US20130105724A1 - Stable 2,3,3,3-tetrafluoropropene composition - Google Patents

Stable 2,3,3,3-tetrafluoropropene composition Download PDF

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US20130105724A1
US20130105724A1 US13/808,326 US201113808326A US2013105724A1 US 20130105724 A1 US20130105724 A1 US 20130105724A1 US 201113808326 A US201113808326 A US 201113808326A US 2013105724 A1 US2013105724 A1 US 2013105724A1
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tetrafluoropropene
ppm
hfo
stable composition
composition according
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Beatrice Boussand
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Arkema France SA
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Arkema France SA
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C09K2205/126—Unsaturated fluorinated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/22—All components of a mixture being fluoro compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
    • C10M2209/043—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09—Characteristics associated with water
    • C10N2020/097—Refrigerants
    • C10N2020/101—Containing Hydrofluorocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention relates to a stable composition including 2,3,3,3-tetrafluoropropene capable of being used in refrigeration and air conditioning.
  • HFCs hydrofluorocarbons
  • HFC-134a hydrofluorocarbon (1,1,1,2-tetrafluoroethane: HFC-134a), which is less harmful to the ozone layer.
  • GWP Global Warning Potential
  • Hydrofluoroolefins have a low heating power and thus meet the objectives set by the Kyoto protocol.
  • the document JP 4-110388 discloses 2,3,3,3-tetrafluoropropene (HFO-1234yf) as heat transfer agent in refrigeration, air conditioning and heat pumps.
  • a refrigerant In addition to having good properties as a heat transfer agent, in order for a refrigerant to be accepted commercially, it must in particular be thermally stable and be compatible with lubricants. This is because it is highly desirable for the refrigerant to be compatible with a lubricant used in the compressor present in the majority of refrigeration systems. This refrigerant and lubricant combination is important for the use and the effectiveness of the refrigeration system; in particular, the lubricant has to be sufficiently soluble in the refrigerant throughout the operating temperature range.
  • fluoroolefins are capable of decomposing on contact with moisture, oxygen or other compounds when they are used as refrigerant, possibly at high temperature, it is recommended to stabilize them with at least one amine.
  • stabilizing agents such as benzophenone derivatives, lactones and some phosphorus-comprising compounds, have also been proposed for stabilizing fluoroolefins (WO 2008/027596, WO 2008/027516 and WO 2008/027515).
  • the document EP 2 149 543 describes a process for the purification of 1,1,1,2,3-pentafluoropropane, a starting material in the manufacture of HFO-1234yf, in order to obtain a product having a 1,1,1,2,3-pentafluoropropene (HFO-1225ye) content of less than 500 ppm and a trifluoropropyne content of less than 50 ppm.
  • the Applicant Company has now developed a 2,3,3,3-tetrafluoropropene composition which makes it possible to improve the thermal stability when it is used in refrigeration systems.
  • a subject-matter of the present invention is thus a stable composition (SC) comprising at least x% by weight of 2,3,3,3-tetrafluoropropene (99.8 ⁇ x ⁇ 100), at most y% by weight of unsaturated compound(s) (Ia) (0 ⁇ y ⁇ 0.2) chosen from 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoropropene, such as 1,3,3,3-tetrafluoropropene (Z and E isomers) and 1,1,2,3-tetrafluoropropene, and optionally at most 500 ppm of 3,3,3-trifluoropropyne and/or at most 200 ppm of 1,1,1,2,3-pentafluoropropene (HFO-1225ye).
  • SC stable composition
  • SC comprising at least x% by weight of 2,3,3,3-tetrafluoropropene (99.8 ⁇ x ⁇
  • the stable composition according to the present invention can additionally comprise at least one of the compounds (Ib) chosen from 1,1,1,2-tetrafluoropropane (HFC-254eb), 1,1,1,2,3-pentafluoropropane (HFC-245eb), 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1,2-trifluoroethane (HFC-143), 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene, cyclohexafluoropropene and 1,1,1,3,3-pentafluoropropene (HFO-1225zc).
  • the compounds (Ib) chosen from 1,1,1,2-tetrafluoropropane (HFC-254eb), 1,1,1,2,3-pentafluoropropane (HFC-245eb), 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1,2-trifluoroethane (HFC
  • the combined compounds (Ib) present in the composition according to the present invention represent at most 500 ppm.
  • the SC composition comprises at least 99.85% by weight of 2,3,3,3-tetrafluoropropene, at most y% by weight of unsaturated compound(s) (Ia) (0 ⁇ y ⁇ 0.15) chosen from 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoropropene, such as 1,3,3,3-tetrafluoropropene (Z and E isomers) and 1,1,2,3-tetrafluoropropene, and optionally at most 250 ppm of 3,3,3-trifluoropropyne and/or at most 50 ppm of 1,1,1,2,3-pentafluoropropene (HFO-1225ye).
  • unsaturated compound(s) (Ia) (0 ⁇ y ⁇ 0.15) chosen from 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoropropene,
  • the SC composition which is particularly preferred comprises at least 99.9% by weight of 2,3,3,3-tetrafluoropropene, at most y% by weight of unsaturated compound(s) (Ia) (0 ⁇ y ⁇ 0.1) chosen from 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoropropene, such as 1,3,3,3-tetrafluoropropene (Z and E isomers) and 1,1,2,3-tetrafluoropropene, and optionally at most 200 ppm of 3,3,3-trifluoropropyne and/or at most 5 ppm of 1,1,1,2,3-pentafluoropropene (HFO-1225ye).
  • unsaturated compound(s) (Ia) (0 ⁇ y ⁇ 0.1) chosen from 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoro
  • the SC composition comprises from 99.85 to 99.98% by weight of 2,3,3,3-tetrafluoropropene, from 0.02 to 0.15% by weight of unsaturated compound(s) (Ia) chosen from 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoropropene, such as 1,3,3,3-tetrafluoropropene (Z and E isomers) and 1,1,2,3-tetrafluoropropene, and optionally at most 200 ppm of 3,3,3-trifluoropropyne and/or at most 5 ppm of 1,1,1,2,3-pentafluoropropene (HFO-1225ye) and/or at most 400 ppm of compounds (Ib).
