CN103642461B - 氟代烯烃制冷剂组合物 - Google Patents
氟代烯烃制冷剂组合物 Download PDFInfo
- Publication number
- CN103642461B CN103642461B CN201310572027.3A CN201310572027A CN103642461B CN 103642461 B CN103642461 B CN 103642461B CN 201310572027 A CN201310572027 A CN 201310572027A CN 103642461 B CN103642461 B CN 103642461B
- Authority
- CN
- China
- Prior art keywords
- compositionss
- lubricant
- fluoroolefin
- alkylene glycol
- poly alkylene
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 239000003507 refrigerant Substances 0.000 title abstract description 20
- 150000001336 alkenes Chemical class 0.000 title description 8
- 239000000314 lubricant Substances 0.000 claims abstract description 97
- 238000005057 refrigeration Methods 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000007791 liquid phase Substances 0.000 claims abstract description 29
- 238000004378 air conditioning Methods 0.000 claims abstract description 25
- 230000006835 compression Effects 0.000 claims abstract description 20
- 238000007906 compression Methods 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 61
- -1 polyol ester Chemical class 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229920001519 homopolymer Polymers 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical class F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical class FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims 4
- BQODPTQLXVVEJG-UHFFFAOYSA-N [O].C=C Chemical group [O].C=C BQODPTQLXVVEJG-UHFFFAOYSA-N 0.000 claims 1
- 229920000891 common polymer Polymers 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 8
- 238000005461 lubrication Methods 0.000 abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 6
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 19
- 239000003921 oil Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000012530 fluid Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000010687 lubricating oil Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229920001281 polyalkylene Polymers 0.000 description 5
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000010696 ester oil Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 239000006200 vaporizer Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- CDOOAUSHHFGWSA-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropene Chemical group FC=CC(F)(F)F CDOOAUSHHFGWSA-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
- C10M107/34—Polyoxyalkylenes
-
- 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
- C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
- C10M111/02—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
-
- 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
- C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
- C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/126—Unsaturated fluorinated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/24—Only one single fluoro component present
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
- C10M2207/2895—Partial esters containing free hydroxy groups used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
- C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
- C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
- C10M2211/063—Perfluorinated compounds 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Abstract
在压缩致冷、空调和热泵系统中使用的液体组合物,其中将一种含3至4个碳原子和至少1个但不超过2个双键的氟代烯烃与一种可基本混溶的有机润滑剂组合,有机润滑剂的量是提供润滑的有效量,含有碳、氢和氧,并且具有的氧碳比有效提供与所述氟代烯烃的一定程度的可混溶性,使得当将至多5重量%润滑剂加入所述氟代烯烃时,该致冷剂在介于‑40和+70℃之间的至少一个温度下具有一个液相。还公开了氟代烯烃单独进行或与所公开的润滑剂组合进行冷却和加热的方法。
Description
相关申请
本申请是中国专利申请号2004800390948、申请日2004年10月25日、发明名称“氟代烯烃制冷剂组合物”的中国专利申请的分案申请。
本申请涉及并要求美国临时申请60/421,263和60/421,435的优先权益,其中每个申请于2002年10月25日递交,且每个申请经引用并入本申请。本申请还涉及并通过引用合并以下同时递交的各美国专利申请:代理人卷号(DocketNumber)H0004412(26,269),Singh等人的标题为“Compositions Containing Fluorine Substituted Olefins(包含氟代烯烃的组合物)”申请,和代理人卷号H0003789(26,267),Tung等人的标题为“Process ForProducing Fluoropropenes(氟代丙烯的制造方法)”申请。
技术领域
本发明涉及在压缩致冷、空调和热泵系统中用作制冷流体的组合物。
背景技术
人们已经变得不赞同使用含氯致冷剂,例如含氯氟烃(chloro-fluorocarbons)(CFC's)、氢化含氯氟烃(hydrochlorofluorocarbons)(HCF's)等作为空调系统和制冷系统的致冷剂,这是因为这些化合物伴有臭氧消耗性能。结果,日益期望用例如氢化氟烃(HFC's)的不消耗臭氧层的非含氯致冷剂化合物代替含氯致冷剂,以改型含氯致冷系统。
作为任何与致冷组合物相关的替代材料,这些材料必须与压缩机中采用的润滑剂相容。遗憾的是,在传统上与CFC's和HFC's一起使用的润滑剂类,包括例如矿物油、烷基苯或聚(α-烯烃)中,包括HFC's的许多非含氯致冷剂流体是相对不可溶的和/或不可混溶的。为了获得一种在压缩致冷、空调或热泵系统中有效工作的致冷流体-润滑剂组合(combination),润滑剂必须在宽泛的操作温度范围里均能足够地溶解在致冷液体中。这种可溶性降低了润滑剂的粘度,并使它能更容易地流过系统。缺少这种可溶性的情况下,润滑剂趋于在压缩致冷、空调和热泵系统的蒸发器以及系统其它部件的蛇行管中滞留,从而降低了系统的效率。
作为HFC致冷液体的可混溶润滑剂,已经开发了聚亚烷基二醇、酯化的聚亚烷基二醇和多元醇酯的润滑油。美国专利4,755,316、4,971,712和4,975,212公开了聚亚烷基二醇致冷润滑剂。美国专利5,008,028公开了聚亚烷基二醇酯。所公开的聚亚烷基二醇和聚亚烷基二醇酯润滑油可混溶于含一个和两个碳原子且无双键的氟代烷烃中。
从而,发现基于氟代烃的流体广泛用于致冷系统应用的工业领域,包括空调系统以及热泵应用,它们均包括压缩致冷。压缩致冷通常包括通过较低压力下热吸收将致冷剂从液相变为汽相,然后通过在高压下排除热量从汽相变为液相。
致冷的首要目的是在低温时除去能量,而热泵的首要目的是在高温时增加能量。热泵因为加热而被认为是逆循环系统,冷凝器的运作与致冷蒸发器的运作互换。
这一技术领域不断寻求基于新的氟代烃和氢化氟代烃的纯流体,其为致冷和热泵应用提供替代物。申请人已经意识到,基于氟代烯烃的材料(氟代烯烃类)尤其有意义,因为它们具有的特性使它们成为比目前使用的氟代烷烃(HFC's)对环境更安全的替代品,HFC's尽管对臭氧层安全,但是令人怀疑使全球变暖。
申请人还认识到,在许多情况下HFC's的致冷组合物替代品优选具有某些性能,使它们被认为是可接受的替代品,包括可接受的致冷特性、化学稳定性、低毒性、不燃性、润滑剂相容性和使用效率。最后的特性在许多致冷系统、空调系统和热泵应用中很重要,尤其在致冷热力学性能或能量效率的损失可能通过电能需求增加引起的矿物燃料使用增加造成二次环境影响时。此外,不需要对传统的蒸汽压缩技术和目前与HFC致冷液体一起使用的润滑剂系统做大的工程变动,这可能也是HFC致冷组合物替代品的优势。
对许多应用来说,可燃性是另一项重要性能。即,在许多应用,尤其是在包括传热的应用中,使用不可燃的组合物被认为是重要或基本的要求。这样,在这类组合物中使用不可燃的化合物常常是有益的。
本申请中使用时,术语“不可燃的”是指化合物或组合物按照ASTM标准E-681,2002年颁,测定会是不可燃的,该标准经引用并入本申请。不幸的是,在所用的致冷剂组合物中别的方面可能可取的许多HFC's却不是不可燃的。例如氟代烷烃二氟乙烷(HFC-152a)和氟代烯烃1,1,1-三氟丙烯(HFO-1243zf)均是可燃的,从而在许多应用中它们是不可用的。
已经提议用更高级的氟代烯烃,即具有至少5个碳原子的氟取代的烯烃,作为致冷剂。Smutry的美国专利4,788,352涉及氟化的C5至C8具有至少一些不饱和度的化合物的生产。Smutry的这项专利视为是这类更高级烯烃,已知它们具有作为致冷剂、杀虫剂、介电流体、传热流体、溶剂和各种化学反应的中间体的实用性。
尽管Smutny专利中描述的氟代烯烃可具有一定效力水平的传热应用,但是据信,这类化合物还可能有某些缺陷。例如其中一些化合物可能倾向于侵蚀基底,特别是一般目的的塑料,例如丙烯酸树脂和ABS树脂。此外,Smutny专利中描述的更高级的烯烃化合物在某些应用中还可能因为这类化合物潜在的毒性水平而是不可取的,之所以这样认为可能是Smutny专利中指出杀虫剂活性所致。这类化合物还可能具有过高的沸点,以致于在某些应用中不能用它们作为致冷剂。
因此申请人已经意识到,需要一些组合物,特别是流体输送组合物,它们可能用在包括蒸汽压缩加热和冷却系统和方法的为数众多的应用中,且同时避免以上指出的一种或多种缺陷。而且,申请人也已经认识到,许多应用中一直需要比HFC's对环境更安全的基于氟代烃和氢化氟代烃的致冷剂液体,相对于至少某些致冷剂的热力学性能,其具有类似或更好的特性,且与现有的润滑剂系统相容。
发明内容
本发明提供一种用于压缩制冷、空调和热泵系统的液体组合物,其包含:
(A)含3至4个碳原子和至少1个但不超过2个双键的氟代烯烃;和
(B)提供润滑有效量的、基本上可混溶的有机润滑剂,其含有碳、氢和氧,并且具有的氧碳比有效提供与所述氟代烯烃的一定程度的可混溶性,使得当将至多5重量%润滑剂加入所述氟代烯烃时,混合物在介于-40和+70℃之间的至少一个温度下具有一个液相。
具体实施方式
本发明涉及如下方案:
项目1.一种用于压缩制冷、空调和热泵系统的液体组合物,其包含:
(A)含3至4个碳原子和至少1个但不超过2个双键的氟代烯烃;和
(B)提供润滑有效量的、基本上可混溶的有机润滑剂,其含有碳、氢和氧,并且具有的氧碳比有效提供与所述氟代烯烃的一定程度的可混溶性,使得当将至多5重量%润滑剂加入所述氟代烯烃时,混合物在介于-40和+70℃之间的至少一个温度下具有一个液相。
2.项目1的组合物,其中当将至多5重量%润滑剂加入所述氟代烯烃时,该混合物具有一个液相。
3.项目2的组合物,其中当将至多20重量%润滑剂加入所述氟代烯烃时,该混合物具有一个液相。
4.项目3的组合物,其中在氟代烯烃和润滑剂的所有比例下,该混合物具有一个液相。
5.项目1的组合物,其中基本覆盖整个温度范围,该混合物具有一个液相。
6.项目1的组合物,其中所述润滑剂选自用于压缩机致冷、空调和热泵系统的聚亚烷基二醇、聚亚烷基二醇酯和多元醇酯润滑剂。
7.项目1的组合物,其中所述氟代烯烃具有如下结构:
XCFzR3-z
其中X是C2或C3不饱和的、取代的或非取代的烷基,R独立地选自Cl、Br、I或H,且z是1至3。
8.项目7的组合物,其中所述氟代烯烃具有如下结构:
其中每个R独立地为Cl、F、Br、I或H;R'为(CR2)nY;Y为CRF2并且n是0或1。
9.项目8的组合物,其中所述氟代烯烃是:1,3,3,3-四氟-丙烯或3,3,3-三氟丙烯。
10.项目1的组合物,其中所述有机润滑剂是聚亚烷基二醇。
11.项目10的组合物,其中所述聚亚烷基二醇具有至少一个端羟基。
12.项目11的组合物,其中所述聚亚烷基二醇的两个端基均是羟基。
