EP3630716A1 - Procede de preparation de composes fluoroorganiques - Google Patents

Procede de preparation de composes fluoroorganiques

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Publication number
EP3630716A1
EP3630716A1 EP18724898.4A EP18724898A EP3630716A1 EP 3630716 A1 EP3630716 A1 EP 3630716A1 EP 18724898 A EP18724898 A EP 18724898A EP 3630716 A1 EP3630716 A1 EP 3630716A1
Authority
EP
European Patent Office
Prior art keywords
formula
ppm
less
compound
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP18724898.4A
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German (de)
English (en)
French (fr)
Inventor
Laurent Wendlinger
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Arkema France SA
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Arkema France SA
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Application filed by Arkema France SA filed Critical Arkema France SA
Publication of EP3630716A1 publication Critical patent/EP3630716A1/fr
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0569—Liquid materials characterised by the solvents
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0028—Organic electrolyte characterised by the solvent
    • H01M2300/0034—Fluorinated solvents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to a process for the preparation of fluoroorganic compounds.
  • Difluorinated organic compounds find many applications as a synthesis intermediate.
  • the difluoropropionic acid type compounds are in particular known as synthesis intermediate in the preparation of fluoroacrylic acid.
  • US 5,072,030 describes the preparation of 2,3-difluoropropionic acid by fluorination of acrylic acid in the presence of fluorine F2.
  • EP 0 132 681 describes the preparation of 2,2-difluoropropionic acid by oxidation of 2,2-difluoronitropropane in the presence of an oxidant such as sulfuric acid. A yield of 85% is obtained.
  • the present invention aims to remedy the drawbacks identified in the prior art.
  • the present invention relates to a process for the preparation of a compound of formula (I) H comprising the steps of:
  • R 1 and R 2 being independently selected from H, F, Cl, Br, I, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl;
  • X 1 and X 2 being independently selected from F, Cl, Br and I with the proviso that X 1 and X 2 are not simultaneously F;
  • Y being selected from the group consisting of H, C 1 -C 20 -alkyl, C 1 -C 20 -haloalkyl, C 6 -C 20 -aryl, -OH, -OR, -NH 2, -NHR, -NR 2 , -SR, C 3 -C 2 o-cycloalkyl, C 3 -C 2 o -cycloalkenyl and C 2 -C 20 -alkenyl;
  • R is independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
  • Step a) of the present process allows the formation of a stream A comprising said compound (I). This is recovered in step b).
  • Y is -OH or -OR.
  • R 1 is H and R 2 is H.
  • the process is carried out in the presence of a catalyst.
  • the method comprises the steps of:
  • Y being as defined above and X 1 is Cl, Br and I;
  • Y is -OH; and the compound of formula (I) wherein Y is -OH is treated under conditions effective to form a compound of formula (I) wherein Y is - OR, R being selected from the group consisting of C 1 -C 20 alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
  • R is a C 1 -C 6 -alkyl, preferably R is -CH 3,
  • X 1 being selected from Cl, Br and I, preferably X 1 is Cl;
  • Y being selected from the group consisting of H, C 1 -C 20 -alkyl, C 1 -C 20 -haloalkyl, C 6 -C 20 -aryl, -OH, -OR, -NH 2 , -NHR, -NR 2 , -SR, C 3 -C 2 o -cycloalkyl, C 3 -C 2 o -cycloalkenyl and C 2 -C 20 -alkenyl, preferably Y is -OH or -OR;
  • R is independently selected from the group consisting of C 1 -C 20 alkyl, C 6 -C 20 aryl and C 2 -C 20 alkenyl, C 3 -C 20 cycloalkenyl and C 3 -C 20 cycloalkyl, preferably R is C 1 -C 6 alkyl, especially R is -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 .
  • the composition is used as a solvent in an electrolytic composition in a battery, preferably a lithium-ion battery.
  • the present invention aims to remedy the drawbacks identified in the prior art.
  • R 1 and R 2 are independently selected from H, F, Cl, Br, I, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl;
  • X 1 and X 2 are independently selected from F, Cl, Br and I with the proviso that X 1 and X 2 are not simultaneously F;
  • Y is selected from the group consisting of H, C 1 -C 20 -alkyl, C 1 -C 20 -haloalkyl, C 6 -C 20 -aryl, -OH, -OR, -NH 2 , -NHR, -NR 2 , -SR, C 3 -C 2 o-cycloalkyl, C 3 -C 2 o -cycloalkenyl and C 2 -C 20 -alkenyl; R is independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
  • alkyl refers to linear or branched hydrocarbon chains containing the specified number of carbon atoms.
  • C1-C6 alkyl means a linear or branched alkyl group containing at least 1 and at most 6 carbon atoms.
  • aryl refers to an aromatic hydrocarbon ring containing the specified number of carbon atoms.
  • aryl may be phenyl, naphthyl, anthracyl or phenanthryl.
  • cycloalkyl refers to a monocyclic or condensed polycyclic non-aromatic hydrocarbon ring having the specified number of carbon atoms.
  • cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • alkenyl refers to linear or branched hydrocarbon chains containing the specified number of carbon atoms and at least one carbon-carbon double bond.
  • cycloalkenyl refers to a fused monocyclic or fused polycyclic non-aromatic hydrocarbon ring having the specified number of carbon atoms and at least one carbon-carbon double bond.
  • R 1 and R 2 are independently selected from H, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
  • R 1 and R 2 are independently selected from H, C 1 -C 10 -alkyl, C 6 -C 10 aryl and C 2 -C 10 -alkenyl , C3-Cio-cycloalkenyl and C3-Cio-cycloalkyl.
  • R 1 and R 2 are independently selected from H, C 1 -C 3 -alkyl, Ce-C 8 -aryl and C 2 -C 6 alkenyl, C3-C6-cycloalkenyl and C3-C6-cycloalkyl.
  • R 1 and R 2 are H.
  • X 1 and X 2 are independently selected from F, Cl and Br with the proviso that X 1 and X 2 are not simultaneously F
  • X 1 and X 2 are independently selected from F and Cl with the proviso that X 1 and X 2 are not simultaneously F.
