FR2912419A1 - Refrigerant fluid with very low ozone depletion potential and global warming potential, especially for vehicle air conditioners, based on optionally fluorinated linear diether such as bis-trifluoromethoxy-methane - Google Patents

Refrigerant fluid with very low ozone depletion potential and global warming potential, especially for vehicle air conditioners, based on optionally fluorinated linear diether such as bis-trifluoromethoxy-methane Download PDF

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FR2912419A1
FR2912419A1 FR0753184A FR0753184A FR2912419A1 FR 2912419 A1 FR2912419 A1 FR 2912419A1 FR 0753184 A FR0753184 A FR 0753184A FR 0753184 A FR0753184 A FR 0753184A FR 2912419 A1 FR2912419 A1 FR 2912419A1
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methane
hydro
chf
trifluoromethoxy
bis
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FR2912419B1 (en
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Wissam Rached
Michel Devic
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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
    • 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

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  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Refrigerant fluid with a very low ozone depletion potential and global warming potential, contains at least one optionally fluorinated linear 3C diether other than perfluorodimethoxymethane. Refrigerant fluid with an ozone depletion potential (ODP) of zero or less than 0.02 and a global warming potential (GWP) of less than 150, containing at least one 3C linear diether of formula R 1-O-R 3-O-R 2(I), in which R 1, R 2methyl (optionally partly or completely fluorinated); R 3optionally fluorinated methylene, i.e. -CH 2-, -CHF- or -CF 2- , not including the compound CF 3-O-CF 2-O-CF 3. An independent claim is also included for a device for transferring heat in a compression cycle containing this fluid.

Description

11

La présente invention concerne des fluides frigorigènes aptes à être utilisés dans les différents types de systèmes à compression et en particulier dans la production d'air conditionné. Elle a plus particulièrement pour objet des fluides frigorigènes dont la contribution à l'effet de serre est très faible.  The present invention relates to refrigerants suitable for use in the various types of compression systems and in particular in the production of air conditioning. It relates more particularly to refrigerants whose contribution to the greenhouse effect is very low.

Les problèmes posés par les substances appauvrissant la couche d'ozone atmosphérique (ODP : ozone depletion potential) ont été traités à Montréal où a été signé le protocole imposant une réduction de la production et de l'utilisation des chlorofluorocarbures (CFC). Ce protocole a fait l'objet d'amendements qui ont imposé l'abandon des CFC et étendu la réglementation à d'autres produits, dont les hydrochlorofluorocarbones (HCFC). L'industrie de la réfrigération et de la production d'air conditionné a beaucoup investi dans la substitution de ces fluides frigorigènes et c'est ainsi que les hydrofluorocarbures (HFC) ont été commercialisés. Dans l'industrie automobile, les systèmes de climatisation des véhicules commercialisés dans de nombreux pays sont passés d'un fluide frigorigène au chlorofluorocarbure (CFC-12) à celui de l'hydrofluorocarbure (1,1,1,2 tetrafluoroéthane : HFC-134a), moins nocif pour la couche d'ozone. Cependant, au regard des objectifs fixés par le protocole de Kyoto, le HFC-134a (GWP = 1300) est considéré comme ayant un pouvoir de réchauffement élevé. La contribution à l'effet de serre d'un fluide est quantifiée par un critère, le GWP (Global Warming Potentials) qui résume le pouvoir de réchauffement en prenant une valeur de référence de 1 pour le dioxyde de carbone. Le dioxyde de carbone étant non-toxique, ininflammable et ayant un très faible GWP, a été proposé comme fluide frigorigène des systèmes de climatisation en remplacement du HFC-134a. Toutefois, l'emploi du dioxyde de carbone présente plusieurs inconvénients, notamment liés à la pression très élevée de sa mise en oeuvre en tant que fluide frigorigène dans les appareils et technologies existantes. Par ailleurs, le document EP 980910 décrit des compositions azéotropiques ou quasi-azéotropiques à base d'hydrofluoropolyéthers en remplacement du CFC-113. 2  The problems posed by ozone depletion potential (ODP) have been addressed in Montreal, where the protocol for reducing the production and use of chlorofluorocarbons (CFCs) has been signed. This protocol has been amended to remove CFCs and extend the regulation to include other products, including hydrochlorofluorocarbons (HCFCs). The refrigeration and air-conditioning industry has invested heavily in the substitution of these refrigerants and so hydrofluorocarbons (HFCs) have been marketed. In the automotive industry, the air conditioning systems of vehicles marketed in many countries have moved from a refrigerant to chlorofluorocarbon (CFC-12) to that of hydrofluorocarbon (1,1,1,2 tetrafluoroethane: HFC-134a ), less harmful for 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 Potentials) which summarizes 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 refrigerant air conditioning systems replacing HFC-134a. However, the use of carbon dioxide has several disadvantages, particularly related to the very high pressure of its implementation as a refrigerant in existing devices and technologies. Furthermore, the document EP 980910 describes azeotropic or quasi-azeotropic compositions based on hydrofluoropolyethers to replace CFC-113. 2

