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A method for preparing 2,5-furandicarboxylic acid diesters from 5-hydroxymethylfurfural

A technology of furandicarboxylate diester and hydroxymethyl furfural, which is applied in the field of organic catalysis synthesis, can solve the problems of long reaction time, difficult large-scale application of catalytic effect catalyst cost, increased production cost, etc., achieves good application prospects, and solves the problems of reaction inefficient effect

Active Publication Date: 2021-08-31
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Prepare 2 by 5-hydroxymethylfurfural oxidative esterification, the method of 5-furandicarboxylic acid diester compound has more reports, what mainly adopt at present is noble metal catalyst (Pd, Au etc.) catalyst (CN 108892652 A, Journal ofCatalysis 326 (2015) 1-8, Journal of Catalysis 265 (2009) 109-116), although they can achieve good catalytic effects, but limited by the cost of catalysts, it is difficult to apply them on a large scale
In addition, Co-N-C catalysts have also been widely used, but such catalysts often require the use of co-catalysts (ChemSusChem 7 (2014) 3334-3340; ChemCatChem 8 (2016) 2907-2911) or longer reaction times ( CN 109293609 A, CN104177319 B), this also increases production cost

Method used

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  • A method for preparing 2,5-furandicarboxylic acid diesters from 5-hydroxymethylfurfural
  • A method for preparing 2,5-furandicarboxylic acid diesters from 5-hydroxymethylfurfural
  • A method for preparing 2,5-furandicarboxylic acid diesters from 5-hydroxymethylfurfural

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Experimental program
Comparison scheme
Effect test

Embodiment 1-11

[0020] Add 0.03g of 5-hydroxymethylfurfural and 3g of methanol (1wt%) to a 20mL autoclave, and then add 0.04g of Co 7 K 3 -N-C, Co 7 Fe 3 -N-C, Co 7 mn 3 -N-C, Co 7 Cu 3 -N-C, Co 7 Bi 3 -N-C, Co 7 Cs 3 -N-C, Co 7 Sr 3 -N-C, Co 7 Mg 3 -N-C, Co 7 Ca 3 -N-C, Co 7 Ni 3 -N-C, Co 7 Ce 3 -N-C (wherein the loading of the metal is 2.4wt%, and the molar ratio of the two metals is 7:3) is used as a catalyst, the reactor is sealed, 2bar oxygen is introduced, vigorously stirred (500rpm), heated to 80°C and maintained for 4 hours , finish the reaction and cool to room temperature and take samples, use GC-MS (Shimadzu) and GC (Agilent) to carry out qualitative and quantitative detection, and the detection results are listed in Table 1 as serial numbers 1-11.

Embodiment 12-15

[0022] Add 0.03g of 5-hydroxymethylfurfural and 3g of methanol (1wt%) to a 20mL autoclave, and then add 0.04g of Co 9 Cu 1 -N-C, Co 4 Cu 1 -N-C, Co 3 Cu 2 -N-C, CoCu-N-C (wherein the load of metal is 2.4wt%, the molar ratio of two kinds of metals is respectively 9:1, 4:1, 3:2, 1:1) as catalyst, seal the reactor, pass into 2bar oxygen, vigorous stirring (500rpm), heated to 80°C and maintained for 4 hours, finished the reaction, cooled to room temperature and took samples, using GC-MS (Shimadzu) and GC (Agilent) for qualitative and quantitative detection, the detection results are listed in the table The serial number in 1 is 12-15.

Embodiment 16-18

[0024] In the autoclave of 20mL, add respectively 0.09g, 0.3g and 0.6g of 5-hydroxymethylfurfural and 3g methanol (substrate concentrations are respectively 2.9wt%, 9.1wt% and 16.7wt%), then add 0.12g , 0.4g and 0.8g Co 7 Cu 3 -N-C (wherein the loading of the metal is 2.4wt%, and the molar ratio of the two metals is 7:3) is used as a catalyst, the reactor is sealed, 2bar oxygen is introduced, vigorously stirred (500rpm), heated to 80°C and maintained for 4 hours , finish the reaction and cool to room temperature and take samples, use GC-MS (Shimadzu) and GC (Agilent) to carry out qualitative and quantitative detection, and the detection results are listed in Table 1 as serial numbers 16-18.

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Abstract

The invention discloses a method for preparing 2,5-furandicarboxylic acid diesters from 5-hydroxymethylfurfural. The invention uses cheap and specific non-precious metals as catalysts, and uses cheap and easily available oxygen or air as oxygen source, under mild reaction conditions, highly efficient preparation of high-purity dimethyl 2,5-furandicarboxylate, solves the problems of low reaction efficiency, low product yield, high cost and the like in the prior art, and has great advantages Good application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic catalytic synthesis, in particular to a method for preparing 2,5-furandicarboxylic acid diester compounds from 5-hydroxymethylfurfural. Background technique [0002] 2,5-furandicarboxylic acid, as a renewable bio-based polymer monomer, has attracted extensive attention from industry and academia, in which 2,5-furandicarboxylic acid and ethylene glycol can be used as raw materials through the polymerization reaction. Preparation of polyethylene furandicarboxylate, which has better gas barrier properties, better mechanical properties and better degradability than the corresponding petroleum-based polymer polyethylene terephthalate, It is a renewable polymer with very broad application prospects. However, due to the inherent high boiling point and poor solubility of 2,5-furandicarboxylic acid, it is difficult to produce 2,5-furandicarboxylic acid on a large scale and to separate and purify it. Comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/68
CPCC07D307/68
Inventor 唐兴刘淮孙勇曾宪海林鹿雷廷宙
Owner XIAMEN UNIV
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