5-Hydroxy-2(5H)-furanone: a new platform chemical for bio-based four carbon chemicals

Industrial chemicals with a four-carbon backbone like maleic acid, 1,4-butanediol, gamma-butyrolactone and pyrrolidones are currently obtained from petroleum. Synthesis of these C4 chemicals from biomass is difficult owing to the low abundance of C4 sugars and development of a suitable C4 platform chemical is necessary. We show that 5-hydroxy-2(5H)-furanone (5H5F) is a versatile platform for above mentioned C4 chemicals. 5H5F was synthesized by oxidation of furfural at room temperature in the presence of TS-1 catalyst with 92 % yield and was isolated by extraction. As a platform chemical, 5H5F was reactive under mild conditions owing to electrophilicity of the carbon atom attached to hydroxyl group. Oxidation, reduction and reductive aminolysis of 5H5F using supported metal catalysts produced industrial C4 chemicals in high yield. We propose that 5H5F can serve as multipurpose platform for C4 chemical synthesis from biomass in industry.