JP2011520870A - 有効な潤滑剤ベースストックとしてのヒマシ油脂肪酸系エストリドエステルおよびそれらの誘導体 - Google Patents
有効な潤滑剤ベースストックとしてのヒマシ油脂肪酸系エストリドエステルおよびそれらの誘導体 Download PDFInfo
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- JP2011520870A JP2011520870A JP2011509083A JP2011509083A JP2011520870A JP 2011520870 A JP2011520870 A JP 2011520870A JP 2011509083 A JP2011509083 A JP 2011509083A JP 2011509083 A JP2011509083 A JP 2011509083A JP 2011520870 A JP2011520870 A JP 2011520870A
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- estolide
- acid
- ester
- castor oil
- fatty acid
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- 150000002149 estolides Chemical class 0.000 title claims abstract description 45
- 239000004359 castor oil Substances 0.000 title claims abstract description 25
- 235000019438 castor oil Nutrition 0.000 title claims abstract description 25
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 title claims abstract description 25
- 235000014113 dietary fatty acids Nutrition 0.000 title abstract description 28
- 239000000194 fatty acid Substances 0.000 title abstract description 28
- 229930195729 fatty acid Natural products 0.000 title abstract description 28
- 150000004665 fatty acids Chemical class 0.000 title abstract description 19
- 239000000314 lubricant Substances 0.000 title abstract description 16
- -1 fatty acid estolide esters Chemical class 0.000 claims abstract description 55
- 239000002253 acid Substances 0.000 claims abstract description 28
- 229960003656 ricinoleic acid Drugs 0.000 claims abstract description 14
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims abstract description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 11
- 229910052802 copper Inorganic materials 0.000 abstract description 11
- 239000010949 copper Substances 0.000 abstract description 11
- 230000007797 corrosion Effects 0.000 abstract description 11
- 238000005260 corrosion Methods 0.000 abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 235000004443 Ricinus communis Nutrition 0.000 abstract description 6
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 230000003595 spectral effect Effects 0.000 description 10
- 239000012345 acetylating agent Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 235000015112 vegetable and seed oil Nutrition 0.000 description 8
- 239000008158 vegetable oil Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 5
- 239000004808 2-ethylhexylester Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 238000006640 acetylation reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000031968 Cadaver Diseases 0.000 description 2