  • unsaturated compound(s) (Ia) chosen from 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-t
  • the stable composition according to the invention exhibits the advantage of being able to be obtained directly by a process for the manufacture of 2,3,3,3-tetrafluoropropene, optionally after at least one separation stage.
  • Another subject-matter of the present invention is 2,3,3,3-tetrafluoropropene which has a purity of greater than or equal to 99.8% by weight and less than 100% by weight and which comprises at most 0.2% by weight of unsaturated compounds (Ia), optionally at most 500 ppm of 3,3,3-trifluoropropyne and/or at most 200 ppm of 1,1,1,2,3-pentafluoropropene and/or at most 500 ppm of compounds (Ib).
  • An additional subject-matter of the present invention is 2,3,3,3-tetrafluoropropene which has a purity of greater than or equal to 99.9% by weight and less than 100% by weight and which comprises at most 0.1% by weight of unsaturated compounds (Ia), optionally at most 200 ppm of 3,3,3-trifluoropropyne and/or at most 5 ppm of 1,1,1,2,3-pentafluoropropene and/or at most 500 ppm of compounds (Ib).
  • 2,3,3,3-Tetrafluoropropene can be obtained from hexafluoropropene (HFP) in at least 4 reaction stages: -(i) hydrogenation of HFP in the presence of a hydrogenation catalyst in a solid phase to give 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in stage (i) in the liquid phase using an alkali metal hydroxide or in the gas phase in the presence of a dehydrohalogenation catalyst to give 1,1,1,2,3-pentafluoropropene; (iii) hydrogenation of the HFO-1225ye obtained in (ii) in the presence of a hydrogenation catalyst in the solid phase to give 1,1,1,2,3-pentafluoropropane; (iv) dehydrofluorination of the HFC-245eb obtained in stage (iii) in the liquid phase using an alkali
  • 2,3,3,3-Tetrafluoropropene can be obtained from hexafluoropropene (HFP) in at least 2 reaction stages: -(i) hydrogenation of HFP in the presence of a hydrogenation catalyst in the solid phase to give 1,1,1,2,3-pentafluoropropane; (ii) dehydrofluorination of the HFC-245eb obtained in stage (i) in the liquid phase using an alkali metal hydroxide or in the gas phase in the presence of a dehydrohalogenation catalyst to give 2,3,3,3-tetrafluoropropene.
  • HFP hexafluoropropene
  • the 2,3,3,3-tetrafluoropropene according to the present invention can be obtained from HFP according to a process as described above after a purification of the HFC-245eb and/or after purification of the 2,3,3,3-tetrafluoropropene
  • the HFC-245eb prior to the dehydrofluorination stage, is, for example, purified by distillation at an absolute pressure of 6 bar and at a column bottom temperature of 80° C. and a top temperature of 50° C. with approximately 30 theoretical plates and a reflux ratio of approximately 37.
  • the HFO-1234yf is subjected to double distillation.
  • the first distillation is carried out at an absolute pressure of approximately 13 bar, a column bottom temperature of approximately 60° C. and a top temperature of approximately 40° C. and with approximately 35 theoretical plates and a reflux ratio of approximately 500.
  • the second distillation is carried out at an absolute pressure of approximately 11 bar, a column bottom temperature of approximately 105° C., and a top temperature of approximately 44° C. and with approximately 30 theoretical plates at a reflux ratio of approximately 4.
  • the 2,3,3,3-tetrafluoropropene can also be obtained from 1,1,1-trifluoro-2-chloropropene by hydrofluorination in the liquid or gas phase in the presence of a fluorination catalyst.
  • the 2,3,3,3-tetrafluoropropene thus obtained can be purified to give the 2,3,3,3-tetrafluoropropene according to the present invention.
  • compositions according to the present invention are capable of being used as heat transfer agent in stationary or motor-vehicle air conditioning, refrigeration and heat pumps.
  • compositions as described above are the compositions as described above in combination with a lubricant.
  • PEOs polyol esters
  • PAGs polyalkylene glycols
  • PVEs polyvinyl ethers
  • the PAG lubricants are in the oxyalkylene homo- or copolymer form.
  • the preferred PAGs are homopolymers composed of oxypropylene groups with a viscosity of 10 to 200 centistokes at 40° C., advantageously between 30 and 80 centistokes.
  • the PAGs which may be suitable are those having hydroxyl groups for each ending or —O—C n H 2n+1 groups.
  • Esters of carboxylic acids having a carbon chain of 4 to 9 atoms are preferred.
  • carboxylic acid of 4 to 9 carbon atoms of n-pentanoic acid, n-hexanoic acid, n-heptanoic acid, n-octanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpentanoic acid, 3,5,5-trimethylhexanoic acid, adipic acid and succinic acid.
  • the POE oils selected can comprise between 0 and 5 relative mol % of CH 2 —O units with respect to the —CH 2 —O—(C ⁇ O)— units.
  • the preferred POE lubricants are those having a viscosity of 1 to 1000 centistokes (cSt) at 40° C., preferably of 10 to 200 cSt and advantageously of 30 to 80 cSt
  • thermal stability trials are carried out according to Standard ASHRAE 97-2007: “sealed glass tube method to test the chemical stability of materials for use within refrigerant systems”.
  • Test conditions are as follows: Weight of fluid: 2.2 g Weight of lubricant: 5 g
  • Lengths of steel are introduced into tubes.
  • the length of steel and the lubricant are introduced into a 42.2 ml glass tube.
  • the tube is subsequently evacuated under vacuum and then the fluid F is added thereto.
  • the tube is then welded in order to close it and placed in an oven at 200° C. for 14 days.
  • the lubricant used in the tests is a commercial PAG oil: PAG ND8.
  • the fluid used for these trials comprises essentially HFO-1234yf (at least 99.9% by weight) and then 300 ppm of HFO-1243zf, 500 ppm of E HFO-1234ze and 300 ppm of HFO-1243zf+500 ppm of E HFO-1234ze are respectively added to the fluid.
  • the examples show that the presence of the compounds (Ia) is not harmful to the thermal stability, either of the HFO-1234yf composition or of the lubricant, and in some cases improves it.

