cu 2 S/imidazole compound/tempo catalyzes the method for preparing aldehyde by air oxidation of alcohol

A technology of compounds and imidazoles is applied in the field of catalytic air oxidation of alcohol to prepare aldehydes, which can solve the problems of difficult recovery of homogeneous catalysts, and achieve the effects of high yield, good substrate applicability and easy operation.

Active Publication Date: 2021-09-17
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Cu / TEMPO catalytic system has been widely used in homogeneously catalyzed oxidation of alcohols, but homogeneous catalysts are not easy to recycle

Method used

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  • cu <sub>2</sub> S/imidazole compound/tempo catalyzes the method for preparing aldehyde by air oxidation of alcohol
  • cu <sub>2</sub> S/imidazole compound/tempo catalyzes the method for preparing aldehyde by air oxidation of alcohol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In a 25mL reaction flask, add cuprous sulfide (19.9mg, 0.125mmol), then add N-methylimidazole (20.5mg, 0.25mmol), TEMPO (19.5mg, 0.125mmol) and benzyl alcohol (540.6mg, 5mmol) ), 6 mL of acetonitrile. Stir vigorously in air at 25 °C for 24 h. After 24 hours of reaction cessation, pipette 0.5 mL of internal standard (o-dichlorobenzene) into a 10 mL volumetric flask and dilute to volume with acetonitrile, use an organic microporous filter membrane to filter, draw and inject 0.2 μL of the filtered solution, The product was analyzed by gas chromatography. According to the internal standard-standard curve method, the calculated yield of benzaldehyde was 98%, and the gas phase analysis purity was 99%. The chemical formula is as follows:

[0017] in,

[0018] N-methylimidazole, referred to as NMI;

Embodiment 2

[0020] In the 25mL reaction flask, add cuprous sulfide (19.9mg, 0.125mmol) respectively, then add N-methylimidazole (20.5mg, 0.25mmol), TEMPO (19.5mg, 0.125mmol) and 4-methylbenzyl alcohol ( 610.9mg, 5mmol), 6mL acetonitrile. Stir vigorously in air at 25 °C for 24 h. Use a pipette to pipette 0.2mL of the reaction solution, then use acetonitrile to make up to volume in a 5mL volumetric flask, filter with an organic microporous membrane, absorb 0.2μL of the filtered solution, and analyze it by gas chromatography-mass spectrometry product. The yield of 4-methylbenzaldehyde is >99%, and the purity by gas phase analysis is 99%.

Embodiment 3

[0022] In the 25mL reaction bottle, add cuprous sulfide (19.9mg, 0.125mmol) respectively, then add N-methylimidazole (20.5mg, 0.25mmol), TEMPO (19.5mg, 0.125mmol) and 2-methylbenzyl alcohol ( 610.9mg, 5mmol), 6mL acetonitrile. Stir vigorously in air at 25 °C for 24 h. Use a pipette to pipette 0.2mL of the reaction solution, then use acetonitrile to make up to volume in a 5mL volumetric flask, filter with an organic microporous membrane, absorb 0.2μL of the filtered solution, and analyze it by gas chromatography-mass spectrometry product. The yield of 2-methylbenzaldehyde is >99%, and the purity by gas phase analysis is 99%.

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PUM

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Abstract

The invention discloses a Cu 2 S / imidazole compound / TEMPO catalyzes the method that air oxidation alcohol prepares aldehyde, is raw material with alcohol, and air is oxidant, in Cu 2 Under the catalysis of S / imidazole compound / TEMPO, the raw material alcohol is oxidized to obtain the corresponding aldehyde; the present invention utilizes Cu 2 S / imidazole compound / TEMPO catalyzes oxyalcohols to obtain the corresponding aldehydes. The catalytic system is simplified, the operation is simple, the substrate applicability is good, the yield is high, the cost is low, and it is easy for industrial production and the catalyst can be recycled. It is a very economical , Simple method for preparing aldehydes from alcohols.

Description

technical field [0001] The invention relates to the field of methods for preparing aldehydes by catalytic air oxidation of alcohols. More specifically, the present invention relates to a Cu 2 S / imidazole compound / TEMPO catalyzed air oxidation method of alcohol to prepare aldehyde. Background technique [0002] As we all know, aldehydes or ketones play an important role in our life. Oxidation of alcohols to aldehydes or ketones is often used in the field of organic synthesis or in industry. The traditional production process is to oxidize alcohols to aldehydes or ketones with chemical doses of chromium reagents, manganese reagents or hypervalent iodides, etc., but this method has the disadvantages of serious pollution and low atom economy. With the development of the times and the popularization of the concept of green chemistry, these production processes can no longer meet the needs of today's society. Therefore, the development of green, economical and efficient cataly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/28C07C45/38C07C47/542C07C47/55C07C47/544C07C47/21C07C47/232C07D333/22C07D213/48
CPCB01J31/006B01J31/28C07C45/38C07C47/542C07C47/55C07C47/544C07C47/21C07C47/232C07D333/22C07D213/48Y02P20/584
Inventor 张培培刘小明钟伟沈忠权
Owner JIAXING UNIV
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