EP0406479B1 - Kältemaschinenschmiermittel - Google Patents
Kältemaschinenschmiermittel Download PDFInfo
- Publication number
- EP0406479B1 EP0406479B1 EP89119265A EP89119265A EP0406479B1 EP 0406479 B1 EP0406479 B1 EP 0406479B1 EP 89119265 A EP89119265 A EP 89119265A EP 89119265 A EP89119265 A EP 89119265A EP 0406479 B1 EP0406479 B1 EP 0406479B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- saturated fatty
- monovalent saturated
- chain monovalent
- carbon number
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000314 lubricant Substances 0.000 title claims description 49
- 238000005057 refrigeration Methods 0.000 title description 20
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical group FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 40
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 40
- 239000003507 refrigerant Substances 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 16
- 150000007519 polyprotic acids Polymers 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 claims description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 3
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 12
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 239000010695 polyglycol Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 5
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- -1 polyoxypropylene monobutyl ether Polymers 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 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
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/40—Esters containing free hydroxy or carboxyl groups
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
- C10M105/44—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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- C—CHEMISTRY; METALLURGY
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/2805—Esters used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/2875—Partial esters used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/288—Partial esters containing free carboxyl groups
- C10M2207/2885—Partial esters containing free carboxyl groups used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2207/287—Partial esters
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- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/11—Complex polyesters
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- C10M2211/0206—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only used as base material
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- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
- C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic used as base material
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- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
- C10M2211/0245—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic used as base material
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- C10M2211/06—Perfluorinated compounds
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- C10N2040/30—Refrigerators lubricants or compressors lubricants
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- C10N2040/32—Wires, ropes or cables lubricants
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/34—Lubricating-sealants
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- C10N2040/36—Release agents or mold release agents
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- C10N2040/38—Conveyors or chain belts
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/40—Generators or electric motors in oil or gas winning field
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/42—Flashing oils or marking oils
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/44—Super vacuum or supercritical use
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N2040/50—Medical uses
Definitions
- This invention relates to lubricants for compressors, and more particularly to lubricants suitable for use in the compression of refrigerants containing no chlorine such as, HFC-134a (1,1,1,2-tetrafluoroethane) and to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine.
- Japanese Patent laid open No. 61-281199 describes a mixture of polyglycol represented by a general formula of R, [O-(R 2 0) m -R 3]n , an alkylbenzene
- Japanese Patent laid open No. 57-63395 describes an oil obtained by mixing a polyether such as high molecular weight polyoxypropylene monobutyl ether with an epoxycycloalkyl compound
- Japanese Patent laid open No. 59-117590 describes a high viscosity mixed oil of a polyether compound and a paraffinic or naphthanic mineral oil.
- the conventional synthetic lubricants as mentioned above cannot be a refrigeration lubricant using HFC-134a as a refrigerant from a viewpoint of compatibility and the like.
- polyoxyalkylene glycol (hereinafter abbreviated as PAG) having hydroxyl groups (-OH) at both terminals is reported as a refrigeration lubricant using HFC-134a.
- PAG polyoxyalkylene glycol
- -OH hydroxyl groups
- HFC-134a is a replacing refrigerant of R-12 and is mainly expected for use in a car air conditioner or a refrigerator, for example.
- the refrigerator it is required to have a good compatibility between lubricant and refrigerant, and further the lubricant itself is necessary to have an electric insulating property because the motor is substantially existent in the refrigeration system.
- the conventional compounds examined as a lubricant for HFC-134a refrigerant inclusive of PAG disclosed in US Patent No. 4,755,316 are remarkably poor in the electric insulating property as compared with the conventional refrigeration mineral oil and high in the hygroscopicity.
- an object of the invention to provide a refrigeration lubricant having an excellent compatibility with a new refrigerant containing no chlorine such as HFC-134a within a wide temperature range, a high electric insulating property and a low hygroscopicity.
- esters At the present, a part of commercially available esters is used in systems using refrigerants R-12 and R-22 for instance, but is incompatible with HFC-134a as a new refrigerant or is very narrow in the compatible range therewith.
- the inventors have aimed at the fact that the ester has a high electric insulating property, a low hygroscopicity, a good lubricity and a high stability as compared with PAG and made various studies with respect to the molecule design of the ester showing a wide range of compatibility with HFC-134a, and found that only esters having a considerably restricted structure can be used in the HFC-134a refrigeration system, and as a result, the invention has been accomplished.
