JPH04314793A - Ester refrigerator oil - Google Patents
Ester refrigerator oilInfo
- Publication number
- JPH04314793A JPH04314793A JP10639791A JP10639791A JPH04314793A JP H04314793 A JPH04314793 A JP H04314793A JP 10639791 A JP10639791 A JP 10639791A JP 10639791 A JP10639791 A JP 10639791A JP H04314793 A JPH04314793 A JP H04314793A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ester
- fatty acids
- mol
- carbon atoms
- 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
- 150000002148 esters Chemical class 0.000 title abstract description 31
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 31
- 239000000194 fatty acid Substances 0.000 claims abstract description 31
- 229930195729 fatty acid Natural products 0.000 claims abstract description 31
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 8
- -1 neopentyl polyol Chemical class 0.000 claims abstract description 8
- 229920005862 polyol Polymers 0.000 claims abstract description 8
- 239000010721 machine oil Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 12
- 239000003507 refrigerant Substances 0.000 abstract description 11
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 4
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000006078 metal deactivator Substances 0.000 abstract description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 description 8
- 230000003301 hydrolyzing effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000005057 refrigeration Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 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
- 125000002252 acyl group Chemical group 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-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
- DIVCBWJKVSFZKJ-UHFFFAOYSA-N 4-methyl-hexanoic acid Chemical compound CCC(C)CCC(O)=O DIVCBWJKVSFZKJ-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 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
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- CBQQWWYZSKCIRS-UHFFFAOYSA-N 2,2,3,3-tetramethylpentanoic acid Chemical compound CCC(C)(C)C(C)(C)C(O)=O CBQQWWYZSKCIRS-UHFFFAOYSA-N 0.000 description 1
- NPMHELYJLOUPIZ-UHFFFAOYSA-N 2,2,3,4-tetramethylpentanoic acid Chemical compound CC(C)C(C)C(C)(C)C(O)=O NPMHELYJLOUPIZ-UHFFFAOYSA-N 0.000 description 1
- JDIOSVLOJNXZCG-UHFFFAOYSA-N 2,2,5-trimethylhexanedioic acid Chemical compound OC(=O)C(C)CCC(C)(C)C(O)=O JDIOSVLOJNXZCG-UHFFFAOYSA-N 0.000 description 1
- JUQQBXJTNZRORL-UHFFFAOYSA-N 2,2-dibutyldecanoic acid Chemical compound CCCCCCCCC(CCCC)(CCCC)C(O)=O JUQQBXJTNZRORL-UHFFFAOYSA-N 0.000 description 1
- LDJUYMIFFNTKOI-UHFFFAOYSA-N 2,2-dimethylbutanoyl chloride Chemical compound CCC(C)(C)C(Cl)=O LDJUYMIFFNTKOI-UHFFFAOYSA-N 0.000 description 1
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 1
- QRMMMWOSHHVOCJ-UHFFFAOYSA-N 2,2-dimethylheptanoic acid Chemical compound CCCCCC(C)(C)C(O)=O QRMMMWOSHHVOCJ-UHFFFAOYSA-N 0.000 description 1
- OENBKJVGVULJJF-UHFFFAOYSA-N 2,2-dimethylhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(C)(C)C(O)=O OENBKJVGVULJJF-UHFFFAOYSA-N 0.000 description 1
- IKNDGHRNXGEHTO-UHFFFAOYSA-N 2,2-dimethyloctanoic acid Chemical compound CCCCCCC(C)(C)C(O)=O IKNDGHRNXGEHTO-UHFFFAOYSA-N 0.000 description 1
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 1
- AOKKPUNLOQKYSU-UHFFFAOYSA-N 2,3,5,5-tetramethyl-2-propan-2-ylhexanoic acid Chemical compound CC(C)C(C)(C(O)=O)C(C)CC(C)(C)C AOKKPUNLOQKYSU-UHFFFAOYSA-N 0.000 description 1
- GMWSHXONQKXRHS-UHFFFAOYSA-N 2,4-dimethylhexanoic acid Chemical compound CCC(C)CC(C)C(O)=O GMWSHXONQKXRHS-UHFFFAOYSA-N 0.000 description 1
- JOMCVBSBANMVDJ-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-2,3,3-trimethylpentanoic acid Chemical compound CCC(C)(C)C(C)(C(O)=O)CC(C)(C)C JOMCVBSBANMVDJ-UHFFFAOYSA-N 0.000 description 1
- JSWJMZFEMLQSDF-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-2,5-dimethylhexanoic acid Chemical compound CC(C)CCC(C)(C(O)=O)CC(C)(C)C JSWJMZFEMLQSDF-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
