Synthesis of dodecanedioic acid from vernonia galamensis oil

Abstract: Dodecanedioic acid, currently available from elaborate synthesis utilizing petrochemical feedstock, was synthesized fromVernonia galamensis oil via an efficient, relatively simple three-reaction sequence that involved the room temperature oxidation of 12,13-epoxystearic acid. The first and second steps of the reaction scheme were saponification and hydrogenation, both of which were almost quantitative. The third reaction, involving chromic acid oxidation of the resulting epoxy acid, afforded greater than 50% of the theoretical yield of dodecanedioic acid (>95% purity, m.p. 123–125°C; lit. m.p. 128–130°C).