New approaches in the synthesis of furan-based diepoxy monomers

In consideration of the concerns about the lack of petrochemical resources and their associated environmental risks, it is mandatory to research and develop new building blocks and synthetic routes respectful towards the environment. Furanic molecules, bio-derived compounds bearing an aromatic moiety, are valuable building blocks that can substitute petrol-derived molecules. For example, it is already proved that 2,5-furandicarboxylic acid (FDCA) is an excellent substitute of terephtalic acid in the production of polyesters with improved barrier properties. FDCA may also be a substitute of Bispehol A in the production of high-quality epoxy resins but its epoxidation requires long reaction time and hazardous reactants and solvents [1]. Therefore, the achievement of epoxy resins from FDCA monomers through simple, scalable and low environmental and human health impact protocols still represent a challenge. In this work, two innovative synthetic routes are proposed in order to obtain the diglycidyl ester of furan (BOFD, Figure 1). The first one involves FDCA glycidylation with epichlorohydrin (mimicking the consolidated route for glycidylation of Bisphenol A), while the second one is based on the transesterification of dimethyl 2,5-furandicarboxylate (DM-FDCA) in the presence of glycidol. The chemical structures of the obtained monomers following both procedures were validated by 1HNMR, 13CNMR, and FTIR spectroscopies, proving the feasibility of these new routes [2]. More efforts are now devoted to further improve the yield of reaction, through the selection of more efficient catalyst.