  • X 1 and X 2 are Cl.
  • Y is selected from the group consisting of H, C1-C10-alkyl, C1-C10-haloalkyl, C6-C10-aryl, -OH, -OR, -N H2, -NHR, -N R2, -SR, C3-Cio-cycloalkyl, C3-Cio-cycloalkenyl and C2-C10-alkenyl.
  • Y is selected from the group consisting of H, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 6 -C 10 aryl, -OH, -OR, C3-Cio-cycloalkyl, C3-C10-cycloalkenyl and C2-C10-alkenyl.
  • Y is selected from the group consisting of H, -OH and -OR. More particularly, in the compounds of formula (I), (II) and / or (III), Y is selected from the group consisting of -OH and -OR.
  • R is independently selected from the group consisting of C1-C10-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl.
  • R is independently selected from the group consisting of C1-C10-alkyl and C6-C10-aryl. More particularly, R is independently selected from the group consisting of C1-C6-alkyl and C6-C8-aryl.
  • R is independently selected from the group consisting of C 1 -C 3 -alkyl and C 6 -aryl.
  • R 1 and R 2 being independently selected from H, F, Cl, Br, I, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; preferably selected from H, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; in particular selected from H, C1-Cio-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl; preferably selected from H, C1-C3-alkyl, C6-C8-aryl and C2-C6-alkenyl, C3-
  • X 1 and X 2 being independently selected from F, Cl, Br and I with the proviso that X 1 and X 2 are not simultaneously F; preferably selected from F, Cl and Br with the proviso that X 1 and X 2 are not simultaneously F; more preferably selected from F and Cl with the proviso that X 1 and X 2 are not simultaneously F; in particular X 1 and X 2 are Cl;
  • Y being selected from the group consisting of H, C 1 -C 20 -alkyl, C 1 -C 20 -haloalkyl, C 6 -C 20 -aryl, -OH, -OR, -NH 2, -NHR, -NR 2 , -SR, C 3 -C 2 o-cycloalkyl, C 3 -C 2 o -cycloalkenyl and C 2 -C 20 -alkenyl; preferably selected from the group consisting of H, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C6-C10 aryl, -OH, -OR, -NH 2, -NHR, -NR 2, -SR, -C 3 -C 0 -Cycloalkyl, C 3 -C 10 O -cycloalkenyl and C 2 -C 10 O -alkenyl; more preferably selected from the group consisting of H, Ci-Cio-
  • R is independently selected from the group consisting of C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; preferably selected from the group consisting of Ci-Cio-alkyl, C6-Cio-aryl and C2-Cio-alkenyl, C 3 -Cio-cycloalkenyl, C3-C10- cycloalkyl; in particular selected from the group consisting of C1-C10-alkyl and C6-C10-aryl; more particularly selected from the group consisting of C1-C6-alkyl and Ce-C8-aryl; preferably, R is independently selected from the group consisting of C 1 -C 3 -alkyl and C 6 -aryl.
  • the present invention relates to a process for the preparation of a compound of formula (I)
  • the process i.e., step a), a1) and / or a2), is carried out in the presence of a catalyst.
  • Said catalyst may be based on an element or elements selected from the metals and / or metalloids of columns 1 to 15 of the periodic table of the elements and their mixtures.
  • a Lewis acid a catalyst based on a metal halide, in particular based on antimony halide, tin, tantalum, titanium, transition metals such as iron halides, niobium, molybdenum, transition metal oxides, Group 4 metal halides, Group 5 metal halides, fluorinated chromium halide, fluorinated chromium oxide, or a mixture of both. Chlorides and metal fluorides can advantageously be used.
  • Such catalysts include: SbCl 5 , SbCl 3 , TiCl 4 , SnCl 4 , TaCl 5 , NbCl 5 , TiCl 4 , FeCu, MoC and their corresponding fluorinated derivatives. Pentavalent metal halides are suitable.
  • the catalyst is based on an element or elements selected from among the metals and / or metalloids of columns 4 to 6 and 13 to 15 of the periodic table of the elements and their mixtures.
  • said catalyst is based on a member or elements selected from the group consisting of titanium, tantalum, molybdenum, boron, tin and antimony, and mixtures thereof.
  • the catalyst is a halide of a member or elements selected from the group consisting of titanium, tantalum, molybdenum, boron, tin and antimony, and mixtures thereof.
  • the catalyst is a fluoride, chloride or chlorofluoride of a member or elements selected from the group consisting of titanium, tantalum, molybdenum, boron, tin and antimony, and mixtures thereof.
  • said catalyst is based on a metal or metals selected from the group consisting of titanium and tin or their mixture.
  • said catalyst is a halide of a metal or metals selected from the group consisting of titanium and tin or their mixture.
  • said catalyst is a fluoride, a chloride or a chlorofluoride of a metal or metals selected from the group consisting of titanium and tin or their mixture.
  • the catalyst is selected from antimony trichloride, antimony pentachloride, titanium tetrachloride and tin tetrachloride and mixtures thereof.
  • Ionic liquids are particularly interesting for fluorination by HF in the liquid phase.
  • Ionic liquids are ionic nonaqueous salts which are liquid at moderate temperatures (preferably below 120 ° C).
  • the ionic liquids preferably result from the reaction between an organic salt and an inorganic compound.
  • the ionic liquids are preferably obtained by reacting at least one halogenated or oxyhalogenated Lewis acid based on aluminum, titanium, niobium, tantalum, tin, antimony, nickel, zinc or iron with a salt of general formula Y + a "wherein a denotes a halide anion (bromide, iodide and preferably chloride or fluoride) or hexafluoroantimonate (SbF 6 _) and Y + is a quaternary ammonium cation, quaternary phosphonium or sulfonium ternary Halogenated Lewis acid based on aluminum, titanium, niobium, tantalum, antimony, nickel, zinc or iron may be a chlorinated, brominated, fluorinated or mixed derivative, for example a chlorofluorinated acid. Mention may be made more particularly of chlorides, fluorides or chlorofluorides of the following formulas:
  • TiCl 4 TiF 4 , TaCl 2, TaF 5 , NbCl 5 , NbF 5 , SbCl 5 , SbCl 4 F, SbCl 3 F 2 , SbCl 2 F 3 , SbCl 4 , SbF 5 and mixtures thereof.
