CA1042458A - Branched-chain aliphatic ester oils - Google Patents
Branched-chain aliphatic ester oilsInfo
- Publication number
- CA1042458A CA1042458A CA189,336A CA189336A CA1042458A CA 1042458 A CA1042458 A CA 1042458A CA 189336 A CA189336 A CA 189336A CA 1042458 A CA1042458 A CA 1042458A
- Authority
- CA
- Canada
- Prior art keywords
- branched
- ester oil
- acid
- chain
- 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.)
- Expired
Links
- 239000010696 ester oil Substances 0.000 title claims abstract description 17
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 229920005862 polyol Polymers 0.000 claims abstract description 13
- -1 aliphatic polyols Chemical class 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 239000000314 lubricant Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 239000012530 fluid Substances 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 25
- 150000007513 acids Chemical class 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000003077 polyols Chemical class 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 claims description 5
- 238000007869 Guerbet synthesis reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 229940117969 neopentyl glycol Drugs 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 2
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 claims 2
- 230000001050 lubricating effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 101100049938 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) exr-1 gene Proteins 0.000 description 1
- 101100031807 Rattus norvegicus Paics gene Proteins 0.000 description 1
- 241000022563 Rema Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 229940102838 methylmethacrylate Drugs 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 101150101384 rat1 gene Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940113165 trimethylolpropane Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
-
- 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
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
- 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
-
- 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
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2302918A DE2302918C2 (de) | 1973-01-22 | 1973-01-22 | Neue Esteröle, sowie deren Verwendung in Schmiermitteln und Hydraulikflüssigkeiten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042458A true CA1042458A (en) | 1978-11-14 |
Family
ID=5869588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA189,336A Expired CA1042458A (en) | 1973-01-22 | 1974-01-02 | Branched-chain aliphatic ester oils |
Country Status (10)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1050335B (it) * | 1975-12-11 | 1981-03-10 | Snam Progetti | Esteri organici da impiegare in composizioni lubrificanti |
| DE2948020C2 (de) * | 1979-11-29 | 1984-05-03 | Mobil Oil Corp., 10017 New York, N.Y. | Schwer entflammbare Hydraulikflüssigkeit |
| CH649575A5 (de) * | 1982-02-23 | 1985-05-31 | Alusuisse | Hydraulikfluessigkeit. |
| JPS5955853A (ja) * | 1982-09-22 | 1984-03-31 | Daicel Chem Ind Ltd | ２−メチル−１，３−プロパンジオ−ルの脂肪族カルボン酸誘導体 |
| JPS5968397A (ja) * | 1982-10-13 | 1984-04-18 | Cosmo Co Ltd | リヤアクスル用ギヤ油組成物 |
| JPS62592A (ja) * | 1985-06-27 | 1987-01-06 | Nippon Oil & Fats Co Ltd | 高粘度冷凍機油 |
| DE3801476A1 (de) * | 1988-01-20 | 1989-08-03 | Henkel Kgaa | Zusammensetzungen zur befreiung festgesetzter bohrgestaenge |
| DE3907392A1 (de) * | 1989-03-08 | 1990-09-13 | Henkel Kgaa | Ester von carbonsaeuren mittlerer kettenlaenge als bestnadteil der oelphase in invert-bohrspuelschlaemmen |
| GB9007193D0 (en) * | 1990-03-30 | 1990-05-30 | Exxon Chemical Patents Inc | Esters and fluids containing them |
| DE4019266A1 (de) * | 1990-06-16 | 1992-01-23 | Henkel Kgaa | Fliessfaehige bohrlochbehandlungsmittel auf basis von polycarbonsaeureestern |
| DE4128647A1 (de) * | 1991-08-29 | 1993-03-11 | Henkel Kgaa | Verwendung von isopalmitinsaeureestern als schmiermittel fuer zweitaktmotoren |
| DE102006001768A1 (de) | 2006-01-12 | 2007-07-19 | Cognis Ip Management Gmbh | Verwendung von Estern mit verzweigten Alkylgruppen als Schmiermittel |
| JP4000337B1 (ja) | 2006-03-23 | 2007-10-31 | 新日本石油株式会社 | 二酸化炭素冷媒用冷凍機油用基油、二酸化炭素冷媒用冷凍機油 |
| GB2451715B (en) * | 2008-03-03 | 2011-09-21 | Indian Oil Corp Ltd | Synthetic fuels |
| JP2021123632A (ja) * | 2020-02-04 | 2021-08-30 | 花王株式会社 | 金属加工油用基油、及び不水溶性金属加工油組成物 |
| CN112375608B (zh) * | 2020-10-20 | 2022-07-12 | 中国石油化工股份有限公司 | 一种经济型合成难燃液压液组合物及其制备方法 |
| WO2025018281A1 (ja) * | 2023-07-14 | 2025-01-23 | 出光興産株式会社 | グリース組成物及びグリース組成物の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2807155A (en) * | 1956-02-02 | 1957-09-24 | Gen Motors Corp | Working fluids in refrigeration apparatus |
-
1973
- 1973-01-22 DE DE2302918A patent/DE2302918C2/de not_active Expired
-
1974
- 1974-01-02 CA CA189,336A patent/CA1042458A/en not_active Expired
- 1974-01-02 SE SE7400019A patent/SE408793B/xx not_active IP Right Cessation
- 1974-01-18 BR BR388/74A patent/BR7400388D0/pt unknown
- 1974-01-18 BE BE139946A patent/BE809901A/xx not_active IP Right Cessation
- 1974-01-18 GB GB253674A patent/GB1444826A/en not_active Expired
- 1974-01-21 AT AT48274A patent/AT336154B/de not_active IP Right Cessation
- 1974-01-21 JP JP49008645A patent/JPS5928239B2/ja not_active Expired
- 1974-01-22 CH CH83774A patent/CH597139A5/xx not_active IP Right Cessation
- 1974-01-22 FR FR7402128A patent/FR2214680B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU6466774A (en) | 1975-07-24 |
| JPS5928239B2 (ja) | 1984-07-11 |
| DE2302918A1 (de) | 1974-07-25 |
| CH597139A5 (enrdf_load_stackoverflow) | 1978-03-31 |
| DE2302918C2 (de) | 1982-04-08 |
| JPS49109771A (enrdf_load_stackoverflow) | 1974-10-18 |
| SE408793B (sv) | 1979-07-09 |
| ATA48274A (de) | 1976-08-15 |
| AT336154B (de) | 1977-04-25 |
| GB1444826A (en) | 1976-08-04 |
| FR2214680B1 (enrdf_load_stackoverflow) | 1976-11-26 |
| BR7400388D0 (pt) | 1974-08-22 |
| FR2214680A1 (enrdf_load_stackoverflow) | 1974-08-19 |
| BE809901A (fr) | 1974-07-18 |
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