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Method for preparing hydroxymethyl furfural by catalytic dehydration reaction of hexose

A technology of hydroxymethylfurfural and catalysis of six-carbon sugars, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of adding large organic solvents and additives, The solvent ionic liquid is expensive, the catalyst is large, etc., to achieve high selectivity, good application prospects, and good product effects

Inactive Publication Date: 2011-10-12
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above-mentioned catalytic system, when metal chloride is used as a catalyst, the disadvantage is that the catalyst has greater toxicity, and the price of the solvent ionic liquid is more expensive; the disadvantage of using inorganic acid or solid acid as a catalyst is that it can only be applied to D-fructose. Catalytic dehydration process, and need to add a lot of organic solvents and additives

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Catalytic dehydration of D-fructose

[0018] Dissolve 1.0g (5.6mmol) D-fructose in 2mL dimethyl sulfoxide, add 0.28mmol N-bromosuccinimide, stir magnetically at 90°C under nitrogen protection, and react for 2 hours, then use gas- Mass spectrometry instrument and high performance liquid chromatography analyze the reaction results; the conversion rate of fructose is 96%, and the yield of hydroxymethylfurfural can reach 84%; at this time, the reaction solution can be neutralized with saturated sodium bicarbonate, filtered, dried, Distillation to produce high-purity hydroxymethylfurfural.

Embodiment 2

[0019] Example 2: Catalytic dehydration of D-fructose

[0020] Dissolve 1.0 g (5.6 mmol) of D-fructose in 10 mL of N, N-dimethylformamide, add 0.56 mmol of N-chlorosuccinimide, and stir magnetically at 100 °C under the protection of argon to react 1 After one hour, the reaction results were analyzed by gas-mass spectrometry and high-performance liquid chromatography. The fructose conversion rate is 95%, and the yield of hydroxymethylfurfural can reach 82%. At this time, the reaction solution can be neutralized with saturated sodium bicarbonate, filtered, dried, and distilled to produce high-purity hydroxymethylfurfural.

Embodiment 3

[0021] Example 3: Catalytic dehydration of L-fructose

[0022] Dissolve 1.0g (5.6mmol) of L-fructose in 20mL of N, N-dimethylacetamide, add 0.56mmol of N-iodosuccinimide, stir at 90°C under nitrogen protection, and react for 3 hours , with gas-mass spectrometry instrument and high-performance liquid chromatography analysis reaction result; Fructose conversion rate is 93%, and the yield of product hydroxymethylfurfural can reach 79%; Now can neutralize reaction solution with saturated sodium bicarbonate, Filter, dry, and distill to produce high-purity hydroxymethylfurfural.

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Abstract

The invention provides a method for preparing hydroxymethyl furfural by catalytic dehydration reaction of hexose. The method comprises the following steps of: dissolving reaction substrates of hexose into a solvent, and adding a catalyst of halogenated succinimide to form a reaction system; and at the temperature of between 0 and 200 DEG C and under the protection of atmosphere gas, stirring the reaction system by magnetic force for dehydration reaction for 0.5 to 10 hours to prepare the hydroxymethyl furfural, wherein the catalyst of the halogenated succinimide may be N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinimide, N-fluorosuccinimide or any succinimide derivatives with substituted halogen atoms. The method has the advantages that: the catalyst of the halogenated succinimide is low in price and easily bought, and can catalyze the hexose in high efficiency as well as high selectivity to prepare the hydroxymethyl furfural; the method is environment-friendly, and the productis easily disposed; and in the whole process, only regenerated compounds such as fructose are consumed, the cost is low, the technically economical requirement is met, and the application prospect isbroad.

Description

technical field [0001] The invention relates to a method for preparing hydroxymethylfurfural, in particular to a method for preparing hydroxymethylfurfural by catalyzing the dehydration reaction of six-carbon sugar. Background technique [0002] At present, solving the oil energy crisis and developing a low-carbon economy have become the focus of global attention; the production of fine chemicals from renewable biomass has gradually become an important research direction in the field of chemistry and chemical engineering. Among them, the synthesis of 5-hydroxymethylfurfural (HMF) using six-carbon sugar as raw material through dehydration reaction has become one of the research hotspots. Studies have shown that HMF is an important intermediate in the synthesis of a variety of fine chemicals, and as a platform compound connecting biomass conversion and large-scale chemical processes, it can reaction to synthesize new polymer materials and many high value-added products, which...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/48B01J31/02
Inventor 仝新利田果薛松
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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