Preparation method of furanone acid

A technology of furanoic acid and acetylfuran, applied in the field of medicine and chemical industry, can solve the problems of many side reactions of furanoic acid, large amount of oxidant, low toxicity, etc., and achieves the advantages of reducing side reactions, reducing the generation of by-products, and improving yield. Effect

Active Publication Date: 2019-07-12
SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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AI Technical Summary

Problems solved by technology

CN102863407A discloses a method of using acetylfuran as a raw material and using sodium nitrite to oxidize under strong acid conditions. The method obtains furanone acid by one-step reaction, the route is short, the raw material is cheap and easy to obtain, and the toxicity is low, which is more suitable for industrialization. The method uses a large amount of oxidant (the molar ratio of acetylfuran to oxidant sodium nitrite is 1:4.25), and there is a problem that the yield is low due to deep oxidation
[0006] At present, there are many side reactions, low yield, and large amount of oxidant in the preparation of furanone acid from 2-acetylfuran.

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0037] (1) Preparation of nitrite

[0038] Add 120mL of water, 40g of n-butanol, and 31.8g of concentrated sulfuric acid into a 500mL reaction bottle, and cool it to 0°C in an ice bath, and slowly add 112g of 40% sodium nitrite aqueous solution to it for 1.5 hours, and the temperature during the dropping process should not exceed 5 °C, the dropwise addition was completed, stirred for 30 min, and the ester layer was separated to obtain 51 g of butyl nitrite.

[0039] (2) Preparation of furanone acid

[0040] Dissolve 20g of 2-acetylfuran in 150mL of 10% dilute hydrochloric acid solution, add 2g of concentrated sulfuric acid, 0.1g of catalyst γ-Al 2 o 3 / Pd(II), control the temperature to 40-55°C, add 20.6g of n-butyl nitrite dropwise for 1h, continue to stir for 1h after the dropwise addition, adjust the pH to 2.8 after the reaction, filter and recover the catalyst, the filtrate Add 100 mL of dichloromethane to extract n-butanol and unreacted acetylfuran produced by the reac...

Embodiment 2

[0043] The implementation conditions are the same as in Example 1. After the furanone acid aqueous solution is prepared, add 110 g of 10% methoxyamine aqueous solution to the furanone acid aqueous solution for oximation reaction for 4 hours, then add 60 g of industrial salt, acidify to pH<0.5, and use 100 mL×3 extracted three times with dichloromethane, combined the organic phases and added methanolic ammonia dropwise to pH 7.0, filtered to obtain 23 g of ammonium furan salt, and the molar yield was 68% based on acetylfuran.

Embodiment 3

[0045](1) Preparation of nitrite

[0046] Add 120mL of water, 30g of n-hexanol, and 16g of concentrated sulfuric acid into a 500mL reaction bottle, and cool it to 0°C in an ice bath, and slowly add 55.7g of 40% sodium nitrite aqueous solution to it for 1.5 hours, and the temperature during the dropping process should not exceed 5°C , the dropwise addition was completed, stirred for 30 min, and the ester layer was separated to obtain 37 g of hexyl nitrite.

[0047] (2) Preparation of furanone acid

[0048] Dissolve 20g of 2-acetylfuran in 150mL of 10% dilute hydrochloric acid solution, add 2g of concentrated sulfuric acid, 0.1g of catalyst γ-Al 2 o 3 / Pd(II), control the temperature to 45-50°C, add 25g of hexyl nitrite dropwise for 1h, continue to stir for 1h after the dropwise addition, adjust the pH to 3.0 after the reaction, filter and recover the catalyst, add 100mL of The n-hexanol produced by dichloromethane extraction reaction and the unreacted acetylfuran, the water ...

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Abstract

The invention belongs to the technical field of medical chemical industry, and particularly relates to a preparation method of furanone acid. The method comprises the following steps of: adding dropwisely a sodium nitrite aqueous solution into a concentrated sulfuric acid and long-chain alcohol aqueous solution, separating an ester layer to obtain nitrite after the dropwise addition is finished; dissolving 2-acetyl furan in a dilute hydrochloric acid solution, adding concentrated sulfuric acid and a catalyst, controlling temperature, adding dropwisely the nitrite, continuously stirring to react after the dropwise addition is finished, adjusting pH after the reaction is finished, filtering to recover the catalyst, and adding an extracting agent into filtrate to extract long-chain alcohol generated by the reaction and unreacted acetyl furan, wherein a water phase is a furanone acid aqueous solution. By the adoption of the preparation method of the furanone acid, an adopted oxidant only needs to slightly exceed the amount of a substrate, so that generation of toxic gas nitrogen oxide is reduced compared with oxidation of sodium nitrite; and the reaction condition is mild, the use of the catalyst accelerates a hydrolysis process, the side reaction is reduced, the yield is improved and more than 82.5%, and a conversion rate of the 2-acetyl furan reaches more than 95%.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a preparation method of furanone acid. Background technique [0002] Cephalosporin antibiotics, as a new type of β-lactam antibiotics with high efficiency and low toxicity, are the most rapidly developed and most new types of antibiotics at home and abroad in recent years, and dozens of varieties have been used in clinical applications. Cefuroxime sodium or cefuroxime axetil is a second-generation cephalosporin developed by GlaxoSmithKline. It has a wide antibacterial spectrum and a wide range of applications. It can be used for respiratory tract infections and urinary tract infections caused by sensitive bacteria. , skin and soft tissue infections, etc., are cephalosporin antibiotics with a good momentum of development in recent years. They have been among the best in the world's pharmaceutical sales rankings for several years, with a huge cons...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/54
CPCC07D307/54
Inventor 侯乐伟付凯毛相港刘建国马莹翟琦磊阴华栋
Owner SHANDONG JINCHENG PHARMACCUTICAL CHEM CO LTD
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