ARS | Publication request: Room-temperature self-curing ene reactions involving soybean oil

Submitted to: Green Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: November 12, 2007
Publication Date: April 1, 2008
Citation: Biswas, A., Sharma, B.K., Willett, J.L., Erhan, S.Z., Cheng, H.N. 2008. Room-temperature self-curing ene reactions involving soybean oil. Green Chemistry. 10(3):298-303.

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 the 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 mixture of soybean oil with diethyl azodicarboxylate exhibits a remarkable self-curing and thickening behavior at room temperature due to the occurrence of crosslinking ene reactions. The kinetics and the reaction mechanisms have been studied with the help of model compounds, 1H and 13C NMR, and size exclusion chromatography. The reactions are found to be most facile with linolenate, followed by linoleate, and least with oleate. The product from this reaction may be used as an environmentally friendly self-curing agent in appropriate applications.