Efficient dehydration of carbohydrates to 5-hydroxymethylfurfural in ionic liquids catalyzed by tin(IV) phosphonate and zirconium phosphonate
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- Ning, H., Song, J., Hou, M. et al. Sci. China Chem. (2013) 56: 1578. doi:10.1007/s11426-013-4944-3
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In this work, we synthesized tin(IV) phosphonate (SnBPMA) and zirconium phosphonate (ZrBPMA) by the reaction of SnCl4·5H2O or ZrOCl2·8H2O with N,N-bis(phosphonomethyl)aminoacetic acid, which was synthesized from a biomaterial glycine through a Mannich-type reaction. The SnBPMA and ZrBPMA were very efficient heterogeneous catalysts for the dehydration of fructose to produce 5-hydroxymethylfurfural (HMF), and the SnBPMA had higher activity than the ZrBPMA. The effects of solvents, temperature, reaction time, and reactant/solvent weight ratio on the reaction catalyzed by SnBPMA were investigated. It was demonstrated that the yield of HMF could reach 86.5% with 1-ethyl-3-methylimidazolium bromide ([Emim] Br) as solvent, and the SnBPMA and SnBPMA/[Emim]Br catalytic system could be reused five times without considerable reduction in catalytic efficiency. Further study indicated that the SnBPMA and ZrBPMA in [Emim]Br were also effective for the dehydration of sucrose and inulin to produce HMF with satisfactory yields.