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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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

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

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