Novel method for preparing epsilon-caprolactone

A technology of caprolactone and cyclohexanone, which is applied in the field of preparing ε-caprolactone, can solve the problems of lack of industrialization value, high process cost and high price of benzaldehyde, and achieves the advantages of low cost, easy availability and reduced production cost. Effect

Active Publication Date: 2017-07-21
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, the price of benzaldehyde is high,...

Method used

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  • Novel method for preparing epsilon-caprolactone
  • Novel method for preparing epsilon-caprolactone
  • Novel method for preparing epsilon-caprolactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add Fe(NO 3 ) 3 ·9H 2 O 0.323kg, NHPI 0.326kg, toluene 1.840kg, cyclohexanone 0.980kg, acetonitrile 20L. Pour in air, adjust the pressure to 0.2MPa, set the temperature to 40°C, and stir. Start the timing reaction, continue the reaction for 10h, stop the reaction, wait for the reaction solution to cool to room temperature, distill out the acetonitrile solvent under reduced pressure, filter NHPI, Fe(NO) 3 ) 3, washed three times with acetonitrile, and dried to recover the catalyst. Benzaldehyde and benzoic acid were separated by vacuum distillation to obtain 0.602 kg of cyclohexanone, 0.403 kg of ε-caprolactone, 0.090 kg of toluene, 0.464 kg of benzaldehyde and 1.76 kg of benzoic acid. The conversion of cyclohexanone was 38.6%, and the selectivity of ε-caprolactone was 91.5%. The conversion of toluene was 95.1%, the selectivity of benzaldehyde was 23%, and the selectivity of benzoic acid was 75.9%.

Embodiment 2

[0051] Add Fe(NO 3 ) 3 ·9H 2 O 0.323kg, NHPI 0.326kg, toluene 1.840kg, cyclohexanone 0.980kg, ethyl acetate 20L. Pour in air, adjust the pressure to 0.2MPa, set the temperature to 60°C, and stir. Start the timing reaction, continue the reaction for 10h, stop the reaction, wait for the reaction solution to cool to room temperature, distill out the ethyl acetate solvent under reduced pressure, filter NHPI, Fe(NO) 3 ) 3 , washed three times with acetonitrile, and dried to recover the catalyst. Benzaldehyde and benzoic acid were separated by vacuum distillation to obtain 0.546kg of cyclohexanone, 0.465kg of ε-caprolactone, 0.160kg of toluene, 0.472kg of benzaldehyde and 1.357kg of benzoic acid. The conversion of cyclohexanone was 44.3%, and the selectivity of ε-caprolactone was 92.1%. Toluene conversion was 91.3%, benzaldehyde selectivity was 24.4%, and benzoic acid selectivity was 61.0%

Embodiment 3

[0053] Add Fe(NO 3 ) 3 ·9H 2 O 0.323kg, NHPI 0.326kg, toluene 1.840kg, cyclohexanone 0.980kg, dichloroethane 20L. Pour in air, adjust the pressure to 0.2MPa, set the temperature to 60°C, and stir. Start the timing reaction, continue the reaction for 10h, stop the reaction, wait for the reaction solution to cool to room temperature, distill out the dichloroethane solvent under reduced pressure, filter NHPI, Fe(NO) 3 ) 3 , washed three times with acetonitrile, and dried to recover the catalyst. Benzaldehyde and benzoic acid were separated by vacuum distillation to obtain 0.496kg of cyclohexanone, 0.541kg of ε-caprolactone, 0.168kg of toluene, 0.406kg of benzaldehyde and 1.63kg of benzoic acid. The conversion of cyclohexanone was 49.4%, and the selectivity of ε-caprolactone was 96.1%. Toluene conversion was 90.8%, benzaldehyde selectivity was 21.1%, and benzoic acid selectivity was 73.6%

[0054] From Examples 1-3, it can be seen that, compared with acetonitrile and ethyl ...

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Abstract

The invention discloses a method for preparing epsilon-caprolactone. After cyclohexanone, co-oxidation agents, catalysts, radical initiators and solvents are mixed, reaction is performed in air atmosphere, the co-oxidation agents are methylbenzene compounds, the catalysts are at least one of nitrates or oxides of Co, Fe and Cu, the solvents are at least one selected from 1, 2-dichloroethane, ethyl acetate and acetonitrile, and the method for preparing the caprolactone further co-produces aromatic aldehyde and aromatic acid. The method for preparing the epsilon-caprolactone takes aromatic methyl compounds as the co-oxidation agents, benzaldehyde is replaced, production cost is remarkably reduced, industrial production of the epsilon-caprolactone prepared by an oxygen/air oxidation method is possible, and the aromatic aldehyde and the aromatic acid are further co-produced when the epsilon-caprolactone is prepared by the method, so that the method had higher values in industrial application.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a new method for preparing ε-caprolactone. Background technique [0002] ε-Caprolactone is an important organic synthesis intermediate and a new type of polyester monomer. It has a very wide range of applications in polymer synthesis and modification. It can react with a variety of compounds to prepare fine chemicals with unique properties. It can also be used as a raw material for the preparation of nylon 66. Its polymerized product, polycaprolactone (PCL), is known as a "green chemical". The copolymerization of caprolactone with various monomers or the blending of PCL with other resins can improve the gloss, transparency, biodegradability and resistance of the material. stickiness etc. With the increasing dependence of human beings on synthetic polymer materials and polymers, the demand for ε-caprolactone has also increased rapidly. However, due to the common use of peroxy ac...

Claims

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Application Information

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IPC IPC(8): C07D313/04
CPCC07D313/04
Inventor 李浩然袁浩然毛建拥陈志荣
Owner ZHEJIANG UNIV
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