Le document EP 1016839 décrit l'utilisation d'un mélange comprenant au moins un composant provenant du groupe constitué des fluorocarbures, hydrofluorocarbures et fluoroéthers et au moins un composant provenant du groupe constitué des fluorocarbures, hydrofluorocarbures et fluoroéthers et gaz atmosphériques, lesdits composants étant différents pour la production de la réfrigération. Le document WO 94/26837 décrit des compositions pour la réfrigération comprenant au moins un fluoroéther acyclique. Il a maintenant été trouvé des fluides frigorigènes ayant à la fois un ODP nul ou inférieur à 0,02 et un GWP inférieur à 150. Les fluides frigorigènes selon la présente invention comprennent au moins un diéther linéaire à trois atomes de carbone représenté par la formule générale (I) ( R1-O-R3-O- R2) dans laquelle Fn et R2 identiques ou différents, représentent chacun un radical méthyle pouvant être partiellement ou totalement fluoré et F3 représente un radical méthylène éventuellement fluoré choisi parmi ù CH2 -, -CHF ù et -CF2-. Le CF3-O-CF2-O-CF3 est exclu de la formule générale (I). Comme diéthers de formule générale (I) pouvant convenir à la présente invention, on peut citer notamment le dimethoxymethane(CH3-O-CH2-O-CH3), le methane,fluorodimethoxy-(CH3-0-CHF-O-C H3), le fluoro(methoxymethoxy)methane(CH3-O-C H2-O-CH2F), le fluoro(fluoromethoxy)methoxymethane(CH3-O-CHF-O-CH2F), le [methanediylbis(oxy)]bis(fluoromethane) (CH2F-O-CH2-O-CH2F), le difluoro(methoxymethoxy)methane (CH3-O-CH2-O-CHF2), le methane,difluorodimethoxy-(CH3-0-CF2-0-C H3), le fluoro[bis(fluoromethoxy)]methane(CH2F-O-CHF-O-CH2F), le difluoro[(fluoromethoxy)methoxy]methane(CHF2-O-CH2-O-CH2F), le difluoro(fluoromethoxy)methoxymethane(CH3-O-CF2-O-CH2F), le trifluoro(methoxymethoxy)methane(CH3-O-CH2-O-CF3), le trifluoro[fluoro(methoxy)methoxy]methane(CH3-O-CHF-O-CF3), Ie(difluoromethoxy)(difluoro)methoxymethane(CH3-O-CF2-O-CHF2), le methanediylbis(oxy)]bis(difluoromethane)(CHF2-O-CH2-O-CHF2), le 3  EP 1016839 discloses the use of a mixture comprising at least one component from the group consisting of fluorocarbons, hydrofluorocarbons and fluoroethers and at least one component from the group consisting of fluorocarbons, hydrofluorocarbons and fluoroethers and atmospheric gases, said components being different for the production of refrigeration. WO 94/26837 discloses compositions for refrigeration comprising at least one acyclic fluoroether. It has now been found that refrigerants having both ODP zero or less than 0.02 and a GWP of less than 150. The refrigerants according to the present invention comprise at least one linear three-carbon diether represented by the formula general formula (I) (R 1 -O-R 3 -O-R 2) in which Fn and R 2, which are identical or different, each represent a methyl radical which may be partially or completely fluorinated and F 3 represents an optionally fluorinated methylene radical chosen from CH 2 -; CHF ù and -CF2-. CF3-O-CF2-O-CF3 is excluded from the general formula (I). As diethers of general formula (I) which may be suitable for the present invention, there may be mentioned in particular dimethoxymethane (CH3-O-CH2-O-CH3), methane, fluorodimethoxy- (CH3-O-CHF-OCH3), fluoro (methoxymethoxy) methane (CH3-OC H2-O-CH2F), fluoro (fluoromethoxy) methoxymethane (CH3-O-CHF-O-CH2F), [methanediylbis (oxy)] bis (fluoromethane) (CH2F-O- CH2-O-CH2F), difluoro (methoxymethoxy) methane (CH3-O-CH2-O-CHF2), methane, difluorodimethoxy- (CH3-O-CF2-O-H3), fluoro [bis (fluoromethoxy)) methane (CH2F-O-CHF-O-CH2F), difluoro [(fluoromethoxy) methoxy] methane (CHF2-O-CH2-O-CH2F), difluoro (fluoromethoxy) methoxymethane (CH3-O-CF2-O- CH2F), trifluoro (methoxymethoxy) methane (CH3-O-CH2-O-CF3), trifluoro [fluoro (methoxy) methoxy] methane (CH3-O-CHF-O-CF3), and (difluoromethoxy) (difluoro) methoxymethane (CH3-O-CF2-O-CHF2), methanediylbis (oxy)] bis (difluoromethane) (CHF2-O-CH2-O-CHF2), on 3

