Method for preparing 5-formyl-2-furancarboxylic acid through catalytic oxidation of 5-hydroxymethylfurfural

A technology for catalytic oxidation of hydroxymethylfurfural, which is applied in chemical instruments and methods, catalytic reactions, physical/chemical process catalysts, etc., can solve the problems of high energy consumption and equipment requirements, high cost and large-scale application, and achieve selective High stability, mild reaction conditions, and simple process operation

Active Publication Date: 2021-12-28
YANTAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, the activated carbon-supported Pt catalyst (Pt / C) reported by Lilga et al. can achieve 83% FFCA selectivity at 130 °C and 150 psi air conditions, but the high cost of the noble metal platinum in the catalyst limits its large-scale application.
(Lilga, M.A., Top.Catal.2010, 53, 1264-1269.) Dibenedetto et al. developed a new catalytic method using MgO CeO2 mixed oxides in an alkaline-free aqueous solution and 0.9 Under the condition of MPa oxygen pressure, 90% FFCA yield is obtained, but the reaction is carried out under high pressure environment, which requires relatively high energy consumption and equipment

Method used

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  • Method for preparing 5-formyl-2-furancarboxylic acid through catalytic oxidation of 5-hydroxymethylfurfural
  • Method for preparing 5-formyl-2-furancarboxylic acid through catalytic oxidation of 5-hydroxymethylfurfural

Examples

Experimental program
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Effect test

Embodiment 1

[0022] (NH 4 ) 3 h 6 CoMo 6 o 24 Preparation example of

[0023] Weigh 1.0583g CoSO 4 ·7H 2 O, dissolved in 7.5 mL deionized water, added 1.5 mL 30 wt% H 2 o 2 , stirred at room temperature for 30 minutes, recorded as solution 1. At the same time, weigh 7.728g (NH 4 ) 6 Mo 7 o 24 ·6H 2 O, dissolved in 65mL deionized water, placed in an oil bath and heated to boiling, recorded as solution 2. Solution 1 was added dropwise to solution 2, and the resulting solution was refluxed for 10 minutes, then evaporated for 15 minutes, left to stand overnight, filtered, washed with water, and vacuum-dried at 60°C for 12 hours to obtain Anderson type heteropolyacid salt (NH 4 ) 3 h 6 CoMo 6 o 24 .

Embodiment 2

[0025] (NH 4 ) 4 ZnM 6 o 24 Preparation example of

[0026] Weigh 0.5g ZnSO 4 ·7H 2 O, dissolved in 29 mL of deionized water, recorded as solution 1. At the same time, weigh 2.5g (NH 4 ) 6 Mo 7 o 24 ·6H 2 O, dissolved in 40mL deionized water, placed in an oil bath and heated to boiling, recorded as solution 2. Add solution 1 dropwise to solution 2, and the obtained solution is rotary evaporated for 10 minutes, then evaporated for 15 minutes, filtered while it is hot, the filtrate is left to stand for crystallization, filtered, washed with water, and dried in vacuum at 60°C for 12 hours to obtain Anderson type heteropolyacid salt (NH 4 ) 4 ZnM 6 o 24 .

Embodiment 3

[0029] Catalytic oxidation of 5-hydroxymethylfurfural to prepare 5-formyl-2-furanoic acid comprises the following steps:

[0030] (1) Mix 1-butyl-3-methylimidazolium chloride (BmimCl) and caprolactam (CPL) in a molar ratio of 3 / 1, heat and stir at 80°C for 1 hour to obtain a homogeneous and clear liquid, That is, deep eutectic solvent (DES).

[0031] (2) Add 0.4mmol HMF to 4g of DES synthesized in step (1), then add 40mg (NH 4 ) 3 h 6 CoMo 6 o 24 Catalyst, and then continue to feed oxygen at a flow rate of 20mL / min, carry out HMF oxidation reaction at 130°C for 6h, and obtain a mixed liquid containing 5-formyl-2-furancarboxylic acid (FFCA).

[0032] (3) Dilute the mixed solution with water as a solvent, and analyze it with a high-performance liquid chromatograph, and use a standard solution to identify the product type. The results are shown in Table 1, showing that the HMF conversion rate is 100%, and the FFCA yield reaches 74%.

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Abstract

The invention discloses a method for preparing 5-formyl-2-furancarboxylic acid through catalytic oxidation of 5-hydroxymethylfurfural. The method specifically comprises the following steps: dissolving 5-hydroxymethylfurfural and an Anderson type polyoxometallate catalyst in a deep eutectic solvent, introducing oxygen at a specified temperature, and carrying out a reaction to obtain the 5-formyl-2-furancarboxylic acid. According to the above technical process, the 5-formyl-2-furancarboxylic acid (with yield reaching 97%) can be efficiently synthesized, reaction conditions are mild, and the method is a cheap and efficient FFCA preparation method. Meanwhile, the technological process is easy to operate, high in selectivity and low in cost, reference is provided for renewable biomass resource conversion, and the method has important significance on development of novel renewable energy sources.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a method for preparing 5-formyl-2-furancarboxylic acid by catalytically oxidizing 5-hydroxymethylfurfural. Background technique [0002] Biomass is an easy-to-obtain and renewable non-fossil carbon source. It is the fourth largest energy source in my country after coal, oil and natural gas. It is regarded as one of the new energy sources most likely to replace fossil fuels and organic molecules. . The study of 5-hydroxymethylfurfural (HMF), a biobased precursor of many industrially valuable chemicals, has attracted great attention. HMF can be used to synthesize many high value-added products, such as 2,5-furandicarbaldehyde (DFF), 5-formyl-2-furanoic acid (FFCA) and 2,5-furandicarboxylic acid (FDCA), etc. Among them, FFCA has both formyl and carboxyl groups, and is widely used in the fields of chemical intermediates and drug synthesis. Therefore, the highly selective oxidatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68B01J31/34
CPCC07D307/68B01J31/34B01J31/0247B01J27/19B01J27/24B01J2231/70B01J35/19
Inventor 吕宏缨杨凯旋孙艳斌魏星瑶
Owner YANTAI UNIV
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