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United States Department of Agriculture

Agricultural Research Service

Title: Azide derivatives of soybean oil and fatty esters

Authors
item Biswas, Atanu
item Brajendra, Sharma - PENN ST. UNIVERSITY
item Willett, Julious
item Adhvaryu, Atanu - PENN ST. UNIVERSITY
item Erhan, Sevim
item Cheng, H - HERCULES INCORP.

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 16, 2008
Publication Date: June 18, 2008
Citation: Biswas, A., Brajendra, S.K., Willett, J.L., Adhvaryu, A., Erhan, S.Z., Cheng, H.N. 2008. Azide derivatives of soybean oil and fatty esters. Journal of Agricultural and Food Chemistry. 56(14):5611-5616.

Interpretive Summary: Soybean oil (SBO) is a renewable natural resource and is an environmentally friendly alternative to petroleum-based products. The major components of soybean oil are triacylglycerols with a mixture of fatty acids moieties (typically 51% linoleic acid, 25% oleic acid, 10% palmitic acid, 7% linolenic acid, and 5% stearic acid). There has been a fair amount of interest in using SBO as a raw material to produce derivatives and even polymers. We have adopted a novel approach to incorporate nitrogen into the triglyceride structure. In this work we have devised a water-based reaction for the azidization of epoxides in fatty esters and soybean oil. Only a small amount of an ionic liquid is needed to achieve high yields. The placement of azide and alcohol functionalities is approximately random. This reaction has been applied not only to methyl oleate, methyl linoleate, and soybean oil, but also to methyl soyate (biodiesel). The structures have been confirmed by detailed Nuclear Magnetic Resonance (NMR) studies. These new materials perhaps can be used as ingredients in coatings, cosmetics, biodiesel fuel, and oil-based or oil-containing chemical products or easily converted to amine group that may have pharmaceutical activities.

Technical Abstract: An environmentally friendly water-based pathway to form the azide derivatives of soybean oil and fatty esters is hereby reported. This entails first the formation of epoxides and then the azidization of the epoxides. The azidization reaction is carried out at high yields in water with only a small amount of an ionic liquid as a catalyst. The distribution of azide and alcohol functionalities on the fatty acid moiety is approximately random. This reaction has been applied to methyl oleate, methyl linoleate, soybean oil, and methyl soyate.

Last Modified: 10/25/2014
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