trifluoro[(fluoromethoxy)methoxy]methane(CH2F-O-CH2-O-CF3), le (difluoromethoxy)(fluoro)(fluoromethoxy)methane(CH2F-O-CHF-O-CHF2), le difluoro[bis(fluoromethoxy)]methane(CH2F-O-CF2-O-CH2F), le (difluoromethoxy)(difluoro)(fluoromethoxy)methane(CHF2-O-CF2-O-CH2F), le [difluoro(methoxy)methoxy](trifluoro)methane(CF3-0-CF2-0-C H3), le [(difluoromethoxy)methoxy](trifluoro)methane(CF3-O-CH2-O-CHF2), le trifluoro[fluoro(fluoromethoxy)methoxy]methane(CF3-O-CHF-O-CH2F), le [difluoro(fluoromethoxy)methoxy](trifluoro)methane(CF3-O-CF2-O-CH2F), le methane, bis(trifluoromethoxy)-(CF3-O-CH2-O-CF3), le methane, bis(difluoromethoxy)difluoro-(CHF2-O-CF2-O-CHF2), le methane, (difluoromethoxy)fluoro(trifluoromethoxy) -(CF3-O-CHF-O-CHF2), le methane, (difluoromethoxy)difluoro(trifluoromethoxy)-(CF3-O-CF2-O-CHF2), le methane, fluorobis(trifluoromethoxy)-(CF3-O-CHF-O-CF3). Les diéthers préférés sont (difluoromethoxy)(difluoro)(fluoromethoxy)methane(CHF2-O-CF2-O-CH2F), le [difluoro(methoxy)methoxy](trifluoro)methane(CF3-O-CF2-O-C H3), le [(difluoromethoxy)methoxy](trifluoro)methane(CF3-O-CH2-O-CHF2), le trifluoro[fluoro(fluoromethoxy)methoxy]methane(CF3-O-CHF-O-CH2F), le [difluoro(fluoromethoxy)methoxy](trifluoro)methane(CF3-O-CF2-O-CH2F), le methane, bis(trifluoromethoxy)-(CF3-O-CH2-O-CF3), le methane, bis(difluoromethoxy)difluoro-(CHF2-O-CF2-O-CHF2), le methane, (difluoromethoxy)fluoro(trifluoromethoxy) -(CF3-O-CHF-O-CHF2), le methane, (difluoromethoxy)difluoro(trifluoromethoxy)-(CF3-O-CF2-O-CHF2), le methane, fluorobis(trifluoromethoxy)-(CF3-O-CHF-O-CF3).  trifluoro [(fluoromethoxy) methoxy] methane (CH2F-O-CH2-O-CF3), (difluoromethoxy) (fluoro) (fluoromethoxy) methane (CH2F-O-CHF-O-CHF2), difluoro [bis (fluoromethoxy)) methane (CH2F-O-CF2-O-CH2F), (difluoromethoxy) (difluoro) (fluoromethoxy) methane (CHF2-O-CF2-O-CH2F), [difluoro (methoxy) methoxy] (trifluoro) methane ( CF3-O-CF2-O-C H3), [(difluoromethoxy) methoxy] (trifluoro) methane (CF3-O-CH2-O-CHF2), trifluoro [fluoro (fluoromethoxy) methoxy] methane (CF3-O- CHF-O-CH2F), [difluoro (fluoromethoxy) methoxy] (trifluoro) methane (CF3-O-CF2-O-CH2F), methane, bis (trifluoromethoxy) - (CF3-O-CH2-O-CF3) methane, bis (difluoromethoxy) difluoro- (CHF2-O-CF2-O-CHF2), methane, (difluoromethoxy) fluoro (trifluoromethoxy) - (CF3-O-CHF-O-CHF2), methane, (difluoromethoxy) difluoro (trifluoromethoxy) - (CF3-O-CF2-O-CHF2), methane, fluorobis (trifluoromethoxy) - (CF3-O-CHF-O-CF3). Preferred diethers are (difluoromethoxy) (difluoro) (fluoromethoxy) methane (CHF2-O-CF2-O-CH2F), [difluoro (methoxy) methoxy] (trifluoro) methane (CF3-O-CF2-OC H3), [(difluoromethoxy) methoxy] (trifluoro) methane (CF3-O-CH2-O-CHF2), trifluoro [fluoro (fluoromethoxy) methoxy] methane (CF3-O-CHF-O-CH2F), [difluoro (fluoromethoxy) methoxy] (trifluoro) methane (CF3-O-CF2-O-CH2F), methane, bis (trifluoromethoxy) - (CF3-O-CH2-O-CF3), methane, bis (difluoromethoxy) difluoro- (CHF2- O-CF 2 -O-CHF 2), methane, (difluoromethoxy) fluoro (trifluoromethoxy) - (CF 3 -O-CHF-O-CHF 2), methane, (difluoromethoxy) difluoro (trifluoromethoxy) - (CF 3 -O-CF 2 O-CHF2), methane, fluorobis (trifluoromethoxy) - (CF3-O-CHF-O-CF3).