- 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
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- AFPFGRHTBBSNCQ-UHFFFAOYSA-N 2-ethyl-2,3,3,5-tetramethylhexanoic acid Chemical compound CCC(C)(C(=O)O)C(C)(C)CC(C)C AFPFGRHTBBSNCQ-UHFFFAOYSA-N 0.000 description 1
- SXJBHJCKWQIWHA-UHFFFAOYSA-N 2-ethyl-2,3,3-trimethylbutanoic acid Chemical compound CCC(C)(C(O)=O)C(C)(C)C SXJBHJCKWQIWHA-UHFFFAOYSA-N 0.000 description 1
- WUWPVNVBYOKSSZ-UHFFFAOYSA-N 2-ethyl-2-methyl valeric ccid Chemical compound CCCC(C)(CC)C(O)=O WUWPVNVBYOKSSZ-UHFFFAOYSA-N 0.000 description 1
- LHJPKLWGGMAUAN-UHFFFAOYSA-N 2-ethyl-2-methyl-butanoic acid Chemical compound CCC(C)(CC)C(O)=O LHJPKLWGGMAUAN-UHFFFAOYSA-N 0.000 description 1
- YLZIMEJTDZWVJG-UHFFFAOYSA-N 2-heptylundecanoic acid Chemical compound CCCCCCCCCC(C(O)=O)CCCCCCC YLZIMEJTDZWVJG-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
- YNXFWNKTAOTVGR-UHFFFAOYSA-N 2-pentylnonanoic acid Chemical compound CCCCCCCC(C(O)=O)CCCCC YNXFWNKTAOTVGR-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- DUHQIGLHYXLKAE-UHFFFAOYSA-N 3,3-dimethylglutaric acid Chemical compound OC(=O)CC(C)(C)CC(O)=O DUHQIGLHYXLKAE-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
- HHGZJCMMPUJXIF-UHFFFAOYSA-N 4,5-dimethylhexanoic acid Chemical compound CC(C)C(C)CCC(O)=O HHGZJCMMPUJXIF-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 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
- BAZMYXGARXYAEQ-UHFFFAOYSA-N alpha-ethyl valeric acid Chemical compound CCCC(CC)C(O)=O BAZMYXGARXYAEQ-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
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- UPURPFNAFBQPON-UHFFFAOYSA-N beta,beta-dimethyl valeric acid Chemical compound CCC(C)(C)CC(O)=O UPURPFNAFBQPON-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010725 compressor oil Substances 0.000 description 1
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- 230000018044 dehydration Effects 0.000 description 1
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- 230000000994 depressogenic effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 1
- 229950004531 hexyldecanoic acid Drugs 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 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
- 230000003449 preventive effect Effects 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
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 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
- 229940029284 trichlorofluoromethane Drugs 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
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Lubricants (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明はエステル系の冷凍機油に
関し、詳しくは加水分解安定性に優れ、フロン冷媒に対
し充分な相溶性を有するエステル系の冷凍機油に関する
。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an ester-based refrigerating machine oil, and more particularly to an ester-based refrigerating machine oil having excellent hydrolytic stability and sufficient compatibility with fluorocarbon refrigerants.
【０００２】0002
【従来の技術】近年の冷凍機の小型大容量化に伴って、
冷凍機の使用温度は益々高くなってきている。従来、冷
凍機油としてはナフテン系鉱油やパラフィン系鉱油など
が用いられてきたが、これらの鉱油系の冷凍機油は高温
における酸化安定性が十分ではない。酸化安定性の優れ
ているエステル系の潤滑油を冷凍機油として、単独ある
いは配合して使用している（特開昭５６−１２５４９４
号公報、特開昭５９−１６４３９３号公報、特開昭６１
−１８１８９５号公報、特公昭６２−１２７８０号公報
）。[Prior Art] As refrigerators have become smaller and larger in capacity in recent years,
The operating temperature of refrigerators is becoming higher and higher. Conventionally, naphthenic mineral oils, paraffinic mineral oils, and the like have been used as refrigeration oils, but these mineral oil-based refrigeration oils do not have sufficient oxidation stability at high temperatures. Ester-based lubricating oils with excellent oxidation stability are used alone or in combination as refrigerating machine oils (Japanese Unexamined Patent Publication No. 125494/1983).
No. 1, JP-A-59-164393, JP-A-Sho 61
-181895, Japanese Patent Publication No. 62-12780).
