze-E) et HF, ledit mélange étant soumis aux étapes suivantes : characterized in that the first composition is obtained from a mixture C comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E) and HF, said mixture being subjected to the following steps:
i') mise en contact dudit mélange C avec une solution aqueuse d'acide fluorhydrique de concentration supérieure à 40% en poids pour former un courant diphasique comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro- 1-propène (1234ze-E) et HF, i ') bringing said mixture C into contact with an aqueous solution of hydrofluoric acid with a concentration of greater than 40% by weight to form a diphasic stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1 2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and HF,
ii') stockage dudit second courant diphasique dans un réservoir tampon, ledit courant diphasique étant constitué d'une phase liquide et d'une phase gazeuse, ii ') storing said second diphasic current in a buffer tank, said two-phase current consisting of a liquid phase and a gaseous phase,
iii') passage de ladite phase gazeuse dudit second courant diphasique dans une colonne d'absorption alimenté à contre-courant par un flux aqueux pour former un courant Cl comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2-pentafluoropropane (245cb), trans- 1,3,3,3-tetrafluoro-l-propène (1234ze-E) et un courant C2 comprenant HF. iii ') passing said gaseous phase from said second diphasic stream into an absorption column fed countercurrently with an aqueous stream to form a stream C1 comprising 2,3,3,3-tetrafluoro-1-propene, 1,1 1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) and a stream C2 comprising HF.
2. Procédé selon la revendication 1 caractérisé en ce qu'il comprend les étapes iv') neutralisation dudit courant Cl obtenu à l'étape iii') par une solution aqueuse alcaline pour former un courant neutralisé C3, et2. Method according to claim 1 characterized in that it comprises the steps iv ') neutralizing said Cl stream obtained in step iii') with an aqueous alkaline solution to form a C3 neutralized stream, and
') séchage dudit courant neutralisé C3 obtenu à l'étape iv') sur tamis moléculaire pour former un courant neutralisé et séché C4 comprenant 2,3,3,3-tétrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E).  drying said neutralized stream C3 obtained in step iv ') on a molecular sieve to form a neutralized and dried C4 stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2 pentafluoropropane (245cb), trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E).
3. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que la solution aqueuse d'acide fluorhydrique utilisé à l'étape i') est à une température comprise entre 0 à 30°C avant sa mise en contact avec ledit mélange C. 3. Method according to any one of the preceding claims characterized in that the aqueous hydrofluoric acid solution used in step i ') is at a temperature between 0 to 30 ° C before contacting said mixture C .
4. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que la phase liquide résultant du mélange de ladite phase liquide dudit second courant diphasique et dudit courant C2 est distillée pour former un courant D, de préférence en tête de colonne de distillation, comprenant de l'acide fluorhydrique contenant moins de 500 ppm d'eau et un courant E, de préférence en pied de colonne de distillation, comprenant de l'acide fluorhydrique sous forme d'une solution aqueuse de concentration inférieure à 50% en poids. 4. Method according to any one of the preceding claims characterized in that the liquid phase resulting from the mixing of said liquid phase of said second two-phase current and said stream C2 is distilled to form a stream D, preferably at the top of the distillation column, comprising hydrofluoric acid containing less than 500 ppm of water and a stream E, preferably at the bottom of the distillation column, comprising hydrofluoric acid in the form of an aqueous solution with a concentration of less than 50% by weight.
5. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que le rapport entre le débit du flux aqueux exprimé en kg/h alimentant la colonne d'absorption à l'étape iii') et la quantité d'acide fluorhydrique dans ledit mélange C exprimée en kg/h est compris entre 0,05 et 1,22, de préférence entre 0,33 et 0,54. 5. Method according to any one of the preceding claims, characterized in that the ratio between the flow rate of the aqueous flow expressed in kg / h feeding the absorption column in step iii ') and the amount of hydrofluoric acid in said mixture C expressed in kg / h is between 0.05 and 1.22, preferably between 0.33 and 0.54.
6. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce qu'il comprend également une étape de récupération dudit courant ii) comprenant le 2,3,3,3- tétrafluoro-l-propène et le 1,1,1,2,2-pentafluoropropane (245cb) obtenu à l'étape b), et de distillation de celui-ci pour former un courant A comprenant 2,3,3,3-tétrafluoro-l-propène et un courant B comprenant 1,1,1,2,2-pentafluoropropane (245cb). 6. Method according to any one of the preceding claims, characterized in that it also comprises a step of recovering said stream ii) comprising 2,3,3,3-tetrafluoro-1-propene and 1,1,1, 2,2-pentafluoropropane (245cb) obtained in step b), and of distillation thereof to form a stream A comprising 2,3,3,3-tetrafluoro-1-propene and a stream B comprising 1.1 1,2,2-pentafluoropropane (245cb).
7. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que ladite première composition comprend également au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis- 1,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf). 7. Method according to any one of the preceding claims characterized in that said first composition also comprises at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1 , 2-tetrafluoroethane (134a), chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z) 3,3,3-trifluoropropene (1243zf).
8. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que ledit agent d'extraction organique a un facteur de séparation Si,2 supérieur ou égal à 1,1, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(y2,s*P2) dans laquelle 8. Method according to any one of the preceding claims characterized in that said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2) in which
yi,s représente le coefficient d'activité du 2,3,3,3-tétrafluoro-l-propène dans ledit agent d'extraction organique à dilution infinie,  yi, s represents the coefficient of activity of 2,3,3,3-tetrafluoro-1-propene in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 2,3,3,3-tétrafluoro-l-propène, PI represents the saturated vapor pressure of 2,3,3,3-tetrafluoro-1-propene,
Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-Y2, s represents the activity coefficient of trans-1, 3,3,3-tetrafluoro-1-propene (1234
E) dans ledit agent d'extraction organique à dilution infinie, E) in said organic infinite dilution extractant,
P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) ;  P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E);
avantageusement, le facteur de séparation est supérieur ou égal à 1,2, de préférence supérieur ou égal à 1,4, plus préférentiellement supérieur ou égal à 1,6, en particulier supérieur ou égal à 1,8, plus particulièrement supérieur ou égal à 2,0.  advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0.
9. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que ledit agent d'extraction organique a un facteur de séparation Si,2 supérieur ou égal à 1,1, ledit facteur de séparation étant calculé par la formule Si,2 = (yi,s*Pl)/(y2,s*P2) dans laquelle 9. Process according to any one of the preceding claims, characterized in that said organic extraction agent has a separation factor Si, 2 greater than or equal to 1.1, said separation factor being calculated by the formula Si, 2 = (yi, s * P1) / (y2, s * P2) in which
yi,s représente le coefficient d'activité du 1,1,1,2,2-pentafluoropropane (245cb) dans ledit agent d'extraction organique à dilution infinie,  yi, s represents the activity coefficient of 1,1,1,2,2-pentafluoropropane (245cb) in said organic infinite dilution extractant,
PI représente la pression de vapeur saturante du 1,1,1,2,2-pentafluoropropane (245cb), Y2,s représente le coefficient d'activité du trans-l,3,3,3-tetrafluoro-l-propène (1234ze- E) dans ledit agent d'extraction organique à dilution infinie,  PI represents the saturated vapor pressure of 1,1,1,2,2-pentafluoropropane (245cb), Y2, s represents the activity coefficient of trans-1,1,3,3-tetrafluoro-1-propene (1234ze) E) in said organic extraction agent with infinite dilution,
P2 représente la pression de vapeur saturante du trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E) ; avantageusement, le facteur de séparation est supérieur ou égal à 1,2, de préférence supérieur ou égal à 1,4, plus préférentiellement supérieur ou égal à 1,6, en particulier supérieur ou égal à 1,8, plus particulièrement supérieur ou égal à 2,0.  P2 represents the saturated vapor pressure of trans-1, 3,3,3-tetrafluoro-1-propene (1234ze-E); advantageously, the separation factor is greater than or equal to 1.2, preferably greater than or equal to 1.4, more preferably greater than or equal to 1.6, in particular greater than or equal to 1.8, more particularly greater than or equal to at 2.0.
10. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que ledit agent d'extraction organique a une capacité d'absorption C2,s supérieure ou égale à 0,20, ladite capacité d'absorption étant calculé par la formule C2,s = l/(y2,s) dans laquelle y2,s représente le coefficient d'activité dudit au moins un des composés consistant en trans-l,3,3,3-tetrafluoro-l- propène (1234ze-E) dans ledit agent d'extraction organique à dilution infinie, de préférence y2,s représente le coefficient d'activité dudit au moins un des composés consistant en trans-1,3,3,3- tetrafluoro-l-propène (1234ze-E), dans ledit agent d'extraction organique à dilution infinie ; avantageusement, la capacité d'absorption C2,s est supérieure ou égale à 0,40, de préférence supérieure ou égale à 0,60, plus préférentiellement supérieure ou égale à 0,80, en particulier supérieure ou égale à 1,0. 10. Process according to any one of the preceding claims, characterized in that said organic extraction agent has an absorption capacity C2, s greater than or equal to 0.20, said absorption capacity being calculated by the formula C2, where y2, s is the activity coefficient of said at least one of trans-1,3,3,3-tetrafluoro-1-propene compounds (1234ze-E) in said organic extraction agent with infinite dilution, preferably y2, s represents the activity coefficient of said at least one of trans-1,3,3,3-tetrafluoro-1-propene (1234ze-E) compounds in said organic infinite dilution extractant; advantageously, the absorption capacity C2, s is greater than or equal to 0.40, preferably greater than or equal to 0.60, more preferably greater than or equal to 0.80, in particular greater than or equal to 1.0.
