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A kind of method that cyclohexane prepares ε-caprolactone

A technology of cyclohexane and caprolactone, applied in the field of organic synthesis, can solve the problems of cumbersome preparation process, high cost and difficulty in large-scale application of NHPI, and achieve the effects of low cost, simple operation and simple catalyst

Active Publication Date: 2022-03-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the advantages of mild reaction conditions, friendly catalyst environment, and the main product of the reaction is lactone. However, due to the cumbersome preparation process and high cost of NHPI, this method is difficult to be widely applied.

Method used

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  • A kind of method that cyclohexane prepares ε-caprolactone
  • A kind of method that cyclohexane prepares ε-caprolactone

Examples

Experimental program
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Effect test

Embodiment 1

[0026] A method for preparing ε-caprolactone from cyclohexane, comprising the following steps:

[0027] Add 40 mg of NCNTs, 25 mL of 1,2-dichloroethane, 2.5 mmol of cyclohexane, and 12.5 mmol of benzaldehyde (the molar ratio of cyclohexane to benzaldehyde is 1:5) into the miniature autoclave in sequence , adjust the stirring speed to 1200rpm, and heat the reactor to 60°C, feed oxygen, start timing, keep the reaction pressure at 0.5MPa, react for 4h, and then cool the reactor to room temperature to obtain a reaction mixture (gas chromatogram as shown in figure 1 shown).

[0028] Gas chromatography (GC) detection results: the conversion rate of cyclohexane was 17.0%, and the selectivity of ε-caprolactone was 82.4%.

Embodiment 2

[0030] A method for preparing ε-caprolactone from cyclohexane, comprising the following steps:

[0031] Add 40 mg of NCNTs, 25 mL of 1,2-dichloroethane, 2.5 mmol of cyclohexane, and 12.5 mmol of benzaldehyde (the molar ratio of cyclohexane to benzaldehyde is 1:5) into the miniature autoclave in sequence , adjust the stirring speed to 1200rpm, and heat the reactor to 50°C, feed oxygen, start timing, keep the reaction pressure at 0.5MPa, react for 4h, and then cool the reactor to room temperature to obtain a reaction mixture.

[0032] Gas chromatography (GC) detection results: the conversion rate of cyclohexane is 26.2%, and the selectivity of ε-caprolactone is 87.4%.

[0033] The NCNTs in the reaction mixture are reclaimed (filtered, then washed and dried) and recycled, and cyclohexane is used to prepare ε-caprolactone (operation as above), and recycled 5 times, the cyclohexane detected by gas chromatography Alkane conversion and ε-caprolactone selectivity are shown in the tab...

Embodiment 3

[0038] A method for preparing ε-caprolactone from cyclohexane, comprising the following steps:

[0039] Add 40mg of NCNTs, 25mL of 1,2-dichloroethane, 2.5mmol of cyclohexane and 7.5mmol of benzaldehyde (the molar ratio of cyclohexane to benzaldehyde is 1:3) into the mini autoclave , adjust the stirring speed to 1200rpm, and heat the reactor to 50°C, feed oxygen, start timing, keep the reaction pressure at 0.5MPa, react for 4h, and then cool the reactor to room temperature to obtain a reaction mixture.

[0040] Gas chromatography (GC) detection results: the conversion rate of cyclohexane is 20.2%, and the selectivity of ε-caprolactone is 78.3%.

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Abstract

The invention discloses a method for preparing ε-caprolactone from cyclohexane, which comprises the following steps: in a solvent system, oxygen is used as an oxidant, an aldehyde compound is used as a pro-oxidant, and nitrogen-doped carbon nanotubes are used as a catalyst. Carry out the oxidation reaction of cyclohexane to obtain ε-caprolactone. The invention has the advantages of high efficiency of the oxidizing agent, simple and easy-to-obtain and recycle catalyst, green and environment-friendly oxidizing agent, simple operation, low cost and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing ε-caprolactone from cyclohexane. Background technique [0002] ε-caprolactone is a non-toxic organic chemical intermediate. It is mainly used as a monomer to prepare high-performance polymers. It can also be used as a good solvent and has good solubility for some polymer materials. The main method for industrially synthesizing ε-caprolactone is the Baeyer-Villiger oxidation method, that is, to obtain ε-caprolactone by directly oxidizing cyclohexanone. This method has the advantages of simple operation and high yield. At present, the oxidants used in the Baeyer-Villiger oxidation method are mainly peroxyacids or high-concentration hydrogen peroxide. These oxidants have high requirements for safe production during preparation, storage and reaction, and eventually lead to the production of ε-caprolactone higher cost. Oxygen is a cheap and clean oxi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/04
CPCC07D313/04
Inventor 曹永海柏佳彤江琦彭峰余皓王红娟
Owner SOUTH CHINA UNIV OF TECH