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The method for the selective hydrogenation of 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol

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

Active Publication Date: 2019-12-27
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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  • The method for the selective hydrogenation of 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol
  • The method for the selective hydrogenation of 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol
  • The method for the selective hydrogenation of 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol

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 chlorid...

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 selectively hydrogenating 5-hydroxymethylfurfural to synthesize 2,5-furandimethanol. The method uses a magnetic metal-organic coordination polymer as an acid-base bifunctional catalyst and uses low-cost and easily available Carbon alcohol is an in-situ hydrogen donor, and 5-hydroxymethylfurfural is efficiently converted into 2,5-furandimethanol through selective transfer hydrogenation under mild operating conditions, with a maximum yield of 98.6%. The magnetic metal-organic coordination polymer used in the present invention not only has higher acid-base strength, more acid-base sites, larger specific surface area and suitable pore size, but also has a simple production process and is easy to separate and recover, showing Excellent catalytic activity and catalytic stability. In addition, the present invention uses low-carbon alcohol as an in-situ hydrogen donor, which not only avoids the use of molecular hydrogen and increases the safety of the reaction process, but also serves as a reaction solvent to reduce the introduction of exogenous substances and further reduce production costs.

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 as...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/28C07D307/42C07D307/44C07D307/58C08G83/00
CPCC07D307/42C07D307/44C07D307/58C08G83/008B01J31/28B01J2531/0216B01J2531/31B01J2531/26B01J2531/49B01J2531/48B01J2531/42B01J2531/57B01J35/33
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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