Utilization method of solid catalyst for cyclohexanone self-condensation reaction

A technology of solid catalyst and condensation reaction, applied in chemical instruments and methods, preparation of organic compounds, physical/chemical process catalysts, etc., can solve problems such as large limitations, deactivation, and poor catalyst activity

Inactive Publication Date: 2008-06-25
CHINA UNIV OF PETROLEUM (EAST CHINA) +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been a small number of literature reports on solid catalysts that can be applied to the condensation reaction of cyclohexanone. For example, the Shanxi Coal Chemical Industry Institute has developed a modified α-Al catalyst for the condensation reaction of cyclohexanone. 2 o 3 Or magnesium-aluminum spinel catalyzes the condensation reaction of cyclohexanone, adopts gas phase reaction, and the temperature is 350-400 ° C, but the activity of the catalyst is poor (the highest conversion rate is 44%) and it is rapidly deactivated
There are also acidic cationic resins that have been studied in China and Japan, which also have a certain catalytic effect, but for industrial production, this type of catalyst has relatively large limitations.

Method used

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  • Utilization method of solid catalyst for cyclohexanone self-condensation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] This example is a comparative example of concentrated sulfuric acid catalyst. Put 100mL of cyclohexanone into a three-neck flask equipped with a thermometer, agitator and water separator, add 2mL of 98% concentrated sulfuric acid as a catalyst, and 60mL of cyclohexane as a water-carrying agent, reflux at 110°C for 2 hours, and the reaction stops Finally, the reaction system was adjusted to neutral with 10% NaOH solution, and after the water layer was separated, the oil phase was taken for chromatographic analysis. The conversion rate of cyclohexanone was about 85.7%, the selectivity was about 83.5%, and the dimer yield was 71.6%. .

Embodiment 2

[0023] Put 100mL of cyclohexanone in a three-neck flask equipped with a thermometer, agitator and water separator, add water in n-heptane (amount of 60mL), add 4g of γ-Al obtained by roasting at 500°C for 4 hours in advance 2 o 3 Catalyst (pore volume 0.52mL / g, specific surface area 207m 2 / g), heated to system boiling reflux reaction for 6 hours, cyclohexanone conversion rate 75.7%, dimer selectivity 99.0%, dimer yield 74.9%; water-carrying agent is unchanged, and replacement catalyst is 5% K 2 O-Al 2 o 3 Composite catalyst, cyclohexanone conversion rate 82.1%, dimer selectivity 96.6%, dimer yield 79.3%; the water-carrying agent remains unchanged, and the catalyst is replaced with 10% TiO 2 -Al 2 o 3Compound catalyst catalyst, cyclohexanone conversion rate 78.3%, dimer selectivity 98.6%, dimer yield 77.2%; catalyst is γ-Al 2 o 3 , replacing the water-carrying agent with toluene (consumption unchanged), the conversion rate of cyclohexanone is 88.8%, the dimer selectivit...

Embodiment 3

[0025] Put 100mL of cyclohexanone into a three-neck flask equipped with a thermometer, agitator and water separator, add water in n-heptane (amount of 60mL), add 4g of industrial macroporous Al obtained by roasting at 500°C for 4 hours in advance 2 o 3 Catalyst (pore volume 0.79mL / g, specific surface 281m 2 / g), heated until the system boiled and refluxed for 6 hours, the conversion rate of cyclohexanone was 81.8%, the dimer selectivity was 96.5%, and the dimer yield was 78.9%. Other conditions remain unchanged, the replacement catalyst is 33.5% MgO-macroporous Al 2 o 3 With the compound catalyst, the conversion rate of cyclohexanone is 76.5%, the dimer selectivity is 95.2%, and the dimer yield is 72.8%.

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Abstract

The invention relates to a method for using a solid catalyst for the self-condensing reaction of a cyclohexanone, which comprises the steps that an alumina-based solid catalyst is used in the first step of condensing and dehydrogenating the cyclohexanone to prepare the O-phenylphenol, namely the step of the self-condensing of the cyclohexanone, and a certain used amount of the appropriate water-carrying agents are used in the process of using the alumina-based solid catalyst for the condensation reaction of the cyclohexanone; wherein, the used amount of the solid catalysts corresponds to 2 per cent to 5 per cent of that of the cyclohexanone and the reaction time ranges from 4 to 8 hours; also that any water-carrying agents is unused is okay and the characteristic that the cyclohexanone carries water is utilized to accomplish the reaction; the cyclohexanone undergoes the self-condensing reaction so as to generate two resonance isomers, 2-(1-cyclohexenyl) (I) cyclohexanone and 2-cyclohexenyl alkylidene cyclohexanone (II), under the effect of the prepared solid catalysts, and two demeric products can be both used as the raw materials for carrying out the dehydrogenation to prepare the O-phenylphenol.

Description

technical field [0001] The invention relates to a method for using a solid catalyst for the self-condensation reaction of cyclohexanone. The method is to use a Alumina-based solid catalysts can use suitable water-carrying agents in the use of alumina-based solid catalysts for the condensation reaction of cyclohexanone, and can also use cyclohexanone itself to carry water to complete the reaction without using any water-carrying agents. Ketone, under the effect of prepared solid catalyst, self-condensation reaction occurs and generates two kinds of resonance isomers 2-(1-cyclohexenyl) (I) cyclohexanone and 2-cyclohexylene alkyl cyclohexanone (II ), both dimerization products can be used as raw materials for the preparation of o-phenylphenol by dehydrogenation. Background technique [0002] Ortho-phenylphenol (OPP) is an important organic chemical product with a wide range of uses and good development prospects. There are many production processes, but many of them have been ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/06C07C37/18B01J21/04
CPCY02P20/52
Inventor 刘晨光李彦鹏赵会吉邢金仙
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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