13.项目10的组合物,其中所述聚亚烷基二醇具有至少一个烷基封端基团。
14.项目13的组合物,其中所述聚亚烷基二醇的至少一个端烷基含有至少一个杂原子。
15.项目14的组合物,其中所述聚亚烷基二醇具有至少一个氟代烷基端基。
16.项目1的组合物,其中所述有机润滑剂是聚亚烷基二醇酯。
17.项目1的组合物,进一步包含适量的烃润滑剂,其基本上与所述氟代烯烃和所述有机润滑剂可混溶。
18.项目17的组合物,进一步包含表面活性剂,其用于增加所述烃润滑剂与所述有机润滑剂的溶解性,其含量使得有效地形成一种基本可混溶的混合物。
19.一种进行致冷的方法,其包括冷凝一种包含氟代烯烃的致冷剂组合物,该氟代烯烃含3至4个碳原子和至少1个但不超过2个双键,并随后在待冷却的物体附近蒸发所述致冷剂组合物。
20.项目19的方法,其中所述氟代烯烃具有如下结构:
XCFzR3-z
其中X是C2或C3不饱和的、取代的或非取代的烷基,R独立地选自Cl、Br、I或H,且z是1至3。
21.项目20的方法,其中所述氟代烯烃具有如下结构:
其中每个R独立地为Cl、F、Br、I或H;R'为(CR2)nY;Y为CRF2并且n是0或1。
22.项目21的方法,其中所述氟代烯烃是:1,3,3,3-四氟丙烯或3,3,3-三氟丙烯。
23.项目19的方法,其中所述致冷方法在压缩致冷系统中执行。
24.项目19的方法,其中所述致冷方法在空调系统中执行。
25.项目19的方法,其中将有机润滑剂以有效提供润滑的量添加到所述致冷剂中,该有机润滑剂含有碳、氢和氧,并且具有的氧碳比有效提供与所述氟代烯烃的一定程度的可混溶性,使得当将至多5重量%润滑剂加入所述氟代烯烃时,致冷剂在介于-40和+70℃之间的至少一个温度下具有一个液相。
26.项目25的方法,其中当将至多20重量%润滑剂加入所述氟代烯烃时,该致冷剂具有一个液相。
27.项目26的方法,其中在氟代烯烃和润滑剂的所有比例下,该致冷剂具有一个液相。
28.项目25的方法,其中基本覆盖整个温度范围,该致冷剂具有一个液相。
29.项目25的方法,其中所述润滑剂选自用于压缩机致冷和空调系统的聚亚烷基二醇、聚亚烷基二醇酯和多元醇酯润滑剂。
30.项目25的方法,其中向所述致冷剂中进一步添加适量的烃润滑剂,其基本上与所述氟代烯烃和所述有机润滑剂可混溶。
31.项目30的方法,其中向所述致冷剂中进一步添加表面活性剂,其用于增加所述烃润滑剂与所述氟代烯烃和所述有机润滑剂的溶解性,其含量使得有效地形成一种基本混溶的混合物。
32.一种进行加热的方法,其包括在待加热的物体附近冷凝一种氟代烯烃组合物,其含3至4个碳原子和至少1个但不超过2个双键,并随后蒸发所述氟代烯烃组合物。
33.项目32的方法,其中所述氟代烯烃具有如下结构:
XCFzR3-z
其中X是C2或C3不饱和的、取代的或非取代的烷基,R独立地选自Cl、Br、I或H,且z是1至3。
34.项目33的方法,其中所述氟代烯烃具有如下结构:
其中每个R独立地为Cl、F、Br、I或H;R'为(CR2)nY;Y为CRF2并且n是0或1。
35.项目34的方法,其中所述氟代烯烃是:1,3,3,3-四氟丙烯或3,3,3-三氟丙烯。
36.项目32的方法,其中将一种有机润滑剂以有效提供润滑的量添加到所述氟代烯烃组合物中,该有机润滑剂含有碳、氢和氧,并且具有的氧碳比有效提供与所述氟代烯烃组合物的一定程度的可混溶性,使得当将至多5重量%润滑剂加入所述氟代烯烃组合物时,所述组合物在介于-40和+70℃之间的至少一个温度下具有一个液相。
37.项目36的方法,其中当将至多20重量%润滑剂加入该氟代烯烃组合物时,该氟代烯烃组合物具有一个液相。
38.项目37的方法,其中在氟代烯烃组合物和润滑剂的所有比例下,该氟代烯烃组合物具有一个液相。
39.项目36的方法,其中基本覆盖整个温度范围,该氟代烯烃组合物具有一个液相。
40.项目36的方法,其中所述润滑剂选自用于压缩机致冷和空调系统的聚亚烷基二醇、聚亚烷基二醇酯和多元醇酯润滑剂。
41.项目36的方法,其中向所述氟代烯烃组合物中进一步添加适量的烃润滑剂,其基本上与所述氟代烯烃和所述有机润滑剂可混溶。
42.项目41的方法,其中向所述氟代烯烃组合物中进一步添加表面活性剂,其用于增加所述烃润滑剂与所述氟代烯烃和所述有机润滑剂的溶解性,其含量使得有效地形成一种基本可混溶的混合物。
通过在待加热的物体附近压缩含2至5个碳原子并至少含1个但不超过2个双键的氟代烯烃而产生热,从而蒸发氟代烯烃。再次地,优选含3个碳原子和1个双键的氟代烯烃。
还发现,本发明的氟代烯烃可与存在的聚亚烷基二醇、聚亚烷基二醇酯和多元醇酯润滑油混溶。因此,按照本发明的另一个方面,提供用于压缩致冷、空调和热泵系统中的液体组合物,其中将含2至5个碳原子且至少1个但不超过2个双键的氟代烯烃与足够提供润滑量的基本混溶的有机润滑剂组合,该润滑剂选自用于压缩致冷、空调和热泵系统中的聚亚烷基二醇、聚亚烷基二醇酯和多元醇酯润滑剂。在某些优选实施方案中,本发明的润滑剂是含碳、氢和氧的有机化合物,且氧对碳的比例足以提供与氟代烯烃的一定混溶度,使得,当约1至5重量%的润滑剂加入到致冷剂流体中时,混合物具有一个液相。优选,在混合物中存在1至20重量%的润滑剂时,混合物具有一个液相。更优选,在混合物各组分的全部比例下,混合物是一个液相。这种溶解性或混溶性优选存在于约-40℃至70℃的至少一个温度下,更优选基本覆盖整个温度范围。
如本文中所用的,术语“致冷系统”是指采用提供冷却的致冷液体或致冷剂的任何系统或设备、或者这种系统或设备的任何部件或部分。这种致冷系统包括,例如空调、电冰箱、深冷器、运输致冷系统、商业致冷系统等等。
本发明的HFC's替代品HFO's尽管对臭氧层安全,但是其被怀疑促使全球变暖。至少按照本发明优选的某些HFO's具有使他们仅以最小的设备改变即可替代HFC's的物理特性。
适于本发明使用的聚亚烷基二醇润滑剂一般含有约5至50个氧化烯(oxylakylene)重复单元,该重复单元含1至5个碳原子。这种聚亚烷基二醇可以是直链或支链的,而且可以是均聚物或2、3或更多种氧乙烯、氧丙烯、氧丁烯或氧戊烯基或其组合以任意比例的共聚物。优选的聚亚烷基二醇含至少50%的氧丙烯基。按照本发明的组合物可含有:一种或多种作为润滑剂的聚亚烷基二醇,一种或多种作为润滑剂的聚亚烷基二醇酯,一种或多种作为润滑剂的多元醇酯,或者一种或多种聚亚烷基二醇、一种或多种聚亚烷基二醇酯和一种或多种多元醇酯的混合物。乙烯醚类也可用于本发明。
合适的聚亚烷基二醇包括:美国专利4,971,712中的聚亚烷基二醇和美国专利4,755,316所公开的每端具有羟基的聚亚烷基二醇。两项专利所公开的内容经引用并入本申请。
虽然合适的聚亚烷基二醇包括每一端以羟基封端的二醇,但是其它合适的HFO润滑剂包括一端或双端羟基被封端的聚亚烷基二醇。羟基可被以下基团封端:含1至10个碳原子的烷基、含杂原子例如氮的1至10个碳原子的烷基、美国专利4,975,212所描述的氟代烷基(该专利的公开内容经引用并入本申请)等。当聚亚烷基二醇的两个羟基都被封端时,可使用相同类型或组合两种不同类型的封端基团。
还可以如美国专利5,008,028(其公开内容经引用并入本申请)所公开的,通过羧酸与一个或两个羟基形成其酯,将其封端。这一专利中的润滑油是指多元醇酯和聚亚烷基二醇酯。羧酸还可以被氟化。当聚亚烷基二醇的两端均被封端时,一端或两端以酯封端、或者一端可以以酯封端而另一端未封端或用前述烷基、杂化烷基或氟代烷基之一封端。
市售可获得的聚亚烷基二醇润滑剂包括:General Motors出售的用于HFC-134a系统的Goodwrench Refrigeration Oil,和Daimler-Chrysler出售的MOPAR-56,这是一种用乙酰基双封端的聚亚烷基二醇。市售可获得的聚亚烷基二醇酯包括:Exxon-Mobil出售的Mobil EAL22cc和CPI Engineering Services,Inc.出售的Solest120。还可从DowChemical获得多种多样的聚亚烷基二醇润滑剂。
在优选的实施方案中,本发明的润滑剂的粘度在约37℃时为约1至1000厘沲,更优选在约37℃时为约10至约200厘沲,并更优选为约30至约150厘沲。
除了HFO致冷剂和润滑剂以外,按照本发明的组合物可包括致冷、空调和热泵的组合物的用于增强它们性能的其它类型添加剂或材料。例如,这些组合物还可包括:耐极压添加剂和耐磨添加剂、氧化和热稳定性改进剂、降倾点剂和降絮凝点剂、消泡剂、可溶于HFO's的其它润滑剂等等。这类添加剂的实例公开在美国专利5,254,280中,经引用将其公开内容并入本申请。从而,本发明的组合物可进一步包括一定量的矿物油润滑剂,其尽管不能与HFO混溶或不可溶,但是当与聚亚烷基二醇、聚亚烷基二醇酯或多元醇酯组合加入HFO时,至少部分混溶或部分可溶。典型地,这是至多约5-20重量%的量。还可添加表面活性剂以使矿物油与聚亚烷基二醇、聚亚烷基二醇酯或多元醇酯及HFO相容,这些内容在美国专利6,516,837中公开,这项专利的公开内容经引用并入本申请。
本发明可使用将本发明致冷组合物引入压缩致冷、空调和热泵系统中的任何方法。例如,一种方法包括将致冷剂容器连接到致冷系统的低压侧,并打开致冷系统的压缩机,以便将这种致冷组合物推入系统中。在这类实施方案中,致冷剂容器可被置于称上,使得能够监控进入系统的致冷组合物的量。当已经将需要量的致冷组合物引入系统时,停止加料。替换地,可以购买到本领域技术人员已知的各种各样的加料工具。因此,鉴于上述内容,本领域技术人员会容易地将本发明的HFO致冷剂和致冷组合物引入压缩致冷、空调和热泵系统中,而且无需过度实验。
实施例
提供以下实施例的目的是为了举例说明本发明,但不限定本发明的范围。
实施例1
性能系数(COP)是普遍接受的致冷剂性能的量度,尤其用于表示,在包括致冷剂蒸发或冷凝的特定加热或冷却循环中,致冷剂的相对热力学效率。在致冷工程中,这个术语表达有用的致冷相对压缩机压缩蒸汽所施加能量的比率。致冷剂的容量表示致冷剂的容积效率,并为压缩机以一定的致冷剂体积流速泵送热量能力来提供某种度量。换句话说,给定了特定的压缩机,致冷剂的容量越高,则输送的冷却或加热功率越大。估算特定操作条件下致冷剂COP的一种手段是基于该致冷剂的热力学性能,使用标准致冷循环分析技术(参见,例如R.C.Downing,FLUOROCARBON REFRIGERANTS HANDBOOK,Chapter3,Prentice-Hall,1988(R.C.Downing,氟代烃致冷剂手册,第3章,Prentice-Hall,1988))。
提供了致冷/空调循环系统,其中冷凝器温度为约150°F,且蒸发器温度为约-35°F,处于标称等熵压缩下,压缩机入口温度为约50°F。对本发明的数种组合物测定COP,测定覆盖了冷凝器和蒸发器的温度范围,并将COP记录在下表1中,基于HFC-134a,其具有1.00的COP值,1.00的容量值和175°F的排出温度。
表I
这一实施例显示,与本组合物一起使用的优选化合物确实每一个都比HFC-134a具有更好的能量效率(1.02、1.04和1.13相比于1.00),而且使用本致冷剂组合物的压缩机将产生排出温度(158、165和155相比于175),这是有利的,因为这种结果可能会导致减少维护问题。
实施例2
试验HFO-1225ye和HFO-1234ze与各种致冷润滑剂的混溶性。受试的润滑剂是矿物油(C3),烷基苯(Zerol150),酯油(Mobil EAL22cc和Solest120),聚亚烷基二醇(PAG)油(134a系统使用的Goodwrench致冷油)和聚(α-烯烃)油(CP-6005-100)。对每种致冷剂/油组合,试验3个组合物,即5、20和50重量%的润滑剂,使每个的余量为受试的本发明化合物。
将润滑剂组合物装入厚壁玻璃管中。使这些管排气(evacuated),加入按照本发明的致冷剂,然后密封这些管。接着将这些管放入空气浴环境模拟箱,其温度从约-50℃到70℃变化。在粗略10℃间隔的各点,肉眼观察管的内容物,判断存在一个或多个液相。在观察到多于一个液相的情况下,将该混合物记录为不可混溶的。在只观察到一个液相的情况下,将这一混合物记录为可混溶的。在观察到两个液相但一个液相仅占有很小体积的情况下,将混合物记录为部分可混溶的。
聚亚烷基二醇及酯油润滑剂被判定在所有试验比例和整个温度范围是可混溶的,除了HFO-1225ye与聚亚烷基二醇的混合物,发现这种致冷剂混合物在-50℃至-30℃温度范围是不可混溶的,而在-20至50℃是部分可混溶的。在致冷剂中PAG的浓度为50重量%时而且在60(℃)时,致冷剂/PAG混合物是可混溶的。70℃时,致冷剂中润滑剂为5重量%至50重量%时,它是可混溶的。
实施例3
在350℃试验与用于致冷和空调系统的金属接触时,本发明的致冷剂化合物和组合物与PAG润滑油的相容性,这代表了比许多致冷和空调应用中严重得多的条件。
将铝、铜和钢取样管加入厚壁玻璃管中。向管中加入2克油。然后使这些管排气并加入1克致冷剂。将这些管放入350°F的烘箱中1个星期并进行肉眼观察。在曝置期结束时,取出这些管。
对以下油与本发明化合物的组合完成这一工序:
a)HFC-1234ze和GM Goodwrench PAG油
b)HFC1243zf和GM Goodwrench油PAG油
c)HFC-1234ze和MOPAR-56PAG油
d)HFC-1243zf和MOPAR-56PAG油
e)HFC-1225ye和MOPAR-56PAG油。
在所有情形中,管的内容物外观变化极小。这表示,本发明的致冷剂化合物和组合物在与致冷和空调系统中存在的铝、钢和铜以及可能会包括在这类组合物中的,或者与这类组合物在这些类系统中一起使用的这些类型的润滑油接触时是稳定的。
对比例
将铝、铜和钢取样管加入装有矿物油和CFC-12的厚壁玻璃管中,并如实施例3中那样于350℃加热1个星期。在曝置期结束时,取出这些管并进行肉眼观察。观察到液体内容物变黑,这表示管的内容物存在严重的分解。
在此以前,CFC-12和矿物油已经是许多致冷系统和方法中选择的组合。因此,与广泛使用的已有技术中的致冷剂-润滑油组合相比,本发明的致冷剂化合物和组合物与许多通常使用的润滑油具有明显更优的稳定性。
Claims (32)
1.一种用于压缩制冷、空调和热泵系统的组合物,其包含:
(A) 包括氟代烯烃的制冷剂,其中所述氟代烯烃是反式-1,3,3,3-四氟丙烯或2,3,3,3-四氟烯烃;和
(B) 选自聚亚烷基二醇润滑剂和多元醇酯润滑剂的润滑剂,
其中所述润滑剂在37℃时具有10-200厘沲范围的粘度,
且其中所述润滑剂提供与所述氟代烯烃的一定程度的可混溶性,使得当将5重量%所述润滑剂加入所述氟代烯烃时,混合物在介于-50和+70℃之间的至少一个温度下具有一个液相。
2.权利要求1的组合物,其中所述制冷剂由2,3,3,3-四氟烯烃组成并且所述润滑剂是聚亚烷基二醇。
3.权利要求1的组合物,其中所述制冷剂包括2,3,3,3-四氟丙烯且所述润滑剂是多元醇酯。
4.权利要求1的组合物,其中所述制冷剂由2,3,3,3-四氟丙烯组成且所述润滑剂是多元醇酯。
5.权利要求1的组合物,其中所述制冷剂包括反式-1,3,3,3-四氟丙烯且所述润滑剂是多元醇酯。
6.权利要求1的组合物,其中所述制冷剂由反式-1,3,3,3-四氟丙烯组成且所述润滑剂是多元醇酯。
7.权利要求1-6任一项的组合物,其中所述润滑剂提供与所述氟代烯烃的一定程度的可混溶性,使得当将5重量%所述润滑剂加入所述氟代烯烃时,该混合物在-40到+20℃的整个温度范围具有一个液相,
或其中所述润滑剂提供与所述氟代烯烃的一定程度的可混溶性,使得当将20重量%所述润滑剂加入所述氟代烯烃时,该混合物在介于-40到+20℃的整个温度范围具有一个液相。
8.权利要求1-6任一项的组合物,其中所述润滑剂提供与所述氟代烯烃的一定程度的可混溶性,使得当将5重量%所述润滑剂加入所述氟代烯烃时,该混合物在-50到+70℃的整个温度范围具有一个液相,
或其中所述润滑剂提供与所述氟代烯烃的一定程度的可混溶性,使得当将20重量%所述润滑剂加入所述氟代烯烃时,该混合物在-50到+70℃的整个温度范围具有一个液相。
