JPH0388892A - Refrigeration machine oil - Google Patents
Refrigeration machine oilInfo
- Publication number
- JPH0388892A JPH0388892A JP1226845A JP22684589A JPH0388892A JP H0388892 A JPH0388892 A JP H0388892A JP 1226845 A JP1226845 A JP 1226845A JP 22684589 A JP22684589 A JP 22684589A JP H0388892 A JPH0388892 A JP H0388892A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- oil
- fluoroethane
- ester
- present
- 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.)
- Pending
Links
- 239000010721 machine oil Substances 0.000 title claims description 9
- 238000005057 refrigeration Methods 0.000 title description 8
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000002148 esters Chemical class 0.000 claims abstract description 22
- -1 saturated aliphatic monocarboxylic acid Chemical class 0.000 claims abstract description 9
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 239000002199 base oil Substances 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 239000003507 refrigerant Substances 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000002826 coolant Substances 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 12
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 12
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 5
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- YSEQNZOXHCKLOG-UHFFFAOYSA-N 2-methyl-octanoic acid Chemical compound CCCCCCC(C)C(O)=O YSEQNZOXHCKLOG-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- NZQMQVJXSRMTCJ-UHFFFAOYSA-N 3-Methyl-hexanoic acid Chemical compound CCCC(C)CC(O)=O NZQMQVJXSRMTCJ-UHFFFAOYSA-N 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
- IGIDLTISMCAULB-UHFFFAOYSA-N 3-methylvaleric acid Chemical compound CCC(C)CC(O)=O IGIDLTISMCAULB-UHFFFAOYSA-N 0.000 description 2
- DIVCBWJKVSFZKJ-UHFFFAOYSA-N 4-methyl-hexanoic acid Chemical compound CCC(C)CCC(O)=O DIVCBWJKVSFZKJ-UHFFFAOYSA-N 0.000 description 2
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 229960002446 octanoic acid Drugs 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 1
- AAKKZDBDOJWNQA-UHFFFAOYSA-N 1,4-dioctylcyclohexa-2,4-dien-1-amine Chemical compound C(CCCCCCC)C1(CC=C(C=C1)CCCCCCCC)N AAKKZDBDOJWNQA-UHFFFAOYSA-N 0.000 description 1
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 description 1
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- YTTWDTVYXAEAJA-UHFFFAOYSA-N 2,2-dimethyl-hexanoic acid Chemical compound CCCCC(C)(C)C(O)=O YTTWDTVYXAEAJA-UHFFFAOYSA-N 0.000 description 1
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 1
- YURQLUXJGMVKDT-UHFFFAOYSA-N 2-(hydroxymethyl)-2-octylpropane-1,3-diol Chemical compound CCCCCCCCC(CO)(CO)CO YURQLUXJGMVKDT-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical class OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
- KTWWTCBUJPAASC-UHFFFAOYSA-N 3,5-dimethylhexanoic acid Chemical compound CC(C)CC(C)CC(O)=O KTWWTCBUJPAASC-UHFFFAOYSA-N 0.000 description 1
- YKSWLQPMYFCNBG-UHFFFAOYSA-N 3-methyl-octanoic acid Chemical compound CCCCCC(C)CC(O)=O YKSWLQPMYFCNBG-UHFFFAOYSA-N 0.000 description 1
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- RHXIYCXNOQKKMZ-UHFFFAOYSA-N diethoxy(dihydroxy)silane Chemical compound CCO[Si](O)(O)OCC RHXIYCXNOQKKMZ-UHFFFAOYSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Lubricants (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はフルオロエタン雰囲気下で用いる潤滑油に関す
るものであり、特に水素含有フルオロエタン系冷媒雰囲
気下で用いる冷凍機油に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a lubricating oil used in a fluoroethane atmosphere, and particularly to a refrigerating machine oil used in a hydrogen-containing fluoroethane refrigerant atmosphere.
〔従来の技術及び発明が解決しようとする課題〕最近、
オゾン層保護のため冷蔵庫やカークーラーに使用されて
いるジクロロジフルオロメタン（フロン１２）が使用規
制され、将来的には使用禁止されようとしている。その
ため、このフロン１２の代替品として、オゾン層を破壊
することのない各種のフルオロエタン系の冷媒が開発さ
れている。[Problems to be solved by conventional techniques and inventions] Recently,
In order to protect the ozone layer, dichlorodifluoromethane (CFC-12), which is used in refrigerators and car coolers, has been regulated and is likely to be banned in the future. Therefore, various fluoroethane-based refrigerants that do not destroy the ozone layer have been developed as substitutes for Freon 12.
これらのフルオロエタン系の冷媒はフロン１２に比べて
極性が高く、従来より冷凍機油として使用されているナ
フテン系鉱油やポリα−オレフィン、アルキルベンゼン
等の潤滑油ではこれらのフルオロエタン系冷媒との相溶
性が悪く、低温において二層分離を起こす、二層分離を
起こすと、オイル戻りが悪くなり、熱交換器としての凝
縮器や蒸発器の付近に厚い油膜を付着して伝熱を妨げた
り、潤滑不良や起動時の発泡の発生等の重要欠陥の原因
となる。そのために、従来の冷凍機油はこれらの新しい
冷媒雰囲気下での冷凍機油として使用することができな
い。These fluoroethane-based refrigerants have higher polarity than Freon-12, and lubricating oils such as naphthenic mineral oils, polyα-olefins, and alkylbenzenes, which have traditionally been used as refrigerating machine oils, do not phase with these fluoroethane-based refrigerants. It has poor solubility and causes two-layer separation at low temperatures.When two-layer separation occurs, oil return becomes poor and a thick oil film forms near the condenser and evaporator, which serve as heat exchangers, impeding heat transfer. This can cause important defects such as poor lubrication and foaming during startup. Therefore, conventional refrigeration oil cannot be used as refrigeration oil under these new refrigerant atmospheres.
