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Method for preparing aromatic aldehyde ketone by utilizing air as oxidant in hydro solvent system

A technology of air oxidation and aromatic aldehydes and ketones, which is applied in the direction of oxidation to prepare carbonyl compounds, etc., can solve the problems of a large amount of inorganic waste, achieve the effect of small risk, less inorganic waste, and reduce safety problems

Inactive Publication Date: 2006-06-21
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalytic system is highly efficient but produces large amounts of inorganic waste

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] In a 300 mL Teflon-lined autoclave, add 3.24 g benzyl alcohol (30 mmol), 46.8 mg TEMPO (0.3 mmol), 343 mg 1,3-dibromo-5,5-dimethylhydantoin (1.2 mmol ), 84mg NaNO 2 (1.2mmol), 10mL water, airtight autoclave, inflated with air until the pressure gauge is 0.9MPa, put the autoclave into an oil bath preheated to 80 degrees, and react for 1.5 hours. After lowering the temperature and carefully releasing the pressure, it was extracted three times with an organic solvent, and the organic phase was analyzed by gas chromatography (GC). The conversion rate was 99.8%, and the selectivity of the product benzaldehyde was 100%. The isolated yield was 88%.

Embodiment 2

[0038] In a 300 mL Teflon-lined autoclave, add 3.66 g of 4-methylbenzyl alcohol (30 mmol), 46.8 mg of TEMPO (0.3 mmol), 343 mg of 1,3-dibromo-5,5-dimethylsea Ethanol (1.2mmol), 84mg NaNO 2 (1.2mmol), 10mL water, airtight autoclave, inflated with air to a pressure gauge of 0.1MPa, put the autoclave into an oil bath preheated to 120 degrees, and react for 2 hours. After lowering the temperature and carefully releasing the pressure, it was extracted three times with an organic solvent, and the organic phase was analyzed by gas chromatography (GC). The conversion rate was 100%, and the selectivity of the product p-tolualdehyde was 100%. The isolated yield was 98%.

Embodiment 3

[0040] In a 300 mL Teflon-lined autoclave, add 3.66 g 3-methylbenzyl alcohol (30 mmol), 46.8 mg 4-benzoyl-TEMPO (0.3 mmol), 343 mg N-bromosuccinimide (1.2mmol), 84mg KNO 2 (1.2mmol), 10mL water, airtight autoclave, inflated with air until the pressure gauge is 0.9MPa, put the autoclave into an oil bath preheated to 80 degrees, and react for 2 hours. After lowering the temperature and carefully releasing the pressure, it was extracted three times with an organic solvent, and the organic phase was analyzed by gas chromatography (GC). The conversion rate was 99.7%, and the selectivity of the product m-tolualdehyde was 100%. The isolated yield was 98%.

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PUM

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Abstract

A methid for preparing aromatic keto-aldehyde in water dissolvent system employing air as oxidation agent, employing 2,2,6,6-tetramethylpiperidine-oxygen free radical (TEMPO), 1,3-dibromo-5,5-dimethylhydantoin and sodium nitrite as catalyst, water as dissolvent, air with pressure lower than 1.2 Mpa as oxidation agent, oxidating the serial aromatic alcohol and hetero-aromatic alcohol under temperature of lower than 160 Deg C to relative aromatic aldehyde and ketone.

Description

technical field [0001] The invention relates to a method for preparing aromatic aldehydes and ketones, in particular to a method for preparing aromatic aldehydes and ketones by using water as a solvent and oxygen or air as an oxidant. Background technique [0002] Oxidation of aromatic alcohols to aromatic aldehydes is one of the most important functional group conversion reactions in organic chemistry. Searching for efficient and clean catalytic oxidation systems has always been a research hotspot in organic chemistry. [0003] Over the past few decades, chemists have developed two broad classes of efficient oxidation systems. One is a transition metal-catalyzed catalytic oxidation system that uses oxygen or air as an oxygen source. The products of the catalytic reaction are easily separated and there is not much waste. However, the catalyst is expensive, and commonly used metals include noble metals such as palladium (Pd) and ruthenium (Ru), and ligands with complex struc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29
Inventor 胡信全刘仁华董春燕梁鑫淼
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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