9.一种用于压缩制冷、空调和热泵系统的组合物,其包含:
(A) 包括氟代烯烃的制冷剂,其中所述氟代烯烃是反式-1,3,3,3-四氟丙烯或2,3,3,3-四氟烯烃;和
(B) 聚亚烷基二醇润滑剂,
其中所述聚亚烷基二醇润滑剂包括直链或支链的至少两种氧丙烯基团的均聚物或共聚物,
和
其中所述聚亚烷基二醇润滑剂在37℃时具有10-200厘沲范围的粘度,和
其中所述聚亚烷基二醇润滑剂提供与所述氟代烯烃的一定程度的可混溶性,使得当将5重量%所述聚亚烷基二醇润滑剂加入所述氟代烯烃时,混合物在-40到+20℃的整个温度范围具有一个液相。
10.权利要求9的组合物,其中所述制冷剂包括2,3,3,3-四氟丙烯。
11.权利要求9的组合物,其中所述制冷剂由2,3,3,3-四氟丙烯组成。
12.权利要求9的组合物,其中所述氟代烯烃包括反式1,3,3,3-四氟丙烯。
13.权利要求9的组合物,其中所述氟代烯烃由反式-1,3,3,3-四氟丙烯组成。
14.权利要求1-6和9-13任一项的组合物,其中所述聚亚烷基二醇包括直链或支链的至少两种氧乙烯、氧丙烯、氧丁烯或氧戊烯基或其组合的均聚物或共聚物。
15.权利要求14的组合物,其中所述聚亚烷基二醇是均聚物。
16.权利要求15的组合物,其中所述聚亚烷基二醇是至少两种氧丙烯基团的均聚物。
17.权利要求14的组合物,其中所述聚亚烷基二醇包括至少50%的氧丙烯基团。
18.权利要求1-6和9-13任一项的组合物,其中所述聚亚烷基二醇具有至少一个封端羟基。
19.权利要求18的组合物,其中所述聚亚烷基二醇的两个端基均是羟基。
20.权利要求1-6和9-13任一项的组合物,其中所述聚亚烷基二醇具有至少一个烷基封端基团。
21.权利要求1-6和9-13任一项的组合物,其中所述聚亚烷基二醇的两端羟基都被烷基封端羟基封端。
22.权利要求20的组合物,其中所述烷基是任选被杂原子氮或氟取代的C1-10烷基基团。
23.权利要求1-6和9-13任一项的组合物,其中一端或两端的封端羟基通过与羧酸反应来封端。
24.权利要求1-6和9-13任一项的组合物,其中该聚亚烷基二醇用乙酰基团进行双封端。
25.权利要求20的组合物,其中所述聚亚烷基二醇的至少一个端烷基含有至少一个杂原子。
26.权利要求25的组合物,其中所述聚亚烷基二醇具有至少一个氟代烷基端基。
27.权利要求1-6和9-13任一项的组合物,其中所述聚亚烷基二醇润滑剂具有至少一个酯端基。
28.权利要求1-6和9-13任一项的组合物,其中所述聚亚烷基二醇润滑剂在37℃时具有30-150厘沲范围的粘度。
29.权利要求1-28任一项的组合物在用于产生致冷的方法中的用途。
30.根据权利要求29的用途,其在选自压缩致冷系统、空调系统、电冰箱、深冷器、运输致冷系统和商业致冷系统的系统中进行。
31.根据权利要求29的用途,其中所述方法在深冷器中进行。
32.权利要求1-28任一项的组合物在产生热的方法中的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/695,212 US20040089839A1 (en) | 2002-10-25 | 2003-10-27 | Fluorinated alkene refrigerant compositions |
US10/695212 | 2003-10-27 | ||
CN200480039094.8A CN1898353B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200480039094.8A Division CN1898353B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103642461A CN103642461A (zh) | 2014-03-19 |
CN103642461B true CN103642461B (zh) | 2017-01-18 |
Family
ID=34549972
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201310572027.3A Expired - Lifetime CN103642461B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
CN201410138436.7A Expired - Lifetime CN103923723B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
CN200480039094.8A Expired - Lifetime CN1898353B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
CN201410138211.1A Expired - Lifetime CN103923611B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
CN201410137429.5A Expired - Lifetime CN103923610B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410138436.7A Expired - Lifetime CN103923723B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
CN200480039094.8A Expired - Lifetime CN1898353B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
CN201410138211.1A Expired - Lifetime CN103923611B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
CN201410137429.5A Expired - Lifetime CN103923610B (zh) | 2003-10-27 | 2004-10-25 | 氟代烯烃制冷剂组合物 |
Country Status (14)
Country | Link |
---|---|
US (5) | US20040089839A1 (zh) |
EP (6) | EP3680308A1 (zh) |
JP (6) | JP2007510039A (zh) |
KR (2) | KR101335360B1 (zh) |
CN (5) | CN103642461B (zh) |
DE (1) | DE08011766T1 (zh) |
DK (3) | DK2277976T3 (zh) |
ES (5) | ES2546024T3 (zh) |
HU (2) | HUE032542T2 (zh) |
PL (5) | PL2275509T3 (zh) |
PT (4) | PT2275509T (zh) |
SI (3) | SI2275509T1 (zh) |
TR (1) | TR201708747T4 (zh) |
WO (1) | WO2005042663A1 (zh) |
Families Citing this family (127)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050096246A1 (en) * | 2003-11-04 | 2005-05-05 | Johnson Robert C. | Solvent compositions containing chlorofluoroolefins |
US7279451B2 (en) | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
US8033120B2 (en) | 2002-10-25 | 2011-10-11 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
US9994750B2 (en) * | 2002-10-25 | 2018-06-12 | Honeywell International Inc. | Compositions containing fluorine substituted olefins and methods and systems using same |
ES2728672T3 (es) | 2002-10-25 | 2019-10-28 | Honeywell Int Inc | Composiciones que contienen olefinas sustituidas con flúor |
US20080292564A1 (en) * | 2002-10-25 | 2008-11-27 | Honeywell International, Inc. | Aerosol compositions containing fluorine substituted olefins and methods and systems using same |
WO2007109748A2 (en) * | 2006-03-21 | 2007-09-27 | Honeywell International Inc. | Foaming agents containing fluorine substituted unsaturated olefins |
US20040089839A1 (en) | 2002-10-25 | 2004-05-13 | Honeywell International, Inc. | Fluorinated alkene refrigerant compositions |
US7655610B2 (en) | 2004-04-29 | 2010-02-02 | Honeywell International Inc. | Blowing agent compositions comprising fluorinated olefins and carbon dioxide |
US7524805B2 (en) | 2004-04-29 | 2009-04-28 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons |
US9499729B2 (en) | 2006-06-26 | 2016-11-22 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
US8008244B2 (en) | 2004-04-29 | 2011-08-30 | Honeywell International Inc. | Compositions of tetrafluoropropene and hydrocarbons |
PT3461871T (pt) * | 2005-03-04 | 2021-03-09 | Chemours Co Fc Llc | Composições compreendendo trans hfc-1234ze e hfc-1234yf |
US20220389297A1 (en) * | 2005-03-04 | 2022-12-08 | The Chemours Company Fc, Llc | Compositions comprising a fluoroolefin |
US7569170B2 (en) * | 2005-03-04 | 2009-08-04 | E.I. Du Pont De Nemours And Company | Compositions comprising a fluoroolefin |
US20060243944A1 (en) * | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
TWI645031B (zh) * | 2005-06-24 | 2018-12-21 | 哈尼威爾國際公司 | 含有經氟取代之烯烴之組合物及其用途 |
US8574451B2 (en) * | 2005-06-24 | 2013-11-05 | Honeywell International Inc. | Trans-chloro-3,3,3-trifluoropropene for use in chiller applications |
US7708903B2 (en) | 2005-11-01 | 2010-05-04 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins and uses thereof |
BR122017013121B1 (pt) | 2005-11-01 | 2020-03-10 | E. I. Du Pont De Nemours And Company | Composição, processo de resfriamento, processo de aquecimento, métodos de uso da composição, método de redução do gwp de uma composição e método de preparação de uma composição refrigerante |
EP1951838B1 (en) * | 2005-11-01 | 2013-07-17 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins and uses thereof |
US20070210276A1 (en) * | 2006-03-10 | 2007-09-13 | Honeywell International Inc. | Method for generating pollution credits |
GB0611742D0 (en) | 2006-06-14 | 2006-07-26 | Ineos Fluor Holdings Ltd | Desiccants for fluids |
ES2539939T3 (es) * | 2006-06-27 | 2015-07-07 | E.I. Du Pont De Nemours And Company | Procedimientos de producción de 1,2,3,3,3-pentafluoropropeno |
WO2008006866A1 (en) * | 2006-07-12 | 2008-01-17 | Solvay Fluor Gmbh | Method for heating and cooling using fluoroether compounds, compositions suitable therefore and their use |
ES2608856T5 (es) * | 2006-09-01 | 2020-06-12 | Chemours Co Fc Llc | Estabilizadores que contienen fósforo para fluoroolefinas |
BRPI0714896A2 (pt) * | 2006-09-01 | 2013-05-21 | Du Pont | mÉtodo para o fornecer o transporte |
JP5139665B2 (ja) | 2006-11-02 | 2013-02-06 | 出光興産株式会社 | 冷凍機用潤滑油組成物 |
ES2935119T3 (es) * | 2007-01-31 | 2023-03-01 | Chemours Co Fc Llc | Un sistema de transferencia de calor por compresión de vapor |
