Highly efficient strategies toward sustainable monomers and polymers derived from fatty acids via tetramethylguanidine promoted esterification

Abstract

Three easily performed and efficient strategies for preparing sustainable monomers and polymers derived from renewable fatty acids were investigated. All of these strategies relied on highly efficient esterification between halogenated compounds and fatty acids promoted by 1,1,3,3-tetramethylguanidine (TMG). In strategy 1, fatty acid-derived monomers and polymers were synthesized by TMG-promoted esterification of fatty acids with halogenated compounds followed by polymerization. In strategy 2, TMG-promoted esterification and polymerization reactions were performed in a one-pot process. In strategy 3, TMG-catalyzed esterification between halogenated polymers and fatty acids was conducted to obtain fatty acid-based sustainable polymers. ¹H nuclear magnetic resonance and size-exclusion chromatography were used to characterize the as-prepared fatty acid based monomers and polymers. To demonstrate the versatility of these strategies, a series of fatty acid-based monomers was developed using various halogenated monomers. Moreover, reversible addition–fragmentation chain transfer (RAFT) polymerization was performed successfully on the prepared monomers.