DE2458441A1 - Ester des trimethylolpropans, die als basis- schmiermittel fuer motorenoele brauchbar sind - Google Patents
Ester des trimethylolpropans, die als basis- schmiermittel fuer motorenoele brauchbar sindInfo
- Publication number
- DE2458441A1 DE2458441A1 DE19742458441 DE2458441A DE2458441A1 DE 2458441 A1 DE2458441 A1 DE 2458441A1 DE 19742458441 DE19742458441 DE 19742458441 DE 2458441 A DE2458441 A DE 2458441A DE 2458441 A1 DE2458441 A1 DE 2458441A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carbon atoms
- composition according
- mol
- mixture
- 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.)
- Ceased
Links
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 title claims description 20
- 239000000314 lubricant Substances 0.000 title claims description 15
- 239000010705 motor oil Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 67
- 150000002148 esters Chemical class 0.000 claims description 44
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 24
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 23
- 239000000654 additive Substances 0.000 claims description 14
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000010687 lubricating oil Substances 0.000 claims description 6
- 238000009736 wetting Methods 0.000 claims description 6
- 239000000080 wetting agent Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 18
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 15
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 10
- 239000005639 Lauric acid Substances 0.000 description 9
- 235000011037 adipic acid Nutrition 0.000 description 8
- 239000001361 adipic acid Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- -1 saturated aliphatic monocarboxylic acid Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 229940031826 phenolate Drugs 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 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
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical class OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 1
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical class OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 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
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000004072 triols Chemical class 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
- 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
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7344459A FR2254633B1 (enExample) | 1973-12-12 | 1973-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2458441A1 true DE2458441A1 (de) | 1975-06-19 |
Family
ID=9129144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742458441 Ceased DE2458441A1 (de) | 1973-12-12 | 1974-12-10 | Ester des trimethylolpropans, die als basis- schmiermittel fuer motorenoele brauchbar sind |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4061581A (enExample) |
| BE (1) | BE822831A (enExample) |
| CA (1) | CA1044216A (enExample) |
| DE (1) | DE2458441A1 (enExample) |
| FR (1) | FR2254633B1 (enExample) |
| GB (1) | GB1490707A (enExample) |
| IT (1) | IT1026968B (enExample) |
| NL (1) | NL7416151A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2656079A1 (de) * | 1975-12-11 | 1977-06-23 | Snam Progetti | Estergemische mit schmiermittelwirkung |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144183A (en) * | 1973-01-22 | 1979-03-13 | Henkel Kommanditgesellschaft Auf Aktien | Mixed branched and straight chain ester oils |
| DE2758780A1 (de) * | 1977-12-29 | 1979-07-12 | Bayer Ag | Carbonsaeureester des pentaerythrits |
| US4313890A (en) * | 1980-01-29 | 1982-02-02 | Union Carbide Corporation | Polyol ester functional fluids |
| US4530772A (en) * | 1984-02-22 | 1985-07-23 | Stauffer Chemical Company | Method of electrical contact lubrication |
| US4655947A (en) * | 1986-07-23 | 1987-04-07 | Aluminum Company Of America | Metalworking with a trimethylolalkane ester lubricant |
| JPH082812B2 (ja) * | 1988-05-10 | 1996-01-17 | 花王株式会社 | トリメチロールメチル分岐アルカン |
| GB9007193D0 (en) * | 1990-03-30 | 1990-05-30 | Exxon Chemical Patents Inc | Esters and fluids containing them |
