Enzymatic Products from Modified Soybean Oil Containing Hydrazinoester

Abstract

Efforts have been made in this work to use soybean oil to produce new, non-petroleum based products. The starting material is the ene reaction product of soybean oil and diethyl azodicarboxylate (DEAD), which can then be hydrolyzed chemically and enzymatically. Chemical hydrolysis gives hydrazino-fatty acids, whereas enzymatic hydrolysis gives the fatty acids modified with the diethyl-azadicarboxylate functionality. Moreover, we have examined enzymatic transesterification reactions in order to explore the chemistry and the utility of these materials. Enzymatic transesterification with methanol gives modified methyl soyate, while enzymatic reactions with glycerol and poly(ethylene glycol) give modified fatty acid glycerides and fatty acid ethoxylates. These new materials can potentially be used as ingredients in coatings, cosmetics, biodiesel fuel, and bio-surfactants.