【０００３】現在、冷凍機にはＲ−１１（トリクロロモ
ノフルオロメタン）、Ｒ−１２（ジクロロジフルオロメ
タン）、Ｒ−２２（モノクロロジフルオロメタン）など
のフロンが冷媒として使用されているが、これらのフロ
ンはオゾン層を破壊するため、オゾン層への影響がない
フロンであるＲ−１３４ａ（１，１，１，２−テトラフ
ルオロエタン）などが冷凍機用の代替フロンとして検討
されている。しかし、Ｒ−１３４ａは従来から冷凍機油
として使用されている鉱油に溶けないという問題があり
、ポリアルキレングリコール系の冷凍機油が提案されて
いるが、ポリアルキレングリコール系の冷凍機油は潤滑
性、吸湿性、高温域でのフロンとの相溶性、電気絶縁性
などの点で必ずしも十分満足できるものではない。そこ
で、これに替わるものとしてエステル系の冷凍機油が検
討されている（上村茂弘、代替フロン冷媒の技術開発状
況、平成２年度石油製品討論会講演資料）。Currently, chlorofluorocarbons such as R-11 (trichloromonofluoromethane), R-12 (dichlorodifluoromethane), and R-22 (monochlorodifluoromethane) are used as refrigerants in refrigerators. Since fluorocarbons destroy the ozone layer, fluorocarbons such as R-134a (1,1,1,2-tetrafluoroethane), which do not affect the ozone layer, are being considered as alternative fluorocarbons for refrigerators. However, R-134a has the problem of not being soluble in mineral oil, which has traditionally been used as refrigeration oil, and polyalkylene glycol-based refrigeration oils have been proposed; However, they are not always fully satisfactory in terms of performance, compatibility with fluorocarbons in high-temperature ranges, electrical insulation properties, etc. Therefore, ester-based refrigeration oil is being considered as an alternative to this (Shigehiro Uemura, Status of technological development of alternative fluorocarbon refrigerants, 1990 Petroleum Products Conference Lecture Materials).
【０００４】エステル系の冷凍機油は鉱油系の冷凍機油
にはない特性を持った優れた冷凍機油であるが、エステ
ルには加水分解しやすい欠点がある。加水分解によって
生じた遊離の脂肪酸は、冷凍機の金属部を腐蝕させるな
どの悪影響を及ぼす。電気冷蔵庫などの冷凍機油の場合
、高温で１０〜２０年の長期間にわたって使用されるの
で、エステルの加水分解しやすい欠点は特に問題である
。[0004] Ester-based refrigerating machine oil is an excellent refrigerating machine oil that has properties not found in mineral oil-based refrigerating machine oil, but esters have the disadvantage of being easily hydrolyzed. Free fatty acids produced by hydrolysis have adverse effects such as corroding the metal parts of refrigerators. In the case of refrigerating machine oils such as electric refrigerators, the disadvantage of easy hydrolysis of esters is particularly problematic because they are used at high temperatures for long periods of 10 to 20 years.
【０００５】[0005]
【発明が解決しようとする課題】加水分解を防ぐ方法と
してはエステル中の水分濃度を極力低く保つ水分管理が
有力な方法であるが、極度の水分管理は作業性を悪化さ
せる。本発明は、加水分解安定性に優れ、かつフロン冷
媒との相溶性の良好なエステル系の冷凍機油を提供する
ことを目的としている。[Problems to be Solved by the Invention] An effective way to prevent hydrolysis is to control the water content in the ester to keep it as low as possible, but excessive water control deteriorates workability. An object of the present invention is to provide an ester-based refrigerating machine oil that has excellent hydrolytic stability and good compatibility with fluorocarbon refrigerants.
【０００６】[0006]
【課題を解決するための手段】すなわち、本発明は全脂
肪酸中に占める三級脂肪酸と二級脂肪酸の合計割合が５
０モル％以上であり、かつ炭素数３〜１８の脂肪酸５０
〜１００モル％、炭素数４〜１０の二価カルボン酸０〜
５０モル％である混合酸と炭素数１５以下のネオペンチ
ルポリオールとのエステルを主成分とする冷凍機油であ
る。[Means for Solving the Problems] That is, the present invention provides a method in which the total proportion of tertiary fatty acids and secondary fatty acids in all fatty acids is 5.
0 mol% or more fatty acid having 3 to 18 carbon atoms 50
~100 mol%, 0~ dihydric carboxylic acid having 4 to 10 carbon atoms
This is a refrigeration oil whose main component is an ester of 50 mol% of a mixed acid and a neopentyl polyol having 15 or less carbon atoms.