  • the salt Y + A - the cation Y + may respond to one of the following general formulas:
  • R 1 to R 4 each denote a hydrocarbyl, chlorohydrocarbyl, fluorohydrocarbyl, chlorofluorohydrocarbyl or fluorocarbyl group having from 1 to 10 carbon atoms, saturated or unsaturated, cyclic or otherwise, or aromatic, one or more of these groups may also contain one or more heteroatoms such as N, P, S or O.
  • the ammonium cation, phosphonium or sulfonium Y + may also be part of a saturated or unsaturated heterocycle, or aromatic having 1 to 3 nitrogen, phosphorus or sulfur atoms, and any of the following general formulas:
  • R 1 and R 2 are as defined above.
  • a salt containing 2 or 3 ammonium, phosphonium or sulfonium sites in their formula may also be suitable.
  • salts Y + A that may be mentioned include tetraalkyl ammonium chlorides and fluorides, tetraalkyl phosphonium chlorides and fluorides, and trialkyl sulfonium chlorides and fluorides, alkyl pyridinium chlorides and fluorides, chlorides, fluorides and bromides of dialkyl imidazolium, and chlorides and fluorides of trialkyl imidazolium.
  • Ionic liquids can be prepared by appropriately mixing the Lewis acid or halogen oxyhalogenated and the organic salt Y + A ". Reference may be made in particular to the method described in WO 01/81353.
  • the preferred ionic liquids advantageously are those resulting from a molar ratio of Lewis acid / organic salt strictly greater than 1: 1. We may also mention the ionic liquids described the reference “liquid-phase HF Fluorination”, Multiphase Homogeneous Catalysis, Eds Wiley-VCH, (2002 ), 535.
  • the method is implemented in the liquid phase.
  • the process is carried out in continuous mode or in batch mode.
  • stream A recovered in step b) is a gaseous stream.
  • stream A may comprise unreacted hydrofluoric acid, hydrogen halide, and the formula (II) or formula (III) unreacted.
  • the hydrogen halide may be HCl, HBr or H1 depending on the substituents X 1 and X 2 of the compounds of formula (II) or (III).
  • said stream A may comprise less than 15% by weight of hydrofluoric acid, more preferably less than 10% by weight of hydrofluoric acid based on the total weight of composition A.
  • said stream A may comprise less than 10% by weight of hydrogen halide, preferably hydrogen chloride, more preferably less than 5% by weight based on the total weight of composition A.
  • said stream A may comprise less than 10% by weight of water, more preferably less than 5% by weight of water based on the total weight of composition A.
  • said stream A may comprise less than 40% by weight of compounds of formula (II) or (III), more preferably less than 30% by weight, in particular less than 20% by weight, more particularly less than 10% by weight. by weight based on the total weight of composition A.
  • the process can be carried out in the presence or absence of solvent.
  • a solvent may be selected from the group consisting of 1,2-dichloroethane, 1,2,3-trichloropropane, 1-chloro-1-fluoroethane, 1,1-difluoroethane, 1,1-dichloroethane , 1,3-dichloro-1-fluorobutane, the isomers of tetrachlorofluoropropane, the isomers of trichlorodifluoropropane, the isomers of dichlorotrifluoropropane, 1,1,1,3,3-pentafluorobutane, 1,1,2-trichloro-2,2- difluoroethane, 1,1,2-trichloro-2-fluoroethane or perchlorethylene, nitro solvents including nitromethane and nitrobenzene, amides, esters, sulfones including tetramethylene sulfon
  • the HF / compound of formula (II) or (III) molar ratio is greater than or equal to 2, preferably greater than or equal to 3, in particular greater than or equal to 10.
  • the catalyst / compound molar ratio of formula (II) or (III) is greater than or equal to 0.01, preferably greater than or equal to 0.025, in particular greater than or equal to 0.025. equal to 0.05.
  • the molar ratio catalyst / compound of formula (II) or (III) is from 2 to 90 mol%, advantageously from 4 to 80 mol%, preferably from 6 to 75 mol%.
  • the present process is carried out at a temperature of at least 30 ° C, preferably at least 40 ° C, preferably at least 50 ° C, in particular at least 100 ° C.
  • the present process is carried out at a temperature of 30 ° C to 200 ° C, preferably 40 ° C to 170 ° C, in particular 50 ° C to 150 ° C.
  • the present process is carried out at a pressure of at least 1 bara, preferably at least 2 bara, preferably at least 4 bara, in particular at least 5 bara.
  • the present process is carried out at a pressure of from 1 bara to 50 bara, preferably from 2 bara to 50 bara, more preferably from 4 bara to 35 bara, in particular from 5 bara to 25 bara.
  • the stream A comprising said compound (I) obtained in step b) can undergo at least one separation and / or purification step, to form a composition B.
  • separation condensation may be mentioned , evaporation, decantation, absorption, washing, liquid-liquid extraction.
  • purification mention may be made of distillation, for example extractive distillation, azeotropic distillation, membrane separation, adsorption on solid and more particularly adsorption on molecular sieve, alumina or activated carbon and drying.
  • the drying can be carried out on molecular sieves, in particular on molecular sieves of 3 to 4 A.
  • composition B comprises said compound of formula (I) as described above.
  • the composition B comprises less than 500 ppm of water by weight based on the total weight of the composition B, advantageously 400 ppm of water, preferably less than 300 ppm of water, in particular less than 200 ppm of water by weight based on the total weight of composition B.
  • the composition B comprises less than 500 ppm of hydrofluoric acid by weight based on the total weight of the composition B, advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less 200 ppm of hydrofluoric acid, in particular less than 100 ppm of hydrofluoric acid by weight based on the total weight of composition B.
  • composition B comprises less than 100 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, by weight based on the total weight of composition B, advantageously less than 75 ppm.