JP5572284B2 (ja) * | 2007-02-27 | 2014-08-13 | Jx日鉱日石エネルギー株式会社 | 冷凍機油および冷凍機用作動流体組成物 |
JP2009074018A (ja) * | 2007-02-27 | 2009-04-09 | Nippon Oil Corp | 冷凍機油および冷凍機用作動流体組成物 |
RU2454453C2 (ru) * | 2007-02-27 | 2012-06-27 | Ниппон Ойл Корпорейшн | Холодильное масло и композиция рабочей жидкости для холодильника |
JP5914912B2 (ja) * | 2007-02-27 | 2016-05-11 | Jxエネルギー株式会社 | 冷凍機油および冷凍機用作動流体組成物 |
JP5302184B2 (ja) * | 2007-03-08 | 2013-10-02 | 出光興産株式会社 | 圧縮型冷凍機用潤滑油、及びそれを用いた冷凍装置 |
JP5193485B2 (ja) * | 2007-03-27 | 2013-05-08 | Jx日鉱日石エネルギー株式会社 | 冷凍機油及び冷凍機用作動流体組成物 |
US20100112328A1 (en) | 2007-03-29 | 2010-05-06 | Van Horn Brett L | Hydrofluoropropene blowing agents for thermoplastics |
MX2009010853A (es) * | 2007-04-18 | 2010-01-29 | Idemitsu Kosan Co | Composicion de aceite lubricante para refrigeradores y compresores que usan la composicion. |
JP5226242B2 (ja) * | 2007-04-18 | 2013-07-03 | 出光興産株式会社 | 冷凍機用潤滑油組成物 |
JP2008267251A (ja) * | 2007-04-19 | 2008-11-06 | Sanden Corp | 圧縮機 |
KR101477832B1 (ko) * | 2007-06-12 | 2014-12-30 | 이데미쓰 고산 가부시키가이샤 | 냉동기용 윤활유 조성물 및 이것을 사용한 압축기 |
US8388857B2 (en) * | 2007-06-27 | 2013-03-05 | Arkema Inc. | Stabilized hydrochlorofluoroolefins and hydrofluoroolefins |
US9523026B2 (en) | 2007-06-27 | 2016-12-20 | Arkema Inc. | Stabilized hydrochlorofluoroolefins and hydrofluoroolefins |
EP2171012A1 (en) * | 2007-07-27 | 2010-04-07 | E. I. du Pont de Nemours and Company | Compositions comprising fluoroolefins and uses thereof |
US8512591B2 (en) | 2007-10-12 | 2013-08-20 | Mexichem Amanco Holding S.A. De C.V. | Heat transfer compositions |
GB201002625D0 (en) * | 2010-02-16 | 2010-03-31 | Ineos Fluor Holdings Ltd | Heat transfer compositions |
US8333901B2 (en) | 2007-10-12 | 2012-12-18 | Mexichem Amanco Holding S.A. De C.V. | Heat transfer compositions |
US8628681B2 (en) | 2007-10-12 | 2014-01-14 | Mexichem Amanco Holding S.A. De C.V. | Heat transfer compositions |
EP2719750A1 (en) * | 2007-10-29 | 2014-04-16 | Nippon Oil Corporation | Refrigerator oil and working fluid composition for refrigerating machine |
JP5241261B2 (ja) * | 2008-02-15 | 2013-07-17 | 出光興産株式会社 | 冷凍機用潤滑油組成物 |
JP5241263B2 (ja) * | 2008-02-15 | 2013-07-17 | 出光興産株式会社 | 冷凍機用潤滑油組成物 |
JP5241262B2 (ja) * | 2008-02-15 | 2013-07-17 | 出光興産株式会社 | 冷凍機用潤滑油組成物 |
JP4665976B2 (ja) | 2008-02-22 | 2011-04-06 | 株式会社デンソー | 車両用冷凍サイクル装置 |
JP5612250B2 (ja) | 2008-03-07 | 2014-10-22 | 出光興産株式会社 | 冷凍機用潤滑油組成物 |
EP2250144A4 (en) | 2008-03-07 | 2014-06-04 | Arkema Inc | FORMULATED AND STABLE SYSTEMS CONTAINING CHLORO-3,3,3-TRIFLUOROPROPENE |
JP2009222032A (ja) | 2008-03-18 | 2009-10-01 | Daikin Ind Ltd | 冷凍装置 |
JP2009222360A (ja) * | 2008-03-18 | 2009-10-01 | Daikin Ind Ltd | 熱交換器 |
JP5285765B2 (ja) * | 2008-04-01 | 2013-09-11 | ハネウェル・インターナショナル・インコーポレーテッド | ヒートポンプ用の潤滑剤を選択する方法 |
US9994751B2 (en) * | 2008-04-30 | 2018-06-12 | Honeywell International Inc. | Absorption refrigeration cycles using a LGWP refrigerant |
US20110232306A1 (en) * | 2008-04-30 | 2011-09-29 | Honeywell International Inc. | Absorption refrigeration cycles using a lgwp refrigerant |
JP2011163565A (ja) * | 2008-06-09 | 2011-08-25 | Mitsubishi Electric Corp | 空気調和装置 |
JP5339788B2 (ja) * | 2008-06-13 | 2013-11-13 | 三菱電機株式会社 | 圧縮機および冷凍サイクル装置 |
JP5400043B2 (ja) * | 2008-06-16 | 2014-01-29 | 三菱電機株式会社 | スクロール圧縮機 |
US8443624B2 (en) * | 2008-06-16 | 2013-05-21 | Mitsubishi Electric Corporation | Non-Azeotropic refrigerant mixture and refrigeration cycle apparatus |
JP5294719B2 (ja) * | 2008-06-17 | 2013-09-18 | 三菱電機株式会社 | ロータリ圧縮機 |
CN102077040A (zh) * | 2008-06-24 | 2011-05-25 | 三菱电机株式会社 | 冷冻循环装置及空气调节装置 |
US8820079B2 (en) * | 2008-12-05 | 2014-09-02 | Honeywell International Inc. | Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids |
FR2936806B1 (fr) | 2008-10-08 | 2012-08-31 | Arkema France | Fluide refrigerant |
FR2937906B1 (fr) * | 2008-11-03 | 2010-11-19 | Arkema France | Procede de chauffage et/ou climatisation d'un vehicule. |
US8871112B2 (en) * | 2008-11-19 | 2014-10-28 | E I Du Pont De Nemours And Company | Compositions comprising 2,3,3,3-tetrafluoropropene and hydrocarbons and uses thereof |
US20100122545A1 (en) | 2008-11-19 | 2010-05-20 | E. I. Du Pont De Nemours And Company | Tetrafluoropropene compositions and uses thereof |
CN102264877B (zh) | 2008-12-23 | 2014-12-10 | 瑞弗化工有限公司 | 制冷润滑剂组合物 |
JP2012519736A (ja) * | 2009-02-11 | 2012-08-30 | アルケマ フランス | クロロトリフルオロプロペンとペンタンの共沸組成物および共沸様組成物 |
JP2011001897A (ja) | 2009-06-19 | 2011-01-06 | Panasonic Corp | 圧縮機 |
JP2011047329A (ja) * | 2009-08-27 | 2011-03-10 | Panasonic Corp | ロータリ圧縮機 |
CA2773453C (en) | 2009-09-09 | 2018-10-09 | Honeywell International Inc. | Monochlorotrifluoropropene compounds and compositions and methods using same |
FR2950065B1 (fr) | 2009-09-11 | 2012-02-03 | Arkema France | Fluide refrigerant binaire |
FR2950066B1 (fr) | 2009-09-11 | 2011-10-28 | Arkema France | Refrigeration basse et moyenne temperature |
MX341116B (es) | 2009-09-16 | 2016-08-09 | E I Du Pont De Nemours And Company * | Aparato enfriador que contiene trans-1,1,1,4,4,4-hexafluoro-2-bute no y metodos para producir enfriamiento en el mismo. |
JP6141019B2 (ja) | 2009-12-29 | 2017-06-07 | アーケマ・インコーポレイテッド | 冷媒−潤滑剤の組合せを選択する方法 |
GB201002622D0 (en) | 2010-02-16 | 2010-03-31 | Ineos Fluor Holdings Ltd | Heat transfer compositions |
FR2957083B1 (fr) | 2010-03-02 | 2015-12-11 | Arkema France | Fluide de transfert de chaleur pour compresseur centrifuge |
JP5546918B2 (ja) * | 2010-03-19 | 2014-07-09 | Jx日鉱日石エネルギー株式会社 | 冷凍機油および冷凍機用作動流体組成物 |
KR102037782B1 (ko) * | 2010-04-16 | 2019-10-29 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 2,3,3,3-테트라플루오로프로펜 및 1,1,1,2-테트라플루오로에탄을 포함하는 조성물, 이를 함유하는 칠러, 및 그 안에 냉각을 생성하는 방법 |
FR2959997B1 (fr) | 2010-05-11 | 2012-06-08 | Arkema France | Fluides de transfert de chaleur et leur utilisation dans des echangeurs de chaleur a contre-courant |
FR2959999B1 (fr) | 2010-05-11 | 2012-07-20 | Arkema France | Fluides de transfert de chaleur et leur utilisation dans des echangeurs de chaleur a contre-courant |
RU2547118C2 (ru) | 2010-05-20 | 2015-04-10 | Мексичем Аманко Холдинг С.А. Де С.В. | Теплообменные композиции |
CN102947408B (zh) | 2010-05-20 | 2016-04-27 | 墨西哥化学阿玛科股份有限公司 | 传热组合物 |
GB2481443B (en) | 2010-06-25 | 2012-10-17 | Mexichem Amanco Holding Sa | Heat transfer compositions |
CN103415587A (zh) * | 2010-07-06 | 2013-11-27 | 阿科玛股份有限公司 | 四氟丙烯与多元醇酯润滑剂的组合物 |
FR2964977B1 (fr) * | 2010-09-20 | 2013-11-01 | Arkema France | Composition a base de 3,3,3-tetrafluoropropene |
FR2964976B1 (fr) | 2010-09-20 | 2012-08-24 | Arkema France | Composition a base de 1,3,3,3-tetrafluoropropene |
MY161767A (en) * | 2010-12-14 | 2017-05-15 | Du Pont | Combinations of e-1,3,3,3-tetrafluoropropene and at least one tetrafluoroethane and their use for heating |
IT1406472B1 (it) | 2010-12-22 | 2014-02-28 | Nuovo Pignone Spa | Prova per similitudine di prestazione di compressore |
