Possible Role of Vesicles on Metallocatalytic Reduction Reaction of 5-Hydroxymethylfurfural to 2,5-Dimethylfuran

Abstract

A reduction reaction of 5-hydroxymethylfurfural to 2,5-dimethylfuran (2,5-DMF) has been previously performed in an organic solvent under high-temperature conditions. For the relaxation of such reaction conditions, conventional palladium on carbon (Pd/C) was combined with vesicles composed of phospholipids or surfactants. Pd/C combined with 1,2-dioleoyl-sn-glycero-3-phosphocholine indicated a yield (25%) at 60 °C compared with Pd/C (17%). Vesicles at the liquid crystalline phase were advantageous for the reduction reaction of HMF. The yield of 2,5-DMF catalyzed by Pd/C combined with the vesicles depended on the lipid composition of the vesicles. It was clarified that the yield of 2,5-DMF could be controlled by the hydration property of the vesicles. Compared with conventional 2,5-DMF synthesis in an organic solvent, the use of vesicles made it possible to reduce the burden of using organic solvents in high-temperature conditions, although limitedly.