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Green method for synthesizing 2-furylglyoxylic acid

A technology of furylglyoxylic acid and furan, which is applied in chemical recovery, organic chemistry, etc., can solve the problems of poor environmental protection and low addition yield, and achieve easy separation and recovery, reduction of three wastes, increase rate and selectivity Effect

Pending Publication Date: 2019-09-20
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 2-furylglyoxylic acid is a key intermediate for the preparation of ammonium furan salts, and its known synthetic routes mainly include the following: (1) CN 107573305, CN 105330627, CN 105254603, CN 103145656, CN 101538255, CN102952118, CN 103923040, etc. all use furan as the starting material to react with acetic anhydride to prepare acetylfuran, and then oxidize it under the action of sodium nitrite to obtain 2-furylglyoxylic acid. However, this route often produces a large amount of high-salt and high-COD wastewater, which is environmentally friendly. (2) CN 102010390 uses furoic acid as the starting material, obtains 2-furylformyl chloride through chlorination, then cyanides with sodium cyanide, and finally obtains the product by acidic hydrolysis
The addition yield of hydrocyanic acid and furfural is low and hydrocyanic acid is a highly toxic substance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Step (1): Add 200 g of dichloromethane, 100 g of furan, 120 g of chloroacetic acid and 1.2 g of Y-type zeolite molecular sieve into the reaction kettle, stir and react at 15 °C for 8 h, and filter the reaction solution to recover Y-type zeolite molecular sieve, vacuum distillation and filtration gained reaction solution and reclaim dichloromethane to obtain 2-furyl acetic acid;

[0023] Step (2): Add 100 g methanol, 0.1 g tricobalt tetroxide and 0.6 g 2,2,6,6-tetramethylpiperidine oxide to the obtained 2-furyl acetic acid, and feed oxygen until the pressure is 0.4 MPa , heated up to 40 ℃ and reacted for 10 h. After the oxidation was completed, filter the reaction solution to recover tricobalt tetroxide. Distill and filter the reaction solution under reduced pressure and recover methanol to obtain 185.5 g of 2-furylglyoxylic acid (yield 90.13%, purity 99.32 %).

Embodiment 2

[0025] Step (1): Add 322 g of chloroform, 124 g of furan, 161.2 g of chloroacetic acid and 3.5 g of Y-type zeolite molecular sieves into the reaction kettle, stir and react at 22 °C for 6 h, and filter the reaction liquid to recover Y-type zeolite molecular sieve, vacuum distillation and filtration of the resulting reaction solution and recovery of chloroform to obtain 2-furyl acetic acid;

[0026] Step (2): Add 248 g ethanol, 0.4 g tricobalt tetroxide and 1.4 g 2,2,6,6-tetramethylpiperidine oxide to the obtained 2-furyl acetic acid, and feed oxygen until the pressure is 0.7 MPa , heated up to 50 ℃ and reacted for 8 h. After the oxidation was completed, filter the reaction solution to recover tricobalt tetroxide. Distill and filter the reaction solution under reduced pressure and recover ethanol to obtain 236.7 g of 2-furylglyoxylic acid (yield 90.55%, purity 99.37 %).

Embodiment 3

[0028] Step (1): Add 307 g of carbon tetrachloride, 96 g of furan, 134.4 g of chloroacetic acid and 4.1 g of Y-type zeolite molecular sieves into the reactor, and stir for 5 h at 27 °C. Reclaiming Y-type zeolite molecular sieves, depressurizing distillation and filtering the resulting reaction solution and reclaiming carbon tetrachloride to obtain 2-furyl acetic acid;

[0029] Step (2): Add 268 g of acetonitrile, 0.5 g of cobalt tetroxide and 1.8 g of 2,2,6,6-tetramethylpiperidine oxide to the obtained 2-furyl acetic acid, and feed oxygen until the pressure is 0.9 MPa , heated to 58 ℃ and reacted for 6.5 h. After the oxidation was completed, filter the reaction solution to recover tricobalt tetroxide. Distill and filter the obtained reaction solution under reduced pressure and recover acetonitrile to obtain 178.3 g of 2-furylglyoxylic acid (yield 90.24%, purity 99.37 %).

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Abstract

The invention provides a green method for synthesizing 2-furylglyoxylic acid, and belongs to the technical field of pharmaceutical chemical processes. The method includes the following steps: (1) adding solvents, furan, chloroacetic acid and Y-type zeolite molecular sieves to a reaction kettle, and carrying out a reaction to obtain 2-furylacetic acid; (2) adding solvents, cobaltosic oxide and 2,2,6,6-tetramethylpiperidine oxide to the obtained 2-furylacetic acid, and injecting oxygen to oxidize the 2-furylacetic acid to obtain the 2-furylglyoxylic acid. The green method for synthesizing the 2-furylglyoxylic acid has the advantages that a raw material used, namely the chloroacetic acid, is cheap and easy to obtain, heterogeneous catalysts, namely the Y-type zeolite molecular sieves and the cobaltosic oxide, are easy to separate and recover and can be recycled, an auxiliary catalyst, namely the 2,2,6,6-tetramethylpiperidine oxide, is beneficial to acceleration and selectivity improvement of oxidation reactions, the oxygen serving as an oxidant is green and environmentally friendly, and accordingly, costs and generated 'three wastes' of the obtained 2-furylglyoxylic acid are greatly reduced; the purity and the yield of the obtained 2-furylglyoxylic acid are respectively higher than 99% and 90%.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical technology, and in particular relates to a green method for synthesizing 2-furylglyoxylic acid. Background technique [0002] Cefuroxime axetil is an orally effective second-generation cephalosporin-based prodrug of cefuroxime, which is the acetoxyethyl ester of cefuroxime; after oral administration, it is absorbed in the body and hydrolyzed by esterase to release cefuroxime Fuxin can inhibit the synthesis of bacterial cell walls and prevent the growth and reproduction of bacteria, so it has a strong antibacterial effect. [0003] Furan ammonium salt is the key side chain for the synthesis of cefcapene pivoxil. At present, furan is mainly used as the starting material, and the target product is obtained through four steps of acylation, oxidation, oximation and salt formation. [0004] 2-furylglyoxylic acid is a key intermediate for the preparation of ammonium furan salts, and its ...

Claims

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Application Information

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IPC IPC(8): C07D307/54
CPCC07D307/54Y02P20/584
Inventor 郑庚修王彬高令峰管西博侯乐伟
Owner UNIV OF JINAN
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