[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

US20110186772A1 - Heat transfer fluid - Google Patents

Heat transfer fluid Download PDF

Info

Publication number
US20110186772A1
US20110186772A1 US13/122,606 US200913122606A US2011186772A1 US 20110186772 A1 US20110186772 A1 US 20110186772A1 US 200913122606 A US200913122606 A US 200913122606A US 2011186772 A1 US2011186772 A1 US 2011186772A1
Authority
US
United States
Prior art keywords
weight
tetrafluoropropene
difluoromethane
difluoroethane
compositions
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.)
Abandoned
Application number
US13/122,606
Inventor
Wissam Rached
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Arkerna France
Original Assignee
Arkerna France
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40627376&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20110186772(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Arkerna France filed Critical Arkerna France
Assigned to ARKEMA FRANCE reassignment ARKEMA FRANCE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RACHED, WISSAM
Publication of US20110186772A1 publication Critical patent/US20110186772A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
    • C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B31/00—Compressor arrangements
    • F25B31/002—Lubrication
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B45/00—Arrangements for charging or discharging refrigerant
    • 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
    • C09K2205/122—Halogenated 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
    • C09K2205/10—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
    • 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
    • C09K2205/40—Replacement mixtures
    • 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
    • C09K2205/40—Replacement mixtures
    • C09K2205/43—Type R22
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C10M2203/065—Well-defined aromatic 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
    • 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
    • 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
    • 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
    • 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 compositions comprising hydrofluoroolefins and to their uses as heat transfer fluids, blowing agents, solvents and aerosols.
  • HFCs hydrofluorocarbons
  • HFC-134a hydrofluorocarbon (1,1,1,2-tetrafluoroethane: HFC-134a), which is less harmful to the ozone layer.
  • CFC-12 chlorofluorocarbon
  • HFC-134a hydrofluorocarbon (1,1,1,2-tetrafluoroethane: HFC-134a)
  • GWP global warming potential
  • Carbon dioxide being non-toxic, non-flammable and having a very low GWP, has been proposed as a refrigerant fluid for air-conditioning systems, as a replacement for HFC-134a.
  • the use of carbon dioxide presents a number of disadvantages, associated in particular with the very high pressure of its use as a refrigerant fluid in existing apparatus and technologies.
  • the mixture R-404A composed of 44% by weight of pentafluoroethane, 52% by weight of trifluoroethane and 4% by weight of HFC-134a
  • This mixture is widely used as a refrigerant fluid in superstores (supermarket) and in refrigerated transport.
  • This mixture has a GWP of 3900.
  • the mixture R-407C composed of 52% by weight of HFC-134a, 25% by weight of pentafluoroethane and 23% by weight of difluoromethane, is used as a heat transfer fluid in air conditioning and in heat pumps.
  • This mixture however, has a GWP of 1800.
  • Document WO 2004/037913 discloses the use of compositions comprising at least one fluoroalkene having three or four carbon atoms, more particularly pentafluoropropene and tetrafluoropropene, preferably having a GWP of not more than 150, as heat transfer fluids.
  • Document WO 2005/105947 teaches the addition to tetrafluoropropene, preferably 1,3,3,3-tetrafluoropropene, of a co-blowing agent such as difluoro-methane, pentafluoroethane, tetrafluoroethane, difluoroethane, heptafluoro-propane, hexafluoropropane, pentafluoropropane, pentafluorobutane, water or carbon dioxide.
  • a co-blowing agent such as difluoro-methane, pentafluoroethane, tetrafluoroethane, difluoroethane, heptafluoro-propane, hexafluoropropane, pentafluoropropane, pentafluorobutane, water or carbon dioxide.
  • compositions which contain hydrofluoropropenes, which can be used as a heat transfer fluid, which do not have the aforementioned drawbacks and which combine a zero ODP with a GWP lower than that of existing heat transfer fluids such as R-404A or R-407C or R22 (chlorodifluoromethane).
  • compositions according to the present invention are characterized in that they comprise 60% to 90% by weight of 2,3,3,3-tetrafluoropropene and 10% to 40% by weight of at least one compound selected from difluoroethane and difluoromethane.
  • compositions comprise 60% to 79% by weight of 2,3,3,3-tetrafluoropropene and 21% to 40% by weight of a compound selected from difluoroethane and difluoromethane.
  • compositions according to this first embodiment preferably comprise 60% to 70% by weight of 2,3,3,3-tetrafluoropropene and 30% to 40% by weight of a compound selected from difluoroethane and difluoromethane.
  • compositions according to this first embodiment comprise 60% to 65% by weight of 2,3,3,3-tetrafluoropropene and 35% to 40% by weight of a compound selected from difluoroethane and difluoromethane.
  • compositions which are particularly preferred according to this first embodiment comprise 2,3,3,3-tetrafluoropropene and difluoromethane.
  • compositions contain essentially 2,3,3,3-tetrafluoropreopene and difluoromethane.
  • compositions comprise 60% to 90% by weight of 2,3,3,3-tetrafluoropropene and 10% to 40% by weight of a mixture composed of dichloromethane and difluoroethane.
  • compositions which are preferred according to this second embodiment comprise 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 20% to 40% by weight of a mixture composed of difluoromethane and difluoroethane.
  • compositions which are advantageously preferred according to this second embodiment comprise 60% to 75% by weight of 2,3,3,3-tetrafluoropropene and 25% to 40% by weight of a mixture composed of difluoromethane and difluoroethane.
  • compositions comprise 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 5% to 35% by weight of difluoromethane and 5% to 35% by weight of difluoroethane.
  • compositions which are of interest are those comprising or containing essentially 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 10% to 30% by weight of difluoromethane and 10% to 30% by weight of difluoroethane.
  • compositions according to the invention may comprise a stabilizer for 2,3,3,3-tetrafluoropropene.
  • the stabilizer represents not more than 5% by weight, relative to the total composition.
  • Stabilizers include more particularly nitromethane, ascorbic acid, terephthalic acid, azoles such as tolutriazole or benzotriazole, phenolic compounds such as tocopherol, hydroquinone, tert-butylhydroquinone, 2,6-di-tert-butyl-4-methylphenol, epoxides (alkyl, optionally fluorinated or perfluorinated, or alkenyl or aromatic) such as n-butyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether and butylphenyl glycidyl ether, phosphites, phosphates, phosphonates, thiols and lactones.
  • epoxides alkyl, optionally fluorinated or perfluorinated, or alkenyl or aromatic
  • compositions according to the present invention may comprise lubricants such as mineral oil, alkylbenzene, polyalkylene glycol and polyvinyl ether.
  • compositions according to the present invention are suitable for replacing R-404A in refrigeration and/or R-407C in air conditioning and heat pumps in existing systems. They may also be suitable for replacing R-404A in refrigeration systems with a cascaded compression regime in which at least one stage is operated with the compositions according to the present invention.
  • compositions which are of particular interest for the replacement of R-404A in existing systems include those comprising or containing essentially 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoromethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoromethane; and 60% by weight of 2,3,3,3-tetrafluoropropene, 30% by weight of difluoromethane and 10% by weight of difluoroethane.
  • compositions which are of particular interest for the replacement of R-404A in systems operating with a cascaded compression regime include those comprising or containing essentially 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoroethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoroethane; and 75% by weight of 2,3,3,3-tetrafluoropropene, 20% by weight of difluoromethane and 5% by weight of difluoroethane.
  • compositions according to the present invention may also be used as a replacement for R-407C, for example in heat pumps.
  • compositions which are of particular interest for the replacement of R-407C in existing systems include those comprising or containing essentially 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoromethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoromethane; 60% by weight of 2,3,3,3-tetrafluoropropene, 30% by weight of difluoromethane and 10% by weight of difluoroethane; and 70% by weigh of 2,3,3,3-tetrafluoropropene, 25% by weight of difluoromethane and 5% by weight of difluoroethane.
  • compositions according to the present invention can be used, furthermore, as blowing agents, aerosols and solvents.
  • compositions according to the invention under the operating conditions of refrigeration are given in Table 1.
  • values of the constituents (1234yf, 32 and 152a) for each composition are given as percentages by weight.
  • the nominal operating pressure is 18 bar
  • the volumetric capacity is 1500 kJ/m 3
  • the COP is 1.8 under the following operating conditions.
  • Evaporation temperature ⁇ 20° C.
  • Condensation temperature 40° C.
  • Compressor inlet temperature ⁇ 5° C.
  • Super cooled liquid temperature 33° C.
  • Isentropic yield of the compressor 70%
  • BP pressure at the evaporator
  • HP pressure at the condenser Ratio: compression ratio
  • T comp outlet temperature at the compressor outlet
  • COP coefficient of performance—defined, for the purposes of refrigeration, as being the useful cooling power supplied by the system, as a proportion of the power provided or consumed by the system.
  • CAP volumetric capacity (kJ/m 3 ) %
  • CAP or COP is the ratio of the value of the CAP or COP of the mixture in relation to the same value for R404A.
  • compositions according to the present invention under the operating conditions of a heat pump and air conditioning are given in Table 2.
  • values of the constituents (1234yf, 32 and 152a) for each composition are given as percentages by weight.
  • the nominal operating pressure is 34 bar
  • the volumetric capacity is 1461 kJ/m 3
  • the COP is 2.1 under the following operating conditions:
  • Evaporation temperature ⁇ 5° C.
  • Condensation temperature 70° C.
  • Compressor inlet temperature 5° C.
  • Supercooled liquid temperature 65° C.
  • Isentropic yield of the compressor 70%
  • BR pressure at the evaporator HP: pressure at the condenser Ratio: compression ratio
  • T comp outlet temperature at the compressor outlet
  • COP coefficient of performance—defined, for the purposes of a heat pump, as being the useful heating power supplied by the system, as a proportion of the power provided or consumed by the system.
  • CAP volumetric capacity (kJ/m 3 ) %
  • CAP or COP is the ratio of the value of the CAP or COP of the mixture in relation to the same value for the R-407C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

