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Method for preparation of 5-hydroxymethylfurfural catalyzed by methyltrioxorhenium

A technology of methyl rhenium trioxide and hydroxymethylfurfural, which is applied in organic chemistry and other fields, can solve problems not involved in catalytic dehydration of six-carbon sugars, and achieve high selectivity, improved conversion rate and selectivity, and simple process Effect

Active Publication Date: 2019-04-19
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Methyl rhenium trioxide (MTO) is a highly efficient transition metal organocatalyst, which has shown excellent activity in a variety of catalytic reactions, but previous research work has not involved the dehydration reaction of six-carbon sugars

Method used

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  • Method for preparation of 5-hydroxymethylfurfural catalyzed by methyltrioxorhenium
  • Method for preparation of 5-hydroxymethylfurfural catalyzed by methyltrioxorhenium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-15

[0019] Add 2 grams of fructose, a certain amount of MTO and 20 grams of tetrahydrofuran into the reaction kettle respectively, seal it, stir and heat to the set reaction temperature, carry out stirring reaction at a speed of 1000 rpm for a certain period of time, and then stop the reaction. The reaction mixture sample was filtered, and the filtrate was analyzed by a liquid chromatograph through an ultraviolet detector. The reaction results are shown in Table 1.

[0020] Table 1. The reaction results of MTO catalyzing the conversion of fructose to HMF under different conditions in tetrahydrofuran solvent

[0021]

[0022]

[0023] The above examples show that: MTO in tetrahydrofuran solvent catalyzes the conversion of fructose to prepare HMF under the above different conditions and obtains good reaction results.

Embodiment 16～20

[0025] Add 2 grams of reaction substrate, 200 mg of catalyst MTO and 20 grams of tetrahydrofuran into the reaction kettle respectively, seal it and heat it to 150° C. with stirring at a speed of 1000 rpm for 5 hours, then stop the reaction. The reaction mixture sample was filtered, and the filtrate was analyzed by a liquid chromatograph through an ultraviolet detector. The reaction results are shown in Table 2.

[0026] Table 2. MTO-catalyzed conversion of different substrates to prepare HMF in tetrahydrofuran solvent

[0027] Example

[0028] Examples 16-20 show that the conversion of different substrates catalyzed by MTO to prepare HMF in tetrahydrofuran solvent has obtained excellent reaction results.

Embodiment 21～26

[0030] Add 2 grams of reaction substrate, 200 mg of catalyst MTO and 20 grams of reaction solvent into the reaction kettle, seal it and heat it to 150° C. with stirring at a speed of 1000 rpm for 5 hours, then stop the reaction. The reaction mixture sample was filtered, and the filtrate was analyzed by a liquid chromatograph through an ultraviolet detector. The reaction results are shown in Table 3.

[0031] Table 3. The reaction results of MTO-catalyzed conversion of fructose to HMF in different solvents

[0032] Example

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Abstract

The invention relates to a method for preparation of 5-hydroxymethylfurfural catalyzed by methyltrioxorhenium. By using an organic solvent as a reaction medium, using hexose or hexose-source biomass as a substrate and using 1-50% (relative to the mass of the biomass sugar source) methyltrioxorhenium as a catalyst, a reaction is carried out at 80-200 DEG C in an enclosed reaction kettle for 0.5-10h so as to efficiently produce HMF. The method of the invention has the following advantages: the reaction is rapid, HMF selectivity is high, the use of an acid catalyst is not involved, and the process is simple. The invention provides a new method for the preparation of HMF from renewable biological resources.

Description

technical field [0001] The present invention relates to the preparation of 5-hydroxymethylfurfural (HMF), specifically a kind of high-efficiency conversion of six-carbon sugar and six-carbon sugar source biomass into HMF under the action of methyl rhenium trioxide (MTO) in an organic solvent process method. Background technique [0002] 5-Hydroxymethylfurfural is an important fine chemical intermediate and is regarded as a new platform compound based on biomass resources. It is widely used in agricultural chemistry, electrochemistry, cosmetics industry, synthetic pharmaceutical intermediates and other industries. Recently, HMF has been considered as a bridge between carbohydrate resources and the petroleum industry, because 2,5-dimethylfuran (DMF) obtained after selective hydrodeoxygenation of HMF is a high-quality fuel with an energy density ratio Ethanol is 40% higher and less volatile, showing great potential to replace fossil fuels [Román-Leshkov, Y, Barrett, C J, Liu, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46
CPCC07D307/46
Inventor 李昌志张波祁早娟王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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