Submitted to: Polymer Preprints
Publication Type: Proceedings
Publication Acceptance Date: 6/19/2006
Publication Date: 9/18/2006
Citation: Biswas, A., Shogren, R.L., Woods, K.K., Erhan, S.Z., Cheng, H. 2006. New bio-based materials from soybean oil: hydrazine and related derivatives. Polymer Preprints. 47(2):259-260.
Interpretive Summary: There is much current interest in developing bio-based materials to replace those currently made from non-renewable, high priced petroleum feedstocks. However, new methods need to be developed to convert bio-based feedstocks like soybean oil into useful chemical products. This research describes a simple method to create a new modified soybean oil and fatty acids containing different type of organic nitrogen. These new bio-based chemicals should be useful building blocks for further modification into chemicals and polymers. These findings should be of interest to other researchers in industry, academia and industry working to develop new modified vegetable oils and applications for those.
Technical Abstract: Soybean oil is a renewable natural resource and is an environmentally friendly alternative to petroleum-based products. The major components of soybean oil (SBO) 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 SBO derivatives and even polymers. Examples are epoxidized oil, SBO methyl ester (methyl soyate), maleated products, SBO polymers, and others. We have adopted a different approach by incorporating nitrogen into the triglyceride structure. Aminating agent such as diethyl azodicarboxylate (DEAD) can be employed for this reaction. In this work we showed that subsequent hydrolysis can produce azacarboxylate ester and hydrazine derivatives of SBO. The reactions are facile and give high produce yields. 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. It may be noted that the hydrazine chemistry is well known. Hydrazine itself is a chemical intermediate that is used to produce agricultural chemicals, spandex fibers and antioxidants. Some hydrazine derivatives are even known to have pharmaceutical activities.