- 241000390166 Physaria Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated 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
- C10M105/34—Esters of monocarboxylic 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
- C10M105/40—Esters containing free hydroxy or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- 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
- C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
- C10M2207/2895—Partial esters containing free hydroxy groups used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/011—Cloud point
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/081—Biodegradable compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
R1は、C1〜C8の分岐状または非分岐状の炭化水素であり、R2部分は、水素、CH3COからなる群から選択される)
のエストリド化合物を提供する。
(i)ヒマシ油を鹸化してリシノール酸を得て、不活性雰囲気下で175〜190℃の範囲の温度で3〜5時間の範囲の間リシノール酸を加熱して式1(式中、nの平均値は1であり、R1およびR2はHである)のエストリド化合物を得るステップと、
(ii)硫酸もしくはSnCl2から選択される触媒の存在下、還流温度または140〜160℃の範囲の温度で3〜8時間の範囲の間、ステップ(i)で得られたエストリド化合物1をメタノール、イソプロパノール、ブタノール、n−ヘキサノール、2−エチルヘキサノールなどの炭素C1〜C8のアルコールと反応させて対応するエストリドエステルを得るステップと、
(iii)ステップ(ii)で得られたエストリドエステルを無水酢酸およびピリジンと反応させて一般式1(式中、R1部分は、メチル、イソプロピル、ブチル、ヘキシル、2−エチルヘキシルからなる群から選択され、R2部分はCH3COである)のエストリドエステルのアセチル化合物を得るステップ。
ヒマシ油脂肪酸のエストリドの調製:ヒマシ油(1000g)を三つ口丸底フラスコに入れ、80℃まで加熱した。水酸化ナトリウムの溶液(145g、水酸化ナトリウム/1200ml、水)を撹拌しながら該フラスコにゆっくり加えた。85℃で3時間撹拌し続けた。鹸化の完了後、十分な量の希塩酸水溶液(6N)を反応混合物に加えて、4未満のpHで脂肪酸石鹸を完全に分解した。15分間撹拌し続けた。反応混合物を室温まで冷却し、エーテルで抽出した。エーテル層を水で洗浄して塩酸を除去した。有機層を硫酸ナトリウムに通して懸濁水(suspended water)を除去した。エーテルを真空下で除去してヒマシ油脂肪酸を得、その収量は920gであった。リシノール酸(800g)を窒素下で撹拌しながら185℃まで加熱した。周期的に試料を抜き取って酸価をモニターしてエストリド形成の程度を判定した。95という所望の酸価、リシノール酸の2つのユニットを有するエストリドの理論酸価の達成後、反応を停止した。生成物の収量は720gであった。
エストリドメチルエステルの調製:2%硫酸を含有するメタノール(4000ml)で酸価95のヒマシ油脂肪酸エストリド(400g)を還流した。エステル化の過程を薄層クロマトグラフィーによりモニターした。反応の完了後、その内容物を冷却し、酢酸エチルで抽出し、水で洗浄した。有機層を硫酸ナトリウムに通し、過剰なアルコールおよび酢酸エチルを減圧下で蒸留した。生成物の収量は401gであり、以下の特性を有していた。
酸価、mg KOH/g:0.26
40℃での粘度:32.97
100℃での粘度:6.20
粘度指数:162
流動点(℃):−33
引火点(℃):252
銅板腐食:1a
1H NMR (CDCl3,ppm):0.9[m,2x−CH3]、1.2−1.6[m,22x−CH2−]、2.0[m,2x−CH 2 −CH=CH−]、2.1−2.4[m,2x−CO−CH2−]、3.5−3.7[m,−CH−OH,−O−CH3]、4.8[m,−O−CH−]、5.2−5.6[m,2x−CH=CH−CH2−]
エストリドメチルエステルの酢酸エステルの調製:無水酢酸(110ml)とピリジン(330ml)との混合物からなるアセチル化剤を使用することによりエストリドメチルエステルをアセチル化した。アセチル化剤をエストリドメチルエステル(220g)に加え、アセチル化反応が完了するまで還流した。続いて、反応混合物を室温まで冷却し、エーテルで抽出し、十分な量の希塩酸で処理してピリジンを中和した。エーテル層を水で洗浄して酸を除去し、硫酸ナトリウムに通した。減圧下でエーテルを除去した。真空下で乾燥して、以下の特性を有する197gのアセチル化生成物を得た。
酸価、mg KOH/g:0.49
40℃での粘度:17.38
100℃での粘度:4.22
粘度指数:164
流動点(℃):−33
引火点(℃):252
