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Method used for preparing epsilon-hexanolactone

A technology of caprolactone and cyclohexanone, which is applied in the field of preparation of organic compounds, can solve the problems of high cost and low efficiency of pro-oxidant benzaldehyde, achieve high industrial value, facilitate separation and purification, and improve economic feasibility Effect

Active Publication Date: 2017-02-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the invention is to solve existing cyclohexanone Baeyer-Villiger oxidation reaction. 2 In the / aldehyde system, the pro-oxidant benzaldehyde is low in efficiency and high in cost. A new type of pro-oxidant-acrolein is provided, combined with nitrogen-doped carbon nanotubes as a non-metallic catalyst, and a simple operation, easy recovery of the catalyst, and low cost are invented. A low-cost method for the synthesis of ε-caprolactone

Method used

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  • Method used for preparing epsilon-hexanolactone
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  • Method used for preparing epsilon-hexanolactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～5

[0026] Add 25ml 1,2-dichloroethane, 2.6g o-dichlorobenzene (internal standard), 4.75g cyclohexanone, 2.69g acrolein and 100mg nitrogen-doped carbon nanotubes (N content is 4.34at%) Stir and heat to the high-pressure reactor to the temperature shown in Table 1, feed oxygen, start timing, and maintain the pressure at 1 MPa during the reaction. After reacting for 4 hours, stop timing, cool the reactor to room temperature, and filter the liquid-solid phase mixture to obtain a solid catalyst and a liquid phase mixture containing unreacted reactants and reaction products. The liquid phase mixture was detected and analyzed by gas chromatography (GC). The gas chromatogram of the reaction solution after the reaction of embodiment 3 is as follows image 3 shown. The GC detection results are shown in Table 1 (the influence of reaction temperature on the Baeyer-Villiger oxidation reaction of cyclohexanone).

[0027] Table 1

[0028] Example 1 2 3 4 5 Reaction tempe...

Embodiment 6～12

[0031] Add 25ml 1,2-dichloroethane, 2.6g o-dichlorobenzene (internal standard), 4.75g cyclohexanone, 2.69g acrolein and 100mg nitrogen-doped carbon nanotubes (N content is 4.34at%) Stir and heat to 80°C in a high-pressure reactor, feed oxygen, start timing, and maintain the pressure at 1 MPa during the reaction. After reacting to the time shown in Table 2, stop timing, the reactor is cooled to room temperature, and the liquid-solid phase mixture is filtered to obtain a solid catalyst and a liquid phase mixture containing unreacted reactants and reaction products. The liquid phase mixture was detected and analyzed by gas chromatography (GC). The GC detection results are shown in Table 2 (the influence of reaction time on the Baeyer-Villiger oxidation reaction of cyclohexanone).

[0032] Table 2

[0033]

[0034]

[0035] Analysis of the data in Table 2 shows that the conversion rate of cyclohexanone increases with the prolongation of time, the efficiency of acrolein dec...

Embodiment 13～16

[0037]Add 25ml 1,2-dichloroethane, 2.6g o-dichlorobenzene (internal standard), 4.75g cyclohexanone, 2.69g acrolein and 100mg nitrogen-doped carbon nanotubes (N content is 4.34at%) Stir and heat to 80°C in a high-pressure reactor, feed oxygen, start timing, and maintain the pressure as shown in Table 3 during the reaction, stop timing after reacting for 4 hours, cool the reactor to room temperature, and filter the liquid and solid phase mixture to obtain a solid catalyst and a liquid phase mixture containing unreacted reactants and reaction products. The liquid phase mixture was detected and analyzed by gas chromatography (GC). The GC detection results are shown in Table 3 (the influence of reaction pressure on the Baeyer-Villiger oxidation reaction of cyclohexanone).

[0038] table 3

[0039] Example 13 14 3 15 16 Reaction pressure (MPa) 0.1 0.5 1 1.5 2 Cyclohexanone conversion rate (%) 13 19 22 24 27 ε-caprolactone selectivity (%) 88...

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Abstract

The invention discloses a method used for preparing epsilon-hexanolactone. According to the method, cyclohexanone, an auxiliary oxidant, and a certain amount of a catalyst are added into a certain amount of an organic solvent, molecular oxygen is taken as an oxidizing agent, and stirring reaction is carried out for 0.1 to 24h at 60 to 100 DEG C under 0.1 to 2MPa, wherein the auxiliary oxidant is acrolein, and the catalyst is a carbon material. The method is high in auxiliary oxidant efficiency; the catalyst is simple, is easily available, and is convenient to recycle; the oxidizing agent is green, and is friendly to the environment; operation is simple; and cost is low.

Description

technical field [0001] The invention relates to the field of preparation of organic compounds, in particular to a method for preparing ε-caprolactone. Background technique [0002] The Beayer-Viillger oxidation is an important class of reactions that oxidize cyclic ketones or linear ketones to more complex and valuable linear esters or lactones. ε-caprolactone is an important polyester monomer, mainly used for the synthesis of polyε-caprolactone, which can be copolymerized or blended with various resins to improve the gloss, transparency and anti-sticking properties of the product, etc. . With the enhancement of people's awareness of environmental protection, it is also expected to replace the existing ordinary plastics, and enter the market of disposable packaging materials and mulch films in large quantities, with broad prospects. Considering factors such as raw materials, equipment and reaction conditions, the cyclohexanone oxidation method is the most effective method,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/04C07B41/12
CPCC07B41/12C07D313/04B01J21/185
Inventor 余皓侯萌萌曹永海彭峰王红娟
Owner SOUTH CHINA UNIV OF TECH
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