Unlocking the Potential of 5-Hydroxy-2(5H)-furanone as a Platform for Bio-Based Four Carbon Chemicals

Abstract

Industrial chemicals with a four-carbon structure, including maleic acid, 1,4-butanediol, γ-butyrolactone, and pyrrolidones, are derived from petroleum. Catalytic synthesis of these C4 chemicals from biomass is challenging because of the scarcity of C4 sugars in biomass feedstock. We show that 5-hydroxy-2(5H)-furanone (5H5F), produced by catalytic oxidation of biomass-derived furfural, is a versatile platform for several oxygen- and nitrogen-containing C4 chemicals. In our study, 5H5F was synthesized in 92% yield by room-temperature oxidation of furfural using TS-1 catalyst. As a platform chemical, 5H5F’s mild reactivity, attributed to the electrophilic carbon attached to the hydroxyl group, enabled its oxidation, reduction, and reductive aminolysis using carbon-supported noble metal catalysts. Industrial C4 chemicals like maleic acid (93%), γ-butyrolactone (93%), 1,4-butanediol (60%), tetrahydrofuran (64%), and 2-pyrrolidone (67%) were obtained from 5H5F under mild conditions (100–150 °C). We envision that 5H5F will be adopted as a platform for C4 chemicals owing to its ease of synthesis and selective transformation to multiple chemicals using heterogeneous catalysts.