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Method for preparing epsilon-caprolactone through biomimetic catalysis of cyclohexanone oxidation

A technology of biomimetic catalysis and cyclohexanone, applied in the direction of organic chemistry, can solve the problems of industrial application limitations, complex catalytic system, large amount of additives, etc., and achieve the effect of avoiding safety problems, simple operation process and mild conditions

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Problems solved by technology

Chinese patent ZL 101205225A reports a method for preparing lactones by metalloporphyrin biomimetic catalyzed oxidation of ketones. This method involves the process of preparing ε-caprolactone by oxidation of cyclohexanone B-V, but there is a large amount of additives (the raw material 15 times), harsh conditions and other issues, so the industrial application of this method is limited
Patent ZL201110298626.1 reported a method for the preparation of ε-caprolactone through the oxygen oxidation of cyclohexanone catalyzed by a metalloporphyrin with a simple structure. However, in this method, metal oxides or molecular sieves are used as cocatalysts, and the catalytic system is complex and separation is difficult. shortcoming

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  • Method for preparing epsilon-caprolactone through biomimetic catalysis of cyclohexanone oxidation
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  • Method for preparing epsilon-caprolactone through biomimetic catalysis of cyclohexanone oxidation

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Embodiment 1

[0021] Containing 50ppm metal phthalocyanine (M) with general formula (I) in 5mL 1 =Al, R=H) in the sec-butyl acetate solution, add 1mmol of cyclohexanone and 2mmol of benzaldehyde, feed oxygen, stir and react at a temperature of 70°C for 6 hours, and quantitatively detect by gas chromatography internal standard method Analysis showed that the conversion rate of cyclohexanone was 92%, and the yield of ε-caprolactone was 92%.

Embodiment 2

[0023] Containing 0.1ppm metal phthalocyanine (M) with general formula (I) in 5mL 1 =Mg, R=COOH) in the trifluorotoluene solution, add 1mmol of cyclohexanone and 1mmol of benzaldehyde, feed oxygen, stir and react at a temperature of 100°C for 2 hours, and quantitatively detect and analyze by gas chromatography internal standard method , the conversion rate of cyclohexanone was 80%, and the yield of ε-caprolactone was 80%.

Embodiment 3

[0025] Containing 10ppm metal phthalocyanine (M) with general formula (I) in 5mL 1 = Zn, R 1 =COOH,R 2 , R 3 , R 4 , R 5 =H) in the benzotrifluorotoluene solution, add 1mmol of cyclohexanone and 0.1mmol of benzaldehyde, feed oxygen, stir and react at a temperature of 100°C for 8 hours, quantitatively detect and analyze through gas chromatography internal standard method, cyclohexane The conversion of ketone was 83%, and the yield of ε-caprolactone was 83%.

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Abstract

The invention discloses a method for preparing epsilon-caprolactone through biomimetic catalysis of cyclohexanone oxidation. In the method, cyclohexanone is used as a raw material, oxygen is used as an oxidizing agent, a metal phthalocyanine or metalloporphyrin compound is used as a catalyst, the reaction temperature is controlled at 25-120 DEG C, and the epsilon-caprolactone is obtained through a catalytic reaction under normal-pressure conditions. The method disclosed by the invention has the advantages of simple technology, mild conditions, high selectivity, safety, low cost and the like.

Description

technical field [0001] The invention relates to a method for preparing ε-caprolactone, in particular to a method for preparing ε-caprolactone by biomimetic catalysis of cyclohexanone oxidation. Background technique [0002] ε-caprolactone is an important polymer monomer. As a new type of polyester monomer, it is widely used in the synthesis of polycaprolactone (PCL) and blended modified resins for various purposes, and as a It is an excellent organic solvent and an important organic synthesis intermediate. It shows good solubility to some insoluble resins and can react with various compounds to prepare fine chemicals with unique properties. At present, the method of industrial production of ε-caprolactone is mainly realized by the Baeyer-Villiger oxidation reaction. The oxidant used is usually an organic peracid such as peracetic acid. There are problems such as poor safety and high energy consumption during use, which makes the process application is limited. [0003] The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/04
Inventor 纪红兵周贤太陈韶云陶旺聪
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