11. Procédé selon l'une quelconque des revendications précédentes caractérisé en ce que ledit agent d'extraction organique est choisi parmi le groupe consistant en éthylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert- butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3- dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy-2-propanol, 1,2-propanediamine, n- butylacetate, 2-methoxy-l-propanol, hexanal. De préférence, ledit agent d'extraction organique est choisi parmi le groupe consistant en éthylamine, isopropylamine, diethylether, n- propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2- methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, l-methoxy-2-propanol, 1,2- propanediamine, n-butylacetate, 2-methoxy-l-propanol, hexanal. 11. Method according to any one of the preceding claims, characterized in that said organic extraction agent is chosen from the group consisting of ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, propanone, methylacetate, butanone, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy- 2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy-1-propanol, hexanal. Preferably, said organic extractant is selected from the group consisting of ethylamine, isopropylamine, diethylether, n-propylamine, diethylamine, diethoxymethane, isopropylacetate, 3-pentylamine, 2-methoxyethanamine, tert-butylacetate, 1,4-dioxane, 1,1-diethoxyethane, trimethoxymethane, n-pentylamine, 1,3-dioxane, sec-butylacetate, 1,2-diaminoethane, 1-methoxy-2-propanol, 1,2-propanediamine, n-butylacetate, 2-methoxy- 1-propanol, hexanal.
12. Procédé de production et de purification du 2,3,3,3-tetrafluoro-l-propène comprenant les étapes de : A process for producing and purifying 2,3,3,3-tetrafluoro-1-propene comprising the steps of:
A) fluoration en présence d'un catalyseur d'un composé de formule CH(n+2)(X)m- CHp(X)(n+i)-CX(3+p-m) où X représente indépendamment F ou Cl ; n, m, p sont indépendamment les uns des autres 0 ou 1 avec (n+m) = 0 ou 1, (n+p) = 0 ou 1 et (m-p) = 0 ou 1, au moins un X étant Cl; A) fluorination in the presence of a catalyst of a compound of formula CH ( n + 2) (X) m-CH p (X) (n + 1) -CX (3 + pm) where X independently represents F or Cl ; n, m, p are independently of one another 0 or 1 with (n + m) = 0 or 1, (n + p) = 0 or 1 and (mp) = 0 or 1, at least one X being Cl;
B) récupération d'un courant comprenant du 2,3,3,3-tetrafluoro-l-propène, 1,1,1,2,2- pentafluoropropane (245cb), trans-l,3,3,3-tetrafluoro-l-propène (1234ze-E), et optionnellement ou non au moins un des composés sélectionnés parmi le groupe consistant en chlorométhane (40), 1,1-difluoroéthane (152a), 1,1,1,2-tetrafluoroethane (134a), chloropentafluoroéthane (115), trans-l,2,3,3,3-pentafluoropropène (1225ye-E), cis-l,2,3,3,3-pentafluoropropène (1225ye-Z), 3,3,3-trifluoropropène (1243zf) ;  B) recovering a stream comprising 2,3,3,3-tetrafluoro-1-propene, 1,1,1,2,2-pentafluoropropane (245cb), trans-1,3,3,3-tetrafluoropropane, 1-propene (1234ze-E), and optionally at least one of the compounds selected from the group consisting of chloromethane (40), 1,1-difluoroethane (152a), 1,1,1,2-tetrafluoroethane (134a) , chloropentafluoroethane (115), trans-1,2,3,3,3-pentafluoropropene (1225ye-E), cis-1,2,3,3,3-pentafluoropropene (1225ye-Z), 3,3,3- trifluoropropene (1243zf);
C) mise en œuvre du procédé de purification du 2,3,3,3-tetrafluoro-l-propène selon l'une quelconque des revendications 1 à 11 à partir du courant récupéré à l'étape B).  C) implementation of the process for purifying 2,3,3,3-tetrafluoro-1-propene according to any one of claims 1 to 11 from the stream recovered in step B).
PCT/FR2018/050735 2017-03-28 2018-03-27 Method for the production and purification of 2,3,3,3-tetrafluoro-1-propene WO2018178555A1 (en)

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