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Synthesis method of 2-acetylfuran

A technology for the synthesis of acetylfuran and its synthesis method, which is applied in the field of chemical synthesis of 2-acetylfuran, can solve the problems of high price, difficult separation, difficult acetic acidification reagents, etc., and achieve less solid waste, clean production environment, and low reaction cost Effect

Inactive Publication Date: 2020-12-04
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this process uses a large amount of excess acetic acidification reagent, which is difficult to recover, resulting in difficult separation and increased cost.
[0003] Indian,192962,19Jun 2004 mentioned Fe 3+ The exchanged montmorillonite is used as a catalyst, and furan is used as a solvent for the acylation reaction, and the yield reaches 98%.
Chemical Reagents, 23(6), 370-371, 2001 introduces that with dichloroethane as a solvent and phosphoric acid as a catalyst, the reaction yield of equimolar furan and acetic anhydride is 40%, and a large amount of dichloroethane will be used in the reaction process The reagent is used as a solvent, and the yield is low and the cost is high
[0004] CN101357910A discloses an improved synthetic method of furan and acetic anhydride, but still belongs to furan acetylation

Method used

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  • Synthesis method of 2-acetylfuran
  • Synthesis method of 2-acetylfuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] First add MeOH-water solution (100:1, v / v, 300ml) into the reactor, then add Pd(OAc) 2 (4.5mg, 0.02mmol), NPMoV[(NH 4 ) 5 h 6 PMo 4 V 7.8 o 40 .nH 2 O] (39mg, 0.025mmol), NaCl (2.93mg, 0.05mmol) and MeSO 3 H (19.2mg, 0.2mmol), stir well. Oxygen was then passed into the reactor, and then 2-vinylfuran (188mg, 2mmol) in MeOH-water solution ((100:1, v / v, 150ml)) was added dropwise to the catalytic system within 3 hours. After stirring at room temperature for 30 minutes, the solvent was distilled off under reduced pressure, and the obtained residue was separated by column chromatography (the chromatographic column was UltimateXB-C18 column (250mm*4.6mm, 5μm), and the mobile phase was methanol:0.5% formic acid=60:40 ), to obtain the target product 2-acetylfuran (184.24mg, yield 98.0%), liquid phase purity 99.85%.

[0027] The mass spectrum of 2-acetylfuran (using Agilent Technologies 5973Network mass spectrometer, EI, 70ev): m / e: 110 (M + ),95(M-CH 3 ),67(M-COCH 3...

Embodiment 2

[0029] First add MeOH-water solution (80:1, v / v, 200ml) into the reactor, then add Pd(OAc) 2 (9.0mg, 0.04mmol), NPMoV[(NH 4 ) 5 h 6 PMo 4 V 7.8 o 40 .nH 2 O] (42mg, 0.027mmol), NaCl (1.47mg, 0.025mmol) and MeSO 3 H (9.6mg, 0.1mmol), stir well. Oxygen was then passed into the reactor, and then 2-vinylfuran (188g, 2mmol) in MeOH-water solution ((80:1, v / v, 100ml)) was added dropwise to the catalytic system within 3 hours. After stirring at room temperature for 30 minutes, the solvent was distilled off under reduced pressure, and the obtained residue was separated by column chromatography (the chromatographic column was UltimateXB-C18 column (250mm*4.6mm, 5μm), and the mobile phase was methanol:0.5% formic acid=60:40 ), the target product 2-acetylfuran (184.62g, yield 98.2%) was obtained, and the liquid phase purity was 99.7%.

Embodiment 3

[0031] First add MeOH-water solution (60:1, v / v, 160ml) into the reactor, then add Pd(OAc) 2 (13.5mg, 0.06mmol), NPMoV[(NH 4 ) 5 h 6 PMo 4 V 7.8 o 40 .nH 2 O] (45mg, 0.029mmol), NaCl (2.34mg, 0.04mmol) and MeSO 3 H (4.8mg, 0.05mmol), stir well. Oxygen was then passed into the reactor, and then 2-vinylfuran (188g, 2mmol) in MeOH-water solution ((60:1, v / v, 80ml)) was added dropwise to the catalytic system within 3 hours. After stirring at room temperature for 30 minutes, the solvent was distilled off under reduced pressure, and the obtained residue was separated by column chromatography (the chromatographic column was Ultimate XB-C18 column (250mm*4.6mm, 5μm), and the mobile phase was methanol: 0.5% formic acid=60: 40), the target product 2-acetylfuran (184.43g, yield 98.1%) was obtained, and the product liquid phase purity was 99.8%.

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Abstract

The invention discloses a synthesis method of 2-acetyl furan, which is characterized in that palladium salt and heteropolyacid are used as catalysts, 2-vinyl furan is used as a raw material, and oxygen-containing gas is used as an oxidizing agent to carry out an oxidation reaction to obtain the 2-acetyl furan. In the synthesis reaction process, use of organic solvents with strong irritation such as acetic anhydride and acetyl chloride is avoided, the reaction is carried out in a water phase system, and no pungent smell of the organic solvents exists in a production field. The product conversion rate is high, and a high-purity 2-acetyl furan product can be obtained.

Description

technical field [0001] The invention relates to the technical field of compound synthesis methods, in particular to the chemical synthesis method of 2-acetylfuran. Background technique [0002] 2-Acetylfuran is an important raw material for the synthesis of ammonium furan, an intermediate of cefuroxime. Synthetic 2-acetylfuran is the method that carries out acetylation with furan at present, and the acylating agent of prior art has the acetyl chloride mentioned in Synthetic Communications, 38 (2), 255-264, 2008; Chinese Journal of Antibiotics 30 (5) Acetic anhydride mentioned in 304,313,2005,Indian,192962,19Jun2004 etc; 2165-2168, acetic acid mentioned in 2004 et al. However, this process uses a large amount of excess acetic acidification reagent, which is difficult to recover, resulting in difficult separation and increased cost. [0003] Indian,192962,19Jun 2004 mentioned Fe 3+ The exchanged montmorillonite is used as a catalyst, and furan is used as a solvent for the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46B01J31/22
CPCB01J31/2226C07D307/46
Inventor 宋道淮孙智源侯乐伟宋君
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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