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Method for preparing epsilon-caprolactone by catalytic oxidation of cyclohexanone in presence of molecular oxygen

A technology for catalytic oxidation and cyclohexanone, which is applied in the direction of catalyst activation/preparation, chemical instruments and methods, metal/metal oxide/metal hydroxide catalysts, etc., can solve the problem of large amount of pro-oxidant benzaldehyde, difficult catalyst preparation, There are too many reaction solvents to achieve the effect of good catalytic effect, good industrial application prospect and high reaction selectivity

Active Publication Date: 2021-10-01
SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is exactly to provide a kind of method for preparing ε-caprolactone by catalytically oxidizing cyclohexanone in the presence of molecular oxygen in order to solve the above problems, which mainly solves the problems existing in the method for preparing ε-caprolactone in the prior art. Catalyst preparation is difficult, catalytic efficiency is poor, there are too many reaction solvents, and the amount of pro-oxidant benzaldehyde is too much and other technical problems

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation method of 30% active alumina supported copper oxide catalyst

[0028] 1.1406g Cu(NO 3 ) 2 · 3 h 2 O was dissolved in 1.8 ml of deionized aqueous solution, stirred well with a glass rod until the metal Cu salt was dissolved, and then the solution containing Cu salt was slowly added dropwise to the γ-Al 2 o 3 (dried in an oven at 120°C for 4-6 hours before use), after the dropwise addition, soak the mixture at room temperature for about 24 hours, ultrasonic for 2 hours, after the impregnation, dry in an oven at 110°C overnight , and then finely grind the dried catalyst precursor into particles, then put it into a muffle furnace and calcinate at a temperature of 400°C for 4 hours.

[0029] Add 0.02g activated alumina-supported copper oxide catalyst, 0.4907g cyclohexanone, 1.0612g benzaldehyde, 15mL 1,2-dichloroethane in sequence in the three-necked flask, and then feed oxygen at 20ml / min under normal pressure. Stir at a constant temperature of 50°C for 4 ...

Embodiment 2

[0032] Add 0.04g activated alumina-supported copper oxide catalyst, 0.4907g cyclohexanone, 1.0612g benzaldehyde, 15mL 1,2-dichloroethane successively in the three-necked flask, then feed oxygen 20ml / min under normal pressure, Stir at a constant temperature of 50°C for 4 hours, and finally detect and analyze by GC, the conversion rate of cyclohexanone is 92.6%, and the selectivity of ε-caprolactone is higher than 99.0%.

[0033] Wherein the proportioning of cyclohexanone, benzaldehyde and 1,2-dichloroethane is calculated according to the molar volume ratio, that is, cyclohexanone:benzaldehyde:1,2-dichloroethane is 1mmol:2mmol:3mL; The amount of the alumina-supported copper oxide catalyst added is calculated according to its mass ratio to cyclohexanone, that is, the activated alumina-supported copper oxide catalyst:cyclohexanone is 0.08:1.

Embodiment 3

[0035] Add 0.02g activated alumina-supported copper oxide catalyst, 0.4907g cyclohexanone, 1.0612g benzaldehyde, 30mL 1,2-dichloroethane in sequence in the three-necked flask, and then feed oxygen 20ml / min under normal pressure conditions. Stir at a constant temperature of 50°C for 4 hours, and finally detect and analyze by GC, the conversion rate of cyclohexanone is 92.1%, and the selectivity of ε-caprolactone is higher than 99.0%.

[0036] Wherein the proportioning of cyclohexanone, benzaldehyde and 1,2-dichloroethane is calculated according to the molar volume ratio, that is, cyclohexanone:benzaldehyde:1,2-dichloroethane is 1mmol:2mmol:6mL; active The amount of the alumina-supported copper oxide catalyst added is calculated according to its mass ratio to cyclohexanone, that is, the activated alumina-supported copper oxide catalyst:cyclohexanone is 0.04:1.

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Abstract

The invention relates to a method for preparing epsilon-caprolactone by catalytic oxidation of cyclohexanone in the presence of molecular oxygen, the method comprises the following steps: taking active aluminum oxide loaded copper oxide as a catalyst, introducing oxygen into a certain amount of organic solvent, taking cyclohexanone as a raw material, adding a pro-oxidant, and reacting for 1-5 hours at the reaction temperature of 30-60 DEG C under the normal pressure condition to obtain epsilon-caprolactone. Compared with the prior art, the method has the advantages that the activated aluminum oxide loaded copper oxide is innovatively adopted as the catalyst for preparing epsilon-caprolactone through catalytic oxidation of cyclohexanone, the catalytic effect is good, the reaction selectivity is as high as 99%, and almost no by-product is generated in the reaction; green and friendly oxygen is used as the oxidizing agent, and a good oxidizing effect is achieved on the reactant cyclohexanone under the condition that the using amount of a pro-oxidant benzaldehyde is small; the activated aluminum oxide supported copper oxide catalyst is easy to prepare, separate and recycle, and the catalyst is low in use cost and has a good industrial application prospect.

Description

technical field [0001] The invention relates to a method for preparing ε-caprolactone, in particular to a method for preparing ε-caprolactone by catalytically oxidizing cyclohexanone in the presence of molecular oxygen. Background technique [0002] Lactone compounds are a class of key organic intermediates in chemical fine products, and play an important role in the fields of chemistry and biology. As an important lactone intermediate, ε-caprolactone has a good performance on the solubility of polymer resins, such as chlorinated polyolefin resin and polyurethane resin, ε-caprolactone and ε-polycaprolactone Esters are used as raw materials to synthesize environmentally friendly and degradable plastics, which can be used in surgical supplies, release agents, adhesive films, etc. In addition, ε-caprolactone polymers can also be used as modifiers to improve the performance of compounds, such as Color, viscosity, melt resistance, water resistance, etc. The Baeyer-Villiger (B-V...

Claims

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Application Information

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IPC IPC(8): C07D313/04B01J23/72B01J37/02B01J37/08
CPCC07D313/04B01J23/72B01J37/0201B01J37/088Y02P20/584
Inventor 孙小玲肖锦唐志林贾得军
Owner SHANGHAI APPLIED TECHNOLOGIES COLLEGE