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Method for epoxidizing macrocyclic olefin by hydrogen peroxide method

A technology of macrocyclene and hydrogen peroxide, which is applied in the direction of organic chemistry, can solve the problems of difficulty in recycling catalyst raw materials, difficulty in balancing conversion rate and selectivity, and strong limitation of hydrogen peroxide concentration, so as to overcome the limitation of hydrogen peroxide concentration and make the reaction process green Environmental protection, wide concentration range effect

Pending Publication Date: 2021-02-05
CHINA TIANCHEN ENG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

①The reaction system requires the participation of high-concentration hydrogen peroxide, high risk of safety control, and strong limitation of hydrogen peroxide concentration; ②The side reaction of hydrogen peroxide decomposition product water and epoxy product is hydrolysis reaction, and the reaction yield is not high; ③It is very easy to decompose in the organic system of hydrogen peroxide, The effective utilization rate of hydrogen peroxide is low; ④The separation of the catalytic system is complicated, involving the separation of acid and water and the separation of the residue & catalyst, and the recycling of catalyst raw materials is difficult; ⑤It is difficult to balance the conversion rate and selectivity.

Method used

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  • Method for epoxidizing macrocyclic olefin by hydrogen peroxide method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 68.0Kg of 50% hydrogen peroxide, 3.4Kg of trisodium phosphate and 1.1Kg of ethylenediaminetetraacetic acid are mixed evenly and put into the head tank A, 1102.0Kg of cyclooctene and 110.2Kg of tert-butanol are put into the head tank B, and the head tank A and The materials in B are added to the 2 cubic reaction kettle within 0.5 hours, the steam pressure is adjusted during the feeding process, and the temperature of the kettle is maintained at 75°C. The volatilization pipe of the reaction kettle is connected to a 1-meter BX packed rectification tower, and the vacuum degree is controlled at 1000Pa. The tower top effluent has a hydrogen peroxide content of 3.0%, and the water content of the material in the reactor is 1.5%. The hydrogen peroxide content of the material in the reactor is 0.5%, the utilization rate of hydrogen peroxide is 83.2%, and the molar yield of epoxy cyclooctane corresponding to cyclooctene is 89.5%.

Embodiment 2

[0038] Mix 1000Kg of 5% hydrogen peroxide, 1Kg of sodium tripolyphosphate and 22.1Kg of diethylamine pentaacetic acid evenly into the high-level tank A, and put 442.1Kg of cyclotetracene and 221.1Kg of tert-amyl alcohol into the high-level tank B, and the high-level tank A Add the materials in B and B to a 3-cubic reaction kettle within 6 hours, adjust the steam pressure during the feeding process, and keep the kettle temperature at 120°C. The volatilization pipe of the reaction kettle is connected to a 1-meter BX packed rectification tower, and the vacuum degree is controlled to 7000Pa. The tower top effluent has a hydrogen peroxide content of 0.01%, and the water content of the materials in the reactor is 0.1%. The hydrogen peroxide content of the material in the reactor is 0.01%, the utilization rate of hydrogen peroxide is 97.1%, and the molar yield of epoxy cyclotetradecane corresponding to cyclotetracocene is 96.5%.

Embodiment 3

[0040] 100Kg of 80% hydrogen peroxide, 1.5Kg of sodium polyphosphate and 12.1Kg of N-hydroxyethyldiaminetriacetic acid are mixed evenly into the head tank A, 560.2Kg of cyclohexadecene and 221.1Kg of tert-butanol are put into the head tank B , the materials in the head tanks A and B are added to a 1 cubic reaction kettle within 1.5 hours, the steam pressure is adjusted during the feeding process, and the temperature of the kettle is maintained at 90°C. The volatilization pipe of the reaction kettle is connected to a 1-meter BX packed rectification tower, and the vacuum degree is controlled at 3000Pa. The tower top effluent has a hydrogen peroxide content of 0.12%, and the water content of the materials in the reactor is 0.13%. The hydrogen peroxide content of the material in the reactor is 0.11%, the utilization rate of hydrogen peroxide is 97.4%, and the molar yield of epoxycyclohexadecane corresponding to cyclohexadecene is 95.1%.

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Abstract

The invention provides a method for epoxidizing macrocyclic olefin by a hydrogen peroxide method. The method comprises the following steps: putting hydrogen peroxide, a stabilizer, a catalyst, a solvent and macrocyclic olefin into an oxidation reactor, and carrying out oxidation reaction to obtain an epoxidized product. According to the method, the hydrogen peroxide stabilizer, the catalyst and the diluting solvent are superposed to promote reaction, the water content of a reaction system is controlled by adjusting the vacuum degree and the material temperature, the macrocyclic olefin in the reaction system is converted by 90%, the water content is controlled to be 0.01-3wt%, the hydrogen peroxide content of tower top effluent is controlled to be 0.01-0.5%, the utilization rate of hydrogenperoxide can reach 93.2-97.4%, and the molar yield of the epoxidation product corresponding to macrocyclic olefin is 90.5-99.3%. According to the technical scheme, the hydrogen peroxide utilization efficiency is high, the reaction rate is high, a catalytic system is easy to separate, the reaction process is environmentally friendly, and the technology is an ideal replacement process for traditional hydrogen peroxide method macrocyclic olefin epoxidation and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of fine chemicals and new materials, and in particular relates to a method for epoxidizing macrocyclic olefins with hydrogen peroxide. Background technique [0002] The traditional processes of olefin epoxidation mainly include peroxyacid, tert-butanol peroxide, hypochlorite, iodosobenzene, osmium tetroxide, etc. The development of green chemistry promotes the research of epoxidation reaction with hydrogen peroxide as oxygen source, hydrogen peroxide The advantages as an epoxidation reagent are extremely obvious, the raw materials are cheap and easy to obtain, the content of active oxygen is high, the by-product of the oxidant after the reaction is only water, and the environment is friendly. In recent years, the hydrogen peroxide method has become a research hotspot and the preferred solution for industrialization of olefin epoxidation. [0003] A typical industrial case of olefin hydrogen peroxide epoxidation is th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/12C07D303/04C07D493/14
CPCC07D301/12C07D303/04C07D493/14
Inventor 冯传密吴昊史文涛杨光靳权龙滢王聪刘新伟王元平杨克俭
Owner CHINA TIANCHEN ENG
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