Les fluides frigorigènes selon la présente invention peuvent comprendre, en outre, au moins un composé choisi(s) parmi les hydrocarbures, les hydrofluorocarbures, les (hydro)fluorooléfines, les (hydro)fluoro éthers, les cyclo (hydro)fluoro ethers, les (hydro)fluoroolefin ethers, cyclo hydrofluoroolefin ethers, le bis(tri fluoro méthyle) sulfide, le dimethyl éther ou les (hydro)fluoroiodocarbures. Le dioxyde de carbone, les gaz rares, l'azote, l'ammoniac, le dioxyde d'azote ou le sulfure d'hydrogène peuvent être présents dans les fluides 4  The refrigerants according to the present invention may further comprise at least one compound chosen from hydrocarbons, hydrofluorocarbons, (hydro) fluoroolefins, (hydro) fluoro ethers, cyclo (hydro) fluoro ethers, (hydro) fluoroolefin ethers, cyclohydrofluoroolefin ethers, bis (trifluoromethyl) sulfide, dimethyl ether or (hydro) fluorocarbons. Carbon dioxide, rare gases, nitrogen, ammonia, nitrogen dioxide or hydrogen sulphide may be present in fluids 4

frigorigènes. La quantité totale de ces composés ne doit pas dépasser 10 % du poids total du fluide frigorigène. Comme hydrocarbures, on peut citer notamment le méthane, l'éthane, le propane, le n-butane, l'isobutane, le 2-methylbutane, n-pentane, l'iso-pentane, le cyclopentane, l'éthylène et le propylène, Comme (hydro)fluorooléfines, on peut citer notamment les hydrofluoroéthylènes, les hydrofluoropropylènes, et les hydrofluorobutylènes. Les hydrofluoropropylènes sont préférés. Comme (hydro)fluoropropylènes, on peut citer notamment le difluoropropylène (HFO- 1252), le trifluoropropylène (HFO- 1243), le tetrafluoropropylène (HFO- 1234) et le pentafluoropropylène (HFO- 1225). Les hydrofluoropropylènes préférés sont le 1,3,3,3-tetrafluoropropylène (HF0-1234ze), le 2,3,3,3-tetrafluoropropylène (HFO- 1234yf) et le 1,2,3,3,3-pentafluoropropylène (HFO-1225ye) ainsi que chacun des ses stéréoisomères.  refrigerants. The total amount of these compounds should not exceed 10% of the total weight of the refrigerant. As hydrocarbons, mention may in particular be made of methane, ethane, propane, n-butane, isobutane, 2-methylbutane, n-pentane, iso-pentane, cyclopentane, ethylene and propylene As (hydro) fluoroolefins, mention may be made in particular of hydrofluoroethylenes, hydrofluoropropylenes and hydrofluorobutylenes. Hydrofluoropropylenes are preferred. As (hydro) fluoropropylenes, there may be mentioned in particular difluoropropylene (HFO-1252), trifluoropropylene (HFO-1243), tetrafluoropropylene (HFO-1234) and pentafluoropropylene (HFO-1225). The preferred hydrofluoropropylenes are 1,3,3,3-tetrafluoropropylene (HF0-1234ze), 2,3,3,3-tetrafluoropropylene (HFO-1234yf) and 1,2,3,3,3-pentafluoropropylene (HFO -1225ye) as well as each of its stereoisomers.

