ARS | Publication request: Enzymatic Products from Modified Soybean Oil Containing Hydrazinoester

Submitted to: American Chemical Society Symposium Series
Publication Type: Book/Chapter
Publication Acceptance Date: March 1, 2008
Publication Date: August 1, 2008
Citation: Biswas, A., Shogren, R.L., Willett, J.L., Erhan, S.Z., Cheng, H.N. 2008. Enzymatic Products from Modified Soybean Oil Containing Hydrazinoester. American Chemical Society Symposium Series. 999(1):76-85.

Technical Abstract: We 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 derivatized with the diethyl-azadicarboxylate functionality. Furthermore, we examined enzymatic transesterification reactions to explore the chemistry and the utility of these materials. Enzymatic transesterification with methanol gives DEAD-methyl soyate, whereas enzymatic reactions with glycerol and poly(ethylene glycol) give DEAD-fatty acid glycerides and DEAD-fatty acid ethoxylates. These new materials can possibly be used as ingredients in coatings, cosmetics, biodiesel fuel, and bio-surfactants.