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Being a member of the glycosaminoglycan family of carbohydrates, native heparin is a highly sulfated polysaccharide. Herein, heparin was grafted onto polydopamine (PDA)- and poly(ethylene imine) (PEI)-coated multiwalled carbon nanotubes (MWCNTs) (heparin-PEI@PDA@MWCNT). The immobilized heparin consists of a sulfated repeating disaccharide unit, conferring a unique microenvironment when catalyzing fructose dehydration into 5-hydroxymethylfurfural (HMF). The hydrogen bonding interactions naturally occur between the disaccharide unit of heparin and the monosaccharide fructose, and the adjacent sulfonic acid groups catalyze the fructose dehydration. The reactions were performed in water, and heparin-PEI@PDA@MWCNT achieved an HMF yield of 46.2% and an HMF selectivity of 82.2%. For the dehydration of fructose in water, heparin-PEI@PDA@MWCNT exhibits advantages over published heterogeneous catalysts on the basis of HMF yield and HMF selectivity. Three aspects contribute to the environmentally benign processing: (1) the catalyst heparin is a natural sulfated polysaccharide; (2) the catalysis is carried out in water and not in organic solvents; and (3) fructose can be produced from a biomass resource.

Heparin Immobilized on Multiwalled Carbon Nanotubes for Catalytic Conversion of Fructose in Water with High Yield and Selectivity