また、潤滑性についてもフロン１２においては、それが
一部分層して塩化水素を発生させ、この塩化水素が摩擦
面と反応して、塩化物皮膜を形威し潤滑性を良好にする
という効果があった。Regarding lubricity, Freon 12 has the effect of forming a partial layer and generating hydrogen chloride, which reacts with the friction surface to form a chloride film and improve lubricity. there were.
しかしながら、塩素原子を含んでいないペンタフルオロ
エタンや１，１．１−トリフルオロエタン、１．１−ジ
フルオロエタン等のようなフルオロエタン系冷媒にはこ
のような効果が期待できないため、これと共に使用する
冷凍機油には従来のものより一層優れた潤滑性が求めら
れる。However, such effects cannot be expected with fluoroethane-based refrigerants such as pentafluoroethane, 1,1.1-trifluoroethane, 1.1-difluoroethane, etc., which do not contain chlorine atoms, so they should not be used together with fluoroethane refrigerants. Refrigerating machine oil is required to have better lubricity than conventional oils.
更に冷凍機油としては、冷媒雰囲気下での熱安定性の良
いことや、冷蔵庫に用いられる絶縁材、カーエアコンに
用いられるホース等の有機材料に悪影響を及ぼさないこ
とが求められる。Furthermore, refrigeration oil is required to have good thermal stability in a refrigerant atmosphere and not to have an adverse effect on organic materials such as insulating materials used in refrigerators and hoses used in car air conditioners.
これらのフルオロエタン系の冷媒との相溶性の問題に対
しては、ポリエーテル系の潤滑油が提案されている。ポ
リエーテル系潤滑油は、ナフテン系鉱油に比べ極性が高
いので、これらの冷媒との低温での相溶性はたしかに良
好である。Polyether-based lubricating oils have been proposed to solve the problem of compatibility with these fluoroethane-based refrigerants. Since polyether lubricating oils have higher polarity than naphthenic mineral oils, they are certainly more compatible with these refrigerants at low temperatures.
しかしながら、米国特許第４７５５３１６号明細書に述
べられているように、ポリエーテル系潤滑油は逆に温度
が上昇すると二層分離を起こすという問題があり、冷凍
機油として安心して使用することができない。However, as stated in US Pat. No. 4,755,316, polyether lubricating oils have the problem of two-layer separation when the temperature rises, so they cannot be safely used as refrigerating machine oils.
また、ポリエーテル系潤滑油にはこの外にもいくつかの
問題がある。１つは極性が高いために、冷蔵庫に用いら
れているＰＥＴフィルム等の絶縁材料と相互作用し、悪
影響を及ぼす。また、もう１つの問題は吸湿性の大きい
ことである。Additionally, polyether-based lubricating oils have several other problems. One is that it is highly polar, so it interacts with insulating materials such as PET films used in refrigerators, causing adverse effects. Another problem is that it is highly hygroscopic.
この潤滑油中の水分のために、冷媒雰囲気下での熱安定
性を悪くしたり、有機材料であるＰＵＴフィルム等を加
水分解させたりする。This water content in the lubricating oil impairs its thermal stability in a refrigerant atmosphere and causes organic materials such as PUT films to be hydrolyzed.
更に、潤滑性についても、ポリエーテル系潤滑油は十分
良好であるとは言えず、従来のフロン１２−ナフテン系
鉱油の系に比べ、フルオロエタン系冷媒−ポリエーテル
系潤滑油の系は劣っている。Furthermore, polyether-based lubricating oils cannot be said to have sufficiently good lubricity; compared to the conventional fluorocarbon-12-naphthenic mineral oil system, the fluoroethane-based refrigerant-polyether-based lubricating oil system is inferior. There is.
一方、冷凍機油の分野においてエステルをフルオロメタ
ンと共に使用する方法がいくつか提案されており、例え
ば、特開昭５６−１３１５４８号、特開昭５６−１３３
２４１号、特開昭６１−１８１８９５号、特開昭６２−
５９２号各公報等に開示されている。また、特開昭５６
−１２５４９４号、特開昭５６−１２５４９５号、特開
昭６１−６２５９６号各公報には、エステルを他の潤滑
油と混ぜて使用する例が述べられている。On the other hand, in the field of refrigeration oil, several methods have been proposed in which esters are used together with fluoromethane.
No. 241, JP-A-61-181895, JP-A-62-
No. 592 and other publications. In addition, JP-A-56
125494, JP 56-125495, and JP 61-62596 each describe examples in which esters are used in combination with other lubricating oils.