Le perfluoropropylène peut également convenir. Comme hydrofluorocarbures, on peut citer notamment le difluorométhane, le difluoroéthane, le 1,1,1,2 tetrafluoroéthane, le 1,1,2,2 tetrafluoroéthane, le pentafluoroéthane, le pentafluoropropane, l'heptafluoropropane et le pentafluorobutane. Le difluorométhane, le difluoroéthane et le 1,1,1,2 tetrafluoroéthane sont préférés. Comme (hydro)fluoroiodocarbures on peut citer le trifluoroiodométhane (CF3I). Comme (hydro)fluoroethers, on peut citer notamment le fluoromethyl difluoromethyl ether (CH2FOCHF2), methyl trifluoromethyl ether (CH3OCF3), bis(difluoromethyl) ether (CHF2OCHF2), fluoromethyl trifluoromethyl ether (CH2FOCF3), difluoromethyl trifluoromethyl ether (CF3OCHF2), bis(trifluoromethyl) ether (CF3OCF3), 2-(difluoromethoxy)-1,1,1-trifluoroethane (CF3CH2OCHF2), 1,1,1,2,2-pentafluoro-2-methoxyethane (CF3CF2OCH3), 2-(difluoromethoxy)-1,1,1,2-tetrafluoroethane (CF3CHFOCHF2), 1,1,1-trifluoro-2- (trifluoromethoxy)ethane (CF3CH2OCF3), 1,1,1,2-tetrafluoro-2- (trifluoromethoxy)ethane (CF3CH FOCF3), 1-difluoromethoxy-1,1,2,2,2- pentafluoroethane (CF3CF2OCHF2), 1,1,1,2,2-pentafluoro-2- (trifluoromethoxy)ethane (CF3CF2OCF3). Comme (hydro)fluoroolefin ether, on peut citer notamment le (trifluoromethoxy)ethylene (CH2=CH-O-CF3), 1-(difluoromethoxy)-1- 5 fluoroethene (CH2=CF-O-CHF2), 1-(difluoromethoxy)-2-fluoroethene (CHF=CHO-CHF2), 1,1 -difluoro-2-(fluoromethoxy)ethene (CF2=CH-O-CH2F), 1,2-difluoro- 1-(fluoromethoxy)ethene (CHF=CF-O-CH2F), 1,1,2-trifluoro-2-methoxyethene(CF2=CF-O-CH3), (Z)-1-fluoro-2-(trifluoromethoxy)ethylene (CH F=CH-O-CF3), 1 -fluoro-1-(trifluoromethoxy)ethene (CH2=CF-O-C F3), (Z)-1,2-difluoroethenyl difluoromethyl ether (CHF=CF-O-CHF2), 2,2-difluoroethenyl difluoromethyl ether (CF2=CH-O-CHF2), 1,1,2-trifluoro-2- (fluoromethoxy)ethene(CF2=CF-O-CH2F), 1,1-difluoro-2-(trifluoromethoxy)ethylene(CF2=CHOCF3), 1-(difluoromethoxy)-1,2,2-trifluoroethene(CF2=CFOCHF2), 1,1,2 -trifluoro-2-(trifluoromethoxy)ethylene ou (perfluoromethyl vinyl ether) (CF2=CFOCF3). Comme cyclo (hydro)fluoroethers on peut citer notamment le 2,3-difluorooxirane (-CHF-CHF-O-), 2,2-difluorooxirane(-CF2-CH2-O-), 