FR2971512B1 (fr) | 2011-02-10 | 2013-01-18 | Arkema France | Compositions binaires de 2,3,3,3-tetrafluoropropene et d'ammoniac |
FR2974812B1 (fr) * | 2011-05-04 | 2014-08-08 | Arkema France | Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification |
US9187682B2 (en) | 2011-06-24 | 2015-11-17 | Emerson Climate Technologies, Inc. | Refrigeration compressor lubricant |
FR2977707B1 (fr) | 2011-07-05 | 2014-05-23 | Schneider Electric Ind Sas | Utilisation d'une hydrofluoroolefine comme milieu d'isolation et/ou d'extinction d'arc en moyenne tension et appareil electrique moyenne tension a isolation gazeuse le comprenant |
IN2014DN03359A (zh) | 2011-10-26 | 2015-06-05 | Jx Nippon Oil & Energy Corp | |
CA2856196C (en) | 2011-12-06 | 2020-09-01 | Masco Corporation Of Indiana | Ozone distribution in a faucet |
FR2986007B1 (fr) * | 2012-01-25 | 2015-01-23 | Arkema France | Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification |
FR2986236B1 (fr) * | 2012-01-26 | 2014-01-10 | Arkema France | Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification |
IN2014DN07397A (zh) | 2012-03-27 | 2015-04-24 | Jx Nippon Oil & Energy Corp | |
CN104160005A (zh) * | 2012-03-29 | 2014-11-19 | 吉坤日矿日石能源株式会社 | 冷冻机用工作流体组合物 |
TW201410856A (zh) | 2012-08-23 | 2014-03-16 | Du Pont | 含四氟丙烯及二氟甲烷的冷媒混合物及其運用 |
FR3008419B1 (fr) | 2013-07-11 | 2015-07-17 | Arkema France | Compositions a base de 2,3,3,3-tetrafluoropropene presentant une miscibilite amelioree |
JP6224965B2 (ja) | 2013-09-12 | 2017-11-01 | 出光興産株式会社 | 冷凍機用混合組成物 |
CN105683269A (zh) | 2013-09-19 | 2016-06-15 | 陶氏环球技术有限责任公司 | 使用混合发泡剂制备闭孔刚性聚氨酯泡沫体的真空辅助方法 |
BR112016006698A2 (pt) | 2013-10-02 | 2017-08-01 | Jx Nippon Oil & Energy Corp | óleo de refrigerador, e composição do fluido de trabalho para refrigeradores |
JP2017508829A (ja) | 2014-01-16 | 2017-03-30 | シュリーブ ケミカル プロダクツ インコーポレーテッド | 乾燥合成冷却潤滑剤組成物 |
GB201410174D0 (en) | 2014-06-09 | 2014-07-23 | Mexichem Amanco Holding Sa | Process |
US10330364B2 (en) | 2014-06-26 | 2019-06-25 | Hudson Technologies, Inc. | System and method for retrofitting a refrigeration system from HCFC to HFC refrigerant |
JP5681829B1 (ja) * | 2014-07-25 | 2015-03-11 | Jx日鉱日石エネルギー株式会社 | 冷凍機油、冷凍機用作動流体組成物 |
WO2016140187A1 (ja) * | 2015-03-02 | 2016-09-09 | Jxエネルギー株式会社 | 冷凍機油及び冷凍機用作動流体組成物 |
CN105089001B (zh) * | 2015-04-14 | 2017-02-22 | 宁波职业技术学院 | 一种北京郊区pm2.5的治理方法 |
CN108463437B (zh) | 2015-12-21 | 2022-07-08 | 德尔塔阀门公司 | 包括消毒装置的流体输送系统 |
KR102374272B1 (ko) * | 2016-05-09 | 2022-03-15 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 하이드로플루오로올레핀 및 이의 사용 방법 |
JP6381614B2 (ja) * | 2016-11-29 | 2018-08-29 | マクセルホールディングス株式会社 | サポート材組成物 |
US10883063B2 (en) * | 2018-01-23 | 2021-01-05 | The Chemours Company Fc, Llc | Compositions, system and methods for introducing PAG lubricant or refrigerant into an air-conditioning or system using lower or low GWP refrigerant or refrigerant blends |
CA3083293A1 (en) * | 2018-01-23 | 2019-08-01 | The Chemours Company Fc, Llc | Compositions, system and methods for introducing pag lubricant or refrigerant into an air-conditioning or system using lower or low gwp refrigerant or refrigerant blends |
FR3077822B1 (fr) | 2018-02-15 | 2020-07-24 | Arkema France | Compositions de transfert de chaleur en remplacement du r-134a |
US11466225B2 (en) | 2018-03-06 | 2022-10-11 | Shrieve Chemical Products, Inc. | Lubricant and refrigerant compositions comprising polyalkylene glycols and uses thereof |
SI3978580T1 (sl) | 2018-04-30 | 2023-08-31 | The Chemours Company Fc, Llc | Stabilizirani fluorolefinski sestavki in postopek za njihovo proizvodnjo, shranjevanje in uporabo |
BR112021022059A2 (pt) | 2018-10-26 | 2021-12-28 | Chemours Co Fc Llc | Composições de fluoropropeno, métodos de produção de uma mistura e de resfriamento, processos para transferência de calor, para tratamento de uma superfície e para formação de uma composição, sistema de refrigeração, aparelhos de refrigeração, uso da composição de fluoropropeno e método para substituição de um refrigerante |
EP4269377A3 (en) * | 2018-10-26 | 2023-12-27 | The Chemours Company FC, LLC | Hfo-1234ze and hfo-1234yf compositions and processes for producing and using the compositions |
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 |
MX2021007466A (es) | 2018-12-21 | 2021-08-05 | Mexichem Fluor Sa De Cv | Compuestos. |
FR3139342A1 (fr) * | 2022-09-02 | 2024-03-08 | Pascal RETOU | Fluide caloporteur pour des systèmes de réfrigération embarqués. |
Family Cites Families (150)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE536296A (zh) | 1954-03-22 | |||
IT535373A (zh) | 1954-06-10 | |||
US2970988A (en) | 1955-10-14 | 1961-02-07 | Minnesota Mining & Mfg | New fluorine-containing polymers and preparation thereof |
US2846458A (en) | 1956-05-23 | 1958-08-05 | Dow Corning | Organosiloxane ethers |
US2889379A (en) * | 1957-02-06 | 1959-06-02 | Dow Chemical Co | Preparation of 3, 3, 3-trifluoropropene |
US2931840A (en) | 1958-11-25 | 1960-04-05 | Du Pont | Process for preparing 2, 3, 3, 3-tetrafluoropropene |
NL121693C (zh) | 1959-05-22 | |||
US2996555A (en) | 1959-06-25 | 1961-08-15 | Dow Chemical Co | Preparation of 2, 3, 3, 3-tetrafluoropropene |
DE1122697B (de) | 1960-05-06 | 1962-01-25 | Bayer Ag | Verfahren zur Herstellung von Schaumstoffen auf Isocyanatbasis |
US3085065A (en) | 1960-07-11 | 1963-04-09 | Du Pont | Process of transferring heat |
FR1422125A (fr) | 1964-09-23 | 1965-12-24 | Labo Cent Telecommunicat | Perfectionnements aux circuits déphaseurs |
US3472826A (en) | 1968-05-23 | 1969-10-14 | Union Carbide Corp | Saturated hydrocarbon prepolymer and reaction products thereof |
US3659023A (en) | 1970-05-11 | 1972-04-25 | Baxter Laboratories Inc | Method of inducing anesthesia with 2-bromo-1 1 2 3 3-pentafluoropropane |
US3884828A (en) * | 1970-10-15 | 1975-05-20 | Dow Corning | Propellants and refrigerants based on trifluoropropene |
US3726318A (en) * | 1971-10-28 | 1973-04-10 | Pryde Inc | Faucet |
US3723318A (en) * | 1971-11-26 | 1973-03-27 | Dow Corning | Propellants and refrigerants based on trifluoropropene |
US4465786A (en) * | 1982-09-27 | 1984-08-14 | General Electric Company | Catalyst composition for the preparation of 3,3,3-trifluoropropene |
US4650914A (en) | 1983-07-06 | 1987-03-17 | Monsanto Company | Process for producing 1,1,2,3-tetrachloropropene |
US4788352A (en) * | 1986-07-21 | 1988-11-29 | Shell Oil Company | Trifluoroalkenes and a method for their preparation |
JPH0688920B2 (ja) | 1987-02-27 | 1994-11-09 | ダイキン工業株式会社 | 2,3,3,3−テトラフルオロプロペンの製法 |
JPH0749391B2 (ja) | 1987-06-04 | 1995-05-31 | ダイキン工業株式会社 | 含フッ素化合物及びその製法 |
US4755316A (en) * | 1987-10-23 | 1988-07-05 | Allied-Signal Inc. | Refrigeration lubricants |
US4798818A (en) * | 1987-11-27 | 1989-01-17 | Dow Corning Corporation | Catalyst composition and process for its preparation |