The present invention relates to compositions which are based on tetrafluoropropene and more particularly relates to compositions comprising 60% to 90% by weight of 2,3,3,3-tetrafluoropropene and 10% to 40% by weight of at least one compound selected from difluoroethane and difluoromethane, which can be used as a heat transfer fluid.

Description

  • The present invention relates to compositions comprising hydrofluoroolefins and to their uses as heat transfer fluids, blowing agents, solvents and aerosols.
  • The problems posed by substances which deplete the atmospheric ozone layer (ODP: ozone depletion potential) were tackled at Montreal, where a protocol was signed which imposes a reduction on the production and use of chlorofluorocarbons (CFCs). This protocol has been the subject of amendments, which have imposed the abandonment of CFCs and have extended the regulations to other products, among them hydrochlorofluorocarbons (HCFCs).
  • The refrigeration industry and the air conditioning industry have invested much in the replacement of these refrigerant fluids, and a product of this investment has been the commercialization of hydrofluorocarbons (HFCs).
  • (Hydro)chlorofluorocarbons which are used as expandants or solvents have also been replaced by HFCs.
  • In the automotive industry, the air-conditioning systems of vehicles which are sold in many countries have switched from a chlorofluorocarbon (CFC-12) refrigerant fluid to that of a hydrofluorocarbon (1,1,1,2-tetrafluoroethane: HFC-134a), which is less harmful to the ozone layer. However, in view of the objectives set by the Kyoto Protocol, HFC-134a (GWP=1300) is considered to have a high warming potential. The contribution to the greenhouse effect of a fluid is quantified by a criterion, the GWP (global warming potential), which indexes the warming potential by taking a reference value of 1 for carbon dioxide.
  • Carbon dioxide, being non-toxic, non-flammable and having a very low GWP, has been proposed as a refrigerant fluid for air-conditioning systems, as a replacement for HFC-134a. However, the use of carbon dioxide presents a number of disadvantages, associated in particular with the very high pressure of its use as a refrigerant fluid in existing apparatus and technologies.
  • Moreover, the mixture R-404A, composed of 44% by weight of pentafluoroethane, 52% by weight of trifluoroethane and 4% by weight of HFC-134a, is widely used as a refrigerant fluid in superstores (supermarket) and in refrigerated transport. This mixture, however, has a GWP of 3900. The mixture R-407C, composed of 52% by weight of HFC-134a, 25% by weight of pentafluoroethane and 23% by weight of difluoromethane, is used as a heat transfer fluid in air conditioning and in heat pumps. This mixture, however, has a GWP of 1800.
  • Document JP 4110388 describes the use of hydrofluoropropenes of formula C3HmFn, where m and n represent an integer between 1 and 5 inclusive and m+n=6, as heat transfer fluids, especially tetrafluoropropene and trifluoropropene. Document WO 2004/037913 discloses the use of compositions comprising at least one fluoroalkene having three or four carbon atoms, more particularly pentafluoropropene and tetrafluoropropene, preferably having a GWP of not more than 150, as heat transfer fluids.
  • Document WO 2005/105947 teaches the addition to tetrafluoropropene, preferably 1,3,3,3-tetrafluoropropene, of a co-blowing agent such as difluoro-methane, pentafluoroethane, tetrafluoroethane, difluoroethane, heptafluoro-propane, hexafluoropropane, pentafluoropropane, pentafluorobutane, water or carbon dioxide.
  • Document WO 2006/094303 discloses an azeotropic composition containing 7.4% by weight of 2,3,3,3-tetrafluoropropene (1234yf) and 92.6% by weight of difluoromethane (HFC-32). This document likewise discloses an azeotropic composition containing 91% by weight of 2,3,3,3-tetrafluoropropene and 9% by weight of difluoroethane (HFC-152a).
  • The applicant has now developed compositions which contain hydrofluoropropenes, which can be used as a heat transfer fluid, which do not have the aforementioned drawbacks and which combine a zero ODP with a GWP lower than that of existing heat transfer fluids such as R-404A or R-407C or R22 (chlorodifluoromethane).
  • The compositions according to the present invention are characterized in that they comprise 60% to 90% by weight of 2,3,3,3-tetrafluoropropene and 10% to 40% by weight of at least one compound selected from difluoroethane and difluoromethane.
  • According to a first embodiment of the invention the compositions comprise 60% to 79% by weight of 2,3,3,3-tetrafluoropropene and 21% to 40% by weight of a compound selected from difluoroethane and difluoromethane.
  • The compositions according to this first embodiment preferably comprise 60% to 70% by weight of 2,3,3,3-tetrafluoropropene and 30% to 40% by weight of a compound selected from difluoroethane and difluoromethane.
  • Advantageously the compositions according to this first embodiment comprise 60% to 65% by weight of 2,3,3,3-tetrafluoropropene and 35% to 40% by weight of a compound selected from difluoroethane and difluoromethane.
  • The compositions which are particularly preferred according to this first embodiment comprise 2,3,3,3-tetrafluoropropene and difluoromethane.
  • Advantageously these compositions contain essentially 2,3,3,3-tetrafluoropreopene and difluoromethane.
  • According to a second embodiment of the invention the compositions comprise 60% to 90% by weight of 2,3,3,3-tetrafluoropropene and 10% to 40% by weight of a mixture composed of dichloromethane and difluoroethane.
  • The compositions which are preferred according to this second embodiment comprise 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 20% to 40% by weight of a mixture composed of difluoromethane and difluoroethane.
  • The compositions which are advantageously preferred according to this second embodiment comprise 60% to 75% by weight of 2,3,3,3-tetrafluoropropene and 25% to 40% by weight of a mixture composed of difluoromethane and difluoroethane.
  • Particularly preferred compositions comprise 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 5% to 35% by weight of difluoromethane and 5% to 35% by weight of difluoroethane.
  • The compositions which are of interest are those comprising or containing essentially 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 10% to 30% by weight of difluoromethane and 10% to 30% by weight of difluoroethane.
  • The compositions according to the invention may comprise a stabilizer for 2,3,3,3-tetrafluoropropene. The stabilizer represents not more than 5% by weight, relative to the total composition.
  • Stabilizers include more particularly nitromethane, ascorbic acid, terephthalic acid, azoles such as tolutriazole or benzotriazole, phenolic compounds such as tocopherol, hydroquinone, tert-butylhydroquinone, 2,6-di-tert-butyl-4-methylphenol, epoxides (alkyl, optionally fluorinated or perfluorinated, or alkenyl or aromatic) such as n-butyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether and butylphenyl glycidyl ether, phosphites, phosphates, phosphonates, thiols and lactones.
  • The compositions according to the present invention may comprise lubricants such as mineral oil, alkylbenzene, polyalkylene glycol and polyvinyl ether.
  • The compositions according to the present invention are suitable for replacing R-404A in refrigeration and/or R-407C in air conditioning and heat pumps in existing systems. They may also be suitable for replacing R-404A in refrigeration systems with a cascaded compression regime in which at least one stage is operated with the compositions according to the present invention. Examples of compositions which are of particular interest for the replacement of R-404A in existing systems include those comprising or containing essentially 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoromethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoromethane; and 60% by weight of 2,3,3,3-tetrafluoropropene, 30% by weight of difluoromethane and 10% by weight of difluoroethane.
  • Examples of compositions which are of particular interest for the replacement of R-404A in systems operating with a cascaded compression regime include those comprising or containing essentially 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoroethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoroethane; and 75% by weight of 2,3,3,3-tetrafluoropropene, 20% by weight of difluoromethane and 5% by weight of difluoroethane.
  • The compositions according to the present invention may also be used as a replacement for R-407C, for example in heat pumps.
  • Examples of compositions which are of particular interest for the replacement of R-407C in existing systems include those comprising or containing essentially 60% by weight of 2,3,3,3-tetrafluoropropene and 40% by weight of difluoromethane; 70% by weight of 2,3,3,3-tetrafluoropropene and 30% by weight of difluoromethane; 60% by weight of 2,3,3,3-tetrafluoropropene, 30% by weight of difluoromethane and 10% by weight of difluoroethane; and 70% by weigh of 2,3,3,3-tetrafluoropropene, 25% by weight of difluoromethane and 5% by weight of difluoroethane.
  • The compositions according to the present invention can be used, furthermore, as blowing agents, aerosols and solvents.
    • EXPERIMENTAL SECTION
  • The performance data of the compositions according to the invention under the operating conditions of refrigeration are given in Table 1. The values of the constituents (1234yf, 32 and 152a) for each composition are given as percentages by weight.
  • For R404A, the nominal operating pressure is 18 bar, the volumetric capacity is 1500 kJ/m3 and the COP is 1.8 under the following operating conditions.
  • Evaporation temperature: −20° C.
    Condensation temperature: 40° C.
    Compressor inlet temperature: −5° C.
    Super cooled liquid temperature: 33° C.
    Isentropic yield of the compressor: 70%
    BP: pressure at the evaporator
    HP: pressure at the condenser
    Ratio: compression ratio
    T comp outlet: temperature at the compressor outlet
    COP: coefficient of performance—defined, for the purposes of refrigeration, as being the useful cooling power supplied by the system, as a proportion of the power provided or consumed by the system.
    CAP: volumetric capacity (kJ/m3)
    % CAP or COP is the ratio of the value of the CAP or COP of the mixture in relation to the same value for R404A.
  • TABLE 1
    BP HP Ratio T comp.
    Compositions (bar) (bar) (p/p) outlet % COP % CAP
    R404A 3   18 6.10 77 100 100
    1234yf 32 152a
    60 40  0 2.7 21 7.57 111 96 102
    70 30  0 2.4 19 8.02 104 94 89
    75 25  0 2.2 18 8.19 101 94 83
    1234yf 32 152a
    60 20 20 2.0 16 8.01 100 98 76
    60 30 10 2.3 18 7.94 106 96 88
    70 25  5 2.2 18 8.10 101 95 83
    70 20 10 2.0 16 8.07 98 96 77
    75 20  5 2.0 16 8.16 97 95 77
    75 15 10 1.9 15 8.01 93 97 72
    85 10  5 1.8 14 7.92 86 99 67
    1234yf 32 152a
    60  0 40 1.5 10 6.60 79 114 59
    70  0 30 1.5 10 6.53 76 113 59
  • The performance data of the compositions according to the present invention under the operating conditions of a heat pump and air conditioning are given in Table 2. The values of the constituents (1234yf, 32 and 152a) for each composition are given as percentages by weight.
  • For R407c, the nominal operating pressure is 34 bar, the volumetric capacity is 1461 kJ/m3 and the COP is 2.1 under the following operating conditions:
  • Evaporation temperature: −5° C.
    Condensation temperature: 70° C.
    Compressor inlet temperature: 5° C.
    Supercooled liquid temperature: 65° C.
    Isentropic yield of the compressor: 70% BR pressure at the evaporator
    HP: pressure at the condenser
    Ratio: compression ratio
    T comp outlet: temperature at the compressor outlet
    COP: coefficient of performance—defined, for the purposes of a heat pump, as being the useful heating power supplied by the system, as a proportion of the power provided or consumed by the system.
    CAP: volumetric capacity (kJ/m3)
    % CAP or COP is the ratio of the value of the CAP or COP of the mixture in relation to the same value for the R-407C.
  • TABLE 2
    BP HP Ratio T comp.
    Compositions (bar) (bar) (p/p) outlet % COP % CAP
    R407C 3.9 34.4 127 100 100
    1234yf 32 152a
    60 40  0 4.8 39.7 8.30 133 91.9 112
    70 30  0 4.2 36.5 8.69 126 92.4 99
    75 25  0 3.9 34.6 8.85 122 93.2 93
    1234yf 32 152a
    60 20 20 3.5 30.1 8.64 121 101.5 89
    60 30 10 4.1 35.0 8.60 128 97.1 101
    70 25  5 3.9 33.9 8.74 123 95.5 94
    70 20 10 3.6 31.2 8.70 119 98.3 88
    75 20  5 3.6 31.8 8.79 118 96.4 88
    75 15 10 3.3 28.9 8.64 113 99.3 82
    85 10  5 3.1 26.7 8.58 107 99.3 75
    1234yf 32 152a
    60  0 40 2.6 18.9 7.27 98 113.7 67
    70  0 30 2.7 19.1 7.19 95 111.3 66

Claims (8)