2,2,3- trifluorooxirane(-CF2-CHF-O-), tetrafluorooxirane(-CF2-CF2-O-), 2,2,4- trifluorooxetane(-CF2-CH2-CHF-O-), 2,3,4-trifluorooxetane(-CHF-CHF-CHF-O-), 2,3,3-trifluorooxetane(-CHF-CF2-CH2-O-), 2,2,3,3-tetrafluorooxetane(-CF2-CF2- CH2-O-), 2,2,3,4,4-pentafluorooxetane(-CF2-CHF-CF2-O-), 2,2,3,3,4- pentafl uorooxetane(-CF2-CF2-CHF-O-), hexafluorooxetane(-CF2-CF2-CF2-O-). Comme cyclo (hydro)fluoroolefin ethers on peut citer notament le 2,2-difluoro-2H-oxete (-CF2-CH=CH-O-), 2,3-difluoro-2H-oxete(-CHF-CF=CH-O-), 3,4-difluoro-2H-oxete(-CH2-CF=CF-O-), 2,3,4-trifluoro-2H-oxete(-CHF-CF=CFO-), 2,2,3-trifluoro-2H-oxete(-CF2-CF=CH-O-), 2,2,4-trifluoro-2H-oxete(-CF2-CH=CF-O-), 2,2,3,4-tetrafluoro-2H-oxete(-CF2-CF=CF-O-). Les fluides frigorigènes selon la présente invention conviennent particulièrement pour les systèmes de compression dans la fabrication d'air conditionné et plus particulièrement dans la fabrication d'air conditionné des véhicules. Les fluides frigorigènes selon la présente invention sont de préférence utilisés en remplacement, partiel ou total, du 1,1,1,2- 6  Perfluoropropylene may also be suitable. As hydrofluorocarbons, mention may be made in particular of difluoromethane, difluoroethane, 1,1,1,2-tetrafluoroethane, 1,1,2,2-tetrafluoroethane, pentafluoroethane, pentafluoropropane, heptafluoropropane and pentafluorobutane. Difluoromethane, difluoroethane and 1,1,1,2-tetrafluoroethane are preferred. As (hydro) fluoroiodocarbons, mention may be made of trifluoroiodomethane (CF3I). As (hydro) fluoroethers, mention may in particular be made of fluoromethyl difluoromethyl ether (CH 2 FOCHF 2), methyl trifluoromethyl ether (CH 3 OCF 3), bis (difluoromethyl) ether (CHF 2 OCHF 2), fluoromethyl trifluoromethyl ether (CH 2 FOCF 3), difluoromethyl trifluoromethyl ether (CF 3 OCHF 2), bis ( trifluoromethyl) ether (CF3OCF3), 2- (difluoromethoxy) -1,1,1-trifluoroethane (CF3CH2OCHF2), 1,1,1,2,2-pentafluoro-2-methoxyethane (CF3CF2OCH3), 2- (difluoromethoxy) -1 , 1,1,2-tetrafluoroethane (CF3CHFOCHF2), 1,1,1-trifluoro-2- (trifluoromethoxy) ethane (CF3CH2OCF3), 1,1,1,2-tetrafluoro-2- (trifluoromethoxy) ethane (CF3CH FOCF3) 1-Difluoromethoxy-1,1,2,2,2-pentafluoroethane (CF3CF2OCHF2), 