【０００７】本発明に用いる炭素数３〜１８の三級脂肪
酸としては、２，２−ジメチルプロパン酸、２，２−ジ
メチルブタン酸、２，２−ジメチルペンタン酸、２，２
−ジメチルヘキサン酸、２，２−ジメチルヘプタン酸、
２，２−ジメチルオクタン酸、２−メチル−２−エチル
ブタン酸、２−メチル−２−エチルペンタン酸、２−エ
チル−２，３，３−トリメチルブタン酸、２，２，３，
３−テトラメチルペンタン酸、２，２，３，４−テトラ
メチルペンタン酸、２−エチル−２，３，３，５，５−
ペンタメチルペンタン酸、２，４，４−トリメチル−２
−ｔｅｒｔ−ペンチルペンタン酸、２−イソペンチル−
２，４，４−トリメチルペンタン酸、２−イソプロピル
−２，３，５，５−テトラメチルヘキサン酸、２，２−
ジメチルヘキサデカン酸、２，２−ジブチルデカン酸な
どが挙げられ、単独で使用しても良いし、二種以上を混
合使用しても良い。The tertiary fatty acids having 3 to 18 carbon atoms used in the present invention include 2,2-dimethylpropanoic acid, 2,2-dimethylbutanoic acid, 2,2-dimethylpentanoic acid, and 2,2-dimethylpropanoic acid.
-dimethylhexanoic acid, 2,2-dimethylheptanoic acid,
2,2-dimethyloctanoic acid, 2-methyl-2-ethylbutanoic acid, 2-methyl-2-ethylpentanoic acid, 2-ethyl-2,3,3-trimethylbutanoic acid, 2,2,3,
3-tetramethylpentanoic acid, 2,2,3,4-tetramethylpentanoic acid, 2-ethyl-2,3,3,5,5-
Pentamethylpentanoic acid, 2,4,4-trimethyl-2
-tert-pentylpentanoic acid, 2-isopentyl-
2,4,4-trimethylpentanoic acid, 2-isopropyl-2,3,5,5-tetramethylhexanoic acid, 2,2-
Examples include dimethylhexadecanoic acid and 2,2-dibutyldecanoic acid, which may be used alone or in combination of two or more.
【０００８】本発明に用いる炭素数３〜１８の二級脂肪
酸としては、２−メチル酪酸、２−メチルペンタン酸、
２−メチルヘキサン酸、２，４−ジメチルヘキサン酸、
２−エチル酪酸、２−エチルペンタン酸、２−エチルヘ
キサン酸、２−プロピルペンタン酸、２−ペンチルノナ
ン酸、２−ヘキシルデカン酸、２−ノニルノナン酸など
が挙げられ、単独で使用しても良いし、二種以上を混合
使用しても良い。The secondary fatty acids having 3 to 18 carbon atoms used in the present invention include 2-methylbutyric acid, 2-methylpentanoic acid,
2-methylhexanoic acid, 2,4-dimethylhexanoic acid,
Examples include 2-ethylbutyric acid, 2-ethylpentanoic acid, 2-ethylhexanoic acid, 2-propylpentanoic acid, 2-pentylnonanoic acid, 2-hexyldecanoic acid, 2-nonylnonanoic acid, and they may be used alone or , two or more types may be used in combination.
【０００９】本発明では三級脂肪酸および二級脂肪酸と
併用して一級脂肪酸が５０モル％未満まで使用されるが
、一級脂肪酸としては、プロピオン酸、吉草酸、カプロ
ン酸、ヘプタン酸、カプリル酸、ペラルゴン酸、カプリ
ン酸、ウンデカン酸、ラウリン酸、ミリスチン酸、パル
ミチン酸、ステアリン酸、オレイン酸、３，３−ジメチ
ルペンタン酸、４−メチルヘキサン酸、３，５−ジメチ
ルヘキサン酸、４，５−ジメチルヘキサン酸、３，５，
５−トリメチルヘキサン酸などが挙げられ、単独で使用
しても良いし、二種以上を混合使用しても良い。[0009] In the present invention, primary fatty acids are used in combination with tertiary fatty acids and secondary fatty acids up to less than 50 mol%, and primary fatty acids include propionic acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, 3,3-dimethylpentanoic acid, 4-methylhexanoic acid, 3,5-dimethylhexanoic acid, 4,5- dimethylhexanoic acid, 3,5,
Examples include 5-trimethylhexanoic acid, which may be used alone or in combination of two or more.
【００１０】炭素数が２以下であるとエステルの粘度が
低くなり実用的でなく、また金属が腐蝕され易い。炭素
数が１９以上であるとエステルのフロン冷媒への相溶性
が悪くなり、また低温で濁りを生じるために好ましくな
い。三級脂肪酸と二級脂肪酸の合計割合は５０モル％以
上であるが、５０モル％未満となると、加水分解安定性
が悪くなる。[0010] When the number of carbon atoms is 2 or less, the viscosity of the ester becomes low, making it impractical, and metals are likely to be corroded. If the number of carbon atoms is 19 or more, the compatibility of the ester with the fluorocarbon refrigerant becomes poor and turbidity occurs at low temperatures, which is not preferable. The total proportion of tertiary fatty acids and secondary fatty acids is 50 mol% or more, but if it is less than 50 mol%, the hydrolytic stability deteriorates.
