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Method for preparing cyclohexanol and cyclohexanone by catalytic oxidation of cyclohexane

A technology for catalytic oxidation and cyclohexane, applied in the field of catalytic oxidation of cyclohexane to prepare cyclohexanol and cyclohexanone, can solve the problem that high cyclohexane conversion rate and high alcohol ketone selectivity cannot be achieved at the same time, and industrial production cannot be achieved. requirements, low conversion of cyclohexane, etc., to achieve the effect of maintaining low temperature, high activity, high stereoselectivity, and controlling catalytic activity

Inactive Publication Date: 2009-07-08
ZHEJIANG APELOA MEDICAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The results show that: when M is Co, Mn or Ni, only cyclohexanol and cyclohexanone are generated, but the conversion rate of cyclohexane is not high; when M is Fe or there is no metal M, the conversion rate of cyclohexane is high , but the selectivity of alcohol and ketone is poor, and a large amount of peroxycyclohexane is generated in the reaction, that is, [PW 11 o 39 ] 7- and [PW 11 Fe(H 2 O)O 39 ] 4- It has relatively high catalytic activity, and the conversion rate of cyclohexane can reach up to 76% after 9 hours of reaction, but the main product is cyclohexane peroxide, and the conversion rate of cyclohexane can reach more than 96% after continuing to react for 1 hour. However, the obtained products are quite complicated, and the selectivity drops sharply, which cannot meet the requirements of industrial production.
Therefore, this research protocol still cannot achieve high cyclohexane conversion and high alcohol and ketone selectivity at the same time

Method used

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  • Method for preparing cyclohexanol and cyclohexanone by catalytic oxidation of cyclohexane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] In a 2000 ml glass flask, add 1000 ml of acetonitrile, 0.3 g of heteropolyacid catalyst H 2 [V 4 (H 2 O) 9 (PW 9 o 34 ) 2 ], add 14 milliliters of 30% (mass percentage concentration) aqueous hydrogen peroxide solution, stir and reflux at room temperature for half an hour, then add 20 milliliters of hexanaphthene, increase the temperature value to 80 ° C, slowly add the remaining 30% (mass percent concentration) hydrogen peroxide aqueous solution (55 milliliters), constant temperature reaction 9-12 hour, reduce temperature to room temperature, GC analysis mixture, cyclohexane transformation rate is 98%, and the total selectivity of cyclohexanol and cyclohexanone is 97%. The ratio of cyclohexanol to cyclohexanone is 1:2.

Embodiment 2

[0049] In a 2000 ml glass flask, add 1000 ml of water and 0.3 g of heteropolyacid catalyst H 2 [V 4 (H 2 O) 9 (PW 9 o 34 ) 2 ], add 14 milliliters of 30% (mass percentage concentration) aqueous hydrogen peroxide solution, stir and reflux at room temperature for half an hour, then add 20 milliliters of hexanaphthene, increase the temperature value to 80 ° C, slowly add the remaining 30% (mass percentage concentration) hydrogen peroxide aqueous solution (55ml), constant temperature reaction 9-12 hour, reduce temperature to room temperature, GC analysis mixture, cyclohexane conversion efficiency is 91%, and the total selectivity of cyclohexanol and cyclohexanone is 98 %. The ratio of cyclohexanol to cyclohexanone is 1:1.

Embodiment 3

[0051] In a 2000 ml glass flask, add 1000 ml of dichloroethane, 0.3 g of heteropolyacid catalyst H 2 [V4 (H 2 O) 9 (PW 9 o 34 ) 2 ], add 14ml of 30% (mass percent concentration) hydrogen peroxide aqueous solution, stir and reflux at room temperature for half an hour, then add 20 milliliters of hexanaphthene, increase the temperature value to 80 ° C, slowly add dropwise the remaining (55ml) 30% (mass percentage concentration) hydrogen peroxide aqueous solution, constant temperature reaction 9-12 hours, reduce temperature to room temperature, GC analysis mixture, cyclohexane conversion rate is 90%, the total selectivity of cyclohexanol and cyclohexanone is 97% . The ratio of cyclohexanol to cyclohexanone is 1.2:1.

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Abstract

The invention discloses a method for preparing cyclohexanol and cyclohexanone. The method comprises the steps of taking cyclohexane as raw material, taking hydrogen peroxide aqueous solution as oxidant and performing catalytic oxidation under the action of a catalyst so as to prepare the cyclohexanol and the cyclohexanone, wherein the catalyst is (An)[M4(H2O)y(ZW9Ox)2]. The method has the advantages of high conversion rate of the cyclohexane, high selectivity of the cyclohexanol and the cyclohexanone and easy regeneration of the catalyst.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for preparing cyclohexanol and cyclohexanone by catalytic oxidation of cyclohexane. Background technique [0002] Cyclohexanone and cyclohexanol are important organic chemical raw materials and are widely used. At present, the main method of producing cyclohexanone and cyclohexanol at home and abroad is cyclohexane oxidation. The oxidation reaction of cyclohexane is relatively complicated. It first generates cyclohexyl hydroperoxide through free radical reaction, and then the peroxide is decomposed into cyclohexanol and cyclohexanone by heat. Because cyclohexanone and cyclohexanol are easier to oxidize than cyclohexane , There are also a large number of by-products generated during the oxidation of cyclohexane. (see formula 1: cyclohexane oxidation process). [0003] [0004] Formula 1: Cyclohexane oxidation process [0005] Rate constant ratio of each reaction pr...

Claims

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Application Information

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IPC IPC(8): C07C35/08C07C29/48C07C49/403C07C45/28B01J27/199B01J27/188B01J23/30B01J23/888B01J31/02
CPCY02P20/584
Inventor 徐新良王建民郑小明何春杨杰杨晓兵
Owner ZHEJIANG APELOA MEDICAL TECH
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