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  • Chemical & Material Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US13/808,326 2010-07-09 2011-06-20 Stable 2,3,3,3-tetrafluoropropene composition Abandoned US20130105724A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/808,326 US20130105724A1 (en) 2010-07-09 2011-06-20 Stable 2,3,3,3-tetrafluoropropene composition

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR1055628A FR2962442B1 (fr) 2010-07-09 2010-07-09 Composition stable de 2,3,3,3-tetrafluoropropene
FR1055628 2010-07-09
US36453910P 2010-07-15 2010-07-15
PCT/FR2011/051406 WO2012004487A2 (fr) 2010-07-09 2011-06-20 Composition stable de 2,3,3,3-tetrafluoropropene
US13/808,326 US20130105724A1 (en) 2010-07-09 2011-06-20 Stable 2,3,3,3-tetrafluoropropene composition

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PCT/FR2011/051406 A-371-Of-International WO2012004487A2 (fr) 2010-07-09 2011-06-20 Composition stable de 2,3,3,3-tetrafluoropropene

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CN102985397B (zh) 2018-04-17
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JP2018076500A (ja) 2018-05-17
US20180327645A1 (en) 2018-11-15
US10662357B2 (en) 2020-05-26
WO2012004487A3 (fr) 2012-03-29
CN107254296A (zh) 2017-10-17
EP2590916B1 (fr) 2016-10-12
CN102985397A (zh) 2013-03-20
ES2602747T3 (es) 2017-02-22
FR2962442B1 (fr) 2016-02-26
JP2020041147A (ja) 2020-03-19
EP2590916A2 (fr) 2013-05-15
FR2962442A1 (fr) 2012-01-13
WO2012004487A2 (fr) 2012-01-12
JP6615846B2 (ja) 2019-12-04
JP2013544896A (ja) 2013-12-19
US10119055B2 (en) 2018-11-06

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