Free radical additions to esters of unsaturated fatty acids. Preparation of dicarboxylic acids and other polyfunctional products

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Abstract
Peroxide initiated free radical addition of acetic acid, acetic anhydride and ethyl cyanoacetate to methyl undecylenate and methyl oleate gives interesting and important derivatives in fair to excellent yields. Of these, the most important are the dicarboxylic acids, brassylic and carboxymethylstearic acids.Acetic acid and acetic anhydride both give the same ultimate products but because of the greater amount of by‐product in the methyl undecylenate reaction with acetic acid and the need for pressure in the reaction of acetic acid with methyl oleate, acetic anhydride is the preferred addendum for preparing the dicarboxylic acids. There is very little by‐product formed in addition of acetic anhydride to methyl undecylenate and methyl oleate.Ethyl cyanoacetate adds readily to both methyl undecylenate and methyl oleate; however, ethyl cyanoacetate is difficult to remove completely from the reaction products. Hydrolysis to destroy it also causes some hydrolysis of the addition products. On the other hand, it is very difficult to hydrolyze completely and subsequently decarboxylate the ethyl cyanoacetate addition products of methyl undecylenate and methyl oleate to obtain dicarboxylic acids.

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