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A kind of method for producing styrene oxide by styrene epoxidation

A technology of styrene oxide and styrene, which is applied in the direction of organic chemistry, can solve the problems of easy ring opening, troublesome post-processing, and failure to achieve industrial application, and achieve high reactivity, increased selectivity, and high activity.

Inactive Publication Date: 2016-03-16
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, styrene is easy to polymerize, so that the amount of styrene added during the reaction should not be too large, otherwise a large amount of by-products will easily be produced during the reaction, and it will cause trouble for post-processing.
Moreover, the product styrene oxide is easy to ring-open and polymerize during the reaction process, which also makes the selectivity unable to meet the requirements of industrial applications.

Method used

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  • A kind of method for producing styrene oxide by styrene epoxidation

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Experimental program
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Embodiment 1

[0018] [Example 1] Different solvent reaction results

[0019] In a 100ml one-necked flask, add styrene 15mmol, H 2 o 2 10mmol (hydrogen peroxide mass concentration is 50%), solvent 20ml, catalyst [(C 2 h 5 ) 3 NCH 2 Ph] 2 HAsMo 2 o 10 0.1mmol and 5mmol of EDTA were stirred and reacted at 70°C for 6h, and the solid catalyst was separated by centrifugation to obtain the product styrene oxide. The organic phase was subjected to qualitative and quantitative analysis by GC. The reaction results are shown in Table 1. (Conversions are based on H 2 o 2 Addition calculation)

[0020] Table 1 Different solvent reaction results

[0021]

[0022] It can be seen from Table 1 that under the action of EDTA additive, the catalysts maintain a high activity and have a high catalyst recovery rate for the solvents in the table.

Embodiment 2

[0024] In a 100ml one-necked flask, add styrene 30mmol, H 2 o 2 10mmol (hydrogen peroxide mass concentration is 50%), solvent ethyl acetate 20ml, catalyst [(CH 3 ) 3 NCH 2 Ph] 7 PV 4 o 16 0.1mmol and 1mmol of EDTA were stirred and reacted at 70°C for 6 hours, and the solid catalyst was separated by centrifugation to obtain the product styrene oxide. The organic phase was subjected to qualitative and quantitative analysis by GC. The reaction results are shown in Table 2. (Conversions are based on H 2 o 2 Addition calculation)

Embodiment 3

[0026] In a 100ml one-necked flask, add styrene 10mmol, H 2 o 2 10mmol (hydrogen peroxide mass concentration is 30%), solvent dichloroethane 20ml, catalyst [(C 2 h 5 ) 3 NCH 2 Ph] 2 HAsMo 2 o 10 0.09mmol and EDTA2mmol were stirred and reacted at 60°C for 7 hours, and the solid catalyst was separated by centrifugation to obtain the product styrene oxide. The organic phase was subjected to qualitative and quantitative analysis by GC. The reaction results are shown in Table 2. (Conversions are based on H 2 o 2 Addition calculation)

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Abstract

The invention provides a new method for preparing styrene oxide through epoxidation of styrene. H2O2 is used as an oxygen source, a reaction-controlled phase-transfer catalysis system is applied, one of toluene, tributyl phosphate, acetonitrile, dichloroethane and ethyl acetate or a mixture of two thereof is used as a solvent, and ethylenediamine tetraacetic acid (EDTA) is used as an auxiliary agent as well as a stabilizer. The method has the advantages of simple process, environmental protection and mildness, and is a new green technology with high activity and high selectivity.

Description

technical field [0001] The invention relates to the field of catalytic oxidation, in particular to a method for preparing styrene oxide by catalytic oxidation of styrene. Background technique [0002] Styrene oxide, also known as styrene oxide, is an important intermediate in organic synthesis, widely used in organic synthesis, pharmaceutical preparation and spice production. Can be used as epoxy resin diluent, UV-absorber, flavor enhancer, etc. Moreover, styrene oxide can be further added with hydrogen under the action of a catalyst to prepare β-phenylethanol, which has a wide range of functions and can be used in flower-flavored daily essences and food; styrene oxide can also be used to synthesize hydrochloric acid An important intermediate of levamisole, levamisole hydrochloride is a broad-spectrum anthelmintic that can be used by both humans and animals. The market demand for styrene oxide is increasing year by year, therefore, the industrialized production of styrene ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D301/12C07D303/04
CPCC07D301/12C07D303/04
Inventor 高爽吕迎李军张恒耘张毅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI