GB988051A - Process for the production of esters - Google Patents
Process for the production of estersInfo
- Publication number
- GB988051A GB988051A GB228/62A GB22862A GB988051A GB 988051 A GB988051 A GB 988051A GB 228/62 A GB228/62 A GB 228/62A GB 22862 A GB22862 A GB 22862A GB 988051 A GB988051 A GB 988051A
- Authority
- GB
- United Kingdom
- Prior art keywords
- attached
- valencies
- group
- free oxygen
- phosphate
- 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
- 150000002148 esters Chemical class 0.000 title abstract 4
- -1 methylol groups Chemical group 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 150000001721 carbon Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract 2
- 239000000314 lubricant Substances 0.000 abstract 2
- 235000021317 phosphate Nutrition 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 abstract 1
- PBCCGCZHDKGPSH-UHFFFAOYSA-N 2-butoxy-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CCCCOP1(=O)OCCO1 PBCCGCZHDKGPSH-UHFFFAOYSA-N 0.000 abstract 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 abstract 1
- QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 abstract 1
- VOWPVJACXJNHBC-UHFFFAOYSA-N methyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OC)OC1=CC=CC=C1 VOWPVJACXJNHBC-UHFFFAOYSA-N 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 229940113165 trimethylolpropane Drugs 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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- 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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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- C10M137/08—Ammonium or amine salts
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- C10M2207/286—Esters of polymerised unsaturated acids
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- 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
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
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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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
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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
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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
- 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
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Esters are prepared by reacting an alkanoic acid with a carbon chain of 4 to 12 atoms or a mixture of acids with an average length of 4 to 12 atoms with a polyhydric alcohol with two or more methylol groups attached to a quaternary carbon atom in the presence of a phosphorus compound with a structure O=P(O-)3 in which each of the free oxygen valencies is attached to an alkyl group, an alkylene group or an aryl group but in which no more than two are attached to aryl groups. Heptanoic acid is specified and trimethylol-propane and ethane, neopentyl glycol, pentaerythritol, 2-butyl - 2 - ethyl - 1, 3 - propanediol, and 2,2,4-trimethyl - 1,3 - pentanediol are examples of the alcohols. Azeotroping agents such as xylene, toluene, cyclohexane, benzene and petroleum naphtha may be present in the reaction. Phosphates specified are butyl phosphoric acid, dipropyl phosphoric acid, tripropyl, tributyl, and triamyl phosphates, phenyl dibutyl phosphate, diphenyl methyl phosphate, ethylene butyl phosphate and ethylene bis-(dibutyl phosphate) and the ester products show improved yield and may be used in lubricant compositions.ALSO:Lubricant compositions comprise esters of an alkanoic acid (C4-C12) on a mixture of alkanoic acids with carbon chains of average 4C to 12C and a polyhydric alcohol with two or more methylol groups attached to a single quaternary carbon atom prepared in the presence of a phosphorus compound with the group O=P(O-)3 in which each of the free oxygen valencies are attached to an alkyl, alkylene or aryl groups but no more than two of the free oxygen valencies are attached to aryl groups (see Division C2) with anti-oxidant additives such as 0.5-3% of phenyl-a -naphthylamine and N-ethyl-pheno-diphenyl silazine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80046A US3215720A (en) | 1961-01-03 | 1961-01-03 | Methods of producing phosphorus esters of polyol alkanoic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB988051A true GB988051A (en) | 1965-04-07 |
Family
ID=46968431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB228/62A Expired GB988051A (en) | 1961-01-03 | 1962-01-03 | Process for the production of esters |
Country Status (3)
Country | Link |
---|---|
US (1) | US3215720A (en) |
DE (1) | DE1225161B (en) |
GB (1) | GB988051A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3325567A (en) * | 1963-05-17 | 1967-06-13 | Lubrizol Corp | Phosphorus esters and process |
US3800002A (en) * | 1970-03-20 | 1974-03-26 | Japan Synthetic Rubber Co Ltd | Process for preventing the polymerization of conjugated dienes |
US4229310A (en) * | 1978-03-16 | 1980-10-21 | Mobil Oil Corporation | Lubricant compositions |
JPS5845293A (en) * | 1981-09-10 | 1983-03-16 | Idemitsu Kosan Co Ltd | Fluid composition for shock absorber |
US4857215A (en) * | 1986-03-25 | 1989-08-15 | Wong John L | Semi-fluid lubricant for extreme climates |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2177983A (en) * | 1935-12-30 | 1939-10-31 | Benjamin R Harris | Phosphate esters |
US2177984A (en) * | 1937-02-11 | 1939-10-31 | Benjamin R Harris | Phosphoric acid esters and method of producing them |
US2492955A (en) * | 1946-08-31 | 1950-01-03 | Shell Dev | Polyoxyalkylene compounds |
US2643261A (en) * | 1948-10-01 | 1953-06-23 | Standard Oil Dev Co | Phosphorus-containing lubricating oil additives |
US2798083A (en) * | 1954-02-03 | 1957-07-02 | Eastman Kodak Co | Synthetic ester lubricants |
FR1251027A (en) * | 1959-03-12 | 1961-01-13 | Heyden Newport Chemical Corp | Lubricating esters |
US3036005A (en) * | 1959-04-23 | 1962-05-22 | Celanese Corp | High temperature lubricant composition |
FR1251028A (en) * | 1960-03-11 | 1961-01-13 | Heyden Newport Chemical Corp | Lubricating compositions |
-
1961
- 1961-01-03 US US80046A patent/US3215720A/en not_active Expired - Lifetime
- 1961-12-29 DE DEC25865A patent/DE1225161B/en active Pending
-
1962
- 1962-01-03 GB GB228/62A patent/GB988051A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US3215720A (en) | 1965-11-02 |
DE1225161B (en) | 1966-09-22 |
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