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

Author:
Biswas, Atanu, Liu, Zengshe, Berfield, Janet L., Cheng, H. N.
Source:
International Journal of Agricultural Science and Technology 2015 v.3 no.2 pp. 28-35
ISSN:
2327-7246
Subject:
acids, chemical derivatives, cycloaddition reactions, furans, hydrolysis, models, raw materials, soybean oil, synthesis, temperature, yields
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.
Agid:
5642479
Handle:
10113/5642479