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,2x−CH3]、1.2−1.4[m,22x−CH2−]、1.9−2.0[m,2x−CH 2 −CH=CH,−CO−CH3]2.2[m,2x−CO−CH2−]、3.6[s−O−CH3]、4.8[m,2x−O−CH−]、5.2−5.4[m,2x−CH=CH−CH2−]
エストリドイソプロピルエステルの調製:2%硫酸を含有するイソプロパノール(118ml)でヒマシ油脂肪酸エストリド(571g)を還流した。エステル化の過程を薄層クロマトグラフィーによりモニターした。反応の完了後、その内容物を冷却し、酢酸エチルで抽出し、水で洗浄した。有機層を硫酸ナトリウムに通し、過剰なアルコールおよび酢酸エチルを減圧下で蒸留した。生成物の収量は594gであり、以下の特性を有していた。
酸価、mg KOH/g:0.03
40℃での粘度:39.90
100℃での粘度:7.28
粘度指数:149
流動点(℃):−27
引火点(℃):252
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,4x−CH3]、1.2−1.6[m,22x−CH2−]、2.0[m,2x−CH 2 −CH=CH−]、2.2−2.4[m,2x−CO−CH2−]、3.6[m,−CH−OH]、4.8−5.0[m,2x−O−CH−]、5.3−5.5[m,2x CH=CH−CH2−]
エストリドイソプロピルエステルの酢酸エステルの調製:1:3v/v比の無水酢酸(100ml)とピリジン(300ml)との混合物からなるアセチル化剤を使用することによりエストリドイソプロピルエステルをアセチル化した。アセチル化剤をエストリドイソプロピルエステル(220g)に加え、アセチル化反応が完了するまで還流した。続いて、反応混合物を室温まで冷却し、エーテルで抽出し、十分な量の希塩酸で処理してピリジンを中和した。エーテル層を水で洗浄して酸を除去し、硫酸ナトリウムに通した。減圧下でエーテルを除去した。真空下で乾燥して、以下の特性を有する214gのアセチル化生成物を得た。
酸価、mg KOH/g:0.08
40℃での粘度:31.27
100℃での粘度:6.73
粘度指数:181
流動点(℃):−30
引火点(℃):252
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,4x−CH3]、1.2−1.6[m,22 x−CH2−]、2.0[m,2x−CH 2 −CH=CH−,O−CO−CH3]2.2−2.5[m,2x−CO−CH2−]、4.8−5.0[m,2x−O−CH−]、5.3−5.5[m,2x−CH=CH−CH2−]
エストリドブチルエステルの調製:1%硫酸を含有するブタノール(100ml)でヒマシ油脂肪酸エストリド(62.5g)を還流した。反応の完了後、その内容物を冷却し、酢酸エチルで抽出し、水で洗浄した。有機層を硫酸ナトリウムに通し、過剰なアルコールおよび酢酸エチルを減圧下で蒸留した。生成物の収量は64.3gであり、以下の特性を有していた。
酸価、mg KOH/g:0.24
40℃での粘度:70.39
100℃での粘度:12.38
粘度指数:176
流動点(℃):−27
引火点(℃):252
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,3x−CH3]、1.2−1.6[m,24 x−CH2−]、2.0[m,2x−CH 2 −CH=CH−]、2.2−2.3[m,2x−CO−CH2−]、3.5[m,−CH−OH]、4.0[t,−O−CH2−]、4.8[m,O−CH−]、5.3−5.4[m,2x−CH=CH−CH2−]
エストリドブチルエステルの酢酸エステルの調製:1:3v/v比の無水酢酸(100ml)とピリジン(300ml)との混合物からなるアセチル化剤を使用することによりエストリドブチルエステルをアセチル化した。アセチル化剤をエストリドブチルエステル(220g)に加え、アセチル化反応が完了するまで還流した。続いて、反応混合物を室温まで冷却し、エーテルで抽出し、十分な量の希塩酸で処理してピリジンを中和した。エーテル層を水で洗浄して酸を除去し、硫酸ナトリウムに通した。減圧下でエーテルを除去した。真空下で乾燥して、以下の特性を有する204gのアセチル化生成物を得た。
酸価、mg KOH/g:0.1
40℃での粘度:25.40
100℃での粘度:6.30
粘度指数:216
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,3x−CH3]、1.2−1.6[m,24 x−CH2]、2.0[m,2x−CH 2 −CH=CH−,O−CO−CH3]、2.2−2.3[m,2x−CO−CH2−]、2.7[m,−CH−OH]、4.0[t,−O−CH2−]、4.0[m,2x−O−CH−]、5.3−5.4[m,2x−CH=CH−CH2−]
エストリドn−ヘキシルエステルの調製:0.1%SnCl2を含有するn−ヘキサノール(660ml)でヒマシ油脂肪酸エストリド(66g)を還流した。反応の完了後、その内容物を冷却し、酢酸エチルで抽出し、水で洗浄した。有機層を硫酸ナトリウムに通し、過剰なアルコールおよび酢酸エチルを減圧下で蒸留した。生成物の収量は69.2gであり、以下の特性を有していた。
酸価、mg KOH/g:0.074
40℃での粘度:56.3
100℃での粘度:10.13
粘度指数:169
流動点(℃):−24
引火点(℃):252
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,3 x−CH3]、1.2−1.6[m,26 x−CH2]、2.0[m,2x−CH 2 −CH=CH−]、2.2−2.4[m,2x−CO−CH2−]、3.5[m,CH−OH]、4.0[t,O−CH2−]、4.8[m,−O−CH−]、5.2−5.5[m,2x−CH=CH−CH2−]