  • composition B may comprise: optionally at least 1000 ppm by weight of a compound of formula (II)
  • 400 ppm water preferably less than 300 ppm water, in particular less than 200 ppm water by weight;
  • At least 500 ppm of hydrofluoric acid by weight advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less than 200 ppm of hydrofluoric acid, in particular less than 100 ppm hydrofluoric acid by weight; and
  • composition B by weight based on the total weight of composition B.
  • said stream A is purified by distillation and / or a drying step as mentioned above.
  • said stream A may comprise less than 15% by weight of hydrofluoric acid, more preferably less than 10% by weight of hydrofluoric acid based on the total weight of composition A.
  • said stream A may comprise less than 10% by weight of hydrogen halide, preferably hydrogen chloride, more preferably less than 5% by weight based on the total weight of composition A.
  • said stream A may comprise less than 10% by weight of water, more preferably less than 5% by weight of water based on the total weight of composition A.
  • said stream A may comprise less than 40% by weight of compounds of formula (II) or (III), more preferably less than 30% by weight, in particular less than 20% by weight based on the total weight of the composition A.
  • Steps i) and ii) can be implemented simultaneously or sequentially. Steps i) and ii) can be carried out in a reactor or in two different reactors.
  • the molar ratio HF / compound of formula (II) or (III) may be greater than or equal to 1, advantageously greater than or equal to 2, preferably greater than or equal to 3, in particular greater than or equal to to 10. If a catalyst is used for the implementation of step i), the molar ratio catalyst / compound of formula (II) or (III) is greater than or equal to 0.01, preferably greater than or equal to 0.025, in particular greater than or equal to 0.05.
  • the molar ratio catalyst / compound of formula (II) or (III) is from 2 to 90 mol%, advantageously from 4 to 80 mol%, preferably from 6 to 75 mol%.
  • the catalyst may be based on a metal or metals selected from the group consisting of titanium and tin or their mixture, in a preferred manner, said catalyst may be a halide of a metal or metals selected (s) from the group consisting of titanium and tin or their mixture, preferably preferentially, said catalyst may be a fluoride, a chloride or a chlorofluoride of a metal or metals selected from the group consisting of titanium and tin or their mixture.
  • a catalyst is used for the implementation of step i), it is tin tetrachloride, antimony pentachloride, antimony trichloride or titanium tetrachloride or mixtures thereof.
  • Step i) can be carried out at a temperature of at least 30 ° C, preferably at least 40 ° C, preferably at least 50 ° C, in particular at least 100 ° C.
  • step i) can be carried out at a temperature of 30 ° C to 200 ° C, preferably 40 ° C to 170 ° C, in particular 50 ° C to 150 ° C.
  • Step i) can be carried out at a pressure of at least 1 bara, preferably at least 2 bara, preferably at least 4 bara, in particular at least 5 bara.
  • step i) can be carried out at a pressure of 1 bara at 50 bara, preferably from 2 bara to 50 bara, more preferably from 4 bara to 35 bara, in particular from 5 bara to 25 bara.
  • the molar ratio HF / compound of formula (IV) or (V) may be greater than or equal to 1, advantageously greater than or equal to 2, preferably greater than or equal to 3, in particular greater than or equal to to 10.
  • the catalyst / compound molar ratio of formula (IV) or (V) is greater than or equal to 0.01, preferably greater than or equal to 0.025, in particular greater than or equal to 0.05.
  • the molar ratio of catalyst / compound of formula (IV) or (V) is from 2 to 90 mol%, advantageously from 4 to 80 mol%, preferably from 6 to 75 mol%.
  • the catalyst may be based on a metal or metals selected from the group consisting of titanium and tin or their mixture, in a preferred manner, said catalyst may be a halide of a metal or metals selected from the group consisting of titanium and tin or their mixture, preferably favored, said catalyst may be a fluoride, a chloride or a chlorofluoride of a metal or metals selected from the group consisting of titanium and tin or their mixture.
  • a catalyst is used for the implementation of step ii), it is antimony pentachloride, antimony trichloride, tin tetrachloride or titanium tetrachloride or mixtures thereof.
  • Step ii) may be carried out at a temperature of at least 30 ° C, preferably at least 40 ° C, preferably at least 50 ° C, in particular at least 100 ° C.
  • step ii) may be carried out at a temperature of 30 ° C to 300 ° C, preferably 40 ° C to 250 ° C, in particular 50 ° C to 200 ° C.
  • the temperature in step ii) may be equal to, greater than or less than that of step i).
  • the temperature in step ii) is greater than in step i).
  • Step ii) can be carried out at a pressure of at least 1 bara, preferably at least 2 bara, preferably at least 4 bara, in particular at least 5 bara.
  • step ii) may be carried out at a pressure of from 1 bara to 50 bara, preferably from 2 bara to 50 bara, more preferably from 4 bara to 35 bara, in particular from 5 bara to 25 bara.
  • the pressure in step ii) may be equal to, greater than or less than that of step i).