また、エステルに添加剤を加えた使用例が、特開昭５５
−１５５０９３号、特開昭５６−３６５７０号、特開昭
５６−１２５４９４号、特開昭５８−１５５９２号、特
開昭５８−１０３５９４号、特開昭６１−１７１７９９
号、特開昭６２−２９２８９５号各公報に述べられてい
る。しかしながら、これらはいずれもジクロロジフルオ
ロメタン（フロン１２）やモノクロロジフルオロメタン
（フロン２２）系冷媒と共に用いられる系を対象とした
ものであり、フルオロエタン系冷媒についてはまったく
触れられていない。また、その目的もフロン１２やフロ
ン２２雰囲気下での熱安定性の改善を目的としたもので
ある。その他、特開昭５３−１４３６０９号と特開昭５
９−１６４３９３号公報においては、フロン雰囲気下で
の熱安定性の向上とともに、フロンとの相溶性について
も述べられている。しかしながら、前者はフロン１２に
、後者はフロン２２に溶けすぎないことを目的としてお
り、フルオロエタン系冷媒との相溶性を向上させること
については何の記述も見られない。In addition, an example of the use of esters with additives is published in JP-A No. 55
-155093, JP 56-36570, JP 56-125494, JP 58-15592, JP 58-103594, JP 61-171799
No. 62-292895. However, all of these are intended for systems used with dichlorodifluoromethane (Freon 12) and monochlorodifluoromethane (Freon 22) refrigerants, and fluoroethane refrigerants are not mentioned at all. Further, its purpose is to improve thermal stability in a Freon 12 or Freon 22 atmosphere. In addition, JP-A-53-143609 and JP-A-5
Publication No. 9-164393 describes improvement in thermal stability in a fluorocarbon atmosphere as well as compatibility with fluorocarbons. However, the purpose of the former is to prevent excessive dissolution in Freon 12, and the purpose of the latter in Freon 22, and there is no description of improving compatibility with fluoroethane refrigerants.
以上述べてきたように、従来技術においては、フルオロ
エタン系冷媒雰囲気下において、相溶性、熱安定性、潤
滑性に優れた冷凍機用潤滑油の開発が課題とされたこと
はなく、また、そのための具体的提案も全くないのが現
状である。As mentioned above, in the prior art, the development of a lubricating oil for refrigerators that has excellent compatibility, thermal stability, and lubricity in a fluoroethane refrigerant atmosphere has never been an issue; At present, there are no concrete proposals for this purpose.
従って本発明の目的は、充分な粘度を持ち、低温及び高
温においてフルオロエタン系冷媒との相溶性に優れ、か
つ該冷媒雰囲気下での熱安定性、潤滑性に優れた冷凍機
油を提供することにある。Therefore, an object of the present invention is to provide a refrigerating machine oil that has sufficient viscosity, is excellent in compatibility with fluoroethane refrigerants at low and high temperatures, and has excellent thermal stability and lubricity in the atmosphere of the refrigerant. It is in.
本発明者は、上記目的を達成するために鋭意研究を重ね
た結果、ある種のエステル化合物が上記目的を達威し得
ることを見い出し、本発明を完成するに至った。As a result of extensive research in order to achieve the above object, the present inventor discovered that a certain type of ester compound can achieve the above object, and completed the present invention.
即ち、本発明は、
（ａ） 第１ヒドロキシ基１〜６個を有する脂肪族多
価アルコールと、
（ｂ） 炭素数２〜９の直鎖又は分岐鎖の飽和脂肪族
モノカルボン酸又はその誘導体
とから得られる反応物であって、分子量１４０〜６００
．１００″Ｃにおける動粘度がｌ〜１０ ｃｓｔである
エステルを基油とすることを特徴とする、水素含有フル
オロエタン系冷媒雰囲気下で用いる冷凍機油を提供する
ものである。That is, the present invention comprises: (a) an aliphatic polyhydric alcohol having 1 to 6 primary hydroxy groups; and (b) a linear or branched saturated aliphatic monocarboxylic acid having 2 to 9 carbon atoms or a derivative thereof. A reaction product obtained from and having a molecular weight of 140 to 600
．． The present invention provides a refrigerating machine oil for use in a hydrogen-containing fluoroethane refrigerant atmosphere, characterized in that the base oil is an ester having a kinematic viscosity of 1 to 10 cst at 100''C.
本発明のエステルの製造に用いられる（ａ）成分の脂肪
族多価アルコールは、そのヒドロキシ基の内、１〜６個
が第１ヒドロキシ基となったものであり、具体的には、
ネオペンチルグリコール、２，２−ジエチル−１，３−
プロパンジオール、２−ｎ−ブチル−２−エチル−１，
３−プロパンジオール、トリメチロールエタン、トリメ
チロールプロパン、トリメチロールノナン、ペンタエリ
スリトール及びジペンタエリスリトール等のヒンダード
アルコール、あるいは、エチレングリコール、ジエチレ
ングリコール、ポリエチレングリコール、プロピレング
リコール、ジプロピレングリコール、ポリプロピレング
リコール、２−エチル−１，３−ヘキサンジオール、グ
リセリン、ジグリセリン、ポリグリセリン、１．２．４
−ブタントリオール、１．２．６−ヘキサンジオール、
ソルビトール及びマンニトール等の多価アルコールが挙
げられる。これらの脂肪族多価アルコールの炭素原子数
は２〜３０、好ましくは２〜２０、更に好ましくは２〜
１０である。炭素原子数が３０より多いと、粘度が高く
なり、フルオロエタン系冷媒との相溶性も悪くなる。ま
た、第１とドロキシ基が６個より多いと粘度が高くなり
すぎる。また、耐熱性の面から、ヒンダードアルコール
が特に優れている。The aliphatic polyhydric alcohol as component (a) used in the production of the ester of the present invention is one in which 1 to 6 of its hydroxy groups are primary hydroxy groups, and specifically,
Neopentyl glycol, 2,2-diethyl-1,3-
Propanediol, 2-n-butyl-2-ethyl-1,
Hindered alcohols such as 3-propanediol, trimethylolethane, trimethylolpropane, trimethylolnonane, pentaerythritol and dipentaerythritol, or ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 2 -ethyl-1,3-hexanediol, glycerin, diglycerin, polyglycerin, 1.2.4
-butanetriol, 1.2.6-hexanediol,
Examples include polyhydric alcohols such as sorbitol and mannitol. The number of carbon atoms in these aliphatic polyhydric alcohols is 2 to 30, preferably 2 to 20, more preferably 2 to 30.