| US5151205A (en) * | 1991-05-13 | 1992-09-29 | Texaco Inc. | Chain and drive gear lubricant |
| US5254277A (en) * | 1991-12-20 | 1993-10-19 | Akzo N.V. | Corrosion inhibitor composition for formulated polyol ester fluids |
| DE4214653A1 (de) * | 1992-05-02 | 1993-11-04 | Henkel Kgaa | Motorengrundoele mit verbesserter dichtungsvertraeglichkeit |
| US6656888B1 (en) * | 1992-08-28 | 2003-12-02 | Cognis Corporation | Biodegradable two-cycle engine oil compositions, grease compositions, and ester base stocks use therein |
| NZ255727A (en) * | 1992-08-28 | 1996-06-25 | Henkel Corp | Biodegradable ester base stock for two-stroke engine oils and the engine oil mixture made therefrom |
| FI95367C (fi) * | 1994-09-07 | 1996-01-25 | Raision Tehtaat Oy Ab | Menetelmä synteettisen esterin valmistamiseksi kasviöljystä |
| CN1074451C (zh) * | 1996-03-12 | 2001-11-07 | 通蒂拉润滑中心有限公司 | 液压油及其制备方法 |
| US5798322A (en) * | 1996-08-30 | 1998-08-25 | Gateway Additive Company | Friction-modifying additives for slideway lubricants |
| CN102089270A (zh) | 2008-05-14 | 2011-06-08 | 科学与工业研究委员会 | 中链脂肪酸的多元醇酯及其制备方法 |
| KR102061374B1 (ko) | 2012-02-28 | 2019-12-31 | 페트롤리암 내셔널 버하드 (페트로나스) | 에스테르의 제조 방법 및 그의 용도 |
| DK2820112T3 (en) | 2012-02-28 | 2017-09-11 | Petroliam Nasional Berhad | PROCEDURE FOR PREPARING POLYOLS AND APPLICATIONS THEREOF |
| EP2819990B1 (en) | 2012-02-28 | 2019-03-27 | Petroliam Nasional Berhad | Method for producing an esterified polyol |
| US10131616B2 (en) | 2012-02-28 | 2018-11-20 | Petroliam Nasional Berhad | Lubricant composition of matter and methods of preparation |
| US10654791B2 (en) | 2012-02-28 | 2020-05-19 | Petroliam Nasional Berhad | Composition of matter polyols for polyurethane applications |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
| WO2016198668A1 (en) * | 2015-06-12 | 2016-12-15 | Novamont S.P.A. | Low pour point trimethylolpropane esters. |
| JP6965880B2 (ja) * | 2016-06-14 | 2021-11-10 | 日油株式会社 | 潤滑油組成物 |
| WO2018019379A1 (en) * | 2016-07-28 | 2018-02-01 | Hp Indigo B.V. | Liquid electrophotographic ink composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2798083A (en) * | 1954-02-03 | 1957-07-02 | Eastman Kodak Co | Synthetic ester lubricants |
| US3126344A (en) * | 1961-01-03 | 1964-03-24 | Synthetic ester lubricating oil | |
| GB1129964A (en) * | 1965-01-15 | 1968-10-09 | British Petroleum Co | Synthetic lubricant composition of improved oxidation stability |
| GB1301003A (en) * | 1969-07-10 | 1972-12-29 | Ethyl Corp | Lubricant materials |
| US3778454A (en) * | 1970-02-18 | 1973-12-11 | Ethyl Corp | Complex ester |
| US3697427A (en) * | 1971-04-30 | 1972-10-10 | British Petroleum Co | Lubricants having improved anti-wear and anti-corrosion properties |
| US3790478A (en) * | 1971-04-30 | 1974-02-05 | British Petroleum Co | Synthetic lubricant for aero gas turbines |
| US3790481A (en) * | 1971-04-30 | 1974-02-05 | British Petroleum Co | Synthetic lubricants for aero gas turbines |
| US3756952A (en) * | 1971-07-06 | 1973-09-04 | Texaco Inc | Synthetic aircraft turbine oil |
-
1973
- 1973-12-12 FR FR7344459A patent/FR2254633B1/fr not_active Expired
-
1974
- 1974-12-02 BE BE1006306A patent/BE822831A/xx unknown
- 1974-12-10 DE DE19742458441 patent/DE2458441A1/de not_active Ceased
- 1974-12-11 CA CA215,798A patent/CA1044216A/fr not_active Expired
- 1974-12-11 NL NL7416151A patent/NL7416151A/xx not_active Application Discontinuation
- 1974-12-11 IT IT30412/74A patent/IT1026968B/it active
- 1974-12-12 GB GB53783/74A patent/GB1490707A/en not_active Expired
- 1974-12-12 US US05/532,237 patent/US4061581A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2656079A1 (de) * | 1975-12-11 | 1977-06-23 | Snam Progetti | Estergemische mit schmiermittelwirkung |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1026968B (it) | 1978-10-20 |
| US4061581A (en) | 1977-12-06 |
| NL7416151A (nl) | 1975-06-16 |
| BE822831A (fr) | 1975-06-02 |
| GB1490707A (en) | 1977-11-02 |
| CA1044216A (fr) | 1978-12-12 |
| FR2254633A1 (enExample) | 1975-07-11 |
| FR2254633B1 (enExample) | 1976-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |