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Method for synthesizing epsilon-caprolactone

A technology of caprolactone and cyclohexanone, which is applied in the field of synthesizing ε-caprolactone, can solve the problems of easy explosion in the rectification process and easy hydrolysis of ε-caprolactone, and achieve improved yield and selectivity, safety Strong and practical effect

Active Publication Date: 2012-10-17
山东明厚德新能源科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a method for oxidizing cyclohexanone with solid peroxyacid to synthesize ε-caprolactone, so as to solve the problems that ε-caprolactone is easy to hydrolyze and explode in the rectification process in the traditional process

Method used

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  • Method for synthesizing epsilon-caprolactone
  • Method for synthesizing epsilon-caprolactone

Examples

Experimental program
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Effect test

Embodiment 1

[0041] 19.6g of cyclohexanone was weighed and placed in a 250ml reactor, and 70ml of acetic acid and 3 drops of lutidine were added, and 35g of peroxysuccinic acid content was slowly added to the three-necked flask with a solid peroxyacid content of 76.57%. Then react at 40°C for 2h. Taking samples for analysis, the conversion rate of cyclohexanone can reach 87.07%, the ε-caprolactone can reach 73.57%, and the selectivity can reach 84.50%. Collect the solid precipitated under the reaction conditions, take 30 g of solid (succinic acid content of 70%), 50 ml of tetrahydronaphthalene, 15 ml of o-xylene, and four zeolite particles, and carry out reactive distillation and dehydration at 180-210 ° C for 1 h to obtain Crude succinic anhydride 9.386g. 9.386 g of crude succinic anhydride was added to 40 ml of ethyl acetate, and recrystallized for 1 h at 90°C under boiling and refluxing conditions to obtain 8 g of refined succinic anhydride, and the yield of succinic anhydride was 44.9...

Embodiment 2

[0043] Weigh 14g of cyclohexanone and place it in a 250ml reactor, and add 70ml of acetic acid and 3 drops of lutidine, and 35g of peroxysuccinic acid content is that the solid peroxyacid of 76.57% is slowly added to the there-necked flask, after adding The reaction was carried out at 40°C for 2h. Taking samples for analysis, the conversion rate of cyclohexanone can reach 95.26%, the ε-caprolactone can reach 86.25%, and the selectivity can reach 90.55%. Collect the solid precipitated under the reaction conditions, take 30 g of solid (succinic acid content of 70%), 60 ml of tetrahydronaphthalene, 15 ml of o-xylene, and four zeolite particles, and carry out reactive distillation and dehydration at 180-210 ° C for 1 h to obtain Crude succinic anhydride 12.567 g. 12.567g of crude succinic anhydride was added to 40ml of ethyl acetate, and recrystallized for 1 h at 90°C under boiling reflux state to obtain 10.5g of refined succinic anhydride, and the yield of succinic anhydride was...

Embodiment 3

[0045] 9.8g of cyclohexanone was weighed and placed in a 250ml reactor, and 70ml of acetic acid and 3 drops of lutidine were added, and 35g of peroxysuccinic acid content was slowly added to the three-necked flask with a solid peroxyacid content of 76.57%. Then react at 40°C for 2h. Taking samples for analysis, the conversion rate of cyclohexanone can reach 97.00%, the ε-caprolactone can reach 95.24%, and the selectivity can reach 98.19%. Collect the solid precipitated under the reaction conditions, take 30 g of solid (succinic acid content of 70%), 70 ml of tetrahydronaphthalene, 15 ml of o-xylene, and four zeolite particles, and carry out reactive distillation and dehydration at 180-210 ° C for 1 h to obtain Crude succinic anhydride 13g. Add 13 g of crude succinic anhydride to 40 ml of ethyl acetate, and recrystallize it for 1 hour at 90°C under boiling and refluxing conditions to obtain 12 g of refined succinic anhydride, and the yield of succinic anhydride is 67.42%.

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Abstract

The invention relates to a method for synthesizing epsilon-caprolactone by adopting solid peroxy acid cyclohexanone diperoxide. The method comprises the following steps of: in the absence of catalysts, oxidizing butanedioic anhydride to obtain solid peroxysuccinic acid by using 70% hydrogen peroxide as an oxidizing agent, and reacting the solid peroxysuccinic acid with cyclohexanone diperoxide to synthesize the epsilon-caprolactone, and the method has higher yield and selectivity. Due to the stability of the solid peroxysuccinic acid, a reaction solution is rectified, so compared with the traditional liquid peroxy acid oxidization method, the method provided by the invention is safer; solid separated out in the process of synthesizing the epsilon-caprolactone is reacted, rectified, dewatered and recrystallized to prepare butanedioic anhydride so as to recycle raw materials, so the method has an actual application valve on the industry.

Description

technical field [0001] The present invention relates to a kind of synthesizing ε-caprolactone, specifically a kind of adopting H 2 O 2 A method for synthesizing ε-caprolactone by indirect oxidation of cyclohexanone in two steps and realizing recycling of raw materials. technical background [0002] ε-caprolactone is an important intermediate in organic synthesis, mainly used for the synthesis of polycaprolactone or copolymerization or blending modification with other esters, among which polycaprolactone has unique biocompatibility and degradability , and good permeability, it has a wide range of applications in the field of materials. However, there are still problems in the synthesis of ε-caprolactone, such as production safety and product stability, which make its synthesis technology difficult. At present, only a few companies in the United States, Britain, Japan and other countries are producing, while my country mainly relies on imports. Therefore, the development o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/04C07D307/60
CPCY02P20/10
Inventor 张光旭赵小双陈波
Owner 山东明厚德新能源科技有限公司