Method for preparing cyclohexene by benzene selective hydrogenation

A technology for selective hydrogenation and cyclohexene, applied in the fields of hydrogenation to hydrocarbons, organic chemistry, etc., can solve the problem of low selectivity, and achieve the effects of improving selectivity, increasing the conversion rate of benzene, high activity and selectivity

Active Publication Date: 2013-09-11
BEIJING ENERGY ENG TECH +1
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The purpose of the present invention is to overcome the problem of low selectivity of cyclohexene prepared by selective hydrogenation of benzen

Method used

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  • Method for preparing cyclohexene by benzene selective hydrogenation
  • Method for preparing cyclohexene by benzene selective hydrogenation

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Example Embodiment

[0027] According to the above-mentioned method for preparing cyclohexene of the present invention, the conversion rate of benzene and the selectivity of cyclohexene can be improved. However, in order to better achieve the purpose of the present invention, preferably, the benzene is contacted with hydrogen. It is carried out in the presence of water and / or alcohol, which helps the formation of cyclohexene. The type and method of addition of the alcohol can be added at once or in batches. There is no special requirement in the present invention. Preferably, the alcohol is selected from tetramethylene glycol, benzyl alcohol, α-naphthyl alcohol and 1,4-butane. One or more of the diols. More preferably, the organic alcohol is a mixture of hexanediol and benzyl alcohol to further improve the selectivity of cyclohexene. The volume ratio of hexanediol to benzyl alcohol can be Choose from a wide range, in order to better achieve the purpose of the present invention, the volume ratio of ...

Example

[0046] Preparation Examples 1-6

[0047] This preparation example is used to illustrate the preparation of the hydrogenation catalyst provided by the present invention.

[0048] All the doughnut-shaped SBA-15 prepared by the method of preparing the doughnut-shaped SBA-15 carrier of the present invention is calcined at 400°C for 10 hours (thermal activation) under the protection of nitrogen to remove the hydroxyl group and residual moisture, and obtain the thermally activated post The doughnut-shaped SBA-15, and the hydrogenation catalyst C1-C6 was prepared according to the incipient wetness impregnation method. The hydrogenation catalyst prepared by the incipient wetness impregnation method includes the use of aqueous solutions of ruthenium chloride; aqueous solutions of ruthenium chloride and zinc chloride; aqueous solutions of ruthenium chloride, zinc chloride and nickel nitrate; aqueous solutions of rhodium chloride; rhodium chloride And cobalt sulfate aqueous solution; palladi...

Example Embodiment

[0056] Example 1-6

[0057] This example is used to illustrate the use of the hydrogenation catalyst of the present invention for selective hydrogenation of benzene to produce cyclohexene.

[0058] The catalysts prepared in Preparation Examples 1-6 were reduced at 200° C. for 3 hours in a hydrogen stream to activate the catalysts. The obtained catalyst was analyzed by EPMA (X-ray microanalyzer), and it was confirmed that the active components Ru, Rh, and Pd were uniformly dispersed on the carrier. For EMPA analysis, use JXA-8600M (Nippon Denshi K.K.) as the measuring device, the acceleration voltage of the electron gun is set to 20KV, and the detection current is 2.0×10 -8 A.

[0059] In a 0.5L stainless steel autoclave completely purged with nitrogen in advance, 120 ml of water, 6 g of hydrogenation catalyst (respectively added to the activated hydrogenation catalyst prepared in Examples 1-6) and 80 ml of benzene were added. Introduce hydrogen, and react with stirring (1000 revolu...

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Abstract

The invention discloses a method for preparing cyclohexene by benzene selective hydrogenation, which is implemented by contacting benzene with hydrogen under selective hydrogenation conditions in the presence of a hydrogenation catalyst, wherein the hydrogenation catalyst comprises a supporter and a hydrogenation active component supported on the supporter, the supporter is donut-like SBA-15, and the hydrogenation active component contains one or more of Ru, Rh and Pd. When being used for catalyzing reaction of preparing cyclohexene by benzene selective hydrogenation, the hydrogenation catalyst disclosed by the invention can obviously enhance the selectivity of cyclohexene and the conversion rate of benzene.

Description

technical field [0001] The invention relates to a method for preparing cyclohexene through selective hydrogenation of benzene. Background technique [0002] Cyclohexene and its derived downstream products adipic acid, nylon 6, nylon 66, polyamide and polyester are important organic chemical raw materials with important industrial uses and broad market prospects. Cyclohexene, an important raw material for the synthesis of many other fine chemicals, can be prepared by selective hydrogenation of benzene. [0003] Conventional methods for producing cyclohexene generally fall into two categories. One is a multi-step synthesis route based on benzene as raw material. First, cyclohexane or halogenated cyclohexane is made from benzene, and then cyclohexane is made into cyclohexanol and then dehydrated to form cyclohexene or the halogenated ring Hexane is dehydrohalogenated to form cyclohexene. The other is a one-step synthesis route using benzene as a raw material, that is, partia...

Claims

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Application Information

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IPC IPC(8): C07C13/20C07C5/11
Inventor 曲良龙董维正王月金芃澔南方陈健
Owner BEIJING ENERGY ENG TECH
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