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Method for producing cyclohexene oxide by reacting cumyl hydroperoxide with cyclohexene

A technology of cumene hydrogen peroxide and epoxy cyclohexane is applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc. Problems such as low hexane selectivity and low catalyst activity, to achieve the effect of reducing the amount, improving the catalytic performance, and increasing the hydrophobicity

Active Publication Date: 2013-01-16
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is that there are low catalyst activity and low selectivity of product epoxycyclohexane in the prior art, and a new reaction of cumene hydroperoxide and cyclohexene to produce epoxycyclohexane is provided. alkane method

Method used

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  • Method for producing cyclohexene oxide by reacting cumyl hydroperoxide with cyclohexene
  • Method for producing cyclohexene oxide by reacting cumyl hydroperoxide with cyclohexene
  • Method for producing cyclohexene oxide by reacting cumyl hydroperoxide with cyclohexene

Examples

Experimental program
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Effect test

Embodiment 1

[0015] 7.23 g of n-hexadecylamine was put into a solution consisting of 63 g of deionized water and 32.2 g of ethanol, stirred and dissolved at 50° C. to form solution A. 1 mole of methyltrimethoxysilane and 0.68 g of butyl titanate were dropped into a mixed solution consisting of 6 g of isopropanol and 19 moles of ethyl orthosilicate, and stirred for 30 minutes to form solution B. Pour solution B into solution A, stir for 18 hours, filter, wash and dry, and bake at 350° C. for 8 hours to obtain precursor I. Precursor I was then placed in a quartz tubular reactor at a temperature of 100° C. under a nitrogen atmosphere, passed through N-trimethylsilyl imidazole to react for 1.5 hours, and then purged for 2 hours under a nitrogen atmosphere to obtain HMS structure titanium silicon molecular sieve. Wherein, the molar ratio of each component in the raw material is: methyltrimethoxysilane: ethyl orthosilicate: butyl titanate: hexadecylamine: water = 1: 19: 0.002: 0.03: 3.5, hexame...

Embodiment 2

[0017] Same as [Example 1], except that the molar ratio of each component in the raw material is: methyltrimethoxysilane: ethyl orthosilicate: butyl titanate: hexadecylamine: water=1: 19: 0.004: 0.04: 3.5 , under nitrogen atmosphere, the reaction temperature of precursor I and hexamethyldisilazane is 200°C, the reaction time is 3 hours, and the weight ratio of hexamethyldisilazane to precursor I is 0.05. The obtained product29 Si CP / MAS NMR spectrogram is similar to [Example 1].

Embodiment 3

[0019] Same as [Example 1], except that the molar ratio of each component in the raw material is: methyltrimethoxysilane: ethyl orthosilicate: butyl titanate: octadecylamine: water=1: 5: 0.003: 0.04: 4.5 , under a nitrogen atmosphere, the reaction temperature of precursor I and hexamethyldisilazane is 250°C, the reaction time is 5 hours, and the weight ratio of N, O-bistrimethylsilylacetamide to precursor I is 0.005. The obtained product 29 Si CP / MAS NMR spectrogram is similar to [Example 1].

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Abstract

The invention relates to a method for producing cyclohexene oxide by reacting cumyl hydroperoxide with cyclohexene, mainly solving the problems of low catalyst activity and low selectivity of cyclohexene oxide in the prior art. The method disclosed herein is characterized by using cumyl hydroperoxide and cyclohexene as reaction raw materials, reacting cumyl hydroperoxide with cyclohexene under the reaction conditions comprising a molar ratio of cumyl hydroperoxide to cyclohexene being 1:(0.1-5), a reaction temperature of 50-100 DEG C, a reaction pressure is 1-5MPa, and a cumyl hydroperoxide weight hourly space velocity of 1-30h<-1> to generate cyclohexene oxide. The catalyst used herein is prepared by the following steps: a) uniformly mixing organic silicon source, inorganic silicon source, titanium source, organic template and water, then filtering, washing, drying and roasting the obtained mixture to obtain a precursor I, wherein the inorganic silicon source is selected from at least one of silica sol, silicate ester or solid silicon oxide, and the organic silicon source is methyltrimethoxy silane; and b) using inert gases as the carrier gas, introducing a silylating reagent into the precursor I for reacting to obtain the catalyst; wherein the silylating reagent is selected from at least one of organic silane, organic silyl amine, organic silyl amide or organic silazane. The method disclosed herein well solves the problems and can be used in the industrial production of cyclohexene oxide.

Description

technical field [0001] The invention relates to a method for producing epoxycyclohexane by reacting cumene hydroperoxide and cyclohexene. Background technique [0002] The surface of mesoporous materials such as HMS and MCM-41 is in an amorphous state, rich in a large number of hydroxyl groups, and the surface is highly hydrophilic, which seriously affects the performance of the catalyst. Therefore, it is hoped that the hydroxyl group can be eliminated by means of modification, and the surface hydrophobicity can be increased to improve its epoxidation performance. Work in this area has attracted more and more attention from chemists. [0003] Bhaumik (Organically Modified Titanium-Rich Ti-MCM-41, Efficient Catalysts for Epoxidation Reactions) [J.Catal., 2000, 189(1): 31-39] adopts in-situ condensation method, respectively, on the surface of Ti-MCM-41 Grafted methyl, vinyl, allyl, chloropropyl, pentyl and phenyl groups. Kapoor et al. (Titanium containing inorganic-organic ...

Claims

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Application Information

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IPC IPC(8): C07D303/04C07D301/19B01J31/02
Inventor 陈璐高焕新金国杰康陈军丁琳杨洪云
Owner CHINA PETROLEUM & CHEM CORP
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