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Method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation

A technology for dimethylolfuran and hydroxymethylfurfural, which is applied in the field of 5-hydroxymethylfurfural catalytic transfer hydrogenation to prepare 2,5-dimethylolfuran, can solve the problem of poor recovery and reuse performance, atomic Low utilization rate, low hydrogen solubility, etc., to achieve strong economic advantages and industrialization prospects, easy separation, recovery and reuse, and avoid the use of exogenous solvents.

Active Publication Date: 2016-10-12
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It should be pointed out that hydrogen is currently mainly derived from non-renewable fossil resources, and the cost of hydrogen production is relatively high. Moreover, hydrogen is highly dispersible and flammable, making it difficult to store and transport. Moreover, the solubility of hydrogen in various solvents is not high. High, low atom utilization, therefore, hydrogenation of 5-hydroxymethylfurfural to prepare 2,5-dimethylfuran with hydrogen as a hydrogen donor is uneconomical and has a greater potential safety hazard
At the same time, gold, ruthenium, platinum and iridium, etc. all belong to noble metal catalysts, which are expensive and have poor recovery and reuse performance. These shortcomings have largely limited the actual production and production of 2,5-dimethylolfuran. Subsequent application

Method used

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  • Method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation
  • Method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation
  • Method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Example 1: Under a nitrogen atmosphere, nano-ferric ferric oxide is added to a zirconium chloride solution containing 50 g / L prepared with deoxidized deionized water at a molar ratio of iron / zirconium of 1:1, mechanically stirred for 30 min, Ultrasonic dispersion was performed for 10 min; under the condition of a mechanical stirring speed of 200 rpm, ammonia solution was added dropwise to the above solution at a rate of 3 mL / min until pH = 9, stirring was continued for 30 min, and the solution was left to age for 24 h; The solid precipitate was separated by a magnet, and the precipitate was repeatedly washed with deionized water until no chloride ions existed; the washed solid precipitate was vacuum-dried at 105 °C for 12 h, and ground and pulverized to 200 mesh to obtain a magnetic zirconium hydroxide catalyst. Abbreviated as Zr(OH) 4 @Fe 3 o 4 (1:1); Next, 20 g of ethanol, 0.2 g of 5-hydroxymethylfurfural and 0.04 g of Zr(OH) 4 @Fe 3 o 4 (1:1) was added to a 100 ...

Embodiment 2

[0020] Example 2: Under a nitrogen atmosphere, nanometer iron ferric oxide was added to a zirconium oxychloride solution containing 75 g / L prepared with deoxidized deionized water at an iron / zirconium molar ratio of 1:3, and mechanically stirred for 60 min , ultrasonically dispersed for 30 min; under the condition of a mechanical stirring speed of 400 rpm, the ammonia solution was added dropwise to the above solution at a rate of 4 mL / min until the pH = 10, continued stirring for 30 min, and stood for 24 h; The solid precipitate was separated with the help of a magnet, and the precipitate was repeatedly washed with deionized water until no chloride ions existed; the washed solid precipitate was vacuum-dried at 105°C for 12 h, and ground and pulverized to 200 mesh to obtain a magnetic zirconium hydroxide catalyst , referred to as Zr(OH) 4 @Fe 3 o 4 (3:1); Next, 30 g n-butanol, 0.9 g 5-hydroxymethylfurfural and 0.54 g Zr(OH) 4 @Fe 3 o 4 (3:1) was added to a 100 mL Parr auto...

Embodiment 3

[0022] Example 3: Add nano-ferric oxide ferric oxide into a zirconium chloride solution containing 100 g / L prepared with deoxidized deionized water at a molar ratio of iron / zirconium of 1:6 under a nitrogen atmosphere, and mechanically stir for 90 min. Ultrasonic dispersion was performed for 60 min; under the condition of a mechanical stirring speed of 600 rpm, ammonia solution was added dropwise to the above solution at a rate of 6 mL / min until pH = 11, stirring was continued for 30 min, and the solution was left to age for 24 h; The solid precipitate was separated by a magnet, and the precipitate was repeatedly washed with deionized water until no chloride ions existed; the washed solid precipitate was vacuum-dried at 105 °C for 12 h, and ground and pulverized to 200 mesh to obtain a magnetic zirconium hydroxide catalyst. Abbreviated as Zr(OH) 4 @Fe 3 o 4 (6:1); Next, 50 g of isopropanol, 2.5 g of 5-hydroxymethylfurfural and 2.5 g of Zr(OH) 4 @Fe 3 o 4 (6:1) was added t...

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Abstract

The invention discloses a method for preparing 2,5-dihydroxymethyl furan through 5-hydroxymethyl furfural catalytic transfer hydrogenation. The method uses magnetic zirconium hydroxide as a catalyst, uses low carbon alcohol as a reaction solvent and a hydrogen donor, 5-hydroxymethyl furfural is selectively converted into the 2,5-dihydroxymethyl furan through Meerwein-Ponndorf-Verley (MPV) transfer hydrogenation reaction in a high-pressure reaction kettle, and the highest yield is up to 91.5%. The raw materials for the used catalyst are low in price, the preparation process is simple, and the catalytic performance is good. In addition, the 2,5-dihydroxymethyl furan has strong magnetism and is easy to separate, recycle and reuse. Furthermore, the used low carbon alcohol can serve as the in-situ hydrogen donor, hydrogen usage is omitted, and the safety of the reaction process is further improved. Moreover, the 2,5-dihydroxymethyl furan can also serve as a reaction solvent, introduction of exogenous substances is reduced, the production costs are further reduced, and the method has a high application value and a good industrialized prospect.

Description

technical field [0001] The invention belongs to the field of biomass energy chemical industry, and in particular relates to a method for preparing 2,5-dimethylfuran by catalytic transfer hydrogenation of 5-hydroxymethylfurfural. Background technique [0002] In recent years, it has become one of the most effective ways to utilize biomass resources from the raw material pretreatment of lignocellulose to the selective separation of the three major components and then to the directional conversion of each component (Chemical Reviews, 2011, 111: 397-417). Among them, 5-Hydroxymethylfurfural obtained from the directional conversion of cellulose components is listed by the U.S. Department of Energy as one of the top ten platform compounds based on biomass resources, and is also considered to be a bridge connecting biomass resources and petroleum-based industries and key substances (Chemical Engineering Science, 2016, 142: 318-346). In addition, 2,5-dimethylolfuran obtained by hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/42
CPCC07D307/42
Inventor 胡磊李悦吴真许家兴周守勇徐继明赵宜江
Owner HUAIYIN TEACHERS COLLEGE
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