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Method for preparing aldehyde or ketone by catalyzing oxygen to oxidize organic alcohol

A technology of oxygen oxidation and organic alcohol, which is applied in the preparation of organic compounds, carbon-based compounds, chemical instruments and methods, etc., can solve the problems of troublesome post-processing, high consumption, and environmental friendliness, and achieve low cost and satisfactory The requirements of technology and economy, the effect of good application prospects

Inactive Publication Date: 2014-01-29
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although above-mentioned two kinds of methods have all successfully realized DDQ catalytic oxidation reaction, the consumption of DDQ is 20 times higher than substrate molar number; And, the consumption of oxidant Mn salt is 6 times of substrate, and can produce a large amount of Metal salts are cumbersome to deal with and do not meet the requirements of environmental friendliness

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the catalytic oxidation of benzyl alcohol

[0016] Dissolve 1.0 g (9.2 mmol) benzyl alcohol in 10 mL methylene chloride, add 0.1589 g 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), 0.069 g sodium nitrite, 0.0534 g bromide Succinimide, sealed; feed oxygen 0.3MPa, stir at 80°C for 2h. The liquid phase product was analyzed by GC-Agilent 7890 gas chromatography, using the internal standard method, the conversion rate of p-benzyl alcohol was calculated to be 99%, and the selectivity of p-benzaldehyde was 94.5%.

Embodiment 2

[0017] Embodiment 2: the oxidation of p-methylbenzyl alcohol

[0018] Add 1.2217g of p-methylbenzyl alcohol, 0.1589g of DDQ, 0.069g of sodium nitrite, 0.0534g of bromosuccinimide (NBS) into a 120mL reaction kettle, seal it, feed oxygen at 0.3MPa, and stir at 80°C for 2h. The liquid phase product is analyzed by GC-Agilent 7890 gas chromatography, and the internal standard method is used to analyze and calculate that the transformation rate of p-toluene alcohol is 100%, and the p-tolualdehyde yield is 99%, and the p-tolualdehyde selectivity 99%.

Embodiment 3

[0019] Embodiment 3: Oxidation of p-ethoxybenzyl alcohol

[0020] Add 1.5017g of p-methylbenzyl alcohol, 0.1589g of DDQ, 0.069g of sodium nitrite, 0.1068g of bromosuccinimide into a 120mL reaction kettle, seal it, feed oxygen at 0.3MPa, and stir at 80°C for 2h. The liquid phase product is analyzed by GC-Agilent 7890 gas chromatography, and the internal standard method is used to analyze and calculate that the conversion rate of p-ethoxybenzyl alcohol is 100%, and the yield of p-ethoxybenzaldehyde is 99%. Formaldehyde selectivity is 99%.

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Abstract

The invention relates to a method for preparing aldehyde or ketone by catalyzing oxygen to oxidize organic alcohol. According to the invention, organic alcohol, a composite catalyst, and an organic solvent or deionized water are mixed and uniformly stirred, such that a reaction system is obtained; in oxygen or air, under a temperature of 50-240 DEG C, a reaction is carried out for 0.5-10h, such that a target product can be obtained. The composite catalyst is composed of a mixture of 2,3-dichloro-5,6-dicyano p-benzoquinone, sodium nitrite and halogenated succinimide. The method has the advantages that: the catalytic components in the composite catalyst are cheap and easy to obtain; with the catalyst, oxygen can be catalyzed with high efficiency and high selectivity for oxidizing organic alcohol to produce aldehyde or ketone; reaction byproduct is water, such that pollution is low, the method is environment-friendly, and the product is easy to treat; only organic alcohol and oxygen molecules are consumed during the entire process, such that cost is low, technical and economic requirements can be satisfied, and the method has good application prospect. The reaction system is a catalytic reaction system with wide application prospect.

Description

technical field [0001] The invention relates to a method for preparing aldehyde or ketone, in particular to a method for preparing aldehyde or ketone by catalytic oxygen oxidation of organic alcohol. Background technique [0002] Selective catalytic oxidation of alcohols to aldehydes or corresponding carbonyl compounds is an important reaction in organic synthesis, widely used in laboratory and industrial production, and plays an important role in fine chemical industry and pharmaceutical industry. The literature has reported that the oxidation of alcohols to aldehydes or ketones can be achieved using stoichiometric amounts of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), see Becker et al., The Journal of Organic Chemistry, Vol. 45 , pp. 1596-1600 (1980). But because DDQ is more expensive, and a large number of DDQ use brings pollution, thus limiting the use of DDQ. From the perspective of green chemistry, the development and use of catalytic amounts of DDQ to realize th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/38C07C47/54C07C47/542C07C47/575C07C47/55C07C47/232C07C47/228C07C47/24B01J31/26
CPCC07C45/38B01J27/25B01J31/0271B01J35/393C07C47/54C07C47/542C07C47/575C07C47/55C07C47/232C07C47/228
Inventor 仝新利燕勇涛王艳华孙永发
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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