1. Composition comprising 60% to 90% by weight of 2,3,3,3-tetrafluoropropene and 10% to 40% by weight of at least one compound selected from difluoroethane and difluoromethane.
2. Composition according to claim 1, characterized in that it comprises 60% to 79% by weight of 2,3,3,3-tetrafluoropropene and 21% to 40% by weight of a compound selected from the group consisting of difluoroethane and difluoromethane.
3. Composition according to either of claim 1, characterized in that it comprises 60% to 70% by weight of 2,3,3,3-tetrafluoropropene and 30% to 40% by weight of a compound selected from the group consisting of difluoroethane and difluoromethane.
4. Composition according to claim 1, characterized in that it comprises 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 20% to 40% by weight of a mixture composed of difluoromethane and difluoroethane.
5. Composition according to claim 1, characterized in that it comprises 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 5% to 35% by weight of difluoromethane and 5% to 35% by weight of difluoroethane.
6. Composition according to claim 1, characterized in that it comprises 60% to 80% by weight of 2,3,3,3-tetrafluoropropene and 10% to 30% by weight of difluoromethane and 10% to 30% by weight of difluoroethane.
7. Heat transfer fluid according to claim 1.
8. Composition according to claim 1, characterized in that it is used as a replacement for R-404A in refrigeration and/or as a replacement for R-407C in heat pumps or air conditioning.
US13/122,606 2008-10-08 2009-09-24 Heat transfer fluid Abandoned US20110186772A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR0856817A FR2936806B1 (en) 2008-10-08 2008-10-08 REFRIGERANT FLUID
FR08.56817 2008-10-08
FR08.56836 2008-10-09
FR0856836A FR2936807B3 (en) 2008-10-08 2008-10-09 HEAT TRANSFER FLUID
PCT/FR2009/051814 WO2010040928A1 (en) 2008-10-08 2009-09-24 Heat transfer fluid

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2009/051814 A-371-Of-International WO2010040928A1 (en) 2008-10-08 2009-09-24 Heat transfer fluid

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/873,855 Continuation US9599381B2 (en) 2008-10-08 2015-10-02 Heat transfer fluid

Publications (1)

Publication Number Publication Date
US20110186772A1 true US20110186772A1 (en) 2011-08-04

Family

ID=40627376

Family Applications (4)

Application Number Title Priority Date Filing Date
US13/122,606 Abandoned US20110186772A1 (en) 2008-10-08 2009-09-24 Heat transfer fluid
US14/873,855 Active US9599381B2 (en) 2008-10-08 2015-10-02 Heat transfer fluid
US15/396,855 Abandoned US20170145276A1 (en) 2008-10-08 2017-01-03 Heat transfer fluid
US16/142,492 Active US11130893B2 (en) 2008-10-08 2018-09-26 Heat transfer fluid

Family Applications After (3)

Application Number Title Priority Date Filing Date
US14/873,855 Active US9599381B2 (en) 2008-10-08 2015-10-02 Heat transfer fluid
US15/396,855 Abandoned US20170145276A1 (en) 2008-10-08 2017-01-03 Heat transfer fluid
US16/142,492 Active US11130893B2 (en) 2008-10-08 2018-09-26 Heat transfer fluid

Country Status (10)

Country Link
US (4) US20110186772A1 (en)
EP (2) EP2586842A3 (en)
JP (5) JP5591246B2 (en)
CN (1) CN102171309B (en)
ES (1) ES2663548T3 (en)
FR (2) FR2936806B1 (en)
PL (1) PL2331651T3 (en)
PT (1) PT2331651T (en)
TW (1) TWI406934B (en)
WO (1) WO2010040928A1 (en)

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120267564A1 (en) * 2009-12-21 2012-10-25 Ei Du Pont De Nemours And Company Compositions comprising tetrafluoropropene and difluoromethane and uses thereof
US20130055738A1 (en) * 2010-05-11 2013-03-07 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
WO2013032908A3 (en) * 2011-08-26 2013-07-25 E. I. Du Pont De Nemours And Company Compositions comprising tetrafluoropropene and methods of use thereof
US20150013942A1 (en) * 2008-11-19 2015-01-15 E I Du Pont De Nemours And Company Tetrafluoropropene compositions and uses thereof
US8940180B2 (en) 2012-11-21 2015-01-27 Honeywell International Inc. Low GWP heat transfer compositions
US9011711B2 (en) 2009-09-11 2015-04-21 Arkema France Heat transfer fluid replacing R-410A
US9028706B2 (en) 2011-02-10 2015-05-12 Arkema France Binary compositions of 2,3,3,3-tetrafluoropropene and of ammonia
US9039922B2 (en) 2009-09-11 2015-05-26 Arkema France Low-temperature and average-temperature refrigeration
US9127191B2 (en) 2009-09-11 2015-09-08 Arkema France Use of ternary compositions
US9133379B2 (en) 2009-09-11 2015-09-15 Arkema France Binary refrigerating fluid
US9169427B2 (en) 2011-07-13 2015-10-27 Honeywell International Inc. Low GWP heat transfer compositions containing difluoromethane, a fluorinated ethane and 1,3,3,3-tetrafluoropropene
US9175203B2 (en) 2009-09-11 2015-11-03 Arkema France Ternary compositions for low-capacity refrigeration
US9267064B2 (en) 2009-09-11 2016-02-23 Arkema France Ternary compositions for high-capacity refrigeration
US9315708B2 (en) 2011-05-04 2016-04-19 Arkema France Heat-transfer compositions exhibiting improved miscibility with the lubricating oil
US9512343B2 (en) 2010-09-20 2016-12-06 Arkema France Composition based on 2,3,3,3-tetrafluoropropene
US9528735B2 (en) 2012-09-04 2016-12-27 Daikin Industries, Ltd. Method for filling mixed refrigerant containing 2,3,3,3-tetrafluoropropene
US9599381B2 (en) 2008-10-08 2017-03-21 Arkema France Heat transfer fluid
US9650551B2 (en) 2012-12-26 2017-05-16 Arkema France Composition including 2,3,3,3-tetrafluoropropene
US9650553B2 (en) 2012-12-26 2017-05-16 Arkema France Azeotropic or quasi-azeotropic composition of chloromethane
US9683157B2 (en) 2009-09-11 2017-06-20 Arkema France Heat transfer method
US9683156B2 (en) * 2013-09-11 2017-06-20 Arkema France Heat transfer fluids comprising difluoromethane, pentafluoroethane, tetrafluoropropene and optionally propane
US9683155B2 (en) 2012-12-26 2017-06-20 Arkema France Composition containing 2,3,3,3-tetrafluoropropene and 1,2-difluoroethylene
US9752069B2 (en) 2012-11-20 2017-09-05 Arkema France Refrigerant composition
US9758709B2 (en) 2010-01-27 2017-09-12 Daikin Industries, Ltd. Refrigerant composition comprising difluoromethane (HFC32) and 2,3,3,3-tetrafluoropropene (HFO1234yf)
US9783721B2 (en) 2012-08-20 2017-10-10 Honeywell International Inc. Low GWP heat transfer compositions
US9845419B2 (en) 2009-07-29 2017-12-19 Honeywell International Inc. Low GWP heat transfer compositions containing difluoromethane and 1,3,3,3-tetrafluoropropene
US9908828B2 (en) 2015-03-18 2018-03-06 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US9982180B2 (en) 2013-02-13 2018-05-29 Honeywell International Inc. Heat transfer compositions and methods
US10005940B2 (en) 2015-02-19 2018-06-26 Daikin Industries, Ltd. Composition containing mixture of fluorinated hydrocarbons, and method for producing same
US10023780B2 (en) 2013-07-11 2018-07-17 Arkema France 2,3,3,3-tetrafluoropropene compositions having improved miscibility
US10035938B2 (en) 2009-09-11 2018-07-31 Arkema France Heat transfer fluid replacing R-134a
US10119055B2 (en) 2010-07-09 2018-11-06 Arkema France Stable 2,3,3,3-tetrafluoropropene composition
US10252913B2 (en) 2013-03-20 2019-04-09 Arkema France Composition comprising HF and 2,3,3,3-tetrafluoropropene
US10308853B2 (en) 2009-12-18 2019-06-04 Arkema France Heat-transfer fluids having reduced flammability
US10450488B2 (en) 2012-01-26 2019-10-22 Arkema France Heat transfer compositions having improved miscibility with lubricating oil
US10808157B2 (en) 2008-11-03 2020-10-20 Arkema France Vehicle heating and/or air conditioning method
US10858561B2 (en) 2008-10-16 2020-12-08 Arkema France Heat transfer method
US10954467B2 (en) 2016-10-10 2021-03-23 Arkema France Use of tetrafluoropropene based compositions
US11001546B2 (en) 2018-02-05 2021-05-11 Arkema France Ternary azeotropic or quasi-azeotropic composition comprising HF, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane
US11053420B2 (en) 2017-09-12 2021-07-06 Arkema France Composition on the basis of hydrochlorofluoroolefin and mineral oil
US11306232B2 (en) 2016-10-10 2022-04-19 Arkema France Tetrafluoropropene-based azeotropic compositions
US11359122B2 (en) 2017-03-21 2022-06-14 Arkema France Method for heating and/or air-conditioning in a vehicle
US11370948B2 (en) 2017-03-21 2022-06-28 Arkema France Tetrafluoropropene-based composition
US11629278B2 (en) 2018-02-15 2023-04-18 Arkema France Heat transfer compositions as replacement for R-134A