- the present invention is directed to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, comprising as a main component an ester(s) obtained by reacting (a) neopentyl glycol with (b) a mixture of at least one of straight chain monovalent saturated fatty acids having a carbon number of 5-10 and at least one of branched-chain monovalent saturated fatty acids having a carbon number of 7-9, wherein the amount of the branched-chain monovalent saturated fatty acid is not less than 50 mol% per total monovalent saturated fatty acid used.
- the invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, comprising as a main component an ester(s) obtained by reacting (a) neopentyl glycol with (b) a mixture of at least one of straight chain monovalent saturated fatty acids having a carbon number of 5-10 and at least one of branched-chain monovalent saturated fatty acids having a carbon number of 7-9, wherein the amount of the branched-chain monovalent saturated fatty acid is not less than 50 mol% per total monovalent saturated fatty acid used, and (c) at least one polybasic acid having a carbon number of 4-10, wherein the amount of the polybasic acid is not more than 80 mol% per total monovalent saturated fatty acid used.
- the hydrofluorocarbon refrigerant is 1,1,1,2-tetrafluoroethane (HFC-134a).
- the invention is directed to a lubricant for compressors using 1,1,1,2-tetrafluoroethane refrigerant, comprising as a main component an ester(s) obtained by reacting (a) neopentyl glycol with (b) a mixture of at least one of straight chain monovalent saturated fatty acids having a carbon number of 5-10 and at least one of branched-chain monovalent saturated fatty acids having a carbon number of 7-9, wherein the amount of the branched-chain monovalent saturated fatty acid is not less than 50 mol% per total monovalent saturated fatty acid used.
- the present invention refers to a lubricant for compressors using 1,1,1,2-tetrafluoroethane refrigerant, comprising as a main component an ester(s) obtained by reacting (a) neopentyl glycol with (b) a mixture of at least one of straight chain monovalent saturated fatty acids having a carbon number of 5-10 and at least one of branched-chain monovalent saturated fatty acids having a carbon number of 7-9, wherein the amount of the branched-chain monovalent saturated fatty acid is not less than 50 mol% per total monovalent saturated fatty acid used, and (c) at least one polybasic acid having a carbon number of 4-10, wherein the amount of the polybasic acid is not more than 80 mol% per total monovalent saturated fatty acid used.
- the monovalent fatty acid mention may be made of, pentanoic acid, hexanoic acid, heptanoic acid, isoheptanoic acid, octanoic acid, 2-ethyl hexanoic acid, nonanoic acid, 3,5,5-trimethyl hexanoic acid and decanoic acid.
- a mixture of at least one of straight-chain monovalent fatty acids having a carbon number of 5-10 and at least one of branched-chain monovalent fatty acids having a carbon number of 7-9 is properly mixed and esterified with neopentyl glycol in order to obtain an ester satisfying desirable physical properties required for various refrigerators.
- the amount of the branched-chain fatty acid used is not less than 50 mol% per the total monovalent fatty acid used.
- At least one polybasic acid having a carbon number of 4-10 may be esterified with neopentyl glycol in an amount of not more than 80 mol% per total fatty acid.
- neopentyl glycol in an amount of not more than 80 mol% per total fatty acid.
- a polybasic acid having a carbon number of 4-10 is used.
- the polybasic acid includes succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, maleic acid, trimellitic acid and so on.
- the polybasic acid having a carbon number of not more than 3 is a special product and is difficult to be cheaply available and is poor in the stability of the ester after the synthesis. While, when the carbon number exceeds 36, the compatibility of the resulting ester with HFC-134a and the like is largely lowered.
- the reason why the amount of the polybasic acid added is limited to not more than 80 mol% per the total fatty acid is due to the fact that when it exceeds 80 mol%, the gelation may be caused and it is difficult to obtain desirable physical properties.
- the ester compounds according to the first invention can be obtained by the esterification reaction through dehydration reaction between the specified polyvalent alcohol and the specified fatty acid as mentioned above, or the general esterification reaction through an acid anhydride, an acid chloride or the like as a derivative of the fatty acid.
