A kind of preparation method of cyclohexene

A technology of cyclohexene and phenol, which is applied in the field of preparation of cyclohexene, can solve the problems of low conversion rate of benzene, difficulty in recovery of precious metals, difficulty in catalyst salt, etc., and achieve improved conversion rate, avoid deep hydrogenation, and high catalytic reaction effect Effect

Active Publication Date: 2015-09-30
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

USP4678861 discloses a technology for the partial hydrogenation of benzene to cyclohexene in a suspended state. The catalytic reaction is completed in two phases. The disadvantage of this process is that the catalyst must be separated from the organic phase and compared with possible salts. difficulty
Chinese patent CN1597099A discloses a ruthenium-based supported catalyst prepared by an impregnation precipitation method with metal oxide zirconia as a carrier. The yield of cyclohexene can only reach 40%, and the catalyst uses zirconia as a carrier, and the precious metal difficult to recycle
But the conversion rate of benzene is low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 (if there is no special note below, the percentages are percentages by weight)

[0023] The process conditions are as follows: hydrogen partial pressure 0.8MPa, reaction temperature 160°C, volumetric space velocity 3.0h -1 , gas volume ratio 1200, hydrogenation catalyst E-1 composition and evaluation results are shown in Table 1 and Table 2.

[0024] The preparation process of the hydrogenation catalyst is as follows: (1) Mix 1 mole of ethyl orthosilicate and 20 moles of tetrabutyl titanate, slowly add it dropwise to 100 liters of nitric acid solution with a pH value of 2 at 35°C, quickly Stir, carry out hydrolysis, continue to stir for 20 minutes after the dropwise addition is completed, let it stand for aging for 4 hours, separate the solid therein, dry at 110°C for 8 hours, and roast at 580°C for 3 hours to obtain a molar ratio of silicon dioxide and titanium dioxide of 1:20, the specific surface area is 506m 3 / g, the pore volume is 0.71cm 3SiO 2 and t...

Embodiment 2

[0026] The process conditions are as follows: hydrogen partial pressure 0.8MPa, reaction temperature 180°C, volumetric space velocity 4.0h -1 , gas volume ratio of 1000, hydrogenation catalyst E-2 composition and evaluation results are shown in Table 1 and Table 2.

[0027] The preparation method of the catalyst is the same as in Example 1, except that in the silicon dioxide and titanium dioxide composite oxide prepared in step (1), the molar ratio of silicon dioxide and titanium dioxide is 1:5, and the specific surface area is 537m 3 / g, the pore volume is 0.68cm3 / g; (2) The amount of boric acid used in the step is different. The catalyst E-2 used in the process of the present invention is obtained.

Embodiment 3

[0029] The process conditions are as follows: hydrogen partial pressure 1.5MPa, reaction temperature 160°C, volumetric space velocity 3.0h -1 , gas volume ratio of 900, hydrogenation catalyst E-3 composition and evaluation results are shown in Table 1 and Table 2.

[0030] The preparation method of the catalyst is the same as in Example 1, the difference is that in the silicon dioxide and titanium dioxide composite oxide prepared in step (1), the molar ratio of silicon dioxide and titanium dioxide is 1:10, and the specific surface area is 637m 3 / g, the pore volume is 0.60cm3 / g; (3) The active metal component used in the step is palladium, and the content is different. The catalyst E-3 used in the process of the present invention is obtained.

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Abstract

The invention discloses a cyclohexene preparation process by partial hydrogenation of benzene. The method uses phenol-containing benzene as a raw material, and carries out a partial hydrogenation reaction in the presence of a hydrogenation catalyst to prepare cyclohexene under the following reaction conditions: hydrogen partial pressure of 0.1-5.0 MPa, reaction temperature of 100-300 DEG C, volume space velocity of 0.5-10.0 / h, and volume ratio of gas and agent of 200-2000, wherein the phenol accounts for 0.5-10 wt% in the raw material. The method can simultaneously improve the conversion rate of benzene and the selectivity of cyclohexene.

Description

technical field [0001] The invention relates to a method for preparing cyclohexene, in particular to a method for preparing cyclohexene by partial hydrogenation of benzene. Background technique [0002] Cyclohexene has active double bonds and is an important organic chemical raw material. As an intermediate, cyclohexene can be widely used in the production of medicines, pesticides, dyes, detergents, explosives, feed additives, polyesters and other fine chemicals. [0003] Industrially, there are many ways to obtain cyclohexene. Traditionally, there are methods such as dehydration of cyclohexanol and dehydrohalogenation of halocyclohexane. Due to the use of high-cost cyclohexanol and halocyclohexane as raw materials, and the complicated process, the production cost of cyclohexene obtained by traditional methods is relatively high. The cyclohexene obtained by the traditional method is usually only suitable for the preparation of products with small demand and high added val...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/20C07C5/11B01J23/46
Inventor 徐会青贾立明王伟刘全杰
Owner CHINA PETROLEUM & CHEM CORP
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