エストリド2−エチルヘキシルエステルの調製:0.1%SnCl2を含有する2−エチルヘキサノール(374ml)でヒマシ油脂肪酸エストリド(700g)を還流した。反応の完了後、その内容物を冷却し、酢酸エチルで抽出し、水で洗浄した。有機層を硫酸ナトリウムに通し、過剰なアルコールおよび酢酸エチルを減圧下で蒸留した。生成物の収量は808gであり、以下の特性を有していた。
酸価、mg KOH/g:0.49
40℃での粘度:63.79
100℃での粘度:10.09
粘度指数:144
流動点(℃):−36
引火点(℃):252
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,4 x−CH3]、1.2−1.6[m,26 x−CH2]、2.0[m,2x−CH 2 −CH=CH−]、2.2−2.3[m,2x−CO−CH2−]、3.5[m,−CH−OH]、4.0[d,O−CH2−]、4.8[m,−O−CH−]、5.2−5.5[m,2x CH=CH−CH2−]
エストリド2−エチルヘキシルエステルの酢酸エステルの調製:エストリド2−エチルヘキシルエステルを無水酢酸(153ml)とピリジン(459ml)との混合物からなるアセチル化剤を使用することによりアセチル化した。アセチル化剤をエストリド2−エチルヘキシル(373g)に加え、アセチル化反応が完了するまで還流した。続いて、反応混合物を室温まで冷却し、エーテルで抽出し、十分な量の希塩酸で処理してピリジンを中和した。エーテル層を水で洗浄して酸を除去し、硫酸ナトリウムに通した。減圧下でエーテルを除去した。真空下で乾燥して、以下の特性を有する348gのアセチル化生成物を得た。
酸価、mg KOH/g:0.20
40℃での粘度:42.7
100℃での粘度:8.35
粘度指数:175
流動点(℃):−39
引火点(℃):262
銅板腐食:1a
1H NMR(CDCl3,ppm):0.9[m,4 x−CH3]、1.2−1.6[m,26 x−CH2−]、1.9−2.0[m,2x−CH 2 −CH=CH−,O−CO−CH3]、2.2−2.3[m,2x−CO−CH2−]、3.9−4.0[d,O−CH2−]、4.8[m,−O−CH−]、5.2−5.4[m,2x−CH=CH−CH2−]
1.本発明のエストリド誘導体の利点は、それらの高粘度指数(VI)およびISO VG32の粘度等級であり、それ以上がより望ましい。
2.これらのエストリド誘導体は、粘度、VIを向上させるのに必要であり、調剤された潤滑剤においてポリマー系増粘剤または変性剤の存在が剪断安定性の問題を引き起こす可能性がある増粘剤を必要としない。
3.低温特性は、潤滑剤ポンパビリティー、濾過性、流動性、ならびにコールドクランキングおよびスタートアップにとって重要である。流動点は、低温挙動の最も一般的な指標である。植物油由来のベースストックは、通常、流動点降下剤を添加しないと高流動点を有する。本発明のエストリド誘導体は、より高粘度のトリオレエート、植物油またはポリオールエステルより優れた低温特性を有する。
4.全般的に、本発明のエストリド誘導体は、それらの酸化安定性および低温特性において他の植物油系潤滑剤に勝ると期待されている。
Claims (5)
- R1部分は、メチル、イソプロピル、ブチル、ヘキシル、2−エチルヘキシルからなる群から選択され、R2部分は、水素、CH3COからなる群から選択される、請求項1に記載のエストリド化合物。
- (i)ヒマシ油を鹸化してリシノール酸を得、不活性雰囲気下で175〜190℃の範囲の温度で3〜5時間の範囲の間リシノール酸を加熱して式1(式中、nの平均値は1であり、R1およびR2はHである)のエストリド化合物を得るステップと、
(ii)硫酸もしくはSnCl2から選択される触媒の存在下、還流温度または140〜160℃の範囲の温度で3〜8時間の範囲の間、ステップ(i)で得られたエストリド化合物1をメタノール、イソプロパノール、ブタノール、n−ヘキサノール、2−エチルヘキサノールなどの炭素C1〜C8のアルコールと反応させて対応するエストリドエステルを得るステップと、
(iii)ステップ(ii)で得られたエストリドエステルを無水酢酸およびピリジンと反応させて一般式1(式中、R1部分はメチル、イソプロピル、ブチル、ヘキシル、2−エチルヘキシルからなる群から選択され、R2部分はCH3COである)のエストリドエステルのアセチル化合物を得るステップと
を含む、請求項1に記載の一般式1のエストリドを調製する方法。 - 前記化合物の酸価が0.5mg KOH/gである、請求項1に記載の方法。
- 式1の化合物が単独で、ならびに配合物および添加物と共に機能液のベースストックとして適している、請求項1に記載の方法。
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US20110282084A1 (en) | 2011-11-17 |
BRPI0915054A2 (pt) | 2019-02-26 |
WO2009139003A1 (en) | 2009-11-19 |
CN102066539B (zh) | 2017-02-08 |
US8742150B2 (en) | 2014-06-03 |
JP5646460B2 (ja) | 2014-12-24 |
WO2009139003A4 (en) | 2010-02-18 |
BRPI0915054B1 (pt) | 2019-09-03 |
CN102066539A (zh) | 2011-05-18 |
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