Eco-Friendly Enzymatic Production of 2,5-Bis(hydroxymethyl)furan Fatty Acid Diesters, Potential Biodiesel Additives

Abstract

Due to the increasing need for greener and sustainable alternatives to fossil-based industrial chemicals and products, development of efficient synthesis of biomass-based platform chemicals is an attractive goal. 5-Hydroxymethylfurfural (HMF) derived 2,5-bis(hydroxymethyl)furan (BHMF) is one of the most targeted green chemicals, since it is a valuable building block for production of various useful compounds. Herein we described the efficient enzyme catalyzed double esterification of BHMF with saturated long-chain fatty acids using biomass-derived 2-methyl-tetrahydrofuran (2-MTHF) as solvent, providing an efficient synthetic route with >99% overall conversion (BHMF mono- and diesters) and between 89 and 99% conversion into the targeted BHMF diesters. The optimized large-scale procedure yielded easily isolable and chemically pure products useful to improve the cetane number of biodiesel.