  • the present process comprises the steps of:
  • R 1 and R 2 are independently selected from H, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl;
  • Y is selected from the group consisting of H, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C6-Cio-aryl, - OH, -OR, -N H2, -NHR, -NR 2, -SR, -C 3 -C 0 -Cycloalkyl, C 3 -C 10 O -cycloalkenyl and C 2 -C 10 O -alkenyl;
  • R is independently selected from the group consisting of C1-Cio-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl;
  • X 1 Cl, Br or I
  • R 1 and R 2 are independently selected from H, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl;
  • Y is selected from the group consisting of H, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C6-Cio-aryl, - OH, -OR, -NH 2, -NHR, -NR 2, -SR, -C 3 -C 0 -Cycloalkyl, C 3 -C 10 O -cycloalkenyl and C 2 -C 10 O -alkenyl;
  • R is independently selected from the group consisting of C1-C10-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl, and
  • the present process comprises the steps of:
  • R 1 and R 2 are independently selected from H, C 1 -C 10 -alkyl, C 6 -C 10 aryl and C 2 -C 10 -alkenyl, C 3 -C 10 -cycloalkenyl and C 3 -C 10 -cycloalkyl;
  • Y is selected from the group consisting of H, C1-C10-alkyl, C1-C10-haloalkyl, C6-C10-aryl, -OH, -OR, C3-C10-cycloalkyl, C3-C10-cycloalkenyl and C2-C10- alkenyl;
  • R 1 and R 2 are independently selected from H, C 1 -C 10 -alkyl, C 6 -C 10 aryl and C 2 -C 10 -alkenyl, C 3 -C 10 -cycloalkenyl and C 3 -C 10 -cycloalkyl;
  • Y is selected from the group consisting of H, C1-C10-alkyl, C1-C10-haloalkyl, C6-C10-aryl, -OH, -OR, C3-C10-cycloalkyl, C3-C10-cycloalkenyl and C2-C10- alkenyl;
  • R is independently selected from the group consisting of C1-C10-alkyl and C6-C10-aryl, and
  • R 1 and R 2 are independently selected from H, C 1 -C 3 -alkyl, C 1 -C 8 aryl and C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkenyl and C 3 -C 6 -cycloalkyl;
  • Y is selected from the group consisting of H, -OH and -OR;
  • R 1 and R 2 are independently selected from H, C 1 -C 3 -alkyl, C 1 -C 8 aryl and C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkenyl and C 3 -C 6 -cycloalkyl;
  • Y is selected from the group consisting of H, -OH and -OR;
  • R is independently selected from the group consisting of C1-C6-alkyl and Ce-C8-aryl, b) recovering said stream A comprising said compound of formula (I).
  • the present process comprises the steps of:
  • the stream A comprising said compound (I) recovered in step b) is purified or separated under conditions that are effective to form a composition B comprising a compound of formula (I)
  • separation there may be mentioned condensation, evaporation, decantation, absorption, washing, liquid-liquid extraction.
  • purification mention may be made of distillation, for example distillation extractive, azeotropic distillation, membrane separation, adsorption on solid and more particularly adsorption on molecular sieve, alumina or activated carbon and drying.
  • the drying can be carried out on molecular sieves, in particular on molecular sieves of 3 to 4 A.
  • Composition B comprises said compound of formula (I) as described above.
  • the composition B comprises less than 500 ppm of water by weight based on the total weight of the composition B, advantageously 400 ppm of water, preferably less than 300 ppm of water, in particular less than 200 ppm of water by weight based on the total weight of composition B.
  • the composition B comprises less than 500 ppm of hydrofluoric acid by weight based on the total weight of the composition B, advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less 200 ppm of hydrofluoric acid, in particular less than 100 ppm of hydrofluoric acid by weight based on the total weight of composition B.
  • composition B comprises less than 100 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, by weight based on the total weight of composition B, advantageously less than 75 ppm.
  • composition B can comprise:
  • 400 ppm water preferably less than 300 ppm water, in particular less than 200 ppm water by weight;
  • At least 500 ppm of hydrofluoric acid by weight advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less than 200 ppm of hydrofluoric acid, in particular less than 100 ppm hydrofluoric acid by weight; and
  • composition B by weight based on the total weight of composition B.
  • composition B comprises:
  • ppm water by weight advantageously less than 400 ppm water, preferably less than 300 ppm water, in particular less than 200 ppm water by weight;
  • At least 500 ppm of hydrofluoric acid by weight advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less than 200 ppm of hydrofluoric acid, in particular less than 100 ppm hydrofluoric acid by weight; and optionally not less than 100 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, advantageously less than 75 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, preferably less than 50 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, in particular less than 20 ppm of a hydrogen halide other than that hydrofluoric acid, preferably hydrogen chloride,
  • composition B comprises:
  • ppm of water by weight advantageously less than 400 ppm of water, preferably less than 300 ppm of water, in particular less than 200 ppm of water by weight;
  • ppm of hydrofluoric acid by weight advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, plus preferably less than 200 ppm of hydrofluoric acid, in particular less than 100 ppm of hydrofluoric acid by weight;
  • a hydrogen halide other than hydrofluoric acid preferably hydrogen chloride
  • a hydrogen halide other than hydrofluoric acid advantageously less than 75 ppm of a hydrogen halide other than hydrofluoric acid, preferably chloride hydrogen, preferably less than 50 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, in particular less than 20 ppm of a hydrogen halide other than the acid hydrofluoric, preferably hydrogen chloride
  • Y is -OH; and the compound of formula (I) wherein Y is -OH is treated under conditions effective to form a compound of formula (I) wherein Y is - OR, R being selected from the group consisting of C 1 -C 20 alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
  • the present process may include the steps of:
  • R 1 and R 2 being independently selected from H, F, Cl, Br, I, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; preferably R 1 and R 2 are independently selected from H, C 1 -C 20 -alkyl, C 6 -C 20 -alkyl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; preferably, R 1 and R 2 are independently selected from H, C 1 -C 10 -alkyl, C 6 -C 10 aryl and C 2 -C 10 -alkenyl, C 3 -C 10 -cycloalkenyl and C 3 -C 10 -cycloalkyl; in particular, R 1 and R 2 are independently selected from H
  • step b) carrying out from said stream A recovered in step b) an esterification reaction of the compound of formula (I) under conditions effective to form a compound of formula (I) wherein Y is -OR with R being selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl; preferably R being selected from the group consisting of C1-C10-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl; preferably R being selected from the group consisting of C1-C10-alkyl and C6-C10-aryl; in particular R being selected from the group consisting of C1-C6-alkyl and Ce-C8-aryl; more preferably, R being selected from the group consisting of C1-
  • the group R 1 is identical in the compounds of formula (II), (III) and (I).
  • the group R 2 is identical in the compounds of formula (II), (III) and (I).
  • the present process may comprise the steps of:
  • R 1 and R 2 are H;
  • X 1 and X 2 are Cl;
  • Y is -OH
  • step a) is carried out under operating conditions as described above in connection with the process according to the present invention.
