Conjugated dienes and trienes from methyl oleate and methyl linoleate

Abstract

Methyl oleate and methyl linoleate were converted to conjugated dienes and trienes, respectively, by selecting and modifying the conventional procedures usually applied to the generation and characterization of fatty hydroperoxides. Conditions have been studied in the laboratory for: (a) the optimum production of hydroperoxides with a minimum of by-products, (b) the effective separation and concentration of the resulting hydroperoxide, (c) the economic reduction of the hydroperoxide mixture, (d) simple dehydration of the reduced product, and, (e) recovery of the resulting polyene-rich material. If the processing sequence is halted after the reduction step, the resulting product,is a mixture of allylic hydroxy monoene or diene methyl esters. Our investigations have been extended to include studies on the methyl esters of commercial oleic acid and the mixture of methyl esters resulting from alcoholysis of lard oil. Products containing 20–25% conjugated diene and lesser proportions of conjugated triene were obtained.