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2942237B1 (en) * 2009-02-13 2013-01-04 Arkema France METHOD FOR HEATING AND / OR AIR CONDITIONING A VEHICLE
US20120119136A1 (en) * 2010-11-12 2012-05-17 Honeywell International Inc. Low gwp heat transfer compositions
JP2013120029A (en) * 2011-12-08 2013-06-17 Panasonic Corp Air conditioner
JP2016513749A (en) * 2013-03-15 2016-05-16 ハネウェル・インターナショナル・インコーポレーテッド Low GWP heat transfer composition
US9631779B2 (en) * 2013-08-15 2017-04-25 Star Headlight & Lantern Co., Inc. Optical system utilizing LED illumination for a light bar, and light bar having same
FR3023286B1 (en) * 2014-07-02 2018-02-16 Arkema France PROCESS FOR THE PRODUCTION OF TETRAFLUOROPROPENE
CN112789342A (en) * 2018-10-04 2021-05-11 科慕埃弗西有限公司 Azeotropic compositions of HFO-1234YF and propylene
BR112021022059A2 (en) 2018-10-26 2021-12-28 Chemours Co Fc Llc Fluoropropene compositions, methods of producing a mixture and cooling, processes for transferring heat, for treating a surface and for forming a composition, refrigeration system, refrigeration apparatus, use of the fluoropropene composition and method for replacing a soda
US11209196B2 (en) * 2018-10-26 2021-12-28 The Chemours Company Fc, Llc HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions
KR20210124247A (en) * 2019-02-14 2021-10-14 이데미쓰 고산 가부시키가이샤 composition for refrigerator
EP3969536B1 (en) * 2019-05-17 2024-09-11 The Chemours Company FC, LLC Refrigerant compressor systems

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US20090314015A1 (en) * 2006-09-01 2009-12-24 E. I. Du Pont De Nemours And Company Method for circulating selected heat transfer fluids through a closed loop cycle
US20100044619A1 (en) * 2003-10-27 2010-02-25 Honeywell International Inc. Compositions Containing Difluoromethane and Fluorine Substituted Olefins
US20100235063A1 (en) * 2008-01-21 2010-09-16 Toyota Jidosha Kabushiki Kaisha Vehicle controller and vehicle provided with the controller
US8246850B2 (en) * 2008-06-11 2012-08-21 Arkema France Hydrofluoroolefin compositions
US20140166923A1 (en) * 2002-10-25 2014-06-19 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins

Family Cites Families (91)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH549772A (en) 1972-04-29 1974-05-31 Bertrams Ag Hch CROSS COUNTERFLOW HEAT EXCHANGER AND METHOD OF ITS MANUFACTURING.
FR2256381A1 (en) 1973-12-27 1975-07-25 Tour Agenturer Ab Arrangement for heating or cooling a flow medium - part of air currents diverted to a circuit containing e.g. ammonia in a heat exchanger
JP2852362B2 (en) 1990-04-27 1999-02-03 日本電信電話株式会社 Word line drive
JPH04110388A (en) 1990-08-31 1992-04-10 Daikin Ind Ltd Fluid for heat transfer
ES2168257T3 (en) * 1991-10-11 2002-06-16 Ici Plc WORKING LIQUIDS.
JP3270706B2 (en) 1997-03-24 2002-04-02 三菱電機株式会社 Multi-source refrigeration equipment
US6503417B1 (en) 1998-04-13 2003-01-07 E. I. Du Pont De Nemours And Company Ternary compositions of ammonia, pentafluoroethane and difluoromethane
JP2000161805A (en) 1998-11-27 2000-06-16 Daikin Ind Ltd Refrigerating apparatus
US6176102B1 (en) 1998-12-30 2001-01-23 Praxair Technology, Inc. Method for providing refrigeration
US20040089839A1 (en) 2002-10-25 2004-05-13 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
US9005467B2 (en) 2003-10-27 2015-04-14 Honeywell International Inc. Methods of replacing heat transfer fluids
DE08020700T1 (en) 2002-10-25 2009-08-13 Honeywell International Inc. Compositions with fluoro-substituted olefins
US7279451B2 (en) 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US20090253820A1 (en) 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
JP4110388B2 (en) 2003-01-10 2008-07-02 荒川化学工業株式会社 Cleaning agent and rinsing agent for gold-plated parts, cleaning method and rinsing method
JP2005202637A (en) * 2004-01-15 2005-07-28 Matsushita Electric Ind Co Ltd Automatic vending machine
JP4454324B2 (en) 2004-01-29 2010-04-21 三洋電機株式会社 Booster unit
JP4454323B2 (en) 2004-01-29 2010-04-21 三洋電機株式会社 Refrigeration system
JP4432654B2 (en) 2004-07-22 2010-03-17 パナソニック株式会社 Bathroom ventilation heater
JP4420807B2 (en) * 2004-12-14 2010-02-24 三洋電機株式会社 Refrigeration equipment
US7569170B2 (en) 2005-03-04 2009-08-04 E.I. Du Pont De Nemours And Company Compositions comprising a fluoroolefin
CN100575813C (en) 2005-03-18 2009-12-30 开利商业冷藏公司 Multi-part heat exchanger
JP2007169331A (en) * 2005-12-19 2007-07-05 Kanou Reiki Kogyo:Kk Non-azeotropic mixture coolant for super low temperature and single unit type freezing circuit for super low temperature
GB0614080D0 (en) 2006-07-17 2006-08-23 Ineos Fluor Holdings Ltd Heat transfer compositions
JP5008365B2 (en) 2006-09-21 2012-08-22 旭化成ケミカルズ株式会社 Vinylidene chloride copolymer resin composition
JP2008134031A (en) 2006-11-29 2008-06-12 Hitachi Appliances Inc Refrigerating device using zeotropic refrigerant mixture
CN101622509B (en) 2006-12-19 2011-06-08 纳幕尔杜邦公司 Air conditioner system for automobile
JP2008159353A (en) 2006-12-22 2008-07-10 Matsushita Electric Ind Co Ltd Method and device for manufacturing button type zinc air battery
ES2982776T3 (en) 2007-01-31 2024-10-17 Chemours Co Fc Llc A vapor compression heat transfer system
US8024937B2 (en) 2007-06-21 2011-09-27 E. I. Du Pont De Nemours And Company Method for leak detection in heat transfer systems
WO2009018117A1 (en) 2007-07-27 2009-02-05 E. I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
JP4556001B2 (en) 2007-12-27 2010-10-06 日立化成工業株式会社 Method for forming surface protective film of flexible wiring board
JP2009257652A (en) 2008-02-29 2009-11-05 Daikin Ind Ltd Refrigerating apparatus
JP2009257655A (en) 2008-03-04 2009-11-05 Daikin Ind Ltd Refrigerating apparatus
JP2009257745A (en) * 2008-03-25 2009-11-05 Daikin Ind Ltd Refrigerating device
JP2009257601A (en) * 2008-04-11 2009-11-05 Daikin Ind Ltd Air conditioning device
US8038899B2 (en) 2008-04-28 2011-10-18 Honeywell International Inc. Refrigerant compositions having a siloxane solubilizing agent
FR2932494B1 (en) 2008-06-11 2011-02-25 Arkema France COMPOSITIONS BASED ON HYDROFLUOROOLEFINS
FR2932492B1 (en) 2008-06-11 2010-07-30 Arkema France COMPOSITIONS BASED ON HYDROFLUOROOLEFINS
JP2010002074A (en) * 2008-06-18 2010-01-07 Mitsubishi Electric Corp Mixed refrigerant and refrigerating cycle device using the same
WO2010002023A1 (en) 2008-07-01 2010-01-07 Daikin Industries, Ltd. REFRIGERANT COMPOSITION COMPRISING DIFLUOROMETHANE (HFC32), 2,3,3,3-TETRAFLUOROPROPENE (HFO1234yf) AND 1,1,1,2-TETRAFLUOROETHANE (HFC134a)
WO2010002016A1 (en) 2008-07-01 2010-01-07 Daikin Industries, Ltd. REFRIGERANT COMPOSITION COMPRISING DIFLUOROMETHANE (HFC32) AND 2,3,3,3-TETRAFLUOROPROPENE (HFO1234yf)
CN104059613A (en) * 2008-07-30 2014-09-24 霍尼韦尔国际公司 Compositions Containing Fluorine Substituted Olefins
US11214720B2 (en) 2009-07-29 2022-01-04 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins
EP2149592B1 (en) * 2008-07-30 2016-04-13 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins
FR2936806B1 (en) 2008-10-08 2012-08-31 Arkema France REFRIGERANT FLUID
US20170080773A1 (en) 2008-11-03 2017-03-23 Arkema France Vehicle Heating and/or Air Conditioning Method