  • step c) is carried out by reacting the compound of formula (I) recovered in step b) with a compound of formula R-OH with R being selected from the group consisting of C 1 -C 20 alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20- cycloalkyl; preferably R being selected from the group consisting of C1-C10-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl; preferably R being selected from the group consisting of C1-C10-alkyl and C6-C10-aryl; in particular R being selected from the group consisting of C1-C6-alkyl and Ce-C8-aryl; more preferably, R being selected from the group consisting of C1-C3-alkyl and C6-aryl,
  • the method can be implemented via steps a1) and a2) as described in the present application instead of step a).
  • the present process may include the steps of:
  • step c) carrying out from said stream A recovered in step b) an esterification reaction of the compound of formula (I) under conditions effective to form a compound of formula (I)
  • Said stream A recovered in step b) can be purified as described in the present application to form said composition B prior to the implementation of step c).
  • Step c) is then implemented from said composition B as defined in the present application.
  • step c) is carried out in the presence of an acid catalyst such as a Lewis acid or a Bronsted acid or a basic catalyst or cationic or anionic resins.
  • an acid catalyst such as a Lewis acid or a Bronsted acid or a basic catalyst or cationic or anionic resins.
  • step c) is carried out in the presence of a basic catalyst such as alkali or alkaline-earth hydroxides (for example KOH, NaOH, Ca (OH) 2, Mg (OH) 2), alkaline oxides or alkaline earth (eg Na2O, CaO, MgO, K2O), alkaline carbonates or alkaline earth (for example Na2CC> 3, K2CO3, Ca ⁇ 3, MgCOs), or an acid catalyst such as a mineral acid (for example HCl, HBr, H1, H2SO4), p-toluenesulphonic acid , boron trifluoride.
  • a basic catalyst such as alkali or alkaline-earth
  • step c) can be carried out at a temperature between 10 ° C and 200 ° C, preferably between 20 ° C and 150 ° C.
  • the present invention relates to a composition comprising said compound of formula (I) as described above.
  • the composition comprises less than 500 ppm of water by weight based on the total weight of the composition, advantageously less than 400 ppm of water, preferably less than 300 ppm of water, in particular less than 200 ppm of water. water by weight based on the total weight of the composition.
  • the composition comprises less than 500 ppm of hydrofluoric acid by weight based on the total weight of the composition, advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less than 200. ppm of hydrofluoric acid, in particular less than 100 ppm of hydrofluoric acid by weight based on the total weight of the composition.
  • the composition comprises less than 100 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, by weight based on the total weight of the composition, advantageously less than 75 ppm of a hydrogen halide.
  • hydrogen halide other than hydrofluoric acid preferably hydrogen chloride, preferably less than 50 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, in particular less 20 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, by weight based on the total weight of the composition.
  • composition may comprise:
  • 400 ppm water preferably less than 300 ppm water, in particular less than 200 ppm water by weight;
  • At least 500 ppm of hydrofluoric acid by weight advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less than 200 ppm of hydrofluoric acid, in particular less than 100 ppm hydrofluoric acid by weight; and
  • the composition comprises:
  • ppm water by weight advantageously less than 400 ppm water, preferably less than 300 ppm water, in particular less than 200 ppm water by weight;
  • At least 500 ppm of hydrofluoric acid by weight advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, more preferably less than 200 ppm of hydrofluoric acid, in particular less than 100 ppm hydrofluoric acid by weight; and optionally not less than 100 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, advantageously less than 75 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, preferably less than 50 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, in particular less than 20 ppm of a hydrogen halide other than that hydrofluoric acid, preferably hydrogen chloride,
  • the composition comprises:
  • ppm of water by weight advantageously less than 400 ppm of water, preferably less than 300 ppm of water, in particular less than 200 ppm of water by weight;
  • ppm of hydrofluoric acid by weight advantageously less than 400 ppm of hydrofluoric acid, preferably less than 300 ppm of hydrofluoric acid, plus preferably less than 200 ppm of hydrofluoric acid, in particular less than 100 ppm of hydrofluoric acid by weight;
  • a hydrogen halide other than hydrofluoric acid preferably hydrogen chloride
  • a hydrogen halide other than hydrofluoric acid advantageously less than 75 ppm of a hydrogen halide other than hydrofluoric acid, preferably chloride hydrogen, preferably less than 50 ppm of a hydrogen halide other than hydrofluoric acid, preferably hydrogen chloride, in particular less than 20 ppm of a hydrogen halide other than the acid hydrofluoric, preferably hydrogen chloride
  • composition according to this second aspect of the invention is obtained by the method according to the first aspect of the present invention.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that:
  • R 1 and R 2 are independently selected from H, F, Cl, Br, I, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl;
  • X 1 and X 2 are independently selected from F, Cl, Br and I with the proviso that X 1 and X 2 are not simultaneously F;
  • Y is selected from the group consisting of H, C 1 -C 20 -alkyl, C 1 -C 20 -haloalkyl, C 6 -C 20 -aryl, -OH, -OR, -NH 2, -NHR, -NR 2 , -SR, C 3 -C 2 o-cycloalkyl, C 3 -C 2 o -cycloalkenyl and C 2 -C 20 -alkenyl; R is independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that R 1 and R 2 are independently selected from H, C 1 -C 2 - alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that R 1 and R 2 are independently selected from H, Ci-Cio- alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that R 1 and R 2 are independently selected from H, C 1 -C 3 -alkyl, Ce-C 8 -aryl and C2-C6-alkenyl, C3-C6-cycloalkenyl and C3-C6-cycloalkyl.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that R 1 and R 2 are H.
  • (V) are such that X 1 and X 2 are independently selected from F, Cl and Br with the proviso that X 1 and X 2 are not simultaneously F. More preferably, in said composition, the compounds of formula (I), (II), (III), (IV) and / or (V) are such that X 1 and X 2 are independently selected from F and Cl with the proviso that X 1 and X 2 are not simultaneously F. In particular, in said composition, the compounds of formula (I), (II), (III), (IV) and / or (V) are such that X 1 and X 2 are Cl.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that Y is selected from the group consisting of H, Ci-Cio-alkyl , C 1 -C 1 0- haloalkyl, C 0 -C 6 -aryl, -OH, -OR, -NH 2, -NHR, -NR 2, -SR, -C 0 -C 3 -cycloalkyl, C3-C10- cycloalkenyl and C2-C10-alkenyl.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that Y is selected from the group consisting of H, Ci-Cio-alkyl , Ci-Cio-haloalkyl, C6-Cio-aryl, -OH, -OR, C3-Cio-cycloalkyl, C3-C 1 0- cycloalkenyl and C2-Cio-alkenyl.