JPH01207250A (ja) | 1988-02-12 | 1989-08-21 | Daikin Ind Ltd | 含フツ素オレフインの製造方法 |
US5008428A (en) | 1989-10-26 | 1991-04-16 | W. R. Grace & Co.-Conn. | Integrated process for the production of aminoacetonitriles |
US5008028A (en) * | 1988-12-14 | 1991-04-16 | The Lubrizol Corporation | Liquid compositions containing carboxylic esters |
US5254280A (en) * | 1988-12-27 | 1993-10-19 | Allied-Signal Inc. | Refrigeration compositions having polyoxyalkylene glycols with alkylene groups having at least 4 carbon atoms therein |
US4975212A (en) * | 1988-12-27 | 1990-12-04 | Allied-Signal Inc. | Fluorinated lubricating compositions |
CA2026568C (en) | 1989-02-02 | 1999-12-14 | Shinsuke Morikawa | Process for producing a hydrogen-containing 2,2-difluoropropane |
US4945119A (en) | 1989-05-10 | 1990-07-31 | The Dow Chemical Company | Foaming system for rigid urethane and isocyanurate foams |
US4944890A (en) | 1989-05-23 | 1990-07-31 | E. I. Du Pont De Nemours And Company | Compositions and process of using in refrigeration |
US4971712A (en) * | 1989-06-02 | 1990-11-20 | E. I. Du Pont De Nemours And Company | Compositions for compression refrigeration and methods of using them |
US4971212A (en) * | 1989-10-06 | 1990-11-20 | Owens-Illinois Closure Inc. | Tamper indicating packages |
US4994890A (en) * | 1989-11-27 | 1991-02-19 | Snap-On Tools Corporation | Rectifier structure with individual links |
US5053155A (en) * | 1989-12-19 | 1991-10-01 | E. I. Du Pont De Nemours And Company | Compositions and process for use in refrigeration |
US5094768A (en) * | 1990-03-30 | 1992-03-10 | Lubrizol Genetics, Inc. | Liquid compositions for refrigeration systems containing boron compositions |
CA2086841C (en) | 1990-07-26 | 2000-05-02 | Donald Bernard Bivens | Near-azeotropic blends for use as refrigerants |
JPH04110388A (ja) | 1990-08-31 | 1992-04-10 | Daikin Ind Ltd | 熱伝達用流体 |
US5100569A (en) * | 1990-11-30 | 1992-03-31 | Allied-Signal Inc. | Polyoxyalkylene glycol refrigeration lubricants having pendant, non-terminal perfluoroalkyl groups |
JPH04288452A (ja) | 1991-03-15 | 1992-10-13 | Daikin Ind Ltd | 冷凍機の運転方法 |
AU1642192A (en) | 1991-03-18 | 1992-10-21 | Allied-Signal Inc. | Non-azeotropic refrigerant compositions comprising difluoromethane; 1,1,1-trifluoroethane; or propane |
US5648017A (en) | 1991-03-28 | 1997-07-15 | E. I. Du Pont De Nemours And Company | Azeotropic and azeotrope-like compositions of 1,1,2,2-tetrafluoroethane and (iso) butane |
US5182040A (en) | 1991-03-28 | 1993-01-26 | E. I. Du Pont De Nemours And Company | Azeotropic and azeotrope-like compositions of 1,1,2,2-tetrafluoroethane |
US5155082A (en) | 1991-04-12 | 1992-10-13 | Allied-Signal Inc. | Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons |
BE1005096A3 (fr) | 1991-07-10 | 1993-04-20 | Solvay | Procede pour la preparation de 1-chloro-1,1,3,3,3-pentafluoropropane et de 1,1,1,3,3,3-hexafluoropropane. |
JPH0585970A (ja) * | 1991-09-25 | 1993-04-06 | Daikin Ind Ltd | 冷 媒 |
US7105152B1 (en) | 1991-12-18 | 2006-09-12 | 3M Innovative Properties Company | Suspension aerosol formulations |
US5250208A (en) | 1992-04-02 | 1993-10-05 | E. I. Du Pont De Nemours And Company | Ternary azeotropic compositions |
WO1993024588A1 (en) * | 1992-06-03 | 1993-12-09 | Henkel Corporation | Polyol ester lubricants for high efficiency refrigerators |
US5518643A (en) | 1992-06-04 | 1996-05-21 | Idemitsu Kosan Co., Ltd. | Lubricating oil containing a polyvinyl ether compound for compression-type refrigerators |
EP0644173A1 (en) | 1992-06-05 | 1995-03-22 | Daikin Industries, Limited | Processes for producing 1,1,1,2,3-pentafluoropropene and producing 1,1,1,2,3-pentafluoropropane |
EP0582451B1 (en) * | 1992-08-05 | 1997-12-10 | Nippon Oil Co., Ltd. | Refrigerator oil composition for fluoroalkane refrigerant |
DE4233531A1 (de) * | 1992-10-06 | 1994-04-07 | Hoechst Ag | Perfluorisohexen als Kühl- und Isoliermedium |
DE4241969A1 (de) * | 1992-12-12 | 1994-06-16 | Hoechst Ag | Hochreines Perfluor-(4-methyl-2-penten), seine Herstellung und Verwendung |
GB2276392B (en) | 1993-02-22 | 1997-03-26 | D G P | Improved production of natural flavours and fragrances |
US5611210A (en) | 1993-03-05 | 1997-03-18 | Ikon Corporation | Fluoroiodocarbon blends as CFC and halon replacements |
US5538659A (en) | 1993-03-29 | 1996-07-23 | E. I. Du Pont De Nemours And Company | Refrigerant compositions including hexafluoropropane and a hydrofluorocarbon |
US5370812A (en) * | 1993-06-28 | 1994-12-06 | Union Carbide Chemicals & Plastics Technology Corporation | Lubricant compositions for refrigerators comprising polyalkylene glycol and a hydrocarbon solvent |
US5395997A (en) | 1993-07-29 | 1995-03-07 | Alliedsignal Inc. | Process for the preparation of hydrofluorocarbons having 3 to 7 carbon atoms |
DE69414403T2 (de) | 1993-07-29 | 1999-05-06 | Alliedsignal Inc., Morristown, N.J. | Verfahren zur herstellung von 1,1,1,3,3 pentafluorpropan |
US6809226B1 (en) | 1993-08-04 | 2004-10-26 | Solvay (Societe Anonyme) | Process for the preparation of 1-chloro-1-fluoroethane and/or 1,1-difluoroethane |
US5736062A (en) | 1993-08-13 | 1998-04-07 | Ausimont S.P.A. | Azeotrope-like mixtures utilizable as refrigerating fluids |
US5510173A (en) | 1993-08-20 | 1996-04-23 | Southwall Technologies Inc. | Multiple layer thin films with improved corrosion resistance |
US5578137A (en) | 1993-08-31 | 1996-11-26 | E. I. Du Pont De Nemours And Company | Azeotropic or azeotrope-like compositions including 1,1,1,2,3,4,4,5,5,5-decafluoropentane |
DE69507533T2 (de) | 1994-05-10 | 1999-06-02 | Calsonic Corp., Tokio/Tokyo | Klimaanlage mit Wärmepumpe |
US5446217A (en) * | 1994-05-16 | 1995-08-29 | Alliedsignal Inc. | Processes for the preparation of fluorinated olefins and hydrofluorocarbons using fluorinated olefin |
JP2818035B2 (ja) | 1994-07-11 | 1998-10-30 | アライドシグナル・インコーポレーテッド | 1,1,1,3,3−ペンタフルオロプロパンの製造法 |
EP0770115B1 (en) | 1994-07-14 | 1998-12-09 | E.I. Du Pont De Nemours And Company | Refrigerant compositions |
US5792383A (en) * | 1994-09-07 | 1998-08-11 | Witco Corporation | Reduction of enterfacial tension between hydrocarbon lubricant and immiscible liquid refrigerant |
US5866030A (en) * | 1994-09-07 | 1999-02-02 | Witco Corporation | Enhanced hydrocarbon lubricants for use with immiscible refrigerants |
US5673144A (en) * | 1994-09-14 | 1997-09-30 | International Business Machines, Corporation | Oblique viewing microscope system |
JPH08157847A (ja) * | 1994-12-08 | 1996-06-18 | Japan Energy Corp | Hfcフロン圧縮機用潤滑油組成物、hfcフロン圧縮機の潤滑性向上方法及び同潤滑油組成物を含有する作動流体組成物 |
RU2073058C1 (ru) | 1994-12-26 | 1997-02-10 | Олег Николаевич Подчерняев | Озонобезопасная рабочая смесь |
US5714083A (en) * | 1995-01-30 | 1998-02-03 | Turner; Donald E. | A non-flammable refrigerant fluid containing hexa fluoropropane and hydrocarbons |
US6013609A (en) | 1995-07-10 | 2000-01-11 | Idemitsu Kosan Co., Ltd. | Refrigerator oil and process for lubrication using the refrigerator oil |