FR2937906B1 (en) 2008-11-03 2010-11-19 Arkema France METHOD FOR HEATING AND / OR AIR CONDITIONING A VEHICLE
US20100122545A1 (en) 2008-11-19 2010-05-20 E. I. Du Pont De Nemours And Company Tetrafluoropropene compositions and uses thereof
BR122013002802A2 (en) 2008-11-19 2016-01-05 Du Pont composition, process for producing cooling, process for producing heating, method, apparatus and stationary cooling system
FR2938550B1 (en) 2008-11-20 2010-11-12 Arkema France COMPOSITION COMPRISING 2,3,3,3-TETRAFLUOROPROPENE METHOD FOR HEATING AND / OR AIR CONDITIONING A VEHICLE
FR2938551B1 (en) 2008-11-20 2010-11-12 Arkema France METHOD FOR HEATING AND / OR AIR CONDITIONING A VEHICLE
FR2941039B1 (en) 2009-01-14 2013-02-08 Arkema France HEAT TRANSFER METHOD
JP2010203759A (en) 2009-02-04 2010-09-16 Panasonic Corp Freezer
FR2942237B1 (en) 2009-02-13 2013-01-04 Arkema France METHOD FOR HEATING AND / OR AIR CONDITIONING A VEHICLE
US9845419B2 (en) 2009-07-29 2017-12-19 Honeywell International Inc. Low GWP heat transfer compositions containing difluoromethane and 1,3,3,3-tetrafluoropropene
FR2950066B1 (en) 2009-09-11 2011-10-28 Arkema France LOW AND MEDIUM TEMPERATURE REFRIGERATION
US10035938B2 (en) 2009-09-11 2018-07-31 Arkema France Heat transfer fluid replacing R-134a
FR2950071B1 (en) 2009-09-11 2012-02-03 Arkema France TERNARY COMPOSITIONS FOR LOW CAPACITY REFRIGERATION
FR2950067B1 (en) 2009-09-11 2011-10-28 Arkema France HEAT TRANSFER FLUID IN REPLACEMENT OF R-410A
FR2950069B1 (en) 2009-09-11 2011-11-25 Arkema France USE OF TERNARY COMPOSITIONS
FR2950070B1 (en) 2009-09-11 2011-10-28 Arkema France TERNARY COMPOSITIONS FOR HIGH CAPACITY REFRIGERATION
FR2950065B1 (en) 2009-09-11 2012-02-03 Arkema France BINARY REFRIGERANT FLUID
FR2950068B1 (en) 2009-09-11 2012-05-18 Arkema France HEAT TRANSFER METHOD
FR2954342B1 (en) 2009-12-18 2012-03-16 Arkema France HEAT TRANSFER FLUIDS WITH REDUCED FLAMMABILITY
FR2957083B1 (en) 2010-03-02 2015-12-11 Arkema France HEAT TRANSFER FLUID FOR CENTRIFUGAL COMPRESSOR
FR2959999B1 (en) 2010-05-11 2012-07-20 Arkema France HEAT TRANSFER FLUIDS AND THEIR USE IN COUNTER-CURRENT HEAT EXCHANGERS
FR2959998B1 (en) 2010-05-11 2012-06-01 Arkema France TERNARY HEAT TRANSFER FLUIDS COMPRISING DIFLUOROMETHANE, PENTAFLUOROETHANE AND TETRAFLUOROPROPENE
FR2959997B1 (en) 2010-05-11 2012-06-08 Arkema France HEAT TRANSFER FLUIDS AND THEIR USE IN COUNTER-CURRENT HEAT EXCHANGERS
JP2013529703A (en) 2010-06-22 2013-07-22 アーケマ・インコーポレイテッド Heat transfer composition of hydrofluorocarbon and hydrofluoroolefin
FR2962130B1 (en) 2010-06-30 2012-07-20 Arkema France COMPOSITION BASED ON 2,3,3,3-TETRAFLUOROPROPENE
FR2962442B1 (en) 2010-07-09 2016-02-26 Arkema France STABLE 2,3,3,3-TETRAFLUOROPROPENE COMPOSITION
FR2964975B1 (en) 2010-09-20 2012-08-24 Arkema France COMPOSITION BASED ON 2,3,3,3-TETRAFLUOROPROPENE
FR2971512B1 (en) 2011-02-10 2013-01-18 Arkema France BINARY COMPOSITIONS OF 2,3,3,3-TETRAFLUOROPROPENE AND AMMONIA
FR2974812B1 (en) 2011-05-04 2014-08-08 Arkema France HEAT TRANSFER COMPOSITIONS HAVING IMPROVED MISCIBILITY WITH LUBRICATING OIL
FR2986007B1 (en) 2012-01-25 2015-01-23 Arkema France HEAT TRANSFER COMPOSITIONS HAVING IMPROVED MISCIBILITY WITH LUBRICATING OIL
FR2986236B1 (en) 2012-01-26 2014-01-10 Arkema France HEAT TRANSFER COMPOSITIONS HAVING IMPROVED MISCIBILITY WITH LUBRICATING OIL
FR3000095B1 (en) 2012-12-26 2015-02-20 Arkema France COMPOSITION COMPRISING 2,3,3,3-TETRAFLUOROPROPENE AND 1,2-DIFLUOROETHYLENE
FR3000093B1 (en) 2012-12-26 2015-07-17 Arkema France AZEOTROPIC OR QUASI-AZEOTROPIC COMPOSITION OF CHLOROMETHANE
FR3000096B1 (en) 2012-12-26 2015-02-20 Arkema France COMPOSITION COMPRISING 2,3,3,3-TETRAFLUOROPROPENE
FR3003565B1 (en) 2013-03-20 2018-06-29 Arkema France COMPOSITION COMPRISING HF AND 2,3,3,3-TETRAFLUOROPROPENE
FR3008419B1 (en) 2013-07-11 2015-07-17 Arkema France 2,3,3,3-TETRAFLUOROPROPENE-BASED COMPOSITIONS HAVING IMPROVED MISCIBILITY
FR3033791B1 (en) 2015-03-18 2017-04-14 Arkema France STABILIZATION OF 1-CHLORO-3,3,3-TRIFLUOROPROPENE
FR3057272B1 (en) 2016-10-10 2020-05-08 Arkema France AZEOTROPIC COMPOSITIONS BASED ON TETRAFLUOROPROPENE
FR3057271B1 (en) 2016-10-10 2020-01-17 Arkema France USE OF TETRAFLUOROPROPENE COMPOSITIONS
FR3061906B1 (en) 2017-01-19 2019-03-15 Arkema France COMPOSITION COMPRISING 2,3,3,3-TETRAFLUOROPROPENE
FR3061905B1 (en) 2017-01-19 2019-05-17 Arkema France COMPOSITION COMPRISING 2,3,3,3-TETRAFLUOROPROPENE
FR3070982B1 (en) 2017-09-12 2019-08-30 Arkema France COMPOSITION BASED ON HYDROCHLOROFLUOROOLEFIN AND MINERAL OIL
FR3077572B1 (en) 2018-02-05 2021-10-08 Arkema France TERNARY AZEOTROPIC OR QUASI-AZEOTROPIC COMPOSITION COMPRISING HF, 2,3,3,3-TETRAFLUOROPROPENE AND 1,1,1,2,2, -PENTAFLUOROPROPANE.
FR3077822B1 (en) 2018-02-15 2020-07-24 Arkema France REPLACEMENT HEAT TRANSFER COMPOSITIONS FOR R-134A
FR3080169B1 (en) 2018-04-13 2020-12-18 Arkema France PROCESS FOR COOLING AND / OR HEATING A BODY OR A FLUID IN A MOTOR VEHICLE

