Synthesis of novel plant oil derivatives: Furan and Diels-Alder reaction products

Authors: Biswas, Atanu; Liu, Zengshe - Kevin; Berfield, Janet; Cheng, Huai

Submitted to: International Journal of Agricultural Science and Technology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/11/2015
Publication Date: 8/10/2015
Publication URL: http://handle.nal.usda.gov/10113/5642479
Citation: Biswas, A., Liu, Z., Berfield, J.L., Cheng, H.N. 2015. Synthesis of novel plant oil derivatives: Furan and Diels-Alder reaction products. International Journal of Agricultural Science and Technology. 3(2):28-35.

Interpretive Summary: Plant oils are useful sustainable raw materials for the development of new chemical products. In this work chemically altered soybean oil, having reactive epoxides groups on it (called epoxidized soybean oil), was treated with different acids giving a new functional group called a furan on the oil. Depending on reaction conditions (solvent type, temperature, type of acid) the amount of furan and degraded starting material could be controlled. From process studies, the highest yields of furan were obtained using either fluorosulfonic or sulfuric acid. Using a model compound for the epoxidized soybean oil, called epoxidized methyl linoleate, we obtained up to 14% furan when fluorosulfonic acid was used. Using epoxidized soybean oil, up to about 7% of the furan structure was found. The furan group is a very useful group that can undergo other useful reactions producing a variety of new compounds that may have value in varied end-uses from sunscreens to polymer modifiers. The technology developed here will provide another higher value product for the producers and converters of soybeans. In addition, the products of this reaction would replace products made from petroleum feedstocks resulting in greener processes.

Technical Abstract: Plant oils are useful sustainable raw materials for the development of new chemical products. In this work epoxidized soybean oil was treated with different acids, and variable amounts of furan structures were produced from the epoxidized linoleate moiety. From process studies, the highest yields of furan were obtained with fluorosulfonic and sulfuric acids. Using epoxidized methyl linoleate as a model compound, we obtained up to 14% furan with fluorosulfonic acid. The relationship between furan formation and ester hydrolysis was found to be a function of temperature and amount of acid used. In epoxidized soybean oil, up to about 7% of the furan structure was found. The furan moiety can undergo Diels-Alder reaction with maleimide and N-phenyl maleimide to form novel plant oil derivatives.