JPH09100483A (ja) * | 1995-10-02 | 1997-04-15 | Japan Energy Corp | 冷凍機油およびそれを用いた冷凍機用作動流体 |
IT1277085B1 (it) | 1995-12-14 | 1997-11-04 | Ausimont Spa | Composizioni ternarie quasi azeotropiche costituite da fluorocarburi idrogenati e idrocarburi adatte come fluidi refrigeranti |
US6235951B1 (en) | 1996-01-17 | 2001-05-22 | Central Glass Company, Limited | Method for producing 1,1,1,3,3-pentafluoropropane |
US6316681B1 (en) | 1996-03-05 | 2001-11-13 | Central Glass Company, Limited | Method for producing 1,1,1,3,3-pentafluoropropane |
US6111150A (en) | 1996-06-20 | 2000-08-29 | Central Glass Company, Limited | Method for producing 1,1,1,3,3,-pentafluoropropane |
JP3465865B2 (ja) | 1996-06-20 | 2003-11-10 | セントラル硝子株式会社 | 1,3,3,3−テトラフルオロプロペンの製造法 |
NZ334422A (en) * | 1996-08-08 | 2000-01-28 | Donald E Turner | Nonflammable refrigerant consisting of hexafluoropropylene, chlorodifluoromethane and one or more hydrocarbons |
US5710352A (en) | 1996-09-19 | 1998-01-20 | Alliedsignal Inc. | Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene |
US6300378B1 (en) | 1996-09-27 | 2001-10-09 | University Of New Mexico | Tropodegradable bromine-containing halocarbon additives to decrease flammability of refrigerants foam blowing agents solvents aerosol propellants and sterilants |
US6023004A (en) | 1996-11-12 | 2000-02-08 | Alliedsignal, Inc. | Liquid phase catalytic fluorination of hydrochlorocarbon and hydrochlorofluorocarbon |
US6369284B1 (en) | 1997-01-31 | 2002-04-09 | E. I. Du Pont De Nemours And Company | Catalytic manufacture of pentafluoropropenes |
US5986151A (en) | 1997-02-05 | 1999-11-16 | Alliedsignal Inc. | Fluorinated propenes from pentafluoropropane |
US5788886A (en) | 1997-05-05 | 1998-08-04 | E. I. Du Pont De Nemours And Company | Pentafluoropropane compositions |
US5988517A (en) | 1997-06-09 | 1999-11-23 | Ford Global Technologies, Inc. | Method and system for controlling an automotive HVAC system based on the principle of HVAC work |
FR2764883B1 (fr) | 1997-06-18 | 1999-07-16 | Atochem Elf Sa | Procede de fabrication d'hydrofluoroalcanes |
US5969198A (en) | 1997-06-27 | 1999-10-19 | Alliedsignal Inc. | Process for the preparation of 1,1,1,3,3-pentafluoropropane |
US6031141A (en) | 1997-08-25 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Fluoroolefin manufacturing process |
US6089032A (en) | 1998-10-28 | 2000-07-18 | Interdynamics Inc. | Method of retrofitting air conditioner and system therefor |
JP3886229B2 (ja) | 1997-11-11 | 2007-02-28 | セントラル硝子株式会社 | 1,3,3,3−テトラフルオロプロペンの製造法 |
US5811603A (en) | 1997-12-01 | 1998-09-22 | Elf Atochem North America, Inc. | Gas phase fluorination of 1230za |
US6092589A (en) | 1997-12-16 | 2000-07-25 | York International Corporation | Counterflow evaporator for refrigerants |
US5856595A (en) | 1998-03-03 | 1999-01-05 | Alliedsignal Inc. | Purified 1,1,1,3,3,3-hexafluoropropane and method for making same |
DE19830628C1 (de) | 1998-07-09 | 2000-04-20 | Lauffer Maschf | Verfahren zum Verpressen von Mehrlagenleiterplatten (Multilayer) |
US6124510A (en) | 1998-07-21 | 2000-09-26 | Elf Atochem North America, Inc. | 1234ze preparation |
US6045444A (en) | 1998-08-28 | 2000-04-04 | General Motors Corporation | Compact automotive air conditioning module |
US6059027A (en) | 1998-11-12 | 2000-05-09 | Daimlerchrysler Corporation | Anti-fog controller for reversible air conditioning and heat pump HVAC system for electric vehicles |
JP2000169404A (ja) | 1998-12-11 | 2000-06-20 | Tosoh Corp | 含フッ素オレフィン類の臭素化方法 |
US6041621A (en) | 1998-12-30 | 2000-03-28 | Praxair Technology, Inc. | Single circuit cryogenic liquefaction of industrial gas |
US6076372A (en) * | 1998-12-30 | 2000-06-20 | Praxair Technology, Inc. | Variable load refrigeration system particularly for cryogenic temperatures |
US6327866B1 (en) * | 1998-12-30 | 2001-12-11 | Praxair Technology, Inc. | Food freezing method using a multicomponent refrigerant |
US6176102B1 (en) | 1998-12-30 | 2001-01-23 | Praxair Technology, Inc. | Method for providing refrigeration |
US5969188A (en) * | 1999-01-05 | 1999-10-19 | Nipa Hardwicke, Inc. | Process for producing trifluoromethylacetophenones |
US6374629B1 (en) | 1999-01-25 | 2002-04-23 | The Lubrizol Corporation | Lubricant refrigerant composition for hydrofluorocarbon (HFC) refrigerants |
US6783691B1 (en) | 1999-03-22 | 2004-08-31 | E.I. Du Pont De Nemours And Company | Compositions of difluoromethane, pentafluoroethane, 1,1,1,2-tetrafluoroethane and hydrocarbons |
US6304803B1 (en) | 1999-09-22 | 2001-10-16 | Honda Giken Kogyo Kabushiki Kaisha | HVAC control system for an automobile |
US6382305B1 (en) | 1999-10-15 | 2002-05-07 | Calsonic Kansei Corporation | Heating ventilation, and air conditioning unit for automotive vehicles |
US6589355B1 (en) | 1999-10-29 | 2003-07-08 | Alliedsignal Inc. | Cleaning processes using hydrofluorocarbon and/or hydrochlorofluorocarbon compounds |
GB0001981D0 (en) | 2000-01-31 | 2000-03-22 | Ici Materials | Refrigerant lubricant compositions |
JP2004513189A (ja) | 2000-07-17 | 2004-04-30 | ハネウェル・インターナショナル・インコーポレーテッド | 担持された触媒系 |
KR20020019682A (ko) | 2000-09-06 | 2002-03-13 | 권오석 | 고온용 혼합 냉매 조성물 |
US6516837B2 (en) | 2000-09-27 | 2003-02-11 | Honeywell International Inc. | Method of introducing refrigerants into refrigeration systems |
US6991744B2 (en) | 2000-12-08 | 2006-01-31 | E. I. Du Pont De Nemours And Company | Refrigerant compositions containing a compatibilizer |
US6548719B1 (en) | 2001-09-25 | 2003-04-15 | Honeywell International | Process for producing fluoroolefins |
ES2357225T3 (es) | 2001-11-01 | 2011-04-20 | Uab Research Foundation | Combinaciones de anticuerpos anti-dr5 y anticuerpos anti-dr4 y otros agentes terapéuticos. |
DE10203779A1 (de) | 2002-01-30 | 2003-07-31 | Solvay Fluor & Derivate | Gemische mit 1,1,1,3,3-Pentalfluorbutan und 1,1,1,2,3,3,3-Heptafluorpropan |
US7230146B2 (en) | 2003-10-27 | 2007-06-12 | Honeywell International Inc. | Process for producing fluoropropenes |
ES2728672T3 (es) | 2002-10-25 | 2019-10-28 | Honeywell Int Inc | Composiciones que contienen olefinas sustituidas con flúor |
US7279451B2 (en) | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
US9994750B2 (en) * | 2002-10-25 | 2018-06-12 | Honeywell International Inc. | Compositions containing fluorine substituted olefins and methods and systems using same |
US20080292564A1 (en) * | 2002-10-25 | 2008-11-27 | Honeywell International, Inc. | Aerosol compositions containing fluorine substituted olefins and methods and systems using same |
US20040089839A1 (en) | 2002-10-25 | 2004-05-13 | Honeywell International, Inc. | Fluorinated alkene refrigerant compositions |
JP4110388B2 (ja) * | 2003-01-10 | 2008-07-02 | 荒川化学工業株式会社 | 金めっき部品用洗浄剤およびすすぎ剤並びに洗浄方法およびすすぎ方法 |
US7592494B2 (en) | 2003-07-25 | 2009-09-22 | Honeywell International Inc. | Process for the manufacture of 1,3,3,3-tetrafluoropropene |
