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Method for synthesizing epoxy styrene by direct oxidation of phenylethylene

A technology for the oxidation synthesis of styrene oxide, applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve the problems of difficult synthesis, serious pollution, low conversion rate, etc., and achieve good repeatability and production The effect of simple process

Inactive Publication Date: 2009-06-24
LANZHOU 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

The haloalcohol method is a simple and convenient synthesis method, but the method consumes a lot of materials and energy, and the pollution is serious, so it is a production process that needs to be improved urgently
And with H 2 o 2 In the catalytic system of oxidant (mainly titanium silicon molecular sieve / H 2 o 2 system) is that the conversion rate is low, such as V.Hulea, E.Dumitriu etc. a series of titanium silicon molecular sieves TS, Ti-β, Ti-MCM-41 and H 2 o 2 The catalytic system composed is used in the oxidation reaction of styrene, and it is found that the conversion rate of styrene is only up to 26% (Appl.Catal.A: Gen.2004, 277:99-106), and the highest selectivity to benzaldehyde is 79% , the selectivity to styrene oxide is the highest but only 15%. The domestic patent CN1557553A proposes a system in which molecular oxygen is used as the oxygen source and MCM series molecular sieves are used as the catalyst. The conversion rate of styrene and the selectivity of styrene oxide are respectively 40% vs. 60%, still not very high
It can be seen that although oxygen is the most ideal oxygen source to oxidize styrene, the current technology is far from meeting the production requirements, and most of the systems use complexes, which are difficult to synthesize, difficult to recycle catalysts, or catalytic reactions can only be performed in the gas phase. Under the condition

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: Weighing AgNO 3 Add 25g deionized water to dissolve 0.157g, then add 1.0g of γ-ZrP, and stir at room temperature for 20h; filter the above mixture, wash thoroughly with deionized water to remove unexchanged silver ions; wash the solid matter at 60°C Vacuum drying for 24 hours; the dried solid was ground to obtain a powder, and XRF showed that the silver content in the catalyst was 3.3%. Weigh 0.05g of catalyst powder and put it into a double-necked flask, vacuumize the reactor and protect it with nitrogen; add 5ml of solvent acetonitrile, 10mmol of styrene and stir and mix evenly; inject 5mmol of oxidant tert-butyl hydroperoxide, put the reactor into the The reaction was started in an oil bath heated to 82°C. After 8 hours of reaction, the catalyst was filtered, and the product was analyzed by GC 201 gas chromatography. The conversion rate of styrene was 72%, and the selectivity of styrene oxide was 96%. Weigh 0.05 g of the recovered catalyst and operate...

Embodiment 2

[0015] Example 2: The preparation of the Ag-γ-ZrP catalyst was the same as in Example 1, except that 0.154 g of Ag(OAc) was used as the precursor silver salt. XRF showed that the silver content in the catalyst was 2.1%. Weigh 0.03g of catalyst powder and put it into a double-necked flask, vacuumize the reactor and protect it with nitrogen; add 5ml of solvent acetonitrile, 10mmol of styrene and stir and mix evenly; inject 5mmol of oxidant tert-butyl hydroperoxide, put the reactor into the The reaction was started in an oil bath heated to 82°C. After 8 hours of reaction, the catalyst was filtered, and the product was analyzed by GC 201 gas chromatography. The conversion rate of styrene was 67%, and the selectivity of styrene oxide was 94%.

Embodiment 3

[0016] Embodiment 3: the preparation of Ag-γ-ZrP catalyst is the same as embodiment 1, different is that AgNO 3 The mass of the catalyst is 0.314g, and XRF shows that the silver content in the catalyst is 8%. Weigh 0.05g of the catalyst powder and pack it into a double-necked flask, and the reactor is evacuated and protected by nitrogen; add solvent acetonitrile 5ml, styrene 10mmol and stir and mix evenly; Inject 5 mmol of oxidant tert-butyl hydroperoxide, and place the reactor in an oil bath preheated to 82°C to start the reaction. After 8 hours of reaction, filter the catalyst. The product is analyzed by GC 201 gas chromatography, and the conversion rate of styrene is 76%. , Styrene oxide selectivity 97%.

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Abstract

The invention relates to a method for synthesizing epoxyphenylethane by directly oxidizing styrene. The method is characterized by taking Ag-gamma-ZrP as a catalyst, taking tert-butyl hydroperoxide as an oxygen source, taking acetonitrile as a solvent, and directly epoxidizing the styrene to synthesize the epoxyphenylethane in a nitrogen atmosphere at the temperature of 70-90 DEG C. The maximum conversation rate of the styrene is up to 92%, and selectivity of the epoxyphenylethane is up to 96%.

Description

technical field [0001] The invention relates to a method for directly oxidizing styrene to synthesize styrene oxide. Background technique [0002] Styrene oxide, as an important organic intermediate, can be used as epoxy resin thinner, UV-thinner, flavor enhancer, and is also an important intermediate in organic synthesis, pharmaceutical industry, and fragrance industry, such as epoxybenzene The β-phenylethanol produced by hydrogenation of ethane is the main component of rose oil, clove oil and neroli oil, and is widely used in the preparation of food, tobacco, soap and cosmetic essence. Oxidation of styrene is of practical significance due to the high market price of styrene oxide. At the same time, there is no mature production technology of styrene oxide in China, and most of the required styrene oxide is imported. The difficulties encountered in production are mainly due to the large number of styrene oxidation products, including benzaldehyde, phenylacetaldehyde, and ...

Claims

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Application Information

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IPC IPC(8): C07D301/19C07D303/04B01J27/14
Inventor 徐贤伦刘俊华王芳刘淑文
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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