It is 10. When the number of carbon atoms is more than 30, the viscosity becomes high and the compatibility with fluoroethane refrigerants becomes poor. Moreover, if there are more than 6 primary and doxy groups, the viscosity becomes too high. Furthermore, hindered alcohol is particularly excellent in terms of heat resistance.
本発明のエステルの製造に用いられるカルボン酸又はそ
の誘導体は、炭素数２〜９、好ましくは５〜８の直鎖又
は分岐鎖の飽和脂肪族モノカルボン酸、又はその低級ア
ルキルエステル、酸無水物等の誘導体である。カルボン
酸の炭素数が９より多いとフルオロエタン系冷媒との相
溶性が悪くなる。これらのモノカルボン酸又はその誘導
体の具体例としては、酢酸、プロピオン酸、酪酸、イソ
酪酸、バレリン酸、イソバレリン酸、ピバリン酸、２−
メチル酪酸、カプロン酸、２−メチルバレリン酸、３−
メチルバレリン酸、４−メチルバレリン酸、２．２−ジ
メチル酪酸、２−エチル酪酸、ｔｅｒｔ−ブチル酢酸、
エナント酸、２，２−ジメチルペンタン酸、２−エチル
ペンクン酸、３−エチルペンクン酸、２−メチルヘキサ
ン酸（イソへブタン酸）、３−メチルヘキサン酸、４−
メチルヘキサン酸、５−メチルヘキサン酸、カプリル酸
、２−エチルヘキサン酸、３，５−ジメチルヘキサン酸
、２．２−ジメチルヘキサン酸、２−メチルへブタン酸
（イソオクタン酸）、３−メチルへブタン酸、４−メチ
ルへブタン酸、２−プロピルペンタン酸、ペラルゴン酸
、２．２−ジメチルへブタン酸、３．５．５− トリメ
チルヘキサン酸、２−メチルオクタン酸、２−エチルへ
ブタン酸、３−メチルオクタン酸、あるいはこれらのメ
チルエステル、エチルエステル、酸無水物等が挙げられ
る。The carboxylic acid or its derivative used for producing the ester of the present invention is a linear or branched saturated aliphatic monocarboxylic acid having 2 to 9 carbon atoms, preferably 5 to 8 carbon atoms, or its lower alkyl ester or acid anhydride. It is a derivative of etc. If the number of carbon atoms in the carboxylic acid is more than 9, the compatibility with the fluoroethane refrigerant will be poor. Specific examples of these monocarboxylic acids or derivatives thereof include acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, pivalic acid, 2-
Methylbutyric acid, caproic acid, 2-methylvaleric acid, 3-
Methylvaleric acid, 4-methylvaleric acid, 2,2-dimethylbutyric acid, 2-ethylbutyric acid, tert-butylacetic acid,
Enanthic acid, 2,2-dimethylpentanoic acid, 2-ethylpencunonic acid, 3-ethylpencunonic acid, 2-methylhexanoic acid (isohbutanoic acid), 3-methylhexanoic acid, 4-
Methylhexanoic acid, 5-methylhexanoic acid, caprylic acid, 2-ethylhexanoic acid, 3,5-dimethylhexanoic acid, 2,2-dimethylhexanoic acid, 2-methylhebutanoic acid (isooctanoic acid), to 3-methyl Butanoic acid, 4-methylhebutanoic acid, 2-propylpentanoic acid, pelargonic acid, 2,2-dimethylhebutanoic acid, 3.5.5-trimethylhexanoic acid, 2-methyloctanoic acid, 2-ethylhebutanoic acid , 3-methyloctanoic acid, or their methyl esters, ethyl esters, and acid anhydrides.
本発明に用いられるエステルは上記（ａ）及び６）成分
を反応させて得られるもので、１００℃における動粘度
が１〜１０ ｃｓｔであり、好ましくは２〜６ ｃｓｔ
である。動粘度が１０ ｃｓｔより高いとフルオロエタ
ン系冷媒との相溶性が悪くなる。またエステルの分子量
は１４０〜６００であり、６００より大きいとフルオロ
エタン系冷媒との相溶性が悪くなり、１４０未満である
と粘度が低くなり使用できない。The ester used in the present invention is obtained by reacting the above components (a) and 6), and has a kinematic viscosity at 100°C of 1 to 10 cst, preferably 2 to 6 cst.
It is. If the kinematic viscosity is higher than 10 cst, the compatibility with fluoroethane refrigerants will be poor. The molecular weight of the ester is 140 to 600, and if it is larger than 600, the compatibility with fluoroethane refrigerants will be poor, and if it is less than 140, the viscosity will be too low to be used.