1,1,1,2,2-pentafluoro-2- (trifluoromethoxy) ethane (CF3CF2OCF3). As (hydro) fluoroolefin ether, there may be mentioned in particular (trifluoromethoxy) ethylene (CH2 = CH-O-CF3), 1- (difluoromethoxy) -1-fluoroethene (CH2 = CF-O-CHF2), 1- (difluoromethoxy) -2-Fluoroethene (CHF = CHO-CHF2), 1,1-difluoro-2- (fluoromethoxy) ethene (CF2 = CH-O-CH2F), 1,2-difluoro-1- (fluoromethoxy) ethene (CHF = CF-O-CH2F), 1,1,2-trifluoro-2-methoxyethene (CF2 = CF-O-CH3), (Z) -1-fluoro-2- (trifluoromethoxy) ethylene (CH F = CH-O- CF3), 1-fluoro-1- (trifluoromethoxy) ethene (CH2 = CF-OC F3), (Z) -1,2-difluoroethenyl difluoromethyl ether (CHF = CF-O-CHF2), 2,2-difluoroethenyl difluoromethyl ether (CF2 = CH-O-CHF2), 1,1,2-trifluoro-2- (fluoromethoxy) ethene (CF2 = CF-O-CH2F), 1,1-difluoro-2- (trifluoromethoxy) ethylene (CF2 = CHOCF3 ), 1- (difluoromethoxy) -1,2,2-trifluoroethene (CF2 = CFOCHF2), 1,1,2-trifluoro-2- (trifluoromethoxy) ethylene or (perfluoromethyl vinyl ether) (CF2 = CFOCF3). Examples of cyclo (hydro) fluoroethers that may be mentioned include 2,3-difluorooxirane (-CHF-CHF-O-), 2,2-difluorooxirane (-CF2-CH2-O-), 2,2,3-trifluorooxirane (- CF2-CHF-O-), tetrafluorooxirane (-CF2-CF2-O-), 2,2,4-trifluorooxetane (-CF2-CH2-CHF-O-), 2,3,4-trifluorooxetane (-CHF-CHF -CHF-O-), 2,3,3-trifluorooxetane (-CHF-CF2-CH2-O-), 2,2,3,3-tetrafluorooxetane (-CF2-CF2-CH2-O-), 2,2 , 3,4,4-pentafluorooxetane (-CF 2 -CHF-O 2 -C), 2,2,3,3,4-pentafluorooxetane (-CF 2 -CF 2 -CHF-O), hexafluorooxetane (-CF 2 -CF 2) -CF2-O-). As cyclo (hydro) fluoroolefin ethers there may be mentioned 2,2-difluoro-2H-oxete (-CF 2 -CH = CH-O-), 2,3-difluoro-2H-oxete (-CHF-CF = CH- O-), 3,4-difluoro-2H-oxete (-CH2-CF = CF-O-), 2,3,4-trifluoro-2H-oxete (-CHF-CF = CFO-), 2.2, 3-trifluoro-2H-oxete (-CF2-CF = CH-O-), 2,2,4-trifluoro-2H-oxete (-CF2-CH = CF-O-), 2,2,3,4- tetrafluoro-2H-oxete (-CF2-CF = CF-O-). The refrigerants according to the present invention are particularly suitable for compression systems in the manufacture of air conditioning and more particularly in the manufacture of air conditioning of vehicles. The refrigerants according to the present invention are preferably used as a partial or total replacement for 1,1,1,2-6.

