JP5597539B2 - 冷媒2,3,3,3‐テトラフルオロ‐1‐プロペン用冷凍機油 - Google Patents
冷媒2,3,3,3‐テトラフルオロ‐1‐プロペン用冷凍機油 Download PDFInfo
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- JP5597539B2 JP5597539B2 JP2010528611A JP2010528611A JP5597539B2 JP 5597539 B2 JP5597539 B2 JP 5597539B2 JP 2010528611 A JP2010528611 A JP 2010528611A JP 2010528611 A JP2010528611 A JP 2010528611A JP 5597539 B2 JP5597539 B2 JP 5597539B2
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- acid
- refrigerant
- weight
- ester
- oil
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- 239000003507 refrigerant Substances 0.000 title claims description 44
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims description 31
- 239000010721 machine oil Substances 0.000 title claims description 27
- 150000002148 esters Chemical class 0.000 claims description 37
- 239000003921 oil Substances 0.000 claims description 37
- -1 phenol compound Chemical class 0.000 claims description 25
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 150000004665 fatty acids Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 150000001718 carbodiimides Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 14
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 13
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 13
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 11
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 235000019198 oils Nutrition 0.000 description 34
- 238000012360 testing method Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 9
- 229920001515 polyalkylene glycol Polymers 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 description 5
- 238000010292 electrical insulation Methods 0.000 description 5
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 5
- 238000005057 refrigeration Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GMEUEHIGFJMSTL-UHFFFAOYSA-N n,n'-bis(2,3-dibutylphenyl)methanediimine Chemical compound CCCCC1=CC=CC(N=C=NC=2C(=C(CCCC)C=CC=2)CCCC)=C1CCCC GMEUEHIGFJMSTL-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000010726 refrigerant oil Substances 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 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
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ACVCIJWFRHNPBF-UHFFFAOYSA-N 6-(oxiran-2-ylmethoxy)-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(=O)OCC1CO1 ACVCIJWFRHNPBF-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical compound C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 description 1
- YDKXQROQJPVWJU-UHFFFAOYSA-N C(CCCCCCCC)C1=C(C=CC=C1)N=C=NC1=C(C=CC=C1)CCCCCCCCC Chemical compound C(CCCCCCCC)C1=C(C=CC=C1)N=C=NC1=C(C=CC=C1)CCCCCCCCC YDKXQROQJPVWJU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- WCQUXQDPAFJFHB-UHFFFAOYSA-N n,n'-bis(2-butylphenyl)methanediimine Chemical compound CCCCC1=CC=CC=C1N=C=NC1=CC=CC=C1CCCC WCQUXQDPAFJFHB-UHFFFAOYSA-N 0.000 description 1