本発明に用いられるエステルは、上記に述べた（ａ）の
多価アルコール１種以上と、上記に述べた（口）のモノ
カルボン酸又はその低級アルキルエステル、酸無水物等
の１種以上とより、通常のエステル化反応やエステル交
換反応によって得ることができる。この際、得られるエ
ステルの酸価は低いほど好ましく 、５＋＋＋ｇＫＯＨ
／ｇ以下、特に１ ｍｇＫＯＨ／ｇ以下が好ましい。The ester used in the present invention includes one or more polyhydric alcohols (a) mentioned above, and one or more monocarboxylic acids or lower alkyl esters thereof, acid anhydrides, etc. mentioned above. It can be obtained by ordinary esterification reaction or transesterification reaction. At this time, the lower the acid value of the obtained ester, the better, 5+++gKOH
/g or less, particularly preferably 1 mgKOH/g or less.
本発明の冷凍機油は上記エステルを基油とするが、鉱物
油やポリα−オレフィン、アルキルベンゼン、上記以外
のエステル、ポリエーテル、パーフルオロポリエーテル
、リン酸エステル等の合成油、またはこれらの混合油等
を配合しても良い。但し、合成油は上記の物に限定され
るものではない。本発明のエステル／他の潤滑油の混合
重量比は水素含有フルオロエタン系冷媒との相溶性等の
性能を損なわない範囲ならいくらでも良く、−膜内には
１００１０〜５／９５、好ましくは１００／ Ｏ〜１０
／９０．更に好ましくは１００１０〜３０／７０である
。The refrigeration oil of the present invention uses the above-mentioned ester as a base oil, but may also contain mineral oil, polyα-olefin, alkylbenzene, ester other than the above, polyether, perfluoropolyether, synthetic oil such as phosphoric acid ester, or a mixture thereof. Oil etc. may be added. However, synthetic oils are not limited to those mentioned above. The mixing weight ratio of the ester of the present invention/other lubricating oil may be any value as long as it does not impair performance such as compatibility with the hydrogen-containing fluoroethane refrigerant; O~10
/90. More preferably, it is 10010 to 30/70.
本発明のエステルはフルオロエタン系の冷媒に対して優
れた性能を有するものであって、特に水素含有フルオロ
エタン系冷媒雰囲気下に用いた場合に、相溶性、熱安定
性、潤滑性に優れた冷凍機油とすることができる。ここ
で水素含有フルオロエタン系冷媒とは例えば、１．１，
１．２＝テトラフルオロエタン（フロン１３４ａ） 、
１．１゜１．２−テトラフルオロ−２−クロロエタン（
フロン１２４） 、ペンタフルオロエタン（フロン１２
５）、１．１−ジフルオロ−１−クロロエタン（フロン
１４２ｂ） 、１．１．１−）リフルオロエタン（フロ
ン１４３ａ） 、１．１−ジフルオロエタン（フロン１
５２ａ）等のことである。The ester of the present invention has excellent performance against fluoroethane refrigerants, and has excellent compatibility, thermal stability, and lubricity, especially when used in a hydrogen-containing fluoroethane refrigerant atmosphere. It can be refrigeration oil. Here, the hydrogen-containing fluoroethane refrigerant is, for example, 1.1,
1.2=tetrafluoroethane (Freon 134a),
1.1゜1.2-tetrafluoro-2-chloroethane (
Freon 124), pentafluoroethane (Freon 12
5), 1.1-difluoro-1-chloroethane (Freon 142b), 1.1.1-)lifluoroethane (Freon 143a), 1.1-difluoroethane (Freon 1
52a) etc.
本発明の冷凍機油には、必要により通常使用される酸化
防止剤、極圧剤、油性向上剤、消泡剤、金属不活性剤等
の潤滑油添加剤を添加することもできる。If necessary, commonly used lubricating oil additives such as antioxidants, extreme pressure agents, oiliness improvers, antifoaming agents, and metal deactivators can be added to the refrigeration oil of the present invention.
酸化防止剤として使用可能なものは、２．６−ジーｔ−
ブチル−４−メチルフェノ−、ル、４，４″−メチレン
ビス（２，６−ジーｔ−ブチルフェノール）等のフェノ
ール系酸化防止剤や、ｐ、ｐ−ジオクチルフェニルアミ
ン、モノオクチルジフェニルアミン、フェノチアジン、
３．７−シオクチルフエノチアジン、フェニル−１−ナ
フチルアミン、フェニル−２−ナフチルアミン、アルキ
ルフェニル−１−ナフチルアミン、アルキルフェニル−
２−ナフチルアミン等のアミン系酸化防止剤や、アルキ
ルジサルファイド、チオジプロピオン酸エステル、ベン
ゾチアゾール等の硫黄系酸化防止剤や、ジアルキルジチ
オリン酸亜鉛、ジアリールジチオリン酸亜鉛などである
。What can be used as an antioxidant is 2,6-di-t-
Phenolic antioxidants such as butyl-4-methylphenol, 4,4″-methylenebis(2,6-di-t-butylphenol), p, p-dioctyl phenylamine, monooctyldiphenylamine, phenothiazine,
3.7-Shioctylphenothiazine, phenyl-1-naphthylamine, phenyl-2-naphthylamine, alkylphenyl-1-naphthylamine, alkylphenyl-
These include amine-based antioxidants such as 2-naphthylamine, sulfur-based antioxidants such as alkyl disulfides, thiodipropionic acid esters, and benzothiazole, and zinc dialkyldithiophosphate and zinc diaryldithiophosphate.