- the ester according to the invention can be obtained by the above method, the remaining acid value and hydroxyl value are not particularly critical.
- the acid value exceeds 3 mg KOH/g, there may be caused an unfavorable phenomenon that the metal soap is formed and precipitated by the reaction with a metal used inside the refrigerator, so that the acid value is preferable to be not more than 3 mg KOH/g.
- the hydroxyl value exceeds 50 mg KOH/g, there may be caused an unfavorable phenomenon that the resulting ester becomes cloudy, so that the hydroxyl value is preferable to be not more than 50 mg KOH/g.
- the esters according to the invention exhibit a good compatibility with the refrigerant HFC-134a and the like over a wide range of from low temperature to high temperature as a lubricant for use in a refrigerator using HFC-134a as a refrigerant, whereby the lubricity and thermal stability of the refrigeration lubricant can be considerably improved. Furthermore, they are high in the electric insulating property and small in the hygroscopicity as compared with PAG conventionally examined as a refrigeration lubricant for HFC-134a.
- the refrigeration lubricants comprising the ester according to the invention as a main component can solve the problems on the compatibility with HFC-134a and the hygroscopicity, which have never been solved in the conventional technique, and can further enhance the electric insulating property, which comes into problem when HFC-134a is used in a compressor for a refrigerator.
- additives usually used in the lubricant such as antioxidant, anti-wear agent, epoxy compound and the like may properly be added to the refrigeration lubricant according to the invention.
- Seizuring load (Falex load-carrying capacity) was measured according to ASTM D-3233-73 under a controlled atmosphere of HFC-134a blown.
- test lubricant Into a beaker of 100 m was charged 60 g of the test lubricant, which was left to stand at a temperature of 25 ° C and a humidity of 70% for 3 hours and then the water concentration was measured.
- the electric insulating property represented by the dielectric constant is 100,000 times or more and the two-phase separation at a high temperature is not caused. Furthermore, the seizuring load is excellent and the hygroscopicity is low.
- the thermal stability is equal in case of the HFC-134a system, but is considerably excellent in case of the R-12 system. This is very advantageous in practical use because the mixing of HFC-134a and R-12 is not avoided at a stage of replacing the refrigerant from R-12 to HFC-134a.
- esters according to the invention are compared with the commercially available esters (C-1 - C-2), the two-phase separation temperature is extremely different and the conventional esters are insoluble in HFC-134a. In this point, the molecule designed esters according to the invention have a great merit.
- the esters according to the invention are fairly excellent in the performances as a lubricant as compared with Comparative Examples.
- the HFC-134a has been mentioned as a possible replacement for R-12 and is used for car air conditioner, refrigerator and the like. Particularly, in case of the car air conditioner, the compressor is driven in summer season, so that the compatibility between oil and refrigerant at high temperature becomes important. When the two-phase separation between oil and refrigerant is caused in the compressor during the driving, the refrigerant having a larger specific gravity remains in the lower portion of the compressor, resulting in the occurrence of compressor seizuring.
- the motor is included in the compressor, so that leakage of electricity comes into problem.
- the esters according to the invention have a dielectric constant higher by 100,000 times or more than that of the conventional PAG and are excellent in the electric insulating property, so that they can be said to be a refrigeration lubricant for the refrigerator.
- HFC-134a causing substantially no breakage of ozone layer is closed up instead of R-12 widely used as a refrigerant in order to cope with the breakage of ozone layer through chlorofluorocarbon and hydrochlorofluorocarbon being a greatest problem in world-wide scale, but is poor in the compatibility with the conventional refrigeration lubricant, which is a bar for the development of replacement system.
