Method for synthesizing 2,5-furandimethanol by selective hydrogenation of 5-hydroxymethylfurfural

A technology of hydroxymethylfurfural and furandimethanol, which is applied in the field of selective hydrogenation of 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol, which can solve the problem of low conversion rate of substrate and product yield, limitations of catalytic efficiency and other issues, to achieve good application value and industrialization prospects, multiple acid-base sites, and easy separation and recovery.

Active Publication Date: 2017-12-08
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these novel catalytic reaction systems can be carried out under the conditions of non-noble metal catalysts and exogenous hydrogen, their catalytic efficiencies, including substrate conversion and product yield, are often low, which largely limits2, The actual production and subsequent application of 5-furandimethanol

Method used

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  • Method for synthesizing 2,5-furandimethanol by selective hydrogenation of 5-hydroxymethylfurfural
  • Method for synthesizing 2,5-furandimethanol by selective hydrogenation of 5-hydroxymethylfurfural
  • Method for synthesizing 2,5-furandimethanol by selective hydrogenation of 5-hydroxymethylfurfural

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Preparation of Magnetic Metal-Organic Coordination Polymer

[0041] Add nanometer iron ferric oxide into 400mL dimethylformamide solution containing 30mmol metal chloride according to the metal chloride / iron molar ratio of 2:1, and stir for 30min with the assistance of ultrasound; Slowly add 400mL of dimethylformamide solution containing 10mmol of organic polybasic acid and 240mmol of triethylamine dropwise at 5mL / min and 1mL / min respectively; continue to stir at room temperature for 4h, raise the temperature to 70°C, and then stand and age for 4h ;Separate the solid precipitate with the help of a magnet, and wash the precipitate repeatedly with ethanol and ether until no chloride ions are detected; dry the washed solid precipitate at 80°C for 12 hours in vacuum, and grind it to about 120 meshes. A magnetic metal organic coordination polymer catalyst is obtained.

[0042] The amount of raw materials and the types of reactants when using different metal chloride...

Embodiment 2

[0047] The above-mentioned magnetic metal-organic coordination polymer catalyst is used to carry out selective hydrogenation of 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol. The synthesis method is:

[0048] Add 20g of isopropanol, 0.4g of 5-hydroxymethylfurfural and 0.16g of magnetic metal-organic coordination polymer catalyst in a 50mL reactor, seal and replace the air in the kettle with nitrogen continuously for 6 times; at a stirring speed of 400 rpm Raise the temperature to 130°C and perform selective hydrogenation reaction for 8 hours to obtain 2,5-furandimethanol.

[0049] In order to investigate the reusability of the catalyst, after the reaction was completed, an external magnet was added to separate MZPCP from the reaction solution, and then it was washed and dried to carry out the next selective hydrogenation reaction according to the above reaction conditions.

[0050] As compared with the catalyst provided by the invention and the hydrogenation synth...

Embodiment 3～8

[0054] Examples 3-8 Catalysts in the selective hydrogenation conversion of other carbonyl compounds

[0055] Add low-carbon alcohols, carbonyl-containing compounds and magnetic metal-organic coordination polymer catalysts into a 50mL reactor, and after sealing, replace the air in the reactor with nitrogen continuously for 6 times; heat up at a stirring speed of 400 rpm, and the selective hydrogenation reaction is The corresponding products can be obtained.

[0056] Among them, the reaction substrates, catalysts and reaction conditions used are summarized as follows:

[0057]

[0058] It can be seen from the above table that the catalyst provided by the present invention is also suitable for the selective hydrogenation reaction of other carbonyl compounds, and has a better reaction yield.

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Abstract

The invention discloses a method for synthesizing 2,5-dihydroxymethylfuran by selective hydrogenation of 5-hydroxymethylfurfural. The method is characterized in that a magnetic metal-organic coordination polymer is used as an acid and base bifunctional catalyst, low-price and easily-obtained low carbon alcohol is used as an in-situ hydrogen donor, and the 5-hydroxymethylfurfural is efficiently transformed into the 2,5-dihydroxymethylfuran by a selective transfer hydrogenation reaction under mild operation conditions and the maximum yield of the 2,5-dihydroxymethylfuran can be up to 98.6 percent. The magnetic metal organic coordination polymer used in the method disclosed by the invention has the advantages of relatively-high acid-base strength, more acid-base sites, relatively-large specific surface area and suitable pore size; in addition, the magnetic metal organic coordination polymer is simple in preparation process, is easy to separate and recover and shows excellent catalytic activity and catalytic stability. Furthermore, the low carbon alcohol is used as the in-situ hydrogen donor in the invention, so that the use of molecular hydrogen is avoided and the safety of the reaction process is improved; besides, the low carbon alcohol can be used as a reaction solvent and the introduction of exogenous substances is reduced, and thereby the production cost can be further reduced.

Description

technical field [0001] The invention belongs to the field of biomass energy chemical industry, and specifically relates to a method for selectively hydrogenating 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol. Background technique [0002] In recent years, converting renewable biomass resources into high value-added bio-based chemicals has become an important way to reduce the over-reliance on non-renewable fossil resources in today's society (Chemical Reviews, 2014, 114: 1827-1870; Chemical Reviews, 2017, 117: 6834-6880). Among various bio-based chemicals, 5-Hydroxymethylfurfural is considered to be one of the top ten platform compounds based on biomass resources, because it can prepare a series of high-quality derivatives that can replace fossil-based products (Renewable and Sustainable Energy Reviews, 2017, 74: 230-257). Among them, 2,5-furandimethanol obtained by selective hydrogenation of 5-hydroxymethylfurfural is particularly attractive. It can be used ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/28C07D307/42C07D307/44C07D307/58C08G83/00
CPCB01J31/28B01J35/0033B01J2531/0216B01J2531/26B01J2531/31B01J2531/42B01J2531/48B01J2531/49B01J2531/57C07D307/42C07D307/44C07D307/58C08G83/008
Inventor 胡磊李婷徐宁徐玲胡佩佩许家兴周守勇褚效中戴本林朱安峰
Owner HUAIYIN TEACHERS COLLEGE
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