Method for preparing aldehyde or ketone by copper salt/bidentate ligand/TEMPO catalytic air oxidation alcohol

A bidentate ligand and alcohol oxidation technology, which is applied in the field of copper salt/bidentate ligand/TEMPO catalyzing air oxidation of alcohol to prepare aldehyde or ketone, can solve the problem of increasing the cost of catalytic reaction, inconsistency with green, energy saving and sustainable development, The system composition is complex and other problems, to achieve the effect of high yield, simple operation and simplified catalytic system

Inactive Publication Date: 2018-12-28
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the major defect of this type of homogeneous catalytic system is that the system is complex (basically composed of copper salts, ligands, TEMPO and additives), which greatly increases the cost of catalytic reactions.
None of these unfavorable factors meet the requirements of green, energy saving and sustainable development

Method used

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  • Method for preparing aldehyde or ketone by copper salt/bidentate ligand/TEMPO catalytic air oxidation alcohol
  • Method for preparing aldehyde or ketone by copper salt/bidentate ligand/TEMPO catalytic air oxidation alcohol
  • Method for preparing aldehyde or ketone by copper salt/bidentate ligand/TEMPO catalytic air oxidation alcohol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] In a 25mL reaction flask, copper iodide (47.2mg, 0.25mmol) was added, followed by tetramethylethylenediamine (TMEDA) (29mg, 0.25mmol), TEMPO (39.1mg, 0.25mmol) and n-octanol ( 651mg, 5mmol), 5mL dichloromethane. Stir vigorously in air at 25 °C for 24 h. After 24 hours of reaction stop, pipette 0.5mL internal standard (biphenyl), then dichloromethane to a 10mL volumetric flask to volume, use an organic microporous filter membrane to filter, absorb 0.2μL of the filtered solution into the The product was analyzed by gas chromatography. According to the internal standard-standard curve method, the calculated yield of n-octanal was 86%, and the gas phase analysis purity was 99%.

[0019] Its chemical formula is as follows:

[0020]

Embodiment 2

[0022] To the 25mL reaction flask, add cuprous iodide (47.2mg, 0.25mmol), then add tetramethylethylenediamine (58mg, 0.5mmol), TEMPO (39.1mg, 0.25mmol) and n-octanol (651mg, 5mmol) ), 5 mL of dichloromethane. Stir vigorously in air at 25 °C for 24 h. After 24 hours of reaction stop, pipette 0.5mL internal standard (biphenyl), then dichloromethane to a 10mL volumetric flask to volume, use an organic microporous filter membrane to filter, absorb 0.2μL of the filtered solution into the The product was analyzed by gas chromatography. According to the internal standard-standard curve method, the calculated yield of n-octanal was 35%, and the gas phase analysis purity was 99%.

Embodiment 3

[0024] In a 25mL reaction flask, copper iodide (47.2mg, 0.25mmol) was added, followed by tetramethylethylenediamine (29mg, 0.25mmol), TEMPO (39.1mg, 0.25mmol) and n-octanol (651mg, 5mmol) ), 5mL acetonitrile. Stir vigorously in air at 25 °C for 24 h. After 24 hours of reaction stop, pipette 0.5mL internal standard (biphenyl), then dichloromethane to a 10mL volumetric flask to volume, use an organic microporous filter membrane to filter, absorb 0.2μL of the filtered solution into the The product was analyzed by gas chromatography. According to the internal standard-standard curve method, the calculated yield of n-octanal was 70%, and the gas phase analysis purity was 99%.

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Abstract

The invention discloses a method for preparing aldehyde or ketone by copper salt/bidentate ligand/TEMPO catalytic air oxidation alcohol. The alcohol is used as a raw material, an organic solution is used as a solvent, and the air is used as an oxidant. The raw material alcohol is oxidized to obtain the corresponding aldehyde or ketone under the catalysis of the copper salt/ bidentate ligand /TEMPO. The copper salt/bidentate ligand/TEMPO catalytic air oxidation alcohol is utilized. A technical route has the advantages of simplifying a catalytic system, being simple in operation, good in substrate applicability, high in yield, low in cost and easy to industrialize, so that the method is a very economical simple method for preparing the aldehyde or the ketone from the alcohol.

Description

technical field [0001] The invention relates to the field of catalytic air oxidation of alcohol to prepare aldehyde or ketone. More specifically, the present invention relates to a method for preparing aldehyde or ketone by copper salt / bidentate ligand / TEMPO catalyzed air oxidation of alcohol. Background technique [0002] The selective oxidation of alcohol is a very important functional group conversion reaction in organic synthesis. The reaction product aldehyde or ketone is an important precursor for the synthesis of drugs, vitamins, spices and fibers, etc., and plays an important role in the field of basic research and fine chemical production. status. Traditionally, stoichiometric oxidants are mostly used for this transformation, such as chromium reagents, manganese reagents and other transition metal oxides, hypervalent iodine reagents, etc. These production processes have problems such as poor atom economy, serious environmental pollution and high cost, which have be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07C47/02C07C47/06C07C47/232C07C47/54C07C47/55C07C47/52C07C47/542C07C47/575C07D333/16C07C49/213
CPCC07C45/29C07D333/16C07C47/02C07C47/06C07C47/232C07C47/54C07C47/55C07C47/52C07C47/542C07C47/575C07C49/213
Inventor 钟伟刘小明刘真真沈忠权
Owner JIAXING UNIV
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