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Method for preparing aldehyde and ketone by alcohol oxidation

An alcohol oxidation, -cnh2n technology, applied in the oxidation preparation of carbonyl compounds, organic chemistry, carbonyl formation/introduction, etc., can solve problems such as troublesome post-processing, pollution, etc., and achieve the effects of easy product, environmental friendliness and low cost

Inactive Publication Date: 2013-03-13
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a new method for preparing aldehydes and ketones by catalyzing oxidative oxidation of alcohols with DDQ to overcome the problems of post-processing troubles and pollution in the above-mentioned oxidation system

Method used

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  • Method for preparing aldehyde and ketone by alcohol oxidation
  • Method for preparing aldehyde and ketone by alcohol oxidation

Examples

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Effect test

example 1

[0017] The investigation of example 1 reaction condition

[0018] First, we investigated the reaction conditions using cinnamyl alcohol as a model substrate. The results are shown in Table 1

[0019] The investigation of table 1 reaction conditions

[0020]

[0021] It can be seen from Table 1 that DDQ, nitrite, and oxygen play a vital role in the oxidation reaction and are indispensable. At the same time, acetic acid also plays a very important role in the reaction. If it is not added or the amount added is too small, the reaction will proceed. It's not good. Among the nitrites, sodium nitrite and potassium nitrite gave better results than the other nitrites. Considering that sodium nitrite is an easy-to-get chemical, the price is relatively cheap, and the following examples all use sodium nitrite as a cocatalyst for the reaction. The higher the reaction temperature of the system, the greater the pressure, and the faster the reaction.

[0022] 2. Oxidation of cinnamyl...

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Abstract

The invention provides a method for preparing aldehyde and ketone by alcohol oxidation, which adopts 2,3-dichloro-5,6-dicyan p-benzoquinone as a catalyst, nitrite as a cocatalyst, and oxygen (or air) as an oxidant, and performs oxidation of alcohol in an acetic acid solvent to generate aldehyde and ketone. The method is mild in reaction condition, simple in operation, free of metal, and less in pollution, and is a green, environment-friendly new method for preparing aldehyde and ketone by alcohol oxidation with nonmetal catalysis.

Description

technical field [0001] The invention relates to the field of catalytic oxidation, in particular to a method for preparing aldehydes and ketones by catalytic oxidation of alcohols. Background technique [0002] The selective oxidation of alcohols to carbonyl compounds is an important reaction in organic synthesis, and is widely used in laboratory and industrial production, and plays a key role in the fine chemical industry. The oxidation of alcohols to aldehydes and ketones with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) is known. (See Becker et al., The Journal of Organic Chemistry, Vol. 45, pp. 1596-1600 (1980)). But because DDQ is relatively expensive, $526 / mol (see 2009-2010 Aldrich catalog), and because its structure contains two -CN groups, it is easy to hydrolyze and has certain toxicity. This limits its use. From the perspective of economy and environmental friendliness, people have been looking for a method that can recycle DDQ, as shown in formula 1, that is, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07C47/232C07C45/29C07C47/54C07C47/565C07C49/786C07C49/675C07C49/603C07C49/84C07C47/575C07C49/796C07C49/794
Inventor 高爽李军吕迎张毅赵公大其他发明人请求不公开姓名
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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