tetrafluoroéthane dans la fabrication d'air conditionné et avantageusement dans la fabrication d'air conditionné des véhicules. La présente invention a également pour objet un dispositif pour transfert de chaleur dans un cycle de compression renfermant les fluides frigorigènes 5 décrits précédemment.  tetrafluoroethane in the manufacture of air conditioning and advantageously in the manufacture of air conditioning of vehicles. The present invention also relates to a device for heat transfer in a compression cycle containing the refrigerants 5 described above.

Claims (6)

REVENDICATIONS 1) Fluide frigorigène, ayant à la fois un ODP nul ou inférieur à 0,02 et un GWP inférieur à 150, comprenant au moins un diéther linéaire à trois atomes de carbone représenté par la formule générale (1) (R1-O-R3-O- R2) dans laquelle R1 et R2 identiques ou différents, représentent chacun un radical méthyle pouvant être partiellement ou totalement fluoré et R3 représente un radical méthylène éventuellement fluoré choisi parmi û CH2 -, -CHF û et -CF2- , à l'exclusion du CF3-O-CF2-O-CF3.  1) Refrigerant, having both a zero ODP or less than 0.02 and a GWP of less than 150, comprising at least one linear three-carbon diether represented by the general formula (1) (R1-O-R3 Wherein R1 and R2, which are identical or different, each represent a methyl radical which may be partially or completely fluorinated and R3 represents an optionally fluorinated methylene radical chosen from CH2 -, - CHF - and -CF2 -, and exclusion of CF3-O-CF2-O-CF3. 2) Fluide frigorigène selon la revendication 1 caractérisé en ce qu'il comprend en outre au moins un composé choisi(s) parmi les hydrocarbures, les hydrofluorocarbures, les (hydro)fluorooléfines, les (hydro)fluoro éthers, les cyclo (hydro)fluoro ethers, les (hydro)fluoroolefin ethers, cyclo (hydro)fluoroolefin ethers, le bis(tri fluoro méthyle) sulfide, le dimethyl éther ou les (hydro)fluoroiodocarbures.  2) Refrigerant according to claim 1 characterized in that it further comprises at least one compound selected from hydrocarbons, hydrofluorocarbons, (hydro) fluoroolefins, (hydro) fluoro ethers, cyclo (hydro) fluoro ethers, (hydro) fluoroolefin ethers, cyclo (hydro) fluoroolefin ethers, bis (trifluoromethyl) sulfide, dimethyl ether or (hydro) fluorocarbons. 3) Dispositif pour transfert de chaleur dans un cycle de compression renfermant le fluide frigorigène selon la revendication 1 ou 2.  3) Device for heat transfer in a compression cycle containing the refrigerant according to claim 1 or 2. 4) Dispositif selon la revendication 3 caractérisé en ce qu'il est utilisé dans la fabrication de l'air conditionné.  4) Device according to claim 3 characterized in that it is used in the manufacture of air conditioning. 5) Fluide frigorigène selon la revendication 1 ou 2 caractérisé en ce qu'il est utilisé dans la fabrication d'air conditionné.  5) Refrigerant according to claim 1 or 2 characterized in that it is used in the manufacture of air conditioning. 6) Fluide frigorigène selon la revendication 1 ou 2 caractérisé en ce qu'il est utilisé en remplacement du 1,1,1,2-tetrafluoroéthane.  6) refrigerant according to claim 1 or 2 characterized in that it is used in replacement of 1,1,1,2-tetrafluoroethane.
FR0753184A 2007-02-12 2007-02-12 REFRIGERANT FLUID BASED ON LINEAR DIETHER. Expired - Fee Related FR2912419B1 (en)

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