08-04-1964 дата публикации
Номер: GB954901A
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 ...
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