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that Y is selected from the group consisting of H, -OH and -OR .
  • the compounds of formula (I), (II), (III), (IV) and / or (V) are such that Y is selected from the group consisting of -OH and -OR.
  • R is independently selected from the group consisting of C 1 -C 10 -alkyl, C 6 -C 10 aryl and C 2 -C 10 -alkenyl, C 3 -C 10 -cycloalkenyl and C 3 -C 10 -cycloalkyl.
  • R is independently selected from the group consisting of C1-C10-alkyl and C6-C10-aryl. More particularly, R is independently selected from the group consisting of C1-C6-alkyl and C6-C8-aryl.
  • R is independently selected from the group consisting of C 1 -C 3 -alkyl and C 6 -aryl.
  • the present composition comprises a compound of formula (I)
  • R 1 and R 2 being independently selected from H, F, Cl, Br, I, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; preferably selected from H, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; in particular selected from H, Ci-Cio-alkyl, C6-Cio-aryl and C2-Cio-alkenyl, C3-C 1 0- cycloalkenyl and C3-Cio-cycloalkyl; preferably selected from H, C1-C3-alkyl, C6-C8-aryl and C2-C6-alkenyl
  • Y being selected from the group consisting of H, C 1 -C 20 -alkyl, C 1 -C 20 -haloalkyl, C 6 -C 20 -aryl, -OH, -OR, -NH 2, -NHR, -NR 2 , -SR, C 3 -C 2 o-cycloalkyl, C 3 -C 2 o -cycloalkenyl and C 2 -C 20 -alkenyl; preferably selected from the group consisting of H, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C6-C10 aryl, -OH, -OR, -NH 2, -NHR, -NR 2, -SR, -C 3 -C 0 -Cycloalkyl, C 3 -C 10 O -cycloalkenyl and C 2 -C 10 O -alkenyl; more preferably selected from the group consisting of H, C1-C10-
  • R is independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl; preferably selected from the group consisting of C1-C10-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl; in particular selected from the group consisting of C1-C10-alkyl and C6-C10-aryl; more particularly selected from the group consisting of C1-C6-alkyl and Ce-C8-aryl; preferably, R is independently selected from the group consisting of C 1 -C 3 -alkyl and C 6 -aryl.
  • composition comprises compounds of formula (II), (III), (IV) and / or (V), they are such that:
  • X 1 and X 2 being independently selected from F, Cl, Br and I with the proviso that X 1 and X 2 are not simultaneously F; preferably selected from F, Cl and Br with the proviso that X 1 and X 2 are not simultaneously F; more preferably selected from F and Cl with the proviso that X 1 and X 2 are not simultaneously F; in particular X 1 and X 2 are Cl;
  • R 1 and R 2 being independently selected from H, F, Cl, Br, I, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; preferably selected from H, C 1 -C 20 -alkyl, C 6 -C 20 -aryl and C 2 -C 20 -alkenyl, C 3 -C 20 -cycloalkenyl and C 3 -C 20 -cycloalkyl; in particular selected from H, C1-Cio-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl; preferably selected from H, C1-C3-alkyl, C6-C8-aryl and C2-C6-alkenyl, C3-
  • Y being selected from the group consisting of H, C 1 -C 20 -alkyl, C 1 -C 20 -haloalkyl, C 6 -C 20 -aryl, -OH, -OR, -NH 2 , -NHR, -NR 2 , -SR, C 3 -C 2 o-cycloalkyl, C 3 -C 2 o -cycloalkenyl and C 2 -C 20 -alkenyl; of preferably selected from the group consisting of H, C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 6 -C 10 -aryl, -OH, -OR, -NH 2 , -NHR, -NR 2 , -SR, C 3 - C 0 -C cycloalkyl, C 3 -C 10 O -cycloalkenyl and C 2 -C 10 O -alkenyl; more preferably selected from the
  • R is independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl; preferably selected from the group consisting of C1-C10-alkyl, C6-C10-aryl and C2-C10-alkenyl, C3-C10-cycloalkenyl and C3-C10-cycloalkyl; in particular selected from the group consisting of C1-C10-alkyl and C6-C10-aryl; more particularly selected from the group consisting of C1-C6-alkyl and Ce-C8-aryl; preferably, R is independently selected from the group consisting of C 1 -C 3 -alkyl and C 6 -aryl.
  • the composition comprises a compound of formula (I) wherein R 1 and R 2 are H; Y being selected from the group consisting of -OH and -OR; R being independently selected from the group consisting of C1-C3-alkyl and C6-aryl.
  • Said composition may also comprise compounds of formula (II), (III), (IV) and / or (V) such that R 1 and R 2 being H; Y being selected from the group consisting of -OH and -OR; R being independently selected from the group consisting of C1-C3-alkyl and C6-aryl; and X 1 and X 2 being Cl.
  • composition according to the second aspect of the present invention may be obtained according to the method described according to the first aspect of the invention.
  • the composition according to the second aspect of the present invention is used as a solvent in an electrolytic composition.
  • the electrolytic composition is preferably used in a battery.
  • the electrolytic composition is used in a Li-ion battery.
  • the electrolytic composition comprises in addition to the present composition used as a solvent, at least one lithium salt.
  • said at least one lithium salt is selected from the group consisting L1PF6, LiBF 4, CH3COOL1, CH3SO3L1, CF3SO3L1, CF3COOL1, L12B12F12, L1BC4O8, LiAsF 6, L ⁇ 2S ⁇ F6, ⁇ 2PFO3, L1CIO4, bis (trifluoromethanesulfonyl) lithium imide, Lithium bis (fluorosulfonyl) imide, lithium 2-trifluoromethyl-4,5-dicyanoimidazolate, lithium 2-pentafluoroethyl-4,5-dicyanoimidazolate.
