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Synthesis of 5-hydroxymethylfurfural from glucose in a biphasic medium with AlCl3 and boric acid as the catalyst

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Abstract

In combination with non-corrosive and low-toxic boric acid, AlCl3 · 6H2O was found to be effective for the synthesis of 5-hydroxymethylfurfural (5-HMF) from glucose. In this work, a 5-HMF yield of ≈ 60 % was obtained at 170°C for 40 min in a H2O/THF biphasic solvent mixture. An addition of NaCl not only improved the partition coefficients but also inhibited by-product formation. THF was identified as an ideal extraction solvent in biphasic systems containing C4 solvents. However, low concentration of ZnCl2, CoCl2 · 6H2O, MnCl2 · 4H2O, NiCl2 · 6H2O, FeCl3 · 6H2O were not suitable for the catalyst system, while ZrOCl2 · 8H2O, InCl3 · 4H2O showed high activity for the reaction. Boric acid increased the amount of Lewis acid sites in the reactive phase and enhanced the isomerization of glucose to fructose. A mechanism of the AlCl3 · 6H2O and boric acid catalyzed glucose dehydration reaction was proposed to proceed through the isomerization of glucose to fructose followed by the transformation of fructose to 5-HMF.

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  1. School of Chemical Engineering, Changchun University of Technology, Changchun, 130012, Jilin, China

    Zhi-Lei Xu, Xiao-Yue Wang, Mei-Yu Shen & Chang-Hai Du

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  1. Zhi-Lei Xu
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Xu, ZL., Wang, XY., Shen, MY. et al. Synthesis of 5-hydroxymethylfurfural from glucose in a biphasic medium with AlCl3 and boric acid as the catalyst. Chem. Pap. 70, 1649–1657 (2016). https://doi.org/10.1515/chempap-2016-0101

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