- the refrigeration lubricants according to the invention have a sufficient compatibility with HFC-134a as a refrigerant and a high electric insulating property and also are excellent in the total performances, so that they have an effect that the conventional systems can be used as they are even when HFC-134a is used instead of the conventional R-12 and R-22 as a refrigerant.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (13)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP91121100A EP0480479B2 (de) | 1989-07-05 | 1989-10-17 | Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden |
EP92121965A EP0536814B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
EP91121101A EP0479338B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
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JP17200189 | 1989-07-05 | ||
JP17200089 | 1989-07-05 | ||
JP17200189 | 1989-07-05 | ||
JP172001/89 | 1989-07-05 | ||
JP17200289 | 1989-07-05 | ||
JP17200089 | 1989-07-05 | ||
JP172002/89 | 1989-07-05 | ||
JP17200289 | 1989-07-05 | ||
JP172000/89 | 1989-07-05 |
Related Child Applications (7)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91121100A Division-Into EP0480479B2 (de) | 1989-07-05 | 1989-10-17 | Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden |
EP91121100A Division EP0480479B2 (de) | 1989-07-05 | 1989-10-17 | Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden |
EP92121965A Division-Into EP0536814B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
EP91121101A Division-Into EP0479338B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
EP91121101.9 Division-Into | 1991-12-09 | ||
EP91121100.1 Division-Into | 1991-12-09 | ||
EP92121965.5 Division-Into | 1992-12-23 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0406479A1 EP0406479A1 (de) | 1991-01-09 |
EP0406479B1 true EP0406479B1 (de) | 1994-04-06 |
EP0406479B2 EP0406479B2 (de) | 2002-09-04 |
Family
ID=27323564
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP89119265A Expired - Lifetime EP0406479B2 (de) | 1989-07-05 | 1989-10-17 | Kältemaschinenschmiermittel |
EP91121100A Expired - Lifetime EP0480479B2 (de) | 1989-07-05 | 1989-10-17 | Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden |
EP92121965A Expired - Lifetime EP0536814B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
EP91121101A Expired - Lifetime EP0479338B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91121100A Expired - Lifetime EP0480479B2 (de) | 1989-07-05 | 1989-10-17 | Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden |
EP92121965A Expired - Lifetime EP0536814B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
EP91121101A Expired - Lifetime EP0479338B1 (de) | 1989-07-05 | 1989-10-17 | Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden. |
Country Status (5)
Country | Link |
---|---|
EP (4) | EP0406479B2 (de) |
KR (3) | KR950005694B1 (de) |
DE (4) | DE68914448T3 (de) |
ES (4) | ES2099120T5 (de) |
SG (2) | SG49157A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102020102162A1 (de) | 2020-01-29 | 2021-07-29 | Oq Chemicals Gmbh | TCD-Ester für Niedertemperatur-Schmierstoffanwendungen |
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-
1989
- 1989-10-04 KR KR1019890014232A patent/KR950005694B1/ko not_active IP Right Cessation
- 1989-10-07 SG SG1996007058A patent/SG49157A1/en unknown
- 1989-10-17 DE DE68914448T patent/DE68914448T3/de not_active Expired - Lifetime
- 1989-10-17 ES ES91121100T patent/ES2099120T5/es not_active Expired - Lifetime
- 1989-10-17 EP EP89119265A patent/EP0406479B2/de not_active Expired - Lifetime
- 1989-10-17 ES ES89119265T patent/ES2051340T5/es not_active Expired - Lifetime
- 1989-10-17 DE DE68928281T patent/DE68928281T2/de not_active Expired - Lifetime
- 1989-10-17 DE DE68927916T patent/DE68927916T3/de not_active Expired - Lifetime
- 1989-10-17 DE DE68925537T patent/DE68925537T2/de not_active Expired - Lifetime
- 1989-10-17 SG SG1996007124A patent/SG49165A1/en unknown
- 1989-10-17 ES ES91121101T patent/ES2104650T3/es not_active Expired - Lifetime
- 1989-10-17 EP EP91121100A patent/EP0480479B2/de not_active Expired - Lifetime
- 1989-10-17 ES ES92121965T patent/ES2082341T3/es not_active Expired - Lifetime
- 1989-10-17 EP EP92121965A patent/EP0536814B1/de not_active Expired - Lifetime
- 1989-10-17 EP EP91121101A patent/EP0479338B1/de not_active Expired - Lifetime
-
1996
- 1996-06-04 KR KR1019960019881A patent/KR0131017B1/ko not_active IP Right Cessation
-
1997
- 1997-01-03 KR KR1019970000016A patent/KR0131016B1/ko not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102020102162A1 (de) | 2020-01-29 | 2021-07-29 | Oq Chemicals Gmbh | TCD-Ester für Niedertemperatur-Schmierstoffanwendungen |
WO2021152001A1 (de) | 2020-01-29 | 2021-08-05 | Oq Chemicals Gmbh | Tcd-ester für niedertemperatur-schmierstoffanwendungen |
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