極圧剤、油性向上剤として使用可能なものは、例えば、
ジアルキルジチオリン酸亜鉛、ジアリールジチオリン酸
亜鉛、ジアルキルポリサルファイド、トリアリールフォ
スフェート、トリアルキルフォスフェート、二硫化モリ
ブデン、グラファイト等である。消泡剤として使用され
るものは、ジメチルポリシロキサン等のシリコーン油や
ジエチルシリケート等のオルガノシリケート類等である
。金属不活性剤として使用されるものは、アリザリン、
キニザリン、メルカプトベンゾチアゾール等である。Examples of extreme pressure agents and oiliness improvers include:
These include zinc dialkyl dithiophosphate, zinc diaryldithiophosphate, dialkyl polysulfide, triaryl phosphate, trialkyl phosphate, molybdenum disulfide, and graphite. Antifoaming agents used include silicone oils such as dimethylpolysiloxane and organosilicates such as diethylsilicate. Those used as metal deactivators are alizarin,
Quinizarin, mercaptobenzothiazole, etc.
本発明の冷凍機油は、十分な粘度をもち、水素含有フル
オロエタン系冷媒との相溶性に優れ、該冷媒雰囲気下で
の熱安定性、潤滑性に優れ、冷凍機用潤滑油として優れ
たものである。The refrigerating machine oil of the present invention has sufficient viscosity, excellent compatibility with hydrogen-containing fluoroethane refrigerant, excellent thermal stability and lubricity in the atmosphere of the refrigerant, and is excellent as a lubricating oil for refrigerating machines. It is.
以下、本発明を実施例により具体的に説明するが、本発
明はこれらの実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples.
実施例１
１１の４つロフラスコに撹拌機、温度計、窒素吹き込み
管、及び冷却器付きの脱水管を取り付けた。ネオペンチ
ルグリコール１０４ｇ （１，０ｍｏｌ）とカプリル酸
２８８ｇ （２，０ｍｏｌ）を前記フラスコに取り、窒
素気流下２４０℃で１０時間エステル化反応を行い本発
明品１のエステルを得た。Example 1 An 11 four-loaf flask was equipped with a stirrer, a thermometer, a nitrogen blowing tube, and a dehydration tube with a condenser. 104 g (1.0 mol) of neopentyl glycol and 288 g (2.0 mol) of caprylic acid were placed in the flask, and an esterification reaction was carried out at 240° C. for 10 hours under a nitrogen stream to obtain ester of product 1 of the present invention.
また表−１に示すアルコール及びカルボン酸を用い、以
下同様な反応を行って本発明品２〜１０及び比較品ｌ〜
６のエステルを得た。In addition, using the alcohols and carboxylic acids shown in Table 1, similar reactions were carried out to obtain products of the present invention 2 to 10 and comparative products 1 to 1.
Ester 6 was obtained.
得られた本発明品１−１０及び比較品１〜６のエステル
、更に表−１に示す比較品７〜１１の分子量、４０℃及
び１００℃における動粘度、並びに粘度指数（ＪＩＳ
Ｋ−２２８３）を測定した。また、流動点（ＪＩＳ Ｋ
−２２６９）を測定した。The molecular weights, kinematic viscosities at 40°C and 100°C, and viscosity index (JIS
K-2283) was measured. In addition, pour point (JIS K
-2269) was measured.
その結果を表−１に示す。The results are shown in Table-1.
実施例２
実施例１で得られた本発明品１〜１０及び比較品１〜１
１の１．１．１．２−テトラフルオロエタン（フロン１
３４ａ）との相溶性を調べるため、１．１．１．２−テ
トラフルオロエタンに対する各種試料濃度ＩＱ ｖｏ１
％における低温及び高温での二相分離温度を測定した。Example 2 Inventive products 1 to 10 obtained in Example 1 and comparative products 1 to 1
1 of 1.1.1.2-Tetrafluoroethane (Freon 1
34a), various sample concentrations for 1.1.1.2-tetrafluoroethane IQ vol.
The two-phase separation temperature at low and high temperatures in % was measured.
尚、比較品において、低温二相分離温度が０℃より高温
のものについては高温分離温度の測定を省略した。Note that for comparative products whose low-temperature two-phase separation temperature was higher than 0° C., measurement of the high-temperature separation temperature was omitted.
結果を表−２に示す。The results are shown in Table-2.
表−２から明らかなように、本発明のエステルは低温に
おける１、１．１．２−テトラフルオロエタンとの相溶
性に優れ、かつ高温になっても相溶性が低下することは
なかった。As is clear from Table 2, the ester of the present invention had excellent compatibility with 1,1.1.2-tetrafluoroethane at low temperatures, and the compatibility did not decrease even at high temperatures.
表
実施例３
実施例１で得られた本発明品１．４，５．７．９及び比
較品７〜１０を用い、Ｆａｌｅｘ試験を行い耐荷重性を
調べた。Table Example 3 Using products 1.4, 5.7.9 of the present invention and comparative products 7 to 10 obtained in Example 1, a Falex test was conducted to examine the load resistance.
即ち、１．１．１．２−テトラフルオロエタン（フロン
１３４ａ ）を毎分１５０ｃｃずつ吹き込み、無負荷で
１０分間回転し、続いて２００ ｌｂで５分間予備回転
した後、２分毎に５０ ｌｂ荷重を増加させた時の焼き
付き荷重を調べた。That is, 1.1.1.2-tetrafluoroethane (Freon 134a) was injected at a rate of 150 cc per minute, rotated for 10 minutes without load, then pre-rotated at 200 lb for 5 minutes, then 50 lb was injected every 2 minutes. The seizure load was investigated when the load was increased.
結果を表−３に示す。The results are shown in Table-3.
