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2, 5-dihydroxy methyl furan or 2, 5-dihydroxy methyl tetrahydrofuran synthesis method

A technology of dimethyloltetrahydrofuran and dimethylolfuran, which is applied in the direction of organic chemistry, can solve the problems of high pollution, high energy consumption, and high cost, and achieve the effects of wide sources, high catalytic activity and selectivity

Inactive Publication Date: 2014-05-21
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a simple and economical synthesis method, which can synthesize 2,5-dimethyloltetrahydrofuran (DHMTHF) in high yield from cheap sugar compounds under mild reaction conditions, and can optionally obtain 2,5-Dihydroxymethylfuran (DHMF), which overcomes the disadvantages of high cost, high energy consumption and high pollution of existing technologies

Method used

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  • 2, 5-dihydroxy methyl furan or 2, 5-dihydroxy methyl tetrahydrofuran synthesis method

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Effect test

Embodiment 1

[0024] Embodiment 1 Fructose dehydration prepares HMF

[0025] Dissolve 1.32g fructose in 11.85g isopropanol, add 0.132g Amberlyst-15, heat to 100°C, stir rapidly, and react for 4 hours. Afterwards, the reaction kettle was cooled with ice water to room temperature, the reaction solution was centrifuged, a certain amount of supernatant was taken in a 10mL volumetric flask, and the ethanol was fixed to volume. The concentration of HMF was quantitatively analyzed by gas chromatography, and the yield of HMF reached 65%.

[0026] Table 1 shows the reaction results of HMF prepared by dehydration of fructose in different reaction temperatures, times and solvent systems.

[0027] Table 1 Preparation of HMF by dehydration of fructose

[0028]

[0029] a SBA-15-SO 3 H is the sulfonic acid functionalized SBA-15 synthesized by one-step method.

[0030] b AC-SO 3 H is a sulfonated activated carbon material.

Embodiment 2

[0031] Embodiment 2HMF hydrogenation prepares 2,5-dimethylolfuran or 2,5-dimethyloltetrahydrofuran

[0032] This example studies the preparation of hydrogenation catalysts, including the influence of different main catalysts, auxiliary agents, and supports, and its catalytic performance for the conversion of HMF at room temperature.

[0033]The hydrogenation catalyst was prepared by equal volume impregnation method. Add the dried carrier to the metal salt solution (the amount of the metal salt is determined by the metal content of the active component), stir evenly, soak at room temperature for 24 hours, and dry for 12 hours after the metal ions are adsorbed on the carrier. After the prepared catalyst was reduced in a hydrogen atmosphere at 350 °C, it was used to catalyze the conversion of HMF.

[0034] HMF hydrogenation conversion: add 10mL 1.25wt% HMF solution and 0.1g reduced catalyst into a 50mL autoclave, seal and replace the air 5 times. Charge hydrogen gas at a pressu...

Embodiment 3

[0040] The influence of embodiment 3 solvent on HMF hydrogenation reaction

[0041] The influence of different solvent systems on the hydrogenation performance of HMF at room temperature has been studied. The catalyst is No. 1 in Example 2. Other reaction processes are the same as in Example 2. The reaction results are shown in Table 3. When water is used as a solvent, HMF has the highest hydrogenation activity, 2 , The yield of 5-dimethyloltetrahydrofuran (DHMTHF) was 83.0%.

[0042] The solvent effect of table 3 HMF hydrogenation reaction

[0043]

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Abstract

The invention relates to a method which uses a sugar catalyst to directly synthesize 2, 5-dihydroxy methyl furan or 2, 5-dihydroxy methyl tetrahydrofuran. The method comprises the steps that fructose and other hexose is used as a raw material, and is dehydrated in the presence of a solid acid catalyst to generate 5-hydroxymethyl furfural; the solid acid is separated; a hydrogenation catalyst is added; and reaction with hydrogen inlet is carried out under normal temperature and pressure to generate the 2, 5-dihydroxy methyl furan or 2, 5-dihydroxy methyl tetrahydrofuran. The method has the advantages of mild reaction condition, cheap and easily obtained raw material, easy reaction process operation, and high yield of 2, 5-dihydroxy methyl furan or 2, 5-dihydroxy methyl tetrahydrofuran.

Description

technical field [0001] The invention relates to the field of chemistry and chemical engineering, in particular to a method for preparing 2,5-dimethylfuran (DHMF) or 2,5-dimethyloltetrahydrofuran (DHMTHF) from six-carbon sugar raw materials such as fructose via 5-hydroxymethylfurfural. )Methods. Background technique [0002] 2,5-Dihydroxymethylfuran (DHMF) and its selective hydrogenation product 2,5-Dihydroxymethyltetrahydrofuran (DHMTHF) are organic compounds with important uses, which can be used as raw materials for the synthesis of pharmaceutical intermediates, nucleoside derivatives Compounds, crown ethers and furans, etc., can also be used as solvents, softeners, wetting agents, binders, surfactants, synthetic plasticizers, etc., and secondly, they can be used as monomers to synthesize polymer materials such as polyester and polyurethane. Reducing the content of volatile organic compounds in clothing coatings is expected to completely or partially replace the use of pr...

Claims

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Application Information

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IPC IPC(8): C07D307/42C07D307/12
CPCC07D307/42C07D307/12
Inventor 徐杰陈佳志路芳于维强张俊杰高进苗虹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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