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Method for preparing 2,5-furandicarboxaldehyde through photocatalytic dehydrogenation of 5-hydroxymethylfurfural

A technology for hydroxymethyl furfural and furandiformaldehyde, which is applied in the field of photocatalytic 5-hydroxymethyl furfural dehydrogenation and preparation 2, can solve problems such as explosiveness, side reactions, difficult separation of target products and by-products, etc.

Pending Publication Date: 2021-09-14
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current industrial production chooses the greener H 2 o 2 , air and molecular oxygen are used as terminal oxidants, and noble metals are used as catalysts to catalyze the oxidation of HMF to synthesize DFF, but there are still problems such as high energy consumption in the reaction, easy excessive oxidation leads to side reactions, and difficult separation of target products and by-products.
Moreover, in the oxidation process under oxygen environment, it is often accompanied by problems such as flammability and explosion, which cannot be solved.

Method used

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  • Method for preparing 2,5-furandicarboxaldehyde through photocatalytic dehydrogenation of 5-hydroxymethylfurfural
  • Method for preparing 2,5-furandicarboxaldehyde through photocatalytic dehydrogenation of 5-hydroxymethylfurfural
  • Method for preparing 2,5-furandicarboxaldehyde through photocatalytic dehydrogenation of 5-hydroxymethylfurfural

Examples

Experimental program
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Effect test

Embodiment 1

[0029]

[0030] Put 0.1g of 5-hydroxymethylfurfural (Chinese medicine) into a 25ml schlenk tube after crushing, add 10mg of Rh / C 3 N 4 , 1ml of acetonitrile (Chinese medicine), the residual air in the nitrogen replacement reactor is irradiated with light with a wavelength of 390nm in the light reactor, the temperature is adjusted so that the temperature reaches 25 ° C, the reaction is kept for 12 hours, and the stirring rate is 500r / min. After the reaction, the reaction solution was transferred to a sample bottle, and the sample was centrifuged and then sent to a high-performance liquid chromatograph. Liquid phase conditions: chromatographic column: Zorbax-ODS column, 4 × 150mm; column temperature: 30 ° C; mobile phase: methanol: Water=20:80; flow rate 0.6mL / min; injection volume: 20uL. The resulting product is 2,5-furandicarbaldehyde (see the hydrogen spectrum figure 1 , see liquid phase figure 2 ), and the yield was 96.8%.

Embodiment 2

[0032] The specific preparation process and detection method are the same as in Example 1, the difference is only that the Rh / C 3 N 4 change to C 3 N 4 . The product obtained was 2,5-furandicarbaldehyde, and the yield was 92%.

Embodiment 3

[0034] The specific preparation process and detection method are the same as in Example 1, the difference is only that the Rh / C 3 N 4 Change to Pt / C 3 N 4 . The obtained product was 2,5-furandicarbaldehyde, and the yield was 94.5%.

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Abstract

The invention relates to a method for preparing 2,5-furandicarboxaldehyde through photocatalysis dehydrogenation of 5-hydroxymethylfurfural. The preparation method comprises the following steps: in the presence of a photosensitive catalyst and light, carrying out dehydrogenation reaction on 5-hydroxymethylfurfural so as to convert 5-hydroxymethylfurfural into 2,5-furandicarboxaldehyde, wherein the photosensitive catalyst is selected from one or more of metal-loaded or metal-unloaded iron oxide, aluminum oxide, titanium dioxide, tin dioxide, tungsten trioxide, molybdenum sulfide, cadmium sulfide, indium zinc sulfide and carbon nitride, and the metal is selected from one or more of iron, cobalt, nickel, copper, platinum, palladium, ruthenium, rhodium and iridium. The method can be carried out under mild conditions, the conversion rate of the 5-hydroxymethylfurfural is relatively high, and the reaction selectivity is relatively good.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to a method for preparing 2,5-furandicarbaldehyde through photocatalytic dehydrogenation of 5-hydroxymethylfurfural. Background technique [0002] 2,5-furandicarbaldehyde (DFF) is an important downstream product of selective oxidation of 5-hydroxymethylfurfural (HMF). Its molecule contains 2 active aldehyde groups and 1 furan ring, which can be used to synthesize many useful compounds and new polymer materials through hydrogenation, oxidation, polymerization, hydrolysis and other chemical reactions, including medicine, Organic conductors, fluorescent agents and macrocyclic ligands, etc. The industrial production of 2,5-furandicarbaldehyde mostly uses the oxidation method of HMF, and HMF is selectively oxidized to DFF under the reaction conditions of high temperature, oxidant and catalyst catalysis. Potassium permanganate and other oxidants that are harmful to the environment are ofte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46
CPCC07D307/46
Inventor 傅尧朱瑞梁婉莹李兴龙
Owner UNIV OF SCI & TECH OF CHINA
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