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United States Department of Agriculture

Agricultural Research Service

Research Project: MODIFICATION OF NATURAL POLYMERS BY THERMO-MECHANICAL PROCESSING

Location: Plant Polymer Research

Title: Novel Modified Soybean Oil Containing Hydrazino-Ester: Synthesis and Characterization

Authors
item Biswas, Atanu
item Sharma, Brajendra - PENNSYLVANIA ST.UNIV.
item Willett, Julious
item Vermillion, Karl
item Erhan, Sevim
item Cheng, H. - HERCULES INCORP.

Submitted to: Green Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: October 18, 2006
Publication Date: January 11, 2007
Citation: Biswas, A., Sharma, B.K., Willett, J.L., Vermillion, K., Erhan, S.Z., Cheng, H.N. 2007. Novel modified soybean oil containing hydrazino-ester: synthesis and characterization. Green Chemistry. 9:85-89.

Interpretive Summary: There has been a constant demand for environmentally friendly lubricants. The interest intensified during the last decade due to strict government and environmental regulations. Most of the current lubricants originate from petroleum stock, which is toxic to environment and difficult to dispose of. Vegetable oils with high oleic content are considered to be potential candidates to substitute conventional mineral oil-based lubricating oils and synthetic esters. Vegetable oils are preferred to synthetic fluids because they are renewable resources and potentially cheaper. We have developed a novel solvent/catalyst less green pathway to incorporating nitrogen into the triglyceride structure by using diethyl azodicarboxylate (DEAD). These new materials perhaps can be used as lubricants and as ingredients in coatings, cosmetics, biodiesel fuel, and oil-based or oil-containing chemical products. These hydrazino derivatives may even have pharmaceutical activities as some hydrazine derivatives are known to have pharmaceutical activities.

Technical Abstract: A novel synthetic approach for chemical modification of vegetable oils is presented. The structural modification is carried out using diethyl azodicarboxylate (DEAD) in the absence of catalyst and solvent. In a microwave oven the reaction can be achieved in 5-15 minutes. The reaction can also proceed via conventional heat, albeit for a longer time. The products are characterized by 1H, 13C, and two-dimensional NMR.

Last Modified: 4/20/2014