【００１１】本発明に用いる炭素数４〜１０の二価のカ
ルボン酸としては、こはく酸、グルタル酸、アジピン酸
、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸
、２，２−ジメチルこはく酸、２，２−ジメチルグルタ
ル酸、３，３−ジメチルグルタル酸、２，２，５−トリ
メチルアジピン酸、フタル酸、テレフタル酸、イソフタ
ル酸などが挙げられ、単独で使用しても良いし、二種以
上を混合使用しても良い。炭素数が１１以上であるとエ
ステルのフロン冷媒への相溶性が悪くなり、また低温で
濁りを生じるため好ましくない。本発明で用いる二価の
カルボン酸の割合は、０〜５０モル％であるが、５０モ
ル％を超えるとエステルの粘度が高くなるので実用的で
ない。The divalent carboxylic acids having 4 to 10 carbon atoms used in the present invention include succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 2,2-dimethylsuccinic acid, Examples include 2,2-dimethylglutaric acid, 3,3-dimethylglutaric acid, 2,2,5-trimethyladipic acid, phthalic acid, terephthalic acid, and isophthalic acid, which may be used alone or in combination of two types. The above may be used in combination. If the number of carbon atoms is 11 or more, the compatibility of the ester with the fluorocarbon refrigerant becomes poor and turbidity occurs at low temperatures, which is not preferable. The proportion of the divalent carboxylic acid used in the present invention is 0 to 50 mol%, but if it exceeds 50 mol%, the viscosity of the ester becomes high, which is not practical.
【００１２】本発明に用いる炭素数１５以下のネオペン
チルポリオールとしては、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、ジペンタエリス
リトール、２，２−ジメチル−３−ヒドロキシプロピル
−２，２−ジメチル−３−ヒドロキシプロピオネート、
トリペンタエリスリトールなどが挙げられ、炭素数が１
６以上になると低温で濁りが生じるので好ましくない。The neopentyl polyol having 15 or less carbon atoms used in the present invention includes neopentyl glycol, 2
, 2-diethyl-1,3-propanediol, 2-n-
Butyl-2-ethyl-1,3-propanediol, trimethylolethane, trimethylolpropane, trimethylolnonane, pentaerythritol, dipentaerythritol, 2,2-dimethyl-3-hydroxypropyl-2,2-dimethyl-3 - hydroxypropionate,
Examples include tripentaerythritol, and the number of carbon atoms is 1.
A value of 6 or higher is not preferable because turbidity occurs at low temperatures.
【００１３】本発明のエステルは、通常のエステル化反
応によって得ることができ、また脂肪酸クロリドを用い
たエステル化反応、さらには各々の誘導体のエステル交
換反応によっても得ることができる。通常のエステル化
反応、または脂肪酸クロリドを用いたエステル化反応を
行なう場合、ネオペンチルポリオールの水酸基と、脂肪
酸または脂肪酸クロリドのアシル基の反応当量比につい
てとくに限定はないが、得られるエステルの水酸基価が
高いと、発泡し易い、粘度指数が低くなる、吸湿し易く
なるなどの欠点が生じるため、水酸基１当量に対して、
アシル基 ０．９当量以上となるようにするのが好まし
い。The ester of the present invention can be obtained by a conventional esterification reaction, an esterification reaction using a fatty acid chloride, and further a transesterification reaction of each derivative. When performing a normal esterification reaction or an esterification reaction using a fatty acid chloride, there are no particular limitations on the reaction equivalent ratio of the hydroxyl group of neopentyl polyol and the acyl group of the fatty acid or fatty acid chloride, but the hydroxyl value of the resulting ester If it is high, there will be disadvantages such as easy foaming, low viscosity index, and easy moisture absorption, so for 1 equivalent of hydroxyl group,
It is preferable that the amount of acyl group is 0.9 equivalent or more.
