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Building a biobased economy requires restructuring the chemical industry in such a way that it is based on renewable carbon instead of fossil fuels. Atom-efficient and scalable approaches need to be developed to convert biomass-derived platform molecules into value-added compounds. 5-Hydroxymethylfurfural (5-HMF), which can be derived from lignocellulosic biomass, plays a critical role in this transition. The high reactivity of its formyl group is problematic, because it leads to undesired oligomerization reactions, decreasing the yield of the desired product. This is usually countered by working in dilute non-aqueous solutions. Here, we present a novel approach to convert concentrated aqueous solutions of 5-HMF to 2,5-bishydroxymethylfuran (BHMF), which is a prospective monomer for polyesters and self-healing polymers. Our approach is based on the protection of the formyl group of 5-HMF using acetalization with 1,3-propanediol. Hydrogenation is carried out using an optimized Ni-Re supported on TiO2 at a carefully controlled pH, resulting in balanced rates of deprotection and hydrogenation and high BHMF yield.

green chemistry

Selective hydrogenation of 5-hydroxymethylfurfural and its acetal with 1,3-propanediol to 2,5-bis(hydroxymethyl)furan using supported rhenium-promoted nickel catalysts in water