GB817054A - Manufacture of esters - Google Patents
Manufacture of estersInfo
- Publication number
- GB817054A GB817054A GB22680/55A GB2268055A GB817054A GB 817054 A GB817054 A GB 817054A GB 22680/55 A GB22680/55 A GB 22680/55A GB 2268055 A GB2268055 A GB 2268055A GB 817054 A GB817054 A GB 817054A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sodium
- esters
- ester
- acid
- oleic acid
- 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
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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- 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
Abstract
Lubricating compositions contain, mixed with each other or with natural or synthetic hydrocarbon lubricants, esters of the formula <FORM:0817054/III/1> where R is a divalent hydrocarbon radical or an acyclic radical interrupted by at least one ether oxygen atom, R1 and R3 are C2-C4 alkylene and R2 and R4 are aliphatic hydrocarbon radicals other than methyl. Preferred compounds are those in which R is p-phenylene or octamethylene and R2COO and R4COO are derived from oleic acid. Aliphatic ethers can also be present in the compositions, especially ethers having more than 12 carbon atoms such as diethylhexyl ether. Various suitable esters are mentioned in which R is also tetramethylene, b - methyl - tetramethylene, 3:8 - dioxa - decamethylene and 4 - methyl - 3:7 - dioxa-nonamethylene; R1 and R3 can be ethylene or propylene (both isomers); R2 and R4 can also be ethyl, 3-heptyl or 2:4:4-trimethylpentyl.ALSO:The invention comprises (1) the preparation of esters of the formula R2-COO-R1-OOC-R-COO-R3-OOC-R4 where R is a divalent hydrocarbon radical or an acyclic radical interrupted by at least one ether oxygen atom, R1 and R3 are C2-C4 alkylene and R2 and R5 are aliphatic hydrocarbon radicals other than methyl by reacting alkali metal salts of R(COOH)2 with Hal-R1-OOC-R2 and/or Hal-R3-OOC-R4; (2) the preparation of the same esters by reacting Hal-R1-OOC-R-COO-R3-Hal with alkali metal salts of R2-COOH and/or R4-COOH; and (3) certain esters of the first formula above, viz. those in which R is an aromatic hydrocarbon radical and R2 and R4 have at least 14 carbon atoms and a single double bond which is non-terminal. The starting materials where R contains an ether group can be prepared by condensing a glycol (or reaction product with, e.g. propylene oxide) with an unsaturated nitrile and then hydrolysing. The halo-esters can be made by esterifying alkylene chlorhydrins or reacting alkylene oxides with carboxylic acid chlorides; the corresponding bromine, iodine and fluorine compounds can also be used. The halo-esters can then be mixed with the dicarboxylic acid, alkali carbonate added and the reaction completed by heating to 130-200 DEG C., preferably 140-170 DEG C. Examples show the reaction of (1) sodium terephthalate with oleic acid b -chloroethyl or b -chloroisopropyl ester and with heptane - 3 - carboxylic acid b - chloroethyl or b -chloropropyl ester; sodium adipate with oleic acid b -chloroethyl ester or heptane-3-carboxylic acid b -chloroethyl ester; sodium sebacate with oleic acid b -chloro-isopropyl ester or heptane-3-carboxylic acid b -chloropropyl ester; sodium salt of 1 : 3- or 1 : 4-bis-(b -carboxyethoxy)-butane with oleic acid b -chloroisopropyl ester; (2) adipic acid di-b -chloroethyl ester with sodium propionate, sodium heptane-3-carboxylate and sodium 2 : 2 : 4-trimethylpentene - 5 - carboxylate; b - methyladipic acid di-b -chloroethyl ester with sodium oleate and sodium heptane-3-carboxylate; b -methyladipic acid di-b -chloro-isopropyl ester with sodium oleate; sebacic acid di-b -chloroethyl ester with sodium heptane-3-carboxylate. Other specified starting materials are esters of propionic, butyric, 2 : 2 : 4 : 4 - tetramethylpentene - 1 - carboxylic, lauric, and palmitic acid and of soya bean fatty acids and the acids obtained in the oxidation of paraffin; the esters may be d -chlorobutyl or g -chloro-isobutyl in addition to the above. Oleic acid b -chloro-isopropyl ester is obtained from oleic acid chloride and propylene oxide. Sodium oleate is prepared from sodium carbonate and oleic acid in glycol at 120 DEG C. Specification 438,540, [Group IV], is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE817054X | 1954-08-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB817054A true GB817054A (en) | 1959-07-22 |
Family
ID=6735143
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22680/55A Expired GB817054A (en) | 1954-08-07 | 1955-08-05 | Manufacture of esters |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB817054A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018109125A1 (en) * | 2016-12-16 | 2018-06-21 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
WO2018109123A1 (en) * | 2016-12-16 | 2018-06-21 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
WO2018109128A1 (en) * | 2016-12-16 | 2018-06-21 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
-
1955
- 1955-08-05 GB GB22680/55A patent/GB817054A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018109125A1 (en) * | 2016-12-16 | 2018-06-21 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
WO2018109123A1 (en) * | 2016-12-16 | 2018-06-21 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
WO2018109128A1 (en) * | 2016-12-16 | 2018-06-21 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
CN110462011A (en) * | 2016-12-16 | 2019-11-15 | 卡斯特罗尔有限公司 | Lubricant compositions, method and purposes based on ether |
CN110462011B (en) * | 2016-12-16 | 2022-05-13 | 卡斯特罗尔有限公司 | Ether-based lubricant compositions, methods and uses |
US11492566B2 (en) | 2016-12-16 | 2022-11-08 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
EP4095220A1 (en) * | 2016-12-16 | 2022-11-30 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
EP4108745A1 (en) * | 2016-12-16 | 2022-12-28 | Castrol Limited | Ether-based lubricant compositions, methods and uses |
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