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Process for preparing cyclohexanone and cyclohexanol by cyclohexane selective oxidation

A technology of cyclohexane and cyclohexanone, which is applied in the fields of catalytic chemistry, organic chemistry and industrial chemical synthesis, can solve the problems of low selectivity and harsh catalyst preparation, and achieves simple preparation process, good cycle stability, and preparation of raw materials. Inexpensive and accessible effects

Inactive Publication Date: 2012-10-03
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalyst used is mainly characterized by nitrogen doping. Compared with the above-mentioned patents, the conversion rate of cyclohexane is greatly improved, but the preparation of the catalyst is relatively harsh, and the main products of the reaction are adipic acid, KA oil (cyclohexanol +cyclohexanone) very low selectivity

Method used

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  • Process for preparing cyclohexanone and cyclohexanol by cyclohexane selective oxidation
  • Process for preparing cyclohexanone and cyclohexanol by cyclohexane selective oxidation
  • Process for preparing cyclohexanone and cyclohexanol by cyclohexane selective oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1-4 is to use phenol and furfural as carbon source with Co(NO 3 ) 2 Comparison of Catalytic Selective Oxidation of Cyclohexane to Cyclohexanone and Cyclohexanol Catalyzed by Graphitized Catalysts Obtained at Different Carbonization Temperatures. The experimental conditions are: 125ml stainless steel autoclave, 12g cyclohexane, 8g acetonitrile, 0.3g cyclohexanone, catalyst GMC-Co-800 (carbonization at 800°C, Example 1), GMC-Co-900 (Example 2) , GMC-Co-1000 (Example 3), GMC-Co-1100 (Example 4), 50mg, 1.5MPa O 2 , 140 ° C reaction 2 ~ 10h.

[0024] The comparative results of Examples 1-4 are shown in Table 1.

[0025] Table 1

[0026]

[0027]

Embodiment 5

[0028] Embodiment 5-9 is with glucose and resorcinol as carbon source, with Fe(NO 3 ) 2 Comparison of Catalytic Selective Oxidation of Cyclohexane to Cyclohexanone and Cyclohexanol Catalyzed by Graphitized Catalysts. The experimental conditions are: 125ml stainless steel autoclave, 12g cyclohexane, 8g acetone, 0.3g cyclohexanone, catalyst GMC-Fe-2 (900°C carbonization for 2h, Example 5), GMC-Fe-4 (Example 6) , GMC-Fe-6 (Example 7), GMC-Fe-8 (Example 8), GMC-Fe-10 (Example 9), 100mg, 1.5MPa O 2 , 140 ° C reaction 2 ~ 10h. The comparison results of Examples 5-9 are shown in Table 2.

[0029] Table 2

[0030]

Embodiment 10

[0031] Embodiment 10-12 is with different carbon sources, with Fe(NO 3 ) 2 Comparison of Catalytic Selective Oxidation of Cyclohexane to Cyclohexanone and Cyclohexanol Catalyzed by Graphitized Catalysts. Experimental condition is: 125ml stainless steel autoclave 12g cyclohexane, 8g acetonitrile, 0.3g cyclohexanone, catalyst GMC-Fe-glucose / resorcinol (embodiment 10), GMC-Fe-sucrose / phloroglucinol ( Embodiment 11), GMC-Fe-furfural / phenol (embodiment 12), 50mg, 1.5MPa O 2 , 140 ° C reaction 2 ~ 10h. The comparative results of Examples 10-12 are shown in Table 3.

[0032] table 3

[0033]

[0034]

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PUM

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Abstract

The invention discloses a process for preparing cyclohexanone and cyclohexanol by cyclohexane selective oxidation. The process includes steps of adding cyclohexane, a solvent, a trace initiator and a solid catalyst into a reactor and filling oxygen with high pressure of 0.8-2.5Mpa to react at the temperature of 90-140 DEG C for 2-24 hours so as to obtain reaction products. The solvent can be any one of acetic acid, acetonitrile,acetone and methanol; cyclohexane is taken as the initiator; and carbon materials graphitized partially are taken as the solid catalyst. The solid catalyst is prepared by steps of mixing phenols with glucose or saccharose or furfural, adding Fe3+ or Co2 or Ni2+ salt, performing hydrothermal carbonization at the temperature of 160-200 DEG C, and removing residual metal by acid dissolving after high-temperature carbonization (at the temperature equal to or higher than 800 DEG C). The overall selectivity of cyclohexanone and cyclohexanol can be 57%, the conversion rate of cyclohexane can be 55%, the catalyst in reaction can be recovered, and accordingly the process is environment-friendly and is an easy and convenient method for preparing cyclohexanone and cyclohexanol. Further, pure oxygen is utilized as an oxidant, which is cheaper and much environment-friendly than hydrogen peroxide serving as a conventional oxidant.

Description

technical field [0001] The invention belongs to the fields of catalytic chemistry, organic chemistry and industrial chemical synthesis, in particular to a method for preparing six-membered ring alcohols or ketones, more specifically to a method for preparing cyclohexanone and cyclohexanol. Background technique [0002] The selective oxidation of cyclohexane to prepare cyclohexanol and cyclohexanone is an important reaction in industry. Cyclohexanol and cyclohexanone are important organic chemical raw materials, important intermediates for the synthesis of caprolactam, adipic acid, and fine chemicals such as medicine, paint, dyes, etc. Raw materials such as phenylphenol can also be used as additives for fine chemicals, and also play a significant role in printing and recycling of plastics. At present, the monomer caprolactam and adipic acid of synthetic fiber nylon-6 and nylon-66 are mainly produced from cyclohexanone. At present, the demand for cyclohexanone in the domesti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C27/12C07C35/08C07C29/50C07C45/33C07C49/403
CPCY02P20/584
Inventor 任家文应婷王安苗王艳芹卢冠忠刘晓晖郭耘郭扬龙王筠松张志刚龚学庆
Owner EAST CHINA UNIV OF SCI & TECH
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