Submitted to: American Chemical Society Symposium Series
Publication Type: Book / Chapter
Publication Acceptance Date: 6/5/2013
Publication Date: 11/22/2013
Citation: Cheng, H.N., Rau, M., Dowd, M.K., Easson, M.W., Condon, B.D. 2013. Hydrogenated cottonseed oil as raw material for biobased materials. In: Cheng, H.N., Asakura, T., English, A.D., editors. Green Polymer Chemistry: Biocatalysis and Materials II. ACS Symposium Series, vol. 1144. Washington, DC: American Chemical Society. p. 359-371.
Interpretive Summary: In the past many polymers have been made from vegetable oils, particularly using reactions involving olefinic functionalities on the triglycerides. In many of these applications the amounts of oleic, linoleic, and linolenic functionalities in a vegetable oil have a major role in the reactivities of the oil, the speed of the reactions, and the nature of the polymer products. If we have better control over the amounts of these functionalities, we have better control of the structure of the products and rate of the polymerization. Our approach is to customize the amounts of mono-ene and di-ene functionalities through hydrogenation. Thus, we have carried out a detailed hydrogenation study of cottonseed oil using commercially available Ni, Pt and Pd catalysts under different hydrogenation conditions. Kinetic modeling of the observed data has been done so that a detailed understanding is obtained of the hydrogenation process. With good knowledge of reaction kinetics, hydrogenated cottonseed oil with mono-ene content up to 60% or linoleic acid content up to 53% can be produced. This information will allow biobased products to be made from cottonseed oil with more precise structures and functionalities.
Technical Abstract: There has been a lot of recent interest in using vegetable oils as biodegradable and renewable raw materials for the syntheses of various biobased materials. Although most of the attention has been paid to soybean oil thus far, cottonseed oil is a viable alternative. An advantage of cottonseed oil is that the reactive groups consist primarily of oleic and linoleic moieties, and their amounts can be varied with appropriate hydrogenation. In this work a detailed hydrogenation study is carried out using three commercially available Ni, Pt and Pd catalysts under different hydrogenation conditions. Kinetic modeling of the observed data has also been done. With cottonseed oil and selective use of hydrogenation, oleic acid content up to 40% and linoleic acid content up to 53% can be produced, and these functionalities can be derivatized to produce specific biobased products. In addition, relative to the hydrogenated soybean oil, hydrogenated cottonseed oil exhibits lower trans fatty acid, and this feature may be beneficial in the context of food use.