Hybrid Conversion of 5-Hydroxymethylfurfural to 5-Aminomethyl-2-furancarboxylic acid: Toward New Bio-sourced Polymers

摘要

Hybrid catalysis, which combines chemo- and biocatalytic benefits, is an efficient way to address green chemistry principles. 5-Hydroxymethylfurfural (HMF) is a versatile building block in numerous industrial applications. To date, few studies have described the production of its amine derivatives and their polymers. Finding a good methodology to directly transform HMF to 5-aminomethyl-2-furancarboxylic acid (AMFC) therefore represents an important challenge. After selecting the best oxidation catalyst for HMF conversion to 5-aldehyde-2-furancarboxylic acid and immobilizing a transaminase onto a solid carrier, we implemented the first one-pot/two-steps hybrid catalytic process to produce AMFC (77 % yield); this is the most efficient AMFC catalytic production method from HMF reported to date. This process also produced 2,5-furandicarboxylic acid (21 % yield) as a major secondary product that can be applied to polymer syntheses such as polyethylene furanoate. Herein, we report a novel way to access new biosourced polymers based on HMF oxidized and aminated derivatives.