Efficient dehydration of carbohydrates to 5-hydroxymethylfurfural in ionic liquids catalyzed by tin(IV) phosphonate and zirconium phosphonate

• Published in: Science China. Chemistry 2013-11, Vol.56 (11), p.1578-1585
• Main Authors: Ning, Hui, Song, JinLiang, Hou, MinQiang, Yang, DeZhong, Fan, HongLei, Han, BuXing
• Format: Article
• Language: English
• Subjects: Biomedical materials; Carbohydrates; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Dehydration; Glycine; Hydroxymethylfurfural; Ionic liquids; Phosphonates; Solvents; Stannic chloride; Zirconium
• ISSN: 1674-7291; 1869-1870
• DOI: 10.1007/s11426-013-4944-3

In this work, we synthesized tin(IV) phosphonate (SnBPMA) and zirconium phosphonate (ZrBPMA) by the reaction of SnCl 4 ·5H 2 O or ZrOCl 2 ·8H 2 O 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.