【００１４】本発明の冷凍機油に用いられるエステルは
エステル化反応ののちに、アルカリ水洗、水洗、蒸留、
吸着処理などの精製工程によって精製することができる
。酸化安定性と加水分解安定性の点から、精製したのち
のエステルの酸価は１ｍｇＫＯＨ／ｇ以下、水酸基価は
４０ｍｇＫＯＨ／ｇ以下とするのが望ましい。また、脂
肪酸クロリドを用いてエステル化した場合は、生成した
塩素が多量に残存すると腐蝕の原因となるので、精製に
より塩素濃度を１０ｐｐｍ以下とするのが望ましい。After the esterification reaction, the ester used in the refrigerating machine oil of the present invention is subjected to alkaline water washing, water washing, distillation,
It can be purified by a purification process such as adsorption treatment. From the viewpoint of oxidative stability and hydrolytic stability, it is desirable that the acid value of the purified ester is 1 mgKOH/g or less, and the hydroxyl value is 40 mgKOH/g or less. Furthermore, in the case of esterification using fatty acid chloride, it is desirable to reduce the chlorine concentration to 10 ppm or less through purification, since if a large amount of the produced chlorine remains, it will cause corrosion.
【００１５】本発明の冷凍機油に用いられるエステルは
単独で冷凍機油として使用しても良いし、鉱油、ポリ−
α−オレフィン、ジエステル、ポリフェニレンエーテル
、ふっそ化炭化水素、シリコーン油、ポリアルキレング
リコールなどの他の油と混合して冷凍機油として使用し
ても良いが、その混合割合は１０重量％以下が好ましい
。The ester used in the refrigerating machine oil of the present invention may be used alone as a refrigerating machine oil, or may be used as a refrigerating machine oil.
It may be mixed with other oils such as α-olefins, diesters, polyphenylene ethers, fluorinated hydrocarbons, silicone oils, and polyalkylene glycols for use as refrigeration oil, but the mixing ratio is preferably 10% by weight or less. .
【００１６】また、本発明のエステル系の冷凍機油は、
通常用いられる酸化防止剤、金属不活性化剤、極圧剤、
油性向上剤、消泡剤、塩素補足剤、流動点降下剤、粘度
指数向上剤、防錆剤などの各種の添加剤を必要に応じて
配合することができる。[0016] Furthermore, the ester-based refrigerating machine oil of the present invention is
Commonly used antioxidants, metal deactivators, extreme pressure agents,
Various additives such as an oiliness improver, an antifoaming agent, a chlorine supplement, a pour point depressant, a viscosity index improver, and a rust preventive can be added as necessary.
【００１７】[0017]
【発明の効果】本発明のエステル系の冷凍機油は加水分
解安定性に優れ、フロン冷媒との相溶性も良好であるの
で、電気冷蔵庫、カークーラーなどの長期間にわたって
使用される冷凍機油として用いることができる。また、
電気絶縁油、コンプレッサー油、エンジン油、作動油、
グリース基油、熱媒体などにも使用することができる。Effects of the Invention The ester-based refrigerating machine oil of the present invention has excellent hydrolytic stability and good compatibility with fluorocarbon refrigerants, so it can be used as a refrigerating machine oil used for long periods of time in electric refrigerators, car coolers, etc. be able to. Also,
Electrical insulation oil, compressor oil, engine oil, hydraulic oil,
It can also be used as a grease base oil, heat medium, etc.
【００１８】[0018]
【実施例】以下、本発明を実施例により具体的に説明す
る。
脂肪酸クロリドの合成
１リットルの攪拌機付きガラス製四つ口フラスコに温度
計、冷却管および滴下漏斗を付け、脂肪酸（２，２−ジ
メチルブタン酸）を四つ口フラスコに入れ、三塩化リン
を４０℃で１時間にわたり均等に滴下し、同温度に３時
間保った。反応生成物を１時間静置したのち上層を分離
し、蒸留を行なって脂肪酸クロリドを得た。脂肪酸と三
塩化リンは、１．００：１．３５当量比で合計５００ｇ
を用いて合成を行なった。[Examples] The present invention will be specifically explained below using examples. Synthesis of Fatty Acid Chloride A 1 liter glass four-necked flask with a stirrer was equipped with a thermometer, condenser and dropping funnel. Fatty acid (2,2-dimethylbutanoic acid) was put into the four-necked flask, and 40% of phosphorus trichloride was added. It was added dropwise evenly over 1 hour at ℃ and kept at the same temperature for 3 hours. After the reaction product was allowed to stand for 1 hour, the upper layer was separated and distilled to obtain fatty acid chloride. A total of 500g of fatty acids and phosphorus trichloride at an equivalent ratio of 1.00:1.35
Synthesis was performed using
【００１９】脂肪酸クロリドを使用するエステルの合成
１リットルの攪拌機付きガラス製四つ口フラスコに温度
計、冷却管および滴下漏斗を付け、ネオペンチルポリオ
ール（トリメチロールプロパン）を入れて７０℃で溶解
させ、脂肪酸クロリド（２，２−ジメチルブタン酸クロ
リド）を７０℃で１時間にわたり均等に滴下し、同温度
に３時間保った。得られた反応生成物を５％の水酸化カ
リウム水溶液で洗い、水洗をしたのち、９５℃、２０ｍ
ｍＨｇで１時間脱水をし、さらに瀘過を行なって実施例
１のエステルを得た。水酸基とアシル基の当量比は１．
０：１．３とし、合計５００ｇを用いて合成を行なった
。Synthesis of ester using fatty acid chloride A 1 liter glass four-necked flask equipped with a stirrer was equipped with a thermometer, a cooling tube and a dropping funnel, and neopentyl polyol (trimethylolpropane) was added thereto and dissolved at 70°C. , fatty acid chloride (2,2-dimethylbutanoic acid chloride) was evenly added dropwise at 70° C. over 1 hour, and the same temperature was maintained for 3 hours. The obtained reaction product was washed with a 5% aqueous potassium hydroxide solution, washed with water, and then heated at 95°C for 20 m.