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140166923A1 (en) * 2002-10-25 2014-06-19 Honeywell International Inc. Compositions containing difluoromethane and fluorine substituted olefins
US20100044619A1 (en) * 2003-10-27 2010-02-25 Honeywell International Inc. Compositions Containing Difluoromethane and Fluorine Substituted Olefins
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US20090314015A1 (en) * 2006-09-01 2009-12-24 E. I. Du Pont De Nemours And Company Method for circulating selected heat transfer fluids through a closed loop cycle
US20100235063A1 (en) * 2008-01-21 2010-09-16 Toyota Jidosha Kabushiki Kaisha Vehicle controller and vehicle provided with the controller
US8246850B2 (en) * 2008-06-11 2012-08-21 Arkema France Hydrofluoroolefin compositions

Cited By (82)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9599381B2 (en) 2008-10-08 2017-03-21 Arkema France Heat transfer fluid
US11130893B2 (en) 2008-10-08 2021-09-28 Arkema France Heat transfer fluid
US10858561B2 (en) 2008-10-16 2020-12-08 Arkema France Heat transfer method
US10808157B2 (en) 2008-11-03 2020-10-20 Arkema France Vehicle heating and/or air conditioning method
US10208236B2 (en) 2008-11-19 2019-02-19 The Chemours Company Fc, Llc Tetrafluoropropene compositions and uses thereof
US9540556B2 (en) * 2008-11-19 2017-01-10 The Chemours Company Fc, Llc Tetrafluoropropene compositions and uses thereof
US20150013942A1 (en) * 2008-11-19 2015-01-15 E I Du Pont De Nemours And Company Tetrafluoropropene compositions and uses thereof
US10767092B2 (en) 2008-11-19 2020-09-08 The Chemours Company Fc, Llc Tetrafluoropropene compositions and uses thereof
US9845419B2 (en) 2009-07-29 2017-12-19 Honeywell International Inc. Low GWP heat transfer compositions containing difluoromethane and 1,3,3,3-tetrafluoropropene
US10316231B2 (en) 2009-09-11 2019-06-11 Arkema France Low-temperature and average-temperature refrigeration
US9011711B2 (en) 2009-09-11 2015-04-21 Arkema France Heat transfer fluid replacing R-410A
US10358592B2 (en) 2009-09-11 2019-07-23 Arkema France Heat transfer method
US9127191B2 (en) 2009-09-11 2015-09-08 Arkema France Use of ternary compositions
US9133379B2 (en) 2009-09-11 2015-09-15 Arkema France Binary refrigerating fluid
US9663697B2 (en) 2009-09-11 2017-05-30 Arkema France Use of ternary compositions
US9175203B2 (en) 2009-09-11 2015-11-03 Arkema France Ternary compositions for low-capacity refrigeration
US9683157B2 (en) 2009-09-11 2017-06-20 Arkema France Heat transfer method
US9267064B2 (en) 2009-09-11 2016-02-23 Arkema France Ternary compositions for high-capacity refrigeration
US10858562B2 (en) 2009-09-11 2020-12-08 Arkema France Binary refrigerating fluid
US10125296B2 (en) 2009-09-11 2018-11-13 Arkema France Binary refrigerating fluid
US9039922B2 (en) 2009-09-11 2015-05-26 Arkema France Low-temperature and average-temperature refrigeration
US9399726B2 (en) 2009-09-11 2016-07-26 Arkema France Use of ternary compositions
US10035938B2 (en) 2009-09-11 2018-07-31 Arkema France Heat transfer fluid replacing R-134a
US9505968B2 (en) 2009-09-11 2016-11-29 Arkema France Ternary compositions for low-capacity refrigeration
US9884984B2 (en) 2009-09-11 2018-02-06 Arkema France Binary refrigerating fluid
US11352533B2 (en) 2009-12-18 2022-06-07 Arkema France Heat-transfer fluids having reduced flammability
US10308853B2 (en) 2009-12-18 2019-06-04 Arkema France Heat-transfer fluids having reduced flammability
US20120267564A1 (en) * 2009-12-21 2012-10-25 Ei Du Pont De Nemours And Company Compositions comprising tetrafluoropropene and difluoromethane and uses thereof
US10619082B2 (en) 2010-01-27 2020-04-14 Daikin Industries, Ltd. Refrigerant composition comprising difluoromethane (HFC32) and 2,3,3,3-tetrafluoropropene (HFO1234yf)
US9758709B2 (en) 2010-01-27 2017-09-12 Daikin Industries, Ltd. Refrigerant composition comprising difluoromethane (HFC32) and 2,3,3,3-tetrafluoropropene (HFO1234yf)
US9359540B2 (en) 2010-05-11 2016-06-07 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US20130055738A1 (en) * 2010-05-11 2013-03-07 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US9057010B2 (en) * 2010-05-11 2015-06-16 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US9488398B2 (en) 2010-05-11 2016-11-08 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US10662357B2 (en) 2010-07-09 2020-05-26 Arkema France Stable 2,3,3,3-tetrafluoropropene composition
US10119055B2 (en) 2010-07-09 2018-11-06 Arkema France Stable 2,3,3,3-tetrafluoropropene composition
US9512343B2 (en) 2010-09-20 2016-12-06 Arkema France Composition based on 2,3,3,3-tetrafluoropropene
US9028706B2 (en) 2011-02-10 2015-05-12 Arkema France Binary compositions of 2,3,3,3-tetrafluoropropene and of ammonia
US9676984B2 (en) 2011-05-04 2017-06-13 Arkema France Heat-transfer compositions exhibiting improved miscibility with the lubricating oil
US9315708B2 (en) 2011-05-04 2016-04-19 Arkema France Heat-transfer compositions exhibiting improved miscibility with the lubricating oil
US9169427B2 (en) 2011-07-13 2015-10-27 Honeywell International Inc. Low GWP heat transfer compositions containing difluoromethane, a fluorinated ethane and 1,3,3,3-tetrafluoropropene
JP2014528987A (en) * 2011-08-26 2014-10-30 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ Compositions containing tetrafluoropropene and methods of use thereof
US10836943B2 (en) 2011-08-26 2020-11-17 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and methods of use thereof
US9932507B2 (en) 2011-08-26 2018-04-03 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and methods of use thereof
US11840657B2 (en) 2011-08-26 2023-12-12 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and methods of use thereof