表−３から明らかなように、ナフテン油（比較品７）は
、ジクロロジフルオロメタン（フロン１２）を吹き込ん
だ時（６００ｌｂ）に比べ、１．１．１゜２−テトラフ
ルオロエタンを吹き込んだ時（４５０１ｂ）は耐荷重性
が劣る。ポリα−オレフィン（比較品８）やポリエーテ
ル（比較品９．１０）は１゜１．１．２−テトラフルオ
ロエタン吹き込み下では５５０ ｌｂ以下であり、耐荷
重性が劣っている。−方、本発明のエステルは１．１．
１．２−テトラフルオロエタン吹き込み下でいずれも６
００ ｌｂ以上であり、耐荷重性が優れている。As is clear from Table 3, the naphthenic oil (comparative product 7) was 1.1.1° when 2-tetrafluoroethane was blown, compared to when dichlorodifluoromethane (Freon 12) was blown (600 lb). (4501b) has poor load resistance. Polyα-olefin (comparative product 8) and polyether (comparative product 9.10) have a weight capacity of 550 lb or less under 1°1.1.2-tetrafluoroethane blowing, and thus have poor load resistance. - On the other hand, the ester of the present invention is 1.1.
Both 6 under 1.2-tetrafluoroethane blowing
00 lb or more, and has excellent load resistance.
表−３
実施例４
実施例１で得られた本発明品１．４．５．７．９の１゜
１．１．２−テトラフルオロエタン雰囲気下での熱安定
性を調べるために、鉄、銅、アルミニウムを触媒とした
シールドチューブ試験（１７５℃×１４日）を行った。Table 3 Example 4 In order to investigate the thermal stability of the invention product 1.4.5.7.9 obtained in Example 1 in a 1°1.1.2-tetrafluoroethane atmosphere, iron A shield tube test (175° C. x 14 days) was conducted using copper, aluminum, and aluminum as catalysts.
結果を表−４に示す。The results are shown in Table 4.
表−４から明らかなように、本発明のエステルは、いず
れも外観は良好で析出物も無く、熱安定性は良好である
。As is clear from Table 4, all of the esters of the present invention have good appearance, no precipitates, and good thermal stability.
表−４
実施例５
実施例１で得られた本発明品５．７．９及び比較品９．
１０の吸湿性を調べた。Table 4 Example 5 Invention product 5.7.9 obtained in Example 1 and comparative product 9.
The hygroscopicity of 10 samples was investigated.
即ち、２５℃、湿度８０％の条件下での水分の経時変化
をカールフィッシャー法により求めた。That is, the change in moisture content over time was determined by the Karl Fischer method under conditions of 25° C. and 80% humidity.
結果を表−５に示す。The results are shown in Table-5.
表−５から明らかなように、 本発明のエステ ルは、 比較品のポリエーテルに比べ吸湿性が低い。As is clear from Table-5, Esthetics of the present invention Le is It has lower hygroscopicity than the comparative polyether.
表table
Claims (1)
ルコールと、 （ｂ）炭素数２〜９の直鎖又は分岐鎖の飽和脂肪族モノ
カルボン酸又はその誘導体 とから得られる反応物であって、分子量１４０〜６００
、１００℃における動粘度が１〜１０ｃｓｔであるエス
テルを基油とすることを特徴とする、水素含有フルオロ
エタン系冷媒雰囲気下で用いる冷凍機油。[Scope of Claims] (a) an aliphatic polyhydric alcohol having 1 to 6 primary hydroxy groups; (b) a linear or branched saturated aliphatic monocarboxylic acid having 2 to 9 carbon atoms or a derivative thereof A reaction product obtained from and having a molecular weight of 140 to 600
A refrigerating machine oil used in a hydrogen-containing fluoroethane refrigerant atmosphere, characterized in that the base oil is an ester having a kinematic viscosity of 1 to 10 cst at 100°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1226845A JPH0388892A (en) | 1989-09-01 | 1989-09-01 | Refrigeration machine oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1226845A JPH0388892A (en) | 1989-09-01 | 1989-09-01 | Refrigeration machine oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0388892A true JPH0388892A (en) | 1991-04-15 |
Family
ID=16851470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1226845A Pending JPH0388892A (en) | 1989-09-01 | 1989-09-01 | Refrigeration machine oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0388892A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992012223A1 (en) * | 1990-12-27 | 1992-07-23 | Matsushita Refrigeration Company | Freezer for refrigerator |
| JPH04249593A (en) * | 1990-05-22 | 1992-09-04 | Unichema Chem Bv | Lubricant/working fluid composition for mechanical vapor-compression heat transfer device and lubricant |
| WO1992019704A1 (en) * | 1991-05-07 | 1992-11-12 | Sanyo Electric Co., Ltd. | Refrigerator oil composition |
| EP0514988A2 (en) * | 1991-05-20 | 1992-11-25 | Shell Internationale Researchmaatschappij B.V. | Fluid composition for compression refrigeration |
| JPH0517789A (en) * | 1991-07-09 | 1993-01-26 | Kyoseki Seihin Gijutsu Kenkyusho:Kk | Refrigerating machine oil |
| JPH0617073A (en) * | 1992-07-04 | 1994-01-25 | Kao Corp | Working fluid composition for refrigerator |
| EP0693546A1 (en) | 1994-07-19 | 1996-01-24 | NIPPON OIL Co. Ltd. | Refrigerator oil and fluid composition for refrigerator |
| EP0699742A2 (en) | 1994-08-03 | 1996-03-06 | Nippon Oil Co. Ltd. | Refrigerator oil composition and fluid composition for refrigerator |
| EP0711824A2 (en) | 1994-11-07 | 1996-05-15 | Nippon Oil Co. Ltd. | Lubricating oil and composition for refrigerating machine, and refrigerating machine |
