CA1044216A - Esters du trimethylolpropane utilisables comme lubrifiants de base pour huiles moteurs - Google Patents
Esters du trimethylolpropane utilisables comme lubrifiants de base pour huiles moteursInfo
- Publication number
- CA1044216A CA1044216A CA215,798A CA215798A CA1044216A CA 1044216 A CA1044216 A CA 1044216A CA 215798 A CA215798 A CA 215798A CA 1044216 A CA1044216 A CA 1044216A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- carbon atoms
- mixture
- composition according
- mol
- 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
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical class CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 239000002253 acid Substances 0.000 claims abstract description 54
- 150000002148 esters Chemical class 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 14
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000314 lubricant Substances 0.000 claims abstract description 11
- 229940113165 trimethylolpropane Drugs 0.000 claims abstract description 9
- 230000032050 esterification Effects 0.000 claims abstract description 6
- 238000005886 esterification reaction Methods 0.000 claims abstract description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000654 additive Substances 0.000 claims description 21
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 14
- 239000002270 dispersing agent Substances 0.000 claims description 10
- 239000010687 lubricating oil Substances 0.000 claims description 9
- 230000000996 additive effect Effects 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 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
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 claims 1
- -1 Trimethylol propane ester Chemical class 0.000 abstract description 6
- 239000003921 oil Substances 0.000 description 14
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 10
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 239000001294 propane Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000005639 Lauric acid Substances 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- 239000010705 motor oil Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000357437 Mola Species 0.000 description 1
- 241001077660 Molo Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003570 air Substances 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
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229940116269 uric acid 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
- 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 (cg-RX-API-DMAC7.html) | 1973-12-12 | 1973-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1044216A true CA1044216A (fr) | 1978-12-12 |
Family
ID=9129144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA215,798A Expired CA1044216A (fr) | 1973-12-12 | 1974-12-11 | Esters du trimethylolpropane utilisables comme lubrifiants de base pour huiles moteurs |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4061581A (cg-RX-API-DMAC7.html) |
| BE (1) | BE822831A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1044216A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2458441A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2254633B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1490707A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1026968B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7416151A (cg-RX-API-DMAC7.html) |
Families Citing this family (26)
| 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 |
| IT1050335B (it) * | 1975-12-11 | 1981-03-10 | Snam Progetti | Esteri organici da impiegare in composizioni lubrificanti |
| 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 |
| 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 |
| US6656888B1 (en) * | 1992-08-28 | 2003-12-02 | Cognis Corporation | Biodegradable two-cycle engine oil compositions, grease compositions, and ester base stocks use therein |
| FI95367C (fi) * | 1994-09-07 | 1996-01-25 | Raision Tehtaat Oy Ab | Menetelmä synteettisen esterin valmistamiseksi kasviöljystä |
| US6406643B2 (en) | 1996-03-12 | 2002-06-18 | Voitelukeskus Tonitila Oy | Hydraulic oil based on esters of tall oil and method for its manufacturing |
| US5798322A (en) * | 1996-08-30 | 1998-08-25 | Gateway Additive Company | Friction-modifying additives for slideway lubricants |
| BRPI0915051B1 (pt) | 2008-05-14 | 2021-04-13 | Council Of Scientific & Industrial Research | Óleo básico lubrificante, ésteres de poliol de ácidos graxos de cadeia média e processo para preparação dos mesmos |
| US9260372B2 (en) | 2012-02-28 | 2016-02-16 | Petroliam Nasional Berhad | Method for the production of polyols and uses thereof |
| MY186982A (en) | 2012-02-28 | 2021-08-26 | Petroliam Nasional Berhad | Bio-polyols for bio-lubricant and bio-polymer and methods fo the preparation thereof |
| JP6126138B2 (ja) | 2012-02-28 | 2017-05-10 | ペトロリアム ナショナル ブルハドＰｅｔｒｏｌｉａｍ Ｎａｓｉｏｎａｌ Ｂｅｒｈａｄ | ポリウレタン用途のためのポリオール類の物質組成 |
| WO2013129909A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad | Lubricant composition of matter and methods of preparation |
| CN104271546B (zh) | 2012-02-28 | 2017-06-09 | 马来西亚国家石油公司 | 酯的生产方法及其用途 |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
| ES2751551T3 (es) * | 2015-06-12 | 2020-04-01 | Novamont Spa | Esteres de trimetilolpropano de bajo punto de fluidez |
| CN109072112B (zh) * | 2016-06-14 | 2021-06-11 | 日油株式会社 | 润滑油基油及润滑油组合物 |
| 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 |
| FR2051665A1 (cg-RX-API-DMAC7.html) * | 1969-07-10 | 1971-04-09 | Ethyl Corp | |
| US3778454A (en) * | 1970-02-18 | 1973-12-11 | Ethyl Corp | Complex ester |
| US3790481A (en) * | 1971-04-30 | 1974-02-05 | British Petroleum Co | Synthetic lubricants for aero gas turbines |
| 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 |
| 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 IT IT30412/74A patent/IT1026968B/it active
- 1974-12-11 NL NL7416151A patent/NL7416151A/xx not_active Application Discontinuation
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| FR2254633B1 (cg-RX-API-DMAC7.html) | 1976-10-08 |
| IT1026968B (it) | 1978-10-20 |
| GB1490707A (en) | 1977-11-02 |
| DE2458441A1 (de) | 1975-06-19 |
| NL7416151A (nl) | 1975-06-16 |
| BE822831A (fr) | 1975-06-02 |
| FR2254633A1 (cg-RX-API-DMAC7.html) | 1975-07-11 |
| US4061581A (en) | 1977-12-06 |
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