  • the composition according to the second aspect of the present invention may also be used as an additive in an electrolytic composition.
  • the electrolytic composition is preferably used in a battery.
  • the electrolytic composition is used in a Li-ion battery.
  • the electrolytic composition comprises in addition to the present composition used as a solvent, at least one lithium salt.
  • said at least one lithium salt is selected from the group consisting of LiPF 6, LiBF 4, CH3COOL1, CH3SO3L1, CF3SO3L1, CF3COOL1, U2B12F12, libc 4 0 8, LiAsF 6, Li 2 SiF 6, Li 2 PF0 3 L1CIO4, lithium bis (trifluoromethanesulfonyl) imide, lithium bis (fluorosulfonyl) imide, lithium 2-trifluoromethyl-4,5-dicyanoimidazolate, lithium 2-pentafluoroethyl-4,5-dicyanoimidazolate.
  • the equipment used consists of a 316L stainless steel autoclave with a capacity of 0.8L surmounted by a condenser and a pressure regulating valve.
  • the autoclave is immersed in liquid nitrogen and the following constituents are successively introduced: 140 g (7.0 mol) of hydrofluoric acid, 100 g (0.7 mol) of 2,2-dichloropropionic acid and 13.3 g (0.07) mol of titanium tetrachloride (TiCl 4 ).
  • the temperature of the autoclave is then raised to room temperature (25 ° C).
  • the autoclave is then immersed in an oil bath and the temperature is raised to 125 ° C while the temperature of the condenser is maintained at about 17 ° C.
  • the pressure is set at 20 bara.
  • the yield of 2,2-difluoropropionic acid expressed as the ratio of the number of moles of 2,2-difluoropropionic acid detected to the number of moles of 2,2-dichloropropionic acid initially introduced, is 77.6%. After distillation and drying, the purity of 2,2-difluoropropionic acid is greater than 99%.
  • the content by weight of ethyl 2-chloro-2-fluoropropionate is 320 ppm
  • the weight content of HF is 23 ppm
  • the content by weight of water is 52 ppm
  • the content by weight of HCl is 5 ppm.
  • Example 2 Synthesis of Ethyl 2,2-difluoropropionate CH3CF2CO2CH2CH3
  • the equipment used is similar to that described in Example 1.
  • the autoclave is immersed in liquid nitrogen and the following constituents are introduced successively: 140 g (7.0 mol) of hydrofluoric acid, 100 g ( 0.58 mol) of ethyl 2,2-dichloropropionate (CH3CCI2CO2CH2CH3) and 18.2 g (0.07 mol) of SnCI 4 tin tetrachloride.
  • the autoclave is then immersed in an oil bath and the temperature is raised to 125 ° C while the temperature of the condenser is maintained at about 17 ° C.
  • the pressure is set at 20 bara.
  • the yield of ethyl 2,2-difluoropropionate expressed as the ratio of the number of moles of ethyl 2,2-difluoropropionate detected to the number of moles of ethyl 2,2-dichloropropionate initially introduced, is 62.degree. , 9%. After distillation and drying, the purity of ethyl 2,2-difluoropropionate is greater than 99%.
  • the content by weight of ethyl 2-chloro-2-fluoropropionate is 287 ppm
  • the weight content of HF is 17 ppm
  • the content by weight of water is 43 ppm
  • the content by weight of HCl is 4 ppm.
  • the reaction products are dried and analyzed by gas chromatography.
  • the yield of ethyl 2,2-difluoropropionate expressed as the ratio of the number of moles of 2,2-difluoropropionate of ethyl detected on the number of moles of 2,2-difluoropropionic acid initially introduced, is 91, 6%.
  • the purity of ethyl 2,2-difluoropropionate is greater than 98.3%.

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EP18724898.4A 2017-05-23 2018-05-22 Procede de preparation de composes fluoroorganiques Pending EP3630716A1 (fr)

Applications Claiming Priority (2)

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FR1754557A FR3066760B1 (fr) 2017-05-23 2017-05-23 Procede de preparation de composes fluoroorganiques.
PCT/EP2018/063316 WO2018215418A1 (fr) 2017-05-23 2018-05-22 Procede de preparation de composes fluoroorganiques

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EP3630716A1 true EP3630716A1 (fr) 2020-04-08

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EP (1) EP3630716A1 (he)
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FR (1) FR3066760B1 (he)
IL (1) IL270782B2 (he)
WO (1) WO2018215418A1 (he)

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JPS5569501A (en) 1978-11-21 1980-05-26 Otsuka Yakuhin Kogyo Kk Herbicide
DE3326210A1 (de) 1983-07-21 1985-01-31 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von fluorcarbonsaeuren
DE3904707A1 (de) 1989-02-16 1990-08-23 Bayer Ag Verfahren zur fluorierung von acrylsaeure und derivaten davon sowie neue fluorierte ester der 2,3-difluorpropionsaeure
JP3367861B2 (ja) * 1997-04-15 2003-01-20 セントラル硝子株式会社 ３，３−ジクロロ−１，１，１−トリフルオロアセトンの製造方法
FR2808268B1 (fr) 2000-04-26 2002-08-30 Atofina Liquides ioniques derives d'acides de lewis a base de titane, niobium, tantale, etain ou antimoine, et leurs applications
FR2812632B1 (fr) 2000-08-07 2003-03-07 Solvay Procede pour la synthese de composes fluoroorganiques
FR2975694B1 (fr) * 2011-05-24 2013-08-02 Arkema France Procede de preparation de bis(fluorosulfonyl)imidure de lithium
JP5923747B2 (ja) * 2013-12-04 2016-05-25 パナソニックＩｐマネジメント株式会社 ナトリウム二次電池

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US11981634B2 (en) 2024-05-14
FR3066760A1 (fr) 2018-11-30
US20200223777A1 (en) 2020-07-16
FR3066760B1 (fr) 2020-05-22
WO2018215418A1 (fr) 2018-11-29
CN110662735A (zh) 2020-01-07
IL270782B2 (he) 2023-10-01
IL270782B1 (he) 2023-06-01
IL270782A (he) 2020-01-30

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