The ester of Example 1 was obtained by dehydration at mHg for 1 hour and further filtration. The equivalent ratio of hydroxyl group to acyl group is 1.
0:1.3, and a total of 500 g was used for synthesis.
【００２０】直接エステル化によるエステルの合成１リ
ットルの攪拌機付きガラス製四つ口フラスコに温度計、
窒素吹き込み管および冷却管を付けた懸垂管を付し、表
１，表２に示した組成の原料５００ｇとエステル化触媒
としてｐ−トルエンスルホン酸１．５ｇを入れて２００
℃で２０時間反応させた。得られた反応生成物を５％の
水酸化カリウム水溶液で洗い、水洗をしたのち、９５℃
、２０ｍｍＨｇで１時間脱水をし、さらに瀘過を行なっ
て実施例２〜１２、および比較例１〜６のエステルを得
た。水酸基とアシル基の当量比は、全て１．０：１．５
である。表１，表２に混合酸，ネオペンチルポリオール
の各々の組成をモル％で示した。Synthesis of esters by direct esterification A 1 liter glass four-necked flask equipped with a stirrer was equipped with a thermometer,
A suspension tube equipped with a nitrogen blowing pipe and a cooling pipe was attached, and 500 g of raw materials having the composition shown in Tables 1 and 2 and 1.5 g of p-toluenesulfonic acid as an esterification catalyst were added to the reactor.
The reaction was carried out at ℃ for 20 hours. The obtained reaction product was washed with a 5% aqueous potassium hydroxide solution, washed with water, and then heated to 95°C.
, and 20 mmHg for 1 hour, followed by filtration to obtain esters of Examples 2 to 12 and Comparative Examples 1 to 6. The equivalent ratio of hydroxyl group and acyl group is all 1.0:1.5
It is. Tables 1 and 2 show the compositions of the mixed acid and neopentyl polyol in mol%.
【表１】[Table 1]
【表２】[Table 2]
【００２１】加水分解安定性試験
試料の各エステルを温度４０℃、湿度９０％に保った恒
温恒湿槽内に静置して
、水分濃度を２０００ｐｐｍ以上にした。そののち、室
温で窒素バブリングして試料の溶存酸素の濃度を０．１
ｐｐｍ以下、水分濃度を１４００〜１６００ｐｐｍに調
整した。つぎに内容量１０ミリリットルのガラス製耐圧
アンプルに試料５ミリリットルを窒素雰囲気下で入れ、
アンプル内を減圧し、減圧状態を保ちながら封管した。
封管したアンプルを１８０℃で４００時間加熱したのち
酸価を測定した。試験前、試験後の酸価を表３に示した
。[0021] Each ester of the hydrolytic stability test sample was left standing in a constant temperature and humidity chamber maintained at a temperature of 40°C and a humidity of 90%, and the water concentration was adjusted to 2000 ppm or more. After that, the concentration of dissolved oxygen in the sample was reduced to 0.1 by nitrogen bubbling at room temperature.
The water concentration was adjusted to 1400 to 1600 ppm. Next, 5 ml of the sample was placed in a 10 ml glass pressure-resistant ampoule under a nitrogen atmosphere.
The pressure inside the ampoule was reduced, and the tube was sealed while maintaining the reduced pressure state. After heating the sealed ampoule at 180° C. for 400 hours, the acid value was measured. Table 3 shows the acid values before and after the test.