- POOVXLCLGSARNP-UHFFFAOYSA-N n,n'-bis(2-propan-2-ylphenyl)methanediimine Chemical compound CC(C)C1=CC=CC=C1N=C=NC1=CC=CC=C1C(C)C POOVXLCLGSARNP-UHFFFAOYSA-N 0.000 description 1
- ONWRHZSCWAZSHZ-UHFFFAOYSA-N n,n'-bis[2,3,4-tri(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=C(C(C)C)C(C(C)C)=CC=C1N=C=NC1=CC=C(C(C)C)C(C(C)C)=C1C(C)C ONWRHZSCWAZSHZ-UHFFFAOYSA-N 0.000 description 1
- GPZRJTOZLDJPBA-UHFFFAOYSA-N n,n'-bis[2,3-di(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=CC=CC(N=C=NC=2C(=C(C(C)C)C=CC=2)C(C)C)=C1C(C)C GPZRJTOZLDJPBA-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- IOAASXXXVORBNR-UHFFFAOYSA-N oxiran-2-ylmethyl 7-methyloctanoate Chemical compound CC(C)CCCCCC(=O)OCC1CO1 IOAASXXXVORBNR-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
-
- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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Description
特許文献1および2には、フッ素化アルケン(フッ素置換オレフィン)を冷媒として用いる場合においても、ハイドロフルオロカーボン(HFC)冷媒用に通常用いられてるポリオールエステル類、ポリアルキレングリコール類およびエステル化ポリアルキレングリコール類等の潤滑剤を使用できることが開示されている。しかしながら、冷凍機油に必須の性能である相溶性、溶解性、冷媒混合状態での潤滑性等は、冷媒の種類により異なるので、フッ素化アルカンであるHFC冷媒で良好であったからといって、そのままフッ素化アルケンのHFO‐1234yf冷媒に良好に用いることができるとは一概にはいえない。特に、冷媒が二重結合を有するオレフィンであるために、冷媒と潤滑剤との混合流体の安定性が問題となる。すなわち、冷媒HFO‐1234yfに好適な潤滑剤は、上述したような性能を評価することにより分かるものであり、未だそれはなされておらず、適切な冷凍機油は未だ提案されていない。
(1)実施例1の供試油:ネオペンチルグリコール(NPG)と2‐エチルヘキサン酸(2EH)とのエステル
(2)実施例2の供試油:トリメチロールプロパン(TMP)と3,5,5‐トリメチルヘキサン酸(3,5,5TH)とのエステル
(3)実施例3の供試油:ペンタエリスリトール(PE)と2‐エチルヘキサン酸とのエステル
(4)実施例4の供試油:ペンタエリスリトールと2-エチルヘキサン酸/3,5,5‐トリメチルヘキサン酸がモル比で1/1の混合酸とのエステルに、添加剤としてヒンダードフェノール化合物である、ジ‐tert.‐ブチル‐p‐クレゾール(DBPC)を0.5重量%添加した油
(5)実施例5の供試油:ペンタエリスリトールと3,5,5‐トリメチルヘキサン酸のエステルに、添加剤として芳香族アミン化合物であるジオクチル‐ジフェニルアミン(DODA)を0.3重量%とエポキシ化合物である2‐エチルヘキシルグリシジルエーテル(2‐EHGE)を0.5重量%添加した油
(6)実施例6の供試油:ペンタエリスリトール/ジペンタエリスリトール(D‐PE)がモル比で1/1の混合アルコールと3,5,5‐トリメチルヘキサン酸とのエステルに、添加剤としてジフェニルカルボジイミド(DPCI)を0.1重量%添加した油
(7)実施例7の供試油:ジペンタエリスリトールと2‐エチルヘキサン酸/3,5,5‐トリメチルヘキサン酸がモル比で2/8の混合酸とのエステルに、添加剤としてエポキシ化合物であるネオデシルグリシジルエステル(NDGE)を1.2重量%とカルボジイミドであるビス(ジブチルフェニル)カルボジイミド(BDCI)を1.0重量%添加した油
(8)実施例8の供試油:ジペンタエリスリトールと3,5,5‐トリメチルヘキサン酸のエステルに、添加剤としてジ‐tert.−ブチル‐p‐クレゾールを0.3重量%、2‐エチルヘキシルグリシジルエーテルを0.5重量%、ジフェニルカルボジイミドを0.1重量%添加した油
(9)比較例1の供試油:トリメチロールプロパンとオレイン酸(OA)とのエステル
(10)比較例2の供試油:ペンタエリスリトールとオレイン酸とのエステルに、添加剤としてジ‐tert.‐ブチル‐p‐クレゾールを0.3重量%、2‐エチルヘキシルグリシジルエーテルを0.5重量%、ジフェニルカルボジイミドを0.1重量%添加した油
(11)比較例3の供試油:ペンタエリスリトールとi‐ペンタン酸/n‐ペンタン酸/n‐ヘプタン酸/n‐オクチル酸がモル比で1/3/2/4の混合酸とのエステル
(12)比較例4の供試油:ポリアルキレングリコール(PAG、末端がブチル基と水酸基であり骨格部がオキシプロピレン、平均分子量が1100)に、添加剤としてエポキシ化合物であるネオデシルグリシジルエステル(NDGE)を1.2重量%とカルボジイミドであるビス(ジブチルフェニル)カルボジイミド(BDCI)を1.0重量%添加した油
(13)比較例5の供試油:変性ポリアルキレングリコール(変性PAG)、CH3(PO)m(EO)nCH3(m/n=8/2、POはオキシプロピレン、EOはオキシエチレン、平均分子量=1100)
(14)比較例6の供試油:ポリアルファオレフィン(PAO、デセンの重合体)
なお、動粘度はJIS K2283に、ヨウ素価はJIS K0070に、全酸価及び水酸基価はJIS K2501に、それぞれ準拠し、測定した。
JIS K2211の「冷媒との相溶性試験方法」に準じ、冷媒HFO‐1234yfとの油分率10質量%での二層分離温度を測定した。
(熱安定性)
ANSI/ASHRAE97−1983に準じ、供試油(20g)とHFO‐1234yf(20g)と触媒(鉄、銅、アルミニウムの各線)をステンレス製ボンベ(100ml)に封入し、175℃に加熱して14日間保持した後、供試油の色相(ASTM表示)および酸価を測定した。
(潤滑性)
ASTM D−3233−73に準拠し、ファレックス(Falex)焼付荷重をHFO‐1234yfの吹き込み制御雰囲気下(70ml/min)で測定した。
JIS C2101に基づき80℃における体積抵抗率を求めた。
(吸湿性)
100mlビーカにサンプル油60gを入れ、温度25℃、湿度70%の雰囲気にて開放状態で3時間静置後、水分濃度をカールフィッシャー法により測定した。
比較例1、2のエステルの場合、酸のカ−ボン数が大きすぎるとHFO‐1234yfと相溶せず、またヨウ素価が高いと熱安定性が極めて悪く、添加剤による大幅な改善も見られない。比較例3のエステルは炭素数5の酸(ペンタン酸)が使われているため、冷媒HFO‐1234yfとは相溶するものの、加水分解されやすい短鎖の酸のため熱安定性が悪くなっている。また電気絶縁性も低く、吸湿性が高い。比較例4、5のエーテルは冷媒と相溶するものもあるが(比較例5)、その相溶範囲は狭く、体積抵抗率で示される電気特性が本発明のエステルより約1000倍悪く、かつ熱安定性も悪く、さらには、吸湿性も高く、冷凍機油として適さないことが分かる。比較例6の合成炭化水素油であるPAOは極性が無いためHFO‐1234yfとは全く相溶せず、使えない。
Claims (5)
- ネオペンチルグリコール、トリメチロールプロパン、ペンタエリスリトール、またはジペンタエリスリトールから選択される1種以上と炭素数7〜9の1価脂肪酸から選ばれた1種以上とのエステルを50重量%以上含有し、かつカルボジイミドを0.01〜1重量%含有する40℃における動粘度が5〜300mm2/s、ヨウ素価が10gI2/100g以下、全酸価が0.1mgKOH/g以下である冷媒2,3,3,3‐テトラフルオロ‐1‐プロペン用冷凍機油。
- 1価脂肪酸が2‐エチルヘキサン酸及び/または3,5,5‐トリメチルヘキサン酸であるエステルを50重量%以上含有する請求項1に記載の冷媒2,3,3,3‐テトラフルオロ‐1‐プロペン用冷凍機油。
- ペンタエリスリトールおよび/またはジペンタエリスリトールと2‐エチルヘキサン酸10〜90重量部と3,5,5‐トリメチルヘキサン酸90〜10重量部の酸混合物とのエステルを50重量%以上含有することからなる請求項1または2に記載の冷媒2,3,3,3‐テトラフルオロ‐1‐プロペン用冷凍機油。
- ヒンダードフェノール化合物、芳香族アミン化合物、エポキシ化合物のうち1種以上を、カルボジイミドと合わせて0.05〜3重量%添加したことからなる請求項1〜3のいずれかに記載の冷媒2,3,3,3‐テトラフルオロ‐1‐プロペン用冷凍機油。
- エポキシ化合物およびカルボジイミドを合わせて0.05〜3重量%添加したエステルからなる請求項1〜4のいずれかに記載の冷媒2,3,3,3‐テトラフルオロ‐1‐プロペン用冷凍機油。
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JP2011094039A (ja) * | 2009-10-30 | 2011-05-12 | Hitachi Appliances Inc | 冷媒圧縮機,冷凍サイクル装置 |
FR2962442B1 (fr) | 2010-07-09 | 2016-02-26 | Arkema France | Composition stable de 2,3,3,3-tetrafluoropropene |
US8889031B2 (en) * | 2010-11-30 | 2014-11-18 | Jx Nippon Oil & Energy Corporation | Working fluid composition for refrigerator machine and refrigerating machine oil |
JP6135017B2 (ja) * | 2012-02-01 | 2017-05-31 | Khネオケム株式会社 | 混合エステル |
WO2013115160A1 (ja) * | 2012-02-01 | 2013-08-08 | Khネオケム株式会社 | 混合多価アルコールとカルボン酸との混合エステル |
US9523058B2 (en) * | 2012-03-23 | 2016-12-20 | Kh Neochem Co., Ltd. | Mixed ester |
CA2890948A1 (en) | 2012-11-16 | 2014-05-22 | Basf Se | Lubricant compositions comprising epoxide compounds to improve fluoropolymer seal compatibility |
JP6076876B2 (ja) | 2013-10-02 | 2017-02-08 | Jxエネルギー株式会社 | 冷凍機油組成物、冷凍機用作動流体組成物 |
JP6072706B2 (ja) * | 2014-01-28 | 2017-02-01 | Jxエネルギー株式会社 | 冷凍機用作動流体組成物及び冷凍機油 |
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JPWO2016181910A1 (ja) * | 2015-05-12 | 2018-03-15 | 旭硝子株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
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