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Method for preparing lactone through catalyzing oxidation of ketone compound, and its special catalyst

A compound and catalyst technology, applied in the field of catalyzing the oxidation of ketone compounds to prepare lactones, can solve the problem of large dosage of auxiliary agents, and achieve the effects of reducing dosage, improving utilization rate and mild conditions

Inactive Publication Date: 2014-08-13
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent ZL101205225A reports a method for producing lactones by metalloporphyrin biomimetic catalyzed oxidation of ketones. This method has problems such as a large amount of additives (15 times that of raw materials). A method for preparing caprolactone by oxidation of cyclohexanone, which uses an azo free radical initiator in the reaction process, has safety problems, so the present invention uses π electrons and metalloporphyrin rings on the carbon nanotube tube wall A series of metalloporphyrin-carbon nanotube catalysts were prepared by the π-π stacking effect between the π electrons on the surface. In the presence of oxygen or air, benzaldehyde was used as an auxiliary agent to catalyze the oxidation of ketones to lactones

Method used

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  • Method for preparing lactone through catalyzing oxidation of ketone compound, and its special catalyst
  • Method for preparing lactone through catalyzing oxidation of ketone compound, and its special catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Take 0.020g of carboxylated multi-walled carbon nanotubes (c-MWCNTs), add 20mL of anhydrous N,N-dimethylformamide into a 50mL three-necked flask, and ultrasonicate the reaction solution for 3h. After the reactants are uniformly dispersed, the Add 0.100g FeTPPCl into the flask, heat it in an oil bath to reflux, cool the reaction solution to room temperature after 8 hours, filter it with a 0.22 μm polytetrafluoroethylene microporous membrane, wash it with tetrahydrofuran for more than three times until it is colorless, and then The black substance was dispersed into N,N-dimethylformamide again, ultrasonicated for 20 minutes, filtered through a 0.22 μm polytetrafluoroethylene microporous membrane, washed with tetrahydrofuran until the filtrate was colorless, and could be obtained after repeated operations Unreacted metalloporphyrins are removed. Disperse the obtained black substance into N,N-dimethylformamide again, ultrasonicate it, place it on a centrifuge and centrifuge...

Embodiment 2

[0022] In 10mL containing 5mg metalloporphyrin-carboxylated multi-walled carbon nanotubes (M=Fe, X=F, R 1 , R 2 , R 3 , R 4 , R 5 =H,X 1 In the 1,2-dichloroethane solution of F), add 2mmol of cyclohexanone and 2mmol of benzaldehyde, feed oxygen, and stir the reaction at a temperature of 50°C for 2 hours. After detection and analysis, the cyclohexanone The conversion rate is 89%, and the selectivity of ε-caprolactone is greater than 99%.

Embodiment 3

[0024] In 10mL containing 10mg metalloporphyrin-carboxylated single-walled carbon nanotubes (M = Fe, X = F, R 1 , R 2 , R 3 , R 4 , R 5 =H,X 1 In the 1,2-dichloroethane solution of F), add 2mmol of 4-methylcyclohexanone and 6mmol of benzaldehyde, and stir the reaction at a temperature of 60°C for 5 hours. After detection and analysis, 4-methyl The conversion rate of cyclohexanone is 92%, and the selectivity of 4-methylcyclocaprolactone is greater than 99%.

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Abstract

The invention discloses a method for preparing lactone through catalyzing the oxidation of a ketone compound, and its special catalyst. The catalyst is a metalloporphyrin-carbon nanotube catalyst prepared through a pi-pi accumulation effect between the pi electron on the tube wall of the carbon nanotube and the pi electron on a metalloporphyrin ring. The method for preparing lactone through catalyzing the oxidation of a ketone compound uses a metalloporphyrin-carbon nanotube compound as the catalyst comprises the following steps: adding an organic solvent and an assistant, and carrying out a catalytic reaction at a reaction temperature of 25-100DEG C under normal pressure to highly selectively obtain a lactone compound. The method and the catalyst have the advantages of simple technology, mild conditions, high selectivity, safety and the like.

Description

technical field [0001] The invention relates to a method for preparing lactone, in particular to a method for catalyzing the oxidation of ketone compounds to prepare lactone and a special catalyst thereof. Background technique [0002] Lactone is an important intermediate in organic synthesis, which is widely used in the preparation of blended modified resins and fine chemicals. At present, lactones are mainly prepared by the Baeyer-Villiger oxidation reaction, and organic peracids such as peracetic acid and peroxybenzoic acid are usually used as oxidants. However, in actual operation, there are high oxidant costs, high energy consumption in the process, and safety Many problems, such as poor performance, make the practical application of this process limited. [0003] Therefore, the use of environmentally friendly and safe oxygen / air as an oxidant to prepare lactones has attracted much attention. Among them, metalloporphyrins can activate oxygen and realize the catalytic r...

Claims

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Application Information

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IPC IPC(8): C07B41/12C07D313/04C07D313/10C07D309/30C07C67/42C07C69/24C07C69/78C07C69/14B01J31/22
Inventor 纪红兵陈韶云周贤太
Owner SUN YAT SEN UNIV
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