Organic acids reaction with vegetable oils

By the reaction of epoxidised vegetable oils with HCl, HBr or various organic acids (R-COOH), the epoxidic ring is opened with the formation of polyols having chlorohydrin, bromohydrin or hydroxyalkyl esters structures (reactions 17.17, 17.18 and 17.19) [31-34]. 

Vegetable oil-based poly(ester amide)s are prepared by a three-step reaction procedure in which a base such as sodium methoxide is used as the catalyst for the first two steps and metal oxide/hydroxide is used for the last step of the reaction (Fig. 5.2). In the first step, methyl esters of the fatty acids are produced by transesterifiction of oil with methanol, followed by transformation to dihydroxy fatty amide by amidation reaction with dihydroxyalkylamine and, finally, esterification reaction by treatment with dibasic acid or anhydride at a relatively high temperature to obtain the desired poly (ester amide). This may be done either by azeotropic distillation or by direct polycondensation under an inert atmosphere. Poly(ester amide) can also be synthesised at a low temperature through a condensation polymerisation reaction in the absence of an organic solvent. In this reaction, V,V-bis(2-hydroxyalkyl) fatty amide and dibasic anhydride are heated at a temperature lower than the onset of the melting points of the component. By-products, such as water, are removed by a vacuum technique. 

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