Method for preparing 2, 5-furandicarboxylic acid by conducting catalytic oxidation on 5-hydroxymethylfurfural

A technology of hydroxymethylfurfural and furandicarboxylic acid, which is applied in the field of preparation of 2,5-furandicarboxylic acid, can solve the problems of low FDCA yield, poor stability, and only 4.2%, achieving high yield and selectivity, and reaction Mild conditions and good reusability

Active Publication Date: 2017-04-19
EAST CHINA UNIV OF SCI & TECH
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Problems solved by technology

Although these noble metal catalysts have good catalytic selectivity and high stability, the noble metals are expensive and not suitable for large-scale industrial production.
However, the existing non-noble metal heterogeneous catalysts generally have the problems of low selectivity and poor stability under oxygen or air conditions. For example, Zhang Zehui’s research group used nanometer Fe 3 o 4 -CoOx catalyzes the oxidation of HMF to prepare FDCA, using tert-butanol peroxide as the oxidant, the FDCA yield can reach 68.6%, but if oxygen is used as the oxidant, the FDCA yield is only 4.2% (Shuguo Wang, Zehui Zhang, ACS Sustainable Chem. Eng ., 2015, 3: 406-412)
The porphyrin cobalt catalyst supported by chloromethyl resin can also obtain higher FDCA yield under the condition of tert-butanol peroxide as oxidant, but the FDCA yield is very low when oxygen is used as oxidant (Langchang Gao, Kejian Deng , Zehui Zhang, Chemical Engineering Journal, 2015, 270: 444-449)

Method used

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  • Method for preparing 2, 5-furandicarboxylic acid by conducting catalytic oxidation on 5-hydroxymethylfurfural
  • Method for preparing 2, 5-furandicarboxylic acid by conducting catalytic oxidation on 5-hydroxymethylfurfural
  • Method for preparing 2, 5-furandicarboxylic acid by conducting catalytic oxidation on 5-hydroxymethylfurfural

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Experimental program
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Effect test

Embodiment 1

[0025] Put 600mg of cerium-chromium composite oxide catalyst prepared by co-precipitation method (the mass percentage of cerium oxide is 50%), 10mL of 0.05mol / L HMF aqueous solution, 0.424g of sodium carbonate, into a stainless steel autoclave, and fill it with 3MPa oxygen As an oxygen source, it was reacted at 150° C. for 12 hours while being magnetically stirred. Finally, the reaction solution was analyzed by HPLC for substrate conversion rate and product yield. The conversion rate of HMF was 97.7%, and the yield of FDCA was 86.7%.

Embodiment 2

[0027] Put 100mg of cerium-manganese composite oxide catalyst prepared by hydrothermal method (the mass percentage of cerium oxide is 30%), 10mL of 0.05mol / L HMF aqueous solution, 0.08g of sodium hydroxide, into a stainless steel autoclave, and fill it with a 2MPa Oxygen was used as an oxygen source, and the reaction was carried out at 110° C. for 8 hours while magnetically stirring. Finally, the reaction solution was analyzed by HPLC for substrate conversion rate and product yield. The conversion rate of HMF was 98.5%, and the yield of FDCA was 81.8%.

Embodiment 3

[0029] Add 30mg of cerium-iron composite oxide catalyst prepared by sol-gel method (the mass percentage of cerium oxide is 10%), 10mL of 0.05mol / L HMF aqueous solution, 0.015g of ethylenediamine, into a stainless steel autoclave, and fill it with 0.5 MPa oxygen was used as an oxygen source, and the reaction was carried out at 70° C. for 6 hours while magnetically stirring. Finally, the reaction solution was analyzed by HPLC for substrate conversion rate and product yield. The conversion rate of HMF was 98.6%, and the yield of FDCA was 84.8%.

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Abstract

The invention relates to a method for preparing 2, 5-furandicarboxylic acid (FDCA) by conducting catalytic oxidation on a biomass derivative, namely 5-hydroxymethylfurfural (HMF) and belongs to the field of preparing renewable chemicals through synthesis of biomass and derivatives. The method comprises the steps that non-noble-metal, namely cerium-based composite oxide, is utilized as a catalyst; oxygen or air serves as an oxidizing agent; and effective catalytic oxidation is conducted on the 5-hydroxymethylfurfural for synthesizing the 2, 5-furandicarboxylic acid. The method is easy to operate and mild in condition; the yield of the 2, 5-furandicarboxylic acid can reach 86.7% at a maximum; in addition, the catalyst is easy to separate and recycle and good in reusability; and good industrialized application prospect is achieved.

Description

technical field [0001] The invention relates to a method for preparing 2, 5-furandicarboxylic acid (FDCA), which belongs to the field of synthesis of renewable chemicals from biomass and derivatives. More specifically, it relates to a method for preparing 2,5-furandicarboxylic acid by oxidation of 5-hydroxymethylfurfural. Background technique [0002] 2,5-Furandicarboxylic acid (FDCA), as a furan compound that can be prepared from biomass, was identified as one of the 12 "platform compounds" by the US Department of Energy in 2004. It has a furan ring and two carboxyl groups, and is expected to replace petroleum-based monomer terephthalic acid in the polyester industry to synthesize green degradable plastics; it can also replace phthalic acid to synthesize green non-toxic plasticizers. Introducing the utilization of biomass into the polyester industry can reduce the dependence of the polyester industry on petroleum energy and reduce environmental pollution. In addition, sta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68B01J23/34B01J23/10B01J23/83B01J23/26B01J23/22
CPCB01J23/002B01J23/10B01J23/22B01J23/26B01J23/34B01J23/83C07D307/68Y02P20/584
Inventor 王艳芹李超群韩学旺刘晓晖夏启能
Owner EAST CHINA UNIV OF SCI & TECH
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