| EP0717098A2 (en) | 1994-12-12 | 1996-06-19 | Nippon Oil Co. Ltd. | A refrigerating machine oil and a fluid composition for use in a refrigerating machine |
| US5620950A (en) * | 1991-10-15 | 1997-04-15 | Asahi Denka Kogyo K.K. | Lubricated refrigerant composition containing alicyclic epoxy compounds |
| US6245254B1 (en) | 1991-10-11 | 2001-06-12 | Imperial Chemical Industries Plc | Lubricants |
| WO2008117657A1 (en) | 2007-03-27 | 2008-10-02 | Nippon Oil Corporation | Refrigerator oil and working fluid composition for refrigerating machine |
| WO2013183161A1 (en) * | 2012-06-08 | 2013-12-12 | トヨタ自動車株式会社 | Liquid coolant composition for internal combustion engines and operating method for internal combustion engines |
| GB2525281A (en) * | 2014-02-13 | 2015-10-21 | M & I Materials Ltd | Improvements in and relating to dielectric fluids |
| US9321948B2 (en) | 2007-02-27 | 2016-04-26 | Nippon Oil Corporation | Refrigerator oil and working fluid composition for refrigerator |
-
1989
- 1989-09-01 JP JP1226845A patent/JPH0388892A/en active Pending
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04249593A (en) * | 1990-05-22 | 1992-09-04 | Unichema Chem Bv | Lubricant/working fluid composition for mechanical vapor-compression heat transfer device and lubricant |
| WO1992012223A1 (en) * | 1990-12-27 | 1992-07-23 | Matsushita Refrigeration Company | Freezer for refrigerator |
| EP0522167B1 (en) * | 1990-12-27 | 1997-09-10 | Matsushita Refrigeration Company | Method for manufacturing a refrigerating system |
| EP0522167A1 (en) * | 1990-12-27 | 1993-01-13 | Matsushita Refrigeration Company | Freezer for refrigerator |
| EP0779354A1 (en) * | 1990-12-27 | 1997-06-18 | Matsushita Refrigeration Company | Refrigerating system for refrigerator |
| WO1992019704A1 (en) * | 1991-05-07 | 1992-11-12 | Sanyo Electric Co., Ltd. | Refrigerator oil composition |
| US5369287A (en) * | 1991-05-07 | 1994-11-29 | Sanyo Electric Co., Ltd. | Refrigerator oil composition containing phenolic antioxidant amine and phosphoric triester components |
| EP0514988A2 (en) * | 1991-05-20 | 1992-11-25 | Shell Internationale Researchmaatschappij B.V. | Fluid composition for compression refrigeration |
| TR25716A (en) * | 1991-05-20 | 1993-09-01 | Shell Int Research | LIQUID COMPUTER FOR COMPRESSED COOLING |
| JPH0517789A (en) * | 1991-07-09 | 1993-01-26 | Kyoseki Seihin Gijutsu Kenkyusho:Kk | Refrigerating machine oil |
| US6245254B1 (en) | 1991-10-11 | 2001-06-12 | Imperial Chemical Industries Plc | Lubricants |
| US5620950A (en) * | 1991-10-15 | 1997-04-15 | Asahi Denka Kogyo K.K. | Lubricated refrigerant composition containing alicyclic epoxy compounds |
| JPH0617073A (en) * | 1992-07-04 | 1994-01-25 | Kao Corp | Working fluid composition for refrigerator |
| EP0580308A1 (en) | 1992-07-04 | 1994-01-26 | Kao Corporation | Working fluid composition for refrigeration machine |
| EP0693546A1 (en) | 1994-07-19 | 1996-01-24 | NIPPON OIL Co. Ltd. | Refrigerator oil and fluid composition for refrigerator |
| EP0699742A2 (en) | 1994-08-03 | 1996-03-06 | Nippon Oil Co. Ltd. | Refrigerator oil composition and fluid composition for refrigerator |
| EP0711824A2 (en) | 1994-11-07 | 1996-05-15 | Nippon Oil Co. Ltd. | Lubricating oil and composition for refrigerating machine, and refrigerating machine |
| EP0717098A2 (en) | 1994-12-12 | 1996-06-19 | Nippon Oil Co. Ltd. | A refrigerating machine oil and a fluid composition for use in a refrigerating machine |
| US9321948B2 (en) | 2007-02-27 | 2016-04-26 | Nippon Oil Corporation | Refrigerator oil and working fluid composition for refrigerator |
| US10214671B2 (en) | 2007-02-27 | 2019-02-26 | Jx Nippon Oil & Energy Corporation | Refrigerator oil and working fluid composition for refrigerator |
| WO2008117657A1 (en) | 2007-03-27 | 2008-10-02 | Nippon Oil Corporation | Refrigerator oil and working fluid composition for refrigerating machine |
| US8318040B2 (en) | 2007-03-27 | 2012-11-27 | Nippon Oil Corporation | Refrigerator oil and working fluid composition for refrigerating machine |
| WO2013183161A1 (en) * | 2012-06-08 | 2013-12-12 | トヨタ自動車株式会社 | Liquid coolant composition for internal combustion engines and operating method for internal combustion engines |
| GB2525281A (en) * | 2014-02-13 | 2015-10-21 | M & I Materials Ltd | Improvements in and relating to dielectric fluids |
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