Method for preparing 2, 5-furandicarboxylic acid by taking 2-furancarboxylic acid as raw material through one-pot method

A technology of furandicarboxylic acid and furanic acid, which is applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve problems such as poor purity, achieve mild reaction conditions, The effect of a simple synthesis process

Active Publication Date: 2022-02-25
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the method of preparing 2,5-furandicarboxylic acid from 2-furancarboxylic acid has also been recently reported in literature or patents [ACS Sustainable Chem.Eng. ], but the poor purity of the prepared 2,5-furandicarboxylic acid generally exists, accompanied by the formation of some 2,3-furandicarboxylic acid and 2,4-furandicarboxylic acid

Method used

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  • Method for preparing 2, 5-furandicarboxylic acid by taking 2-furancarboxylic acid as raw material through one-pot method
  • Method for preparing 2, 5-furandicarboxylic acid by taking 2-furancarboxylic acid as raw material through one-pot method
  • Method for preparing 2, 5-furandicarboxylic acid by taking 2-furancarboxylic acid as raw material through one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0019] (1) Effects of catalysts composed of different palladium compounds and ligands on the preparation of 2,5-furandicarboxylic acid from 2-furancarboxylic acid

[0020] Specific experimental steps: Add 5mL of N-methylpyrrolidone solvent, 2.5mL of deionized water, 5mmol of 2-furanoic acid, 0.25mmol of palladium compound, 0.25mmol of ligand, and 10mmol of liquid into a 50mL polytetrafluoroethylene-lined stainless steel autoclave. bromine, 15 mmol sodium acetate and 2.5 mL formic acid. After sealing, replace the air in the reactor with nitrogen, then flush into 1.0 MPa of carbon monoxide, and react at 90°C for 9 hours. After the reaction, cool to room temperature, and calculate 2,5-furan by HPLC (high performance liquid chromatography). The yield of formic acid.

[0021]

[0022]

[0023] Note: XANTPHOS, 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene; BINAP, 1,1'-binaphthyl-2,2'-bisdiphenylphosphine; DPPP, 1 ,3-bis(diphenylphosphino)propane; XANTPHOS-SO 3 Na, water-s...

Embodiment 11-15

[0025] (2) Effects of different bromination reagents on the preparation of 2,5-furandicarboxylic acid from 2-furancarboxylic acid

[0026] Specific experimental steps: Add 5mL of N-methylpyrrolidone solvent, 2.5mL of deionized water, 5mmol of 2-furanoic acid, 0.25mmol of palladium acetate, and 0.25mmol of water-soluble ligand into a 50mL polytetrafluoroethylene-lined stainless steel autoclave XANTPHOS-SO 3Na, 10mmol brominating reagent, 15mmol sodium acetate and 2.5mL formic acid. After sealing, replace the air in the reactor with nitrogen, then flush into 1.0 MPa of carbon monoxide, and react at 90°C for 9 hours. After the reaction, cool to room temperature, and calculate 2,5-furan by HPLC (high performance liquid chromatography). The yield of formic acid.

[0027]

[0028] Note: XANTPHOS, 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene; BINAP, 1,1'-binaphthyl-2,2'-bisdiphenylphosphine; DPPP, 1 ,3-bis(diphenylphosphino)propane; XANTPHOS-SO 3 Na, water-soluble 4,5-bis(d...

Embodiment 16-21

[0030] (3) Effects of different buffers on the preparation of 2,5-furandicarboxylic acid from 2-furancarboxylic acid

[0031] Specific experimental steps: Add 5mL of organic solvent, 2.5mL of deionized water, 15mmol of various sodium salts, 2.5mL of various acids, 5mmol of 2-furancarboxylic acid, 0.25mmol of Palladium chloride, 0.25mmol water-soluble ligand XANTPHOS-SO 3 Na and 10mmol liquid bromine. After sealing, replace the air in the reactor with nitrogen, then flush into 1.0 MPa of carbon monoxide, and react at 90°C for 9 hours. After the reaction, cool to room temperature, and calculate 2,5-furan by HPLC (high performance liquid chromatography). The yield of formic acid.

[0032]

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Abstract

The invention discloses a method for preparing 2, 5-furandicarboxylic acid by taking 2-furancarboxylic acid as a raw material through an one-pot method, which comprises the following steps of: stirring and reacting a solution system containing 2-furancarboxylic acid, a solvent, a bromination reagent, a catalyst and a buffer solution in a carbon monoxide atmosphere at the temperature of 50-150 DEG C for 4-24 hours by taking 2-furancarboxylic acid as the raw material under the action of a catalyst; and then separating out the target product 2, 5-furandicarboxylic acid. The 2, 5-furandicarboxylic acid is prepared from the biomass-derived 2-furancarboxylic acid as a raw material through the one-pot bromination-carbonylation cascade reaction, the synthesis process is a one-pot synthesis technology, the synthesis steps are simple, and the 2, 5-furandicarboxylic acid is directly obtained without acidification after the reaction is finished.

Description

technical field [0001] The invention belongs to the chemical field of homogeneous catalysis and synthesis of fine chemicals, and relates to a method for preparing 2,5-furandicarboxylic acid in a one-pot method using 2-furancarboxylic acid catalyzed by a catalyst of a noble metal palladium compound as a raw material. Background technique [0002] 2,5-furandicarboxylic acid (2,5-FDCA, also known as 2,5-difuroic acid), the structural formula is It is one of the 10 bio-based chemical substances with high added value [Green Chemistry, 2010, 12, 539-554.], which can be used in the fields of synthetic polyester, plasticizer, fire protection and medicine [Chemical Progress, 2021, 40, 1008- 1017.]. Especially in the polyester industry, 2,5-furandicarboxylic acid can replace petroleum-based terephthalic acid as a suitable monomer for polymerization with diols and diamines (preparation of polyester or polyamide). Compared with traditional terephthalic acid polymers, polymeric materi...

Claims

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Application Information

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IPC IPC(8): C07D307/68B01J31/24
CPCC07D307/68B01J31/2404B01J2531/824Y02P20/584
Inventor 刘晔姚垠青路勇
Owner EAST CHINA NORMAL UNIV
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