【００２２】フロン冷媒との相溶性試験試料０．２ｇ、
フロン１．８ｇをガラスチューブに入れ、これを封管し
た。２０℃から１℃／分の割合で冷却および加熱し、二
層分離温度を求めた。結果を表３に示した。なお、試験
に用いたフロンＲ−２２とＲ−１３４ａはいずれもダイ
キン工業（株）製である。0.2 g of compatibility test sample with Freon refrigerant,
1.8 g of Freon was placed in a glass tube and the tube was sealed. The mixture was cooled and heated from 20° C. at a rate of 1° C./min to determine the two-layer separation temperature. The results are shown in Table 3. Note that Freon R-22 and R-134a used in the test were both manufactured by Daikin Industries, Ltd.
【表３】[Table 3]
【００２３】表３から明らかなように、本発明のエステ
ル系の冷凍機油は加水分解安定性に優れ、フロン冷媒と
の相溶性が良好であることがわかる。また、本発明の範
囲外の比較例１〜６は、加水分解安定性あるいはフロン
冷媒との相溶性が悪いことがわかる。As is clear from Table 3, the ester-based refrigerating machine oil of the present invention has excellent hydrolytic stability and good compatibility with fluorocarbon refrigerants. Furthermore, it can be seen that Comparative Examples 1 to 6, which are outside the scope of the present invention, have poor hydrolytic stability or poor compatibility with fluorocarbon refrigerants.
Claims (1)
脂肪酸の合計割合が５０モル％以上であり、かつ炭素数
３〜１８の脂肪酸５０〜１００モル％、炭素数４〜１０
の二価カルボン酸０〜５０モル％である混合酸と炭素数
１５以下のネオペンチルポリオールとのエステルを主成
分とする冷凍機油。Claim 1: The total proportion of tertiary fatty acids and secondary fatty acids in all fatty acids is 50 mol% or more, and 50 to 100 mol% of fatty acids having 3 to 18 carbon atoms and 4 to 10 carbon atoms.
A refrigerating machine oil whose main component is an ester of a mixed acid which is 0 to 50 mol% of a dihydric carboxylic acid and a neopentyl polyol having 15 or less carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10639791A JPH04314793A (en) | 1991-04-12 | 1991-04-12 | Ester refrigerator oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10639791A JPH04314793A (en) | 1991-04-12 | 1991-04-12 | Ester refrigerator oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04314793A true JPH04314793A (en) | 1992-11-05 |
Family
ID=14432561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10639791A Pending JPH04314793A (en) | 1991-04-12 | 1991-04-12 | Ester refrigerator oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04314793A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5716916A (en) * | 1996-04-09 | 1998-02-10 | Mitsubishi Gas Chemical Company, Inc. | Polyol ester based-lubricant |
| US6245254B1 (en) | 1991-10-11 | 2001-06-12 | Imperial Chemical Industries Plc | Lubricants |
| JP2009079143A (en) * | 2007-09-26 | 2009-04-16 | Nippon Oil Corp | Base oil for refrigerator oil for carbon dioxide coolant, and refrigerator oil for carbon dioxide coolant |
| JP2009079146A (en) * | 2007-09-26 | 2009-04-16 | Nippon Oil Corp | Base oil for refrigerator oil for carbon dioxide refrigerant, and refrigerator oil for carbon dioxide refrigerant |
| JP2009079147A (en) * | 2007-09-26 | 2009-04-16 | Nippon Oil Corp | Base oil for refrigerator oil for carbon dioxide refrigerant, and refrigerator oil for carbon dioxide refrigerant |
| JP2011208068A (en) * | 2010-03-30 | 2011-10-20 | Jx Nippon Oil & Energy Corp | Refrigerator oil and working fluid composition for refrigerator |
-
1991
- 1991-04-12 JP JP10639791A patent/JPH04314793A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245254B1 (en) | 1991-10-11 | 2001-06-12 | Imperial Chemical Industries Plc | Lubricants |
| US5716916A (en) * | 1996-04-09 | 1998-02-10 | Mitsubishi Gas Chemical Company, Inc. | Polyol ester based-lubricant |
| JP2009079143A (en) * | 2007-09-26 | 2009-04-16 | Nippon Oil Corp | Base oil for refrigerator oil for carbon dioxide coolant, and refrigerator oil for carbon dioxide coolant |
| JP2009079146A (en) * | 2007-09-26 | 2009-04-16 | Nippon Oil Corp | Base oil for refrigerator oil for carbon dioxide refrigerant, and refrigerator oil for carbon dioxide refrigerant |
| JP2009079147A (en) * | 2007-09-26 | 2009-04-16 | Nippon Oil Corp | Base oil for refrigerator oil for carbon dioxide refrigerant, and refrigerator oil for carbon dioxide refrigerant |
| JP2011208068A (en) * | 2010-03-30 | 2011-10-20 | Jx Nippon Oil & Energy Corp | Refrigerator oil and working fluid composition for refrigerator |
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