Polymerized and functionalized triglycerides

Authors: Cheng, Huai; Biswas, Atanu

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 4/4/2016
Publication Date: 8/21/2016
Citation: Cheng, H.N., Biswas, A. 2016. Polymerized and functionalized triglycerides. (Abstract). ACS Abstract Book for San Diego National Meeting, p. 223, POLY paper #38.

Interpretive Summary:

Technical Abstract: Plant oils are useful sustainable raw materials for the development of new chemical products. As part of our research emphasis in sustainability and green polymer chemistry, we have explored a new method for polymerizing epoxidized triglycerides with the use of fluorosulfonic acid. Depending on the reaction conditions, we can get viscous oils or solid materials as reaction products. The reaction mechanism has been studied through a systematic examination of the fluorosulfonic acid-initiated reaction of epoxidized methyl oleate and epoxidized methyl linoleate. The effects of temperature, initiator dosage, and reaction time have been investigated and shown to affect the nature of polymer products obtained and the distribution of different chemical species present. An interesting finding has been the furan structure produced from the epoxidized linoleate moiety. The relationship between furan formation and ester hydrolysis has been found to be a function of temperature and amount of acid used. Using epoxidized triglyceride (or epoxidized methyl linoleate), we have obtained up to 7% (or 14%) furan with fluorosulfonic acid, respectively. The furan moiety has been shown to undergo Diels-Alder reaction with maleimide and N-phenyl maleimide to form novel plant oil derivatives.