GB954901A - A process for the production of substituted carboxylic acids - Google Patents

A process for the production of substituted carboxylic acids

Info

Publication number
GB954901A
GB954901A GB4010760A GB4010760A GB954901A GB 954901 A GB954901 A GB 954901A GB 4010760 A GB4010760 A GB 4010760A GB 4010760 A GB4010760 A GB 4010760A GB 954901 A GB954901 A GB 954901A
Authority
GB
United Kingdom
Prior art keywords
acid
anhydride
unsaturated
substituted carboxylic
olefines
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
Application number
GB4010760A
Inventor
Shirley Wonnacott
Thomas Frank Thomas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Research Ltd
Original Assignee
Shell Research Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shell Research Ltd filed Critical Shell Research Ltd
Priority to GB4010760A priority Critical patent/GB954901A/en
Publication of GB954901A publication Critical patent/GB954901A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton

Abstract

Alkenyl-substituted carboxylic acids are prepared by reacting a mono-olefine with a compound having a double bond between two carbon atoms conjugated with one or more carbonyloxy groups (i.e. an a , b -unsaturated carboxylic acid or an anhydride or ester thereof) to obtain an alkenyl-substituted carboxylic acid, anhydride or ester; reacting this with an aqueous solution of an inorganic base, separating the aqueous layer containing the salt of the substituted carboxylic acid, acidifying in the presence of a water-insoluble organic solvent (which may be added with or immediately after the acid), and recovering the substituted acid from the solvent layer, e.g. by removal of the solvent. Specified olefines are ethylene, propylene, butylene-1, amylene-1, hexylene-1, octene-1, decene-1, dodecene-1, tetradecene-1, octadecene-1, cosene-1 tetracosene-1, hexacosene-1, the corresponding internally unsaturated olefines, styrene, methyl styrene, and mixtures of olefines, e.g. C14-18 and C18-24 olefine mixtures. Specified unsaturated carbonyloxy compounds are acrylic, crotonic, 1-methylacrylic, angelic, tiglic, 2-hexenoic, 2-heptenoic and other 2-ethylenically unsaturated aliphatic acids and the corresponding esters; maleic, fumaric, ethylidene malonic, propylidene malonic, isopropylidene malonic and butylidene malonic acids and their esters and anhydrides, especially maleic anhydride; cinnamic acid, 4-phenylbut-2-enoic acid, and aralkyl unsaturated dibasic carboxylic acids and their esters and anhydrides. The addition reaction is preferably conducted at at least 100 DEG C. Specified inorganic bases are alkali metal hydroxides. Specified water-insoluble organic solvents are benzene, toluene, isopropyl ether and halogenated hydrocarbons; preferably 20-40% by volume is used, based on the volume of the organic acid salt solution. Suitable acids for acidification are HCl, H2SO4 and HNO3. Examples react maleic anhydride with C18-24 cracked wax olefines. The products of the process are lubricating oil additives (see Division C5). Specifications 657,496, 671,456, 671,457, 671,458, 681,246, 725,598, 736,438 and 879,506 are referred to.ALSO:A rust-inhibiting additive for mineral lubricating oils comprises the alkenyl-substituted carboxylic acids obtained (see Division C2) by reacting a mono-olefine with a compound having a double bond between two carbon atoms conjugated with one or more carbonyloxy groups (i.e. an a ,b -unsaturated carboxylic acid, e.g. mono- or dibasic, or an anhydride or ester thereof) to obtain an alkenyl-substituted carboxylic acid or anhydride or ester; reacting this with an aqueous solution of an inorganic base, separating the aqueous layer containing the salt of the acid, acidifying in the presence of a water-insoluble organic solvent, and recovering the acid from the solvent layer. Suitable reactants are listed (see Division C2). Specifications 657,496, 671,456, 671,457, 671,458, 681,246, 725,598, 736,438 and 879,506 are referred to.
GB4010760A 1960-11-22 1960-11-22 A process for the production of substituted carboxylic acids Expired GB954901A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4010760A GB954901A (en) 1960-11-22 1960-11-22 A process for the production of substituted carboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4010760A GB954901A (en) 1960-11-22 1960-11-22 A process for the production of substituted carboxylic acids

Publications (1)

Publication Number Publication Date
GB954901A true GB954901A (en) 1964-04-08

Family

ID=10413228

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4010760A Expired GB954901A (en) 1960-11-22 1960-11-22 A process for the production of substituted carboxylic acids

Country Status (1)

Country Link
GB (1) GB954901A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2531984A1 (en) * 1982-08-20 1984-02-24 Chevron Res ALKENYLSUCCINIC ANHYDRIDE-BASED COMPOSITION, PROCESS FOR PREPARING THE SAME AND APPLICATION THEREOF FOR BONDING PAPER
GB2137614A (en) * 1983-02-07 1984-10-10 Mitsubishi Oil Co Alkenylsuccinic acid salts of use as paper sizing agents
EP0429123A1 (en) * 1989-11-17 1991-05-29 Akzo Nobel N.V. Compositions from alpha,beta-unsaturated dicarboxylic acid esters and olefinically unsaturated compounds which are particularly suitable for use as lubricants and lubricant additives and a process for the preparation of such compositions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2531984A1 (en) * 1982-08-20 1984-02-24 Chevron Res ALKENYLSUCCINIC ANHYDRIDE-BASED COMPOSITION, PROCESS FOR PREPARING THE SAME AND APPLICATION THEREOF FOR BONDING PAPER
GB2137614A (en) * 1983-02-07 1984-10-10 Mitsubishi Oil Co Alkenylsuccinic acid salts of use as paper sizing agents
EP0429123A1 (en) * 1989-11-17 1991-05-29 Akzo Nobel N.V. Compositions from alpha,beta-unsaturated dicarboxylic acid esters and olefinically unsaturated compounds which are particularly suitable for use as lubricants and lubricant additives and a process for the preparation of such compositions
US5176841A (en) * 1989-11-17 1993-01-05 Akzo N.V. Compositions from α,β-unsaturated dicarboxylic acid esters and olefinically unsaturated compounds which are particularly suitable for use as lubricants and lubricant additives and a process for the preparation of such compositions

Similar Documents

Publication Publication Date Title
GB1105729A (en) Metal salts of organic phosphorus acids
BR8505280A (en) PROCESS TO PRODUCE SUBSTITUTED CARBOXYLIC ACIDS AND DERIVATIVES FROM THE SAME AND SUBSTITUTED ANhydrides REPLACED WITH HYDROCARBONS
GB644043A (en) Mineral oil composition
GB954901A (en) A process for the production of substituted carboxylic acids
US2477327A (en) Hydroxy alkyl thio succinic acids and esters
GB928702A (en) Lubricant compositions and additives therefor
GB1047042A (en) Additive for cutting-oils and for high-pressures lubricating oils
GB964184A (en) Fuel oil compositions
US2037229A (en) Production of sulphonic acids
US2372160A (en) Sulphurized esters of cyclic sulphones
US2413199A (en) Production of aliphatic hydrocarbon sulfonates
DE69023348D1 (en) COATING COMPOSITIONS.
DE902381C (en) Process for the production of ester-like condensation products
US3091635A (en) Alkylation process
GB803768A (en) Improvements in or relating to polymeric basic aluminium salts of organic acids
GB990083A (en) Method of preparing hydrocarbons, chlorinated hydrocarbons or esters of aromatic mono-, di- or tri carboxylic acids
GB989476A (en) Process for the preparation of cyclic carboxylic acids and their esters
GB742949A (en) Improvements in and relating to the condensation of di-alkyl succinates
DE884365C (en) Process for the production of vitamin A esters or free vitamin A.
GB641438A (en) Process for the production of vinyl esters of organic acids
SU865880A1 (en) Water-repulsive composition
ES483369A1 (en) Process for the preparation of glycidyl esters of maleic acid.
GB498008A (en) Improvements in the manufacture and production of capillary-active agents
GB512583A (en) Improvements in preparation of salts of hexamethylenetetramine
GB728772A (en) Improvements in or relating to lubricating grease compositions