US7524805B2 (en) * | 2004-04-29 | 2009-04-28 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons |
US6991532B2 (en) | 2003-12-09 | 2006-01-31 | Valeo Climate Control Corp. | Method and apparatus for decontamination for automotive HVAC systems |
FR2865731B1 (fr) | 2004-01-30 | 2007-09-07 | Solvay | Procede de fabrication d'un hydrofluoroalcane |
US7074751B2 (en) * | 2004-04-16 | 2006-07-11 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane |
US6969701B2 (en) * | 2004-04-16 | 2005-11-29 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane |
AU2005236038B2 (en) | 2004-04-16 | 2008-10-02 | Honeywell International Inc. | Azeotrope-like compositions of difluoromethane and trifluoroiodomethane |
US7341984B2 (en) * | 2004-04-16 | 2008-03-11 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane |
US7622435B2 (en) * | 2004-04-16 | 2009-11-24 | Honeywell International Inc. | Methods of replacing refrigerant |
US7605117B2 (en) * | 2004-04-16 | 2009-10-20 | Honeywell International Inc. | Methods of replacing refrigerant |
JP2008504373A (ja) | 2004-04-16 | 2008-02-14 | ハネウェル・インターナショナル・インコーポレーテッド | ジフルオロメタン及びトリフルオロヨードメタンの共沸混合物様組成物 |
US7098176B2 (en) * | 2004-04-16 | 2006-08-29 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and pentafluoropropene |
US8008244B2 (en) * | 2004-04-29 | 2011-08-30 | Honeywell International Inc. | Compositions of tetrafluoropropene and hydrocarbons |
CA2564903C (en) | 2004-04-29 | 2012-12-04 | Honeywell International Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene |
US6958424B1 (en) | 2004-12-10 | 2005-10-25 | Honeywell International Inc. | Process for fluoroalkenes |
US20060243944A1 (en) | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
TWI645031B (zh) | 2005-06-24 | 2018-12-21 | 哈尼威爾國際公司 | 含有經氟取代之烯烴之組合物及其用途 |
US20070100010A1 (en) | 2005-11-01 | 2007-05-03 | Creazzo Joseph A | Blowing agents for forming foam comprising unsaturated fluorocarbons |
US7708903B2 (en) | 2005-11-01 | 2010-05-04 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins and uses thereof |
US20070098646A1 (en) | 2005-11-01 | 2007-05-03 | Nappa Mario J | Aerosol propellants comprising unsaturated fluorocarbons |
US7759532B2 (en) | 2006-01-13 | 2010-07-20 | E.I. Du Pont De Nemours And Company | Refrigerant additive compositions containing perfluoropolyethers |
US7563384B2 (en) * | 2006-07-28 | 2009-07-21 | Honeywell International Inc. | Essentially non-flammable low global warming compositions |
JP5285765B2 (ja) * | 2008-04-01 | 2013-09-11 | ハネウェル・インターナショナル・インコーポレーテッド | ヒートポンプ用の潤滑剤を選択する方法 |
-
2003
- 2003-10-27 US US10/695,212 patent/US20040089839A1/en not_active Abandoned
-
2004
- 2004-10-25 PL PL10010521T patent/PL2275509T3/pl unknown
- 2004-10-25 PL PL08011766T patent/PL2009075T3/pl unknown
- 2004-10-25 PL PL10011589T patent/PL2277976T3/pl unknown
- 2004-10-25 SI SI200432481T patent/SI2275509T1/sl unknown
- 2004-10-25 PT PT100105212T patent/PT2275509T/pt unknown
- 2004-10-25 PL PL04817445T patent/PL1725628T3/pl unknown
- 2004-10-25 PT PT100105204T patent/PT2277970T/pt unknown
- 2004-10-25 JP JP2006538130A patent/JP2007510039A/ja not_active Withdrawn
- 2004-10-25 EP EP19218149.3A patent/EP3680308A1/en active Pending
- 2004-10-25 CN CN201310572027.3A patent/CN103642461B/zh not_active Expired - Lifetime
- 2004-10-25 ES ES08011766.6T patent/ES2546024T3/es not_active Expired - Lifetime
- 2004-10-25 DK DK10011589.8T patent/DK2277976T3/da active
- 2004-10-25 HU HUE10010520A patent/HUE032542T2/en unknown
- 2004-10-25 EP EP08011766.6A patent/EP2009075B1/en not_active Revoked
- 2004-10-25 EP EP10010521.2A patent/EP2275509B1/en not_active Expired - Lifetime
- 2004-10-25 ES ES10011589T patent/ES2784188T3/es not_active Expired - Lifetime
- 2004-10-25 TR TR2017/08747T patent/TR201708747T4/tr unknown
- 2004-10-25 ES ES10010521T patent/ES2748910T3/es not_active Expired - Lifetime
- 2004-10-25 EP EP04817445A patent/EP1725628B1/en not_active Revoked
- 2004-10-25 ES ES10010520.4T patent/ES2628746T3/es not_active Expired - Lifetime
- 2004-10-25 PT PT100115898T patent/PT2277976T/pt unknown
- 2004-10-25 CN CN201410138436.7A patent/CN103923723B/zh not_active Expired - Lifetime
- 2004-10-25 CN CN200480039094.8A patent/CN1898353B/zh not_active Expired - Lifetime
- 2004-10-25 WO PCT/US2004/035132 patent/WO2005042663A1/en active Application Filing
- 2004-10-25 EP EP10010520.4A patent/EP2277970B1/en not_active Revoked
- 2004-10-25 KR KR1020067010510A patent/KR101335360B1/ko active IP Right Grant
- 2004-10-25 ES ES04817445T patent/ES2385650T3/es not_active Expired - Lifetime
- 2004-10-25 DE DE08011766T patent/DE08011766T1/de active Pending
- 2004-10-25 EP EP10011589.8A patent/EP2277976B1/en not_active Revoked
- 2004-10-25 DK DK04817445.2T patent/DK1725628T3/da active
- 2004-10-25 HU HUE10010521A patent/HUE046570T2/hu unknown
- 2004-10-25 PT PT04817445T patent/PT1725628E/pt unknown
- 2004-10-25 SI SI200431900T patent/SI1725628T1/sl unknown
- 2004-10-25 PL PL10010520T patent/PL2277970T3/pl unknown
- 2004-10-25 SI SI200432490T patent/SI2277976T1/sl unknown
- 2004-10-25 CN CN201410138211.1A patent/CN103923611B/zh not_active Expired - Lifetime
- 2004-10-25 CN CN201410137429.5A patent/CN103923610B/zh not_active Expired - Lifetime
- 2004-10-25 DK DK10010521.2T patent/DK2275509T3/da active
- 2004-10-25 KR KR1020127011477A patent/KR101335358B1/ko active IP Right Grant
-
2006
- 2006-03-20 US US11/385,259 patent/US9631129B2/en not_active Expired - Lifetime
-
2013
- 2013-05-24 JP JP2013110268A patent/JP2013166962A/ja active Pending
-
2014
- 2014-06-10 JP JP2014119442A patent/JP2014159604A/ja not_active Withdrawn
-
2016
- 2016-03-01 JP JP2016038691A patent/JP2016104886A/ja active Pending
- 2016-12-23 US US15/389,697 patent/US20170233624A1/en not_active Abandoned
-
2017
- 2017-04-18 US US15/490,413 patent/US20180094179A1/en not_active Abandoned
- 2017-05-26 JP JP2017104404A patent/JP2017197753A/ja active Pending
-
2018
- 2018-11-13 JP JP2018212825A patent/JP2019048996A/ja active Pending
-
2019
- 2019-10-01 US US16/589,770 patent/US20200208034A1/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103642461B (zh) | 氟代烯烃制冷剂组合物 | |
US9676984B2 (en) | Heat-transfer compositions exhibiting improved miscibility with the lubricating oil | |
US10450488B2 (en) | Heat transfer compositions having improved miscibility with lubricating oil | |
JP2007510039A5 (zh) | ||
CN103215013B (zh) | 氟代烯烃制冷剂组合物 | |
WO2024106514A1 (ja) | 作動流体組成物、冷凍機油及び冷凍機 | |
AU2016231462B2 (en) | Heat-transfer compositions exhibiting improved miscibility with the lubricating oil | |
TWI376409B (en) | Fluorinated alkene refrigerant compositions | |
AU2015202362B2 (en) | Heat-transfer compositions exhibiting improved miscibility with the lubricating oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CX01 | Expiry of patent term |
Granted publication date: 20170118 |