Submitted to: Polymer Preprints
Publication Type: Proceedings
Publication Acceptance Date: November 23, 2010
Publication Date: March 1, 2011
Citation: Biswas, A., Sharma, B., Klasson, K.T., Cheng, H.N. 2011. New Bio-Based Materials From Vegetable Oil: Amination and Click Reactions. Polymer Preprints. v. 52(1): 78-79. Interpretive Summary: Vegetable oils are renewable natural materials and can serve as an environmentally friendly alternative to petroleum-based products. Their methyl esters (e.g., methyl soyate) are gaining increasing attention as a bio-fuel. It will be useful to explore the chemistry of vegetable oils and their methyl esters in order to take advantage of the availability of these materials and to generate new compounds and new polymers that can increase their utility. In this article we show two approaches that can generate new vegetable oil-based products: amination and click reaction. Epoxidized soybean oil and methyl epoxy soyate are amenable to reactions with an amine or an azide to form aminohydrins or azidohydrins. A catalyst is useful to produce higher yields. An azidohydrin thus produced can be subjected to a “click reaction”, whereby a phenyl substituent can be readily grafted onto the soybean oil or methyl soyate backbone. These structural modifications are tools that permit specific molecular groups to be attached to vegetable oils or their methyl esters in order to improve specific properties. With suitable modifications, it may be possible to produce vegetable oil-based materials with potential applications in heat resistance, uv protection, or drug encapsulation.
Technical Abstract: For some time we have been interested in utilizing vegetable oils as cheap and bio-renewable raw materials. We have found derivatization reactions with nitrogen-containing reagents to be good pathways to achieve a range of new vegetable oil-based products. One of our approaches is to derivatize epoxidized soybean oil and methyl epoxy soyate through environmentally friendly reactions. Thus, amination reactions are relatively easy to carry out and provide several examples of interesting products. The click reaction is another example whereby new vegetable oil-based materials can be made through the reaction of an azide and phenylacetylene. The materials generated in this work have been fully characterized by NMR.