WO2013032908A3 (en) * 2011-08-26 2013-07-25 E. I. Du Pont De Nemours And Company Compositions comprising tetrafluoropropene and methods of use thereof
CN103917621A (en) * 2011-08-26 2014-07-09 纳幕尔杜邦公司 Compositions comprising tetrafluoropropene and methods of use thereof
US20140216074A1 (en) * 2011-08-26 2014-08-07 E I Du Pont De Nemours And Company Compositions comprising tetrafluoropropene and methods of use thereof
US9249347B2 (en) * 2011-08-26 2016-02-02 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and methods of use thereof
US10035940B2 (en) 2011-08-26 2018-07-31 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and methods of use thereof
CN106978141A (en) * 2011-08-26 2017-07-25 纳幕尔杜邦公司 Composition comprising tetrafluoropropene and use their method
US20160102231A1 (en) * 2011-08-26 2016-04-14 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and methods of use thereof
TWI585065B (en) * 2011-08-26 2017-06-01 杜邦股份有限公司 Compositions comprising tetrafluoropropene and methods of use thereof
US10184074B2 (en) 2011-08-26 2019-01-22 The Chemours Company Fc, Llc Compositions comprising tetrafluoropropene and methods of use thereof
US10450488B2 (en) 2012-01-26 2019-10-22 Arkema France Heat transfer compositions having improved miscibility with lubricating oil
US9783721B2 (en) 2012-08-20 2017-10-10 Honeywell International Inc. Low GWP heat transfer compositions
US9528735B2 (en) 2012-09-04 2016-12-27 Daikin Industries, Ltd. Method for filling mixed refrigerant containing 2,3,3,3-tetrafluoropropene
US9752069B2 (en) 2012-11-20 2017-09-05 Arkema France Refrigerant composition
US8940180B2 (en) 2012-11-21 2015-01-27 Honeywell International Inc. Low GWP heat transfer compositions
US9650551B2 (en) 2012-12-26 2017-05-16 Arkema France Composition including 2,3,3,3-tetrafluoropropene
US10131829B2 (en) 2012-12-26 2018-11-20 Arkema France Composition containing 2,3,3,3-tetrafluoropropene and 1,2-difluoroethylene
US9969918B2 (en) 2012-12-26 2018-05-15 Arkema France Azeotropic or quasi-azeotropic composition of chloromethane
US10604690B2 (en) 2012-12-26 2020-03-31 Arkema France Composition including 2,3,3,3-tetrafluoropropene
US9683155B2 (en) 2012-12-26 2017-06-20 Arkema France Composition containing 2,3,3,3-tetrafluoropropene and 1,2-difluoroethylene
US9650553B2 (en) 2012-12-26 2017-05-16 Arkema France Azeotropic or quasi-azeotropic composition of chloromethane
US9982180B2 (en) 2013-02-13 2018-05-29 Honeywell International Inc. Heat transfer compositions and methods
US10252913B2 (en) 2013-03-20 2019-04-09 Arkema France Composition comprising HF and 2,3,3,3-tetrafluoropropene
US10023780B2 (en) 2013-07-11 2018-07-17 Arkema France 2,3,3,3-tetrafluoropropene compositions having improved miscibility
US10377935B2 (en) 2013-07-11 2019-08-13 Arkema France 2,3,3,3-tetrafluoropropene compositions having improved miscibility
US9683156B2 (en) * 2013-09-11 2017-06-20 Arkema France Heat transfer fluids comprising difluoromethane, pentafluoroethane, tetrafluoropropene and optionally propane
US10113093B2 (en) 2013-09-11 2018-10-30 Arkema France Heat transfer fluids comprising difluoromethane, pentafluoroethane, tetrafluoropropene and optionally propane
US10005940B2 (en) 2015-02-19 2018-06-26 Daikin Industries, Ltd. Composition containing mixture of fluorinated hydrocarbons, and method for producing same
US10618861B2 (en) 2015-03-18 2020-04-14 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US9908828B2 (en) 2015-03-18 2018-03-06 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US10399918B2 (en) 2015-03-18 2019-09-03 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US10954467B2 (en) 2016-10-10 2021-03-23 Arkema France Use of tetrafluoropropene based compositions
US11306232B2 (en) 2016-10-10 2022-04-19 Arkema France Tetrafluoropropene-based azeotropic compositions
US11359122B2 (en) 2017-03-21 2022-06-14 Arkema France Method for heating and/or air-conditioning in a vehicle
US11370948B2 (en) 2017-03-21 2022-06-28 Arkema France Tetrafluoropropene-based composition
US11053420B2 (en) 2017-09-12 2021-07-06 Arkema France Composition on the basis of hydrochlorofluoroolefin and mineral oil
US11001546B2 (en) 2018-02-05 2021-05-11 Arkema France Ternary azeotropic or quasi-azeotropic composition comprising HF, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane
US11629278B2 (en) 2018-02-15 2023-04-18 Arkema France Heat transfer compositions as replacement for R-134A

Also Published As

Publication number Publication date
EP2331651A1 (en) 2011-06-15
JP2021066889A (en) 2021-04-30
CN102171309A (en) 2011-08-31
JP5591246B2 (en) 2014-09-17
JP2016176082A (en) 2016-10-06
JP2014141681A (en) 2014-08-07
PT2331651T (en) 2018-03-28
WO2010040928A1 (en) 2010-04-15
US20170145276A1 (en) 2017-05-25
US20160025394A1 (en) 2016-01-28
JP2019052317A (en) 2019-04-04
FR2936806A1 (en) 2010-04-09
TWI406934B (en) 2013-09-01
US20190203094A1 (en) 2019-07-04
CN102171309B (en) 2014-06-25
ES2663548T3 (en) 2018-04-13
EP2586842A2 (en) 2013-05-01
EP2331651B1 (en) 2018-02-21
US11130893B2 (en) 2021-09-28
PL2331651T3 (en) 2018-06-29
JP2012505279A (en) 2012-03-01
TW201026835A (en) 2010-07-16
US9599381B2 (en) 2017-03-21
FR2936807A1 (en) 2010-04-09
FR2936806B1 (en) 2012-08-31
EP2586842A3 (en) 2017-03-08
FR2936807B3 (en) 2012-10-26

Similar Documents

Publication Publication Date Title
US11130893B2 (en) Heat transfer fluid
US8246850B2 (en) Hydrofluoroolefin compositions
US8486294B2 (en) Hydrofluoroolefin compositions
US8252198B2 (en) Hydrofluoroolefin compositions
US10858561B2 (en) Heat transfer method
US20190040292A1 (en) Heat transfer process

Legal Events

Date Code Title Description
AS Assignment

Owner name: ARKEMA FRANCE, FRANCE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:RACHED, WISSAM;REEL/FRAME:026151/0049

Effective date: 20110307

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION