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Method for producing furandicarboxylic acid and derivatives thereof from furfural

A technology of furandicarboxylic acid and furfural, applied in the direction of organic chemistry and the like, can solve the problems of high cost, difficult to have recyclability and catalytic stability, harsh reaction conditions, etc., and achieve the effect of reducing the cost of raw materials

Pending Publication Date: 2020-05-15
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the high price of the above-mentioned precious metals and the inactivation characteristics of by-products and intermediates that will be adsorbed or deposited on their active sites in practical applications, it is difficult to have recyclability and catalytic stability.
In order to avoid the problem of high cost of noble metal catalysts, Hayashi (ChemSus Chem, 2017, 10, 654-658), Saha (Journal of Catalysis, 2013, 299, 316-320) and others used MnO 2 , Fe-POP and other transition metal catalysts catalyze the oxidation of 5-HMF, although the catalyst cost is low, the reaction conditions are relatively harsh and the product selectivity is poor
[0004] Although the above-mentioned processes for preparing FDCA from 5-HMF have their own advantages and disadvantages, fundamentally there is a commonality of using 5-HMF as a raw material
In fact, the price of 5-HMF is between US$500-1500 / kg, which is much higher than the petroleum-based chemicals currently used, because the process of producing 5-HMF from glucose / fructose produces many by-products, such as soluble In addition, 5-HMF itself can generate levulinic acid and formic acid, which brings great difficulties to the large-scale separation and purification of 5-HMF, so the price of 5-HMF has always been at the top high
Therefore, any process of preparing FDCA from 5-HMF faces a huge challenge, that is, the extremely high cost of raw materials

Method used

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  • Method for producing furandicarboxylic acid and derivatives thereof from furfural
  • Method for producing furandicarboxylic acid and derivatives thereof from furfural
  • Method for producing furandicarboxylic acid and derivatives thereof from furfural

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Embodiment 1

[0035] (1) Preparation of 2-methylfuran from furfural

[0036] Hydrogenation catalysts are prepared by impregnation. Pd precursor PdCl 2 Dissolved in a certain amount of water. A certain amount of SiO 2 Add PdCl 2 In solution, the metal occupies SiO 2 2% of mass. The mixture was stirred until dry, dried overnight at 80°C, and then ground into powder. The powder was calcined in a nitrogen atmosphere at 350°C, and then reduced with hydrogen at the same temperature to obtain a hydrogenation catalyst.

[0037] The present embodiment takes furfural as raw material. Add 1g of hydrogenation catalyst into the reaction kettle, add 10g of furfural, and then add 80mL of anhydrous methanol as a solvent. After sealing the reactor, first use N 2 Replace the air in the reactor, and then use H 2 Replace the N in the reactor 2 , then filled with 4MPa of H 2 . The temperature of the reaction kettle was raised to 150° C., and the reaction was carried out for 4 hours.

[0038] After...

Embodiment 2

[0054] (1) Preparation of 2-methylfuran from furfural

[0055] Hydrogenation catalysts are prepared by impregnation. Ni precursor Ni(NO 3 ) 2 ·6H 2 O dissolved in a certain amount of water. A certain amount of activated carbon is added to the precursor solution, and the metal accounts for 20% of the mass of the activated carbon. The mixture was stirred until dry, dried overnight at 80°C, and then ground into powder. The powder was calcined in a nitrogen atmosphere at 350°C, and then reduced with hydrogen at the same temperature to obtain a hydrogenation catalyst.

[0056] The present embodiment takes furfural as raw material. Add 1g of hydrogenation catalyst into the reaction kettle, add 10g of furfural, and then add 80mL of anhydrous tetrahydrofuran as a solvent. After sealing the reactor, first use N 2 Replace the air in the reactor, and then use H 2 Replace the N in the reactor 2 , then filled with 2MPa of H 2 . The reaction kettle was heated to 200°C and reacte...

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Abstract

The invention discloses a method for producing furandicarboxylic acid and derivatives thereof from furfural. The method comprises the following steps: furfural is reduced to 2-methylfuran under the hydrogen condition; acetylation reaction is carried out on 2-methylfuran to obtain 5-methyl-2-acetylfuran; 5-methyl-2-acety furan reacts with ester to obtain methyl 5-methyl-2-furanformate, methyl 5-methyl-2-furanformate is oxidized into monomethyl 2,5-furandicarboxylate under the oxygen condition, and monomethyl 2,5-furandicarboxylate is hydrolyzed into monomethyl 2,5-furandicarboxylate or furtheresterified with methyl alcohol to generate dimethyl 2,5-furandicarboxylate. The cheap five-carbon furan compound furfural is used as a raw material, and the 2 5-furandicarboxylic acid and the derivatives thereof are prepared by a strategy of increasing a carbon chain, so that the cost of the raw material is greatly reduced. The product provided by the invention has high purity and can be directlyused as a polymerization monomer of PET polyester.

Description

technical field [0001] The application relates to the technical field of biomass conversion and utilization, in particular to a method for producing furandicarboxylic acid and its derivatives from furfural. Background technique [0002] The shortage of fossil resources such as oil and coal has gradually turned people's attention to the utilization of biomass resources. It is of great significance to use the abundant biomass resources to prepare a series of fine chemicals and polymer materials through catalytic conversion. As an important derivative of biomass resources, 2,5-furandicarboxylic acid (FDCA) has the potential value of replacing terephthalic acid, a petrochemical derivative in the field of polyester, and is listed as 12 high value-added organisms by the US Department of Energy. one of the base chemicals. In addition, 2,5-furandicarboxylic acid is also widely used in the production of fine chemicals, pharmaceuticals and pesticides. [0003] At present, the resea...

Claims

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Application Information

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IPC IPC(8): C07D307/68
CPCC07D307/68Y02P20/584
Inventor 赵晨赵磊李愽龙
Owner EAST CHINA NORMAL UNIVERSITY
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