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Method for preparing aldehyde or ketone by alcohol oxidation

An alcohol oxidation and oxygen technology, which is applied in the oxidation preparation of carbonyl compounds, organic chemistry, carbonyl formation/introduction, etc., can solve problems such as pollution and troublesome post-treatment, and achieve the effects of environmental friendliness, easy products and mild reaction conditions.

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1-11

[0016] The investigation of embodiment 1-11 reaction conditions

[0017] First, we used acetic acid as an additive and cinnamyl alcohol as a model substrate to conduct a preliminary investigation on the reaction conditions, and the results are shown in Table 1

[0018] The investigation of table 1 reaction conditions

[0019]

[0020] Note: The dosage of cinnamyl alcohol is 0.1mol. Dichloromethane was used as solvent 100mL. The reaction time is 25h.

[0021] 0.1 MPaO 2 . DDQ, NaNO 2 , the amount of HOAc is relative to the amount of cinnamyl alcohol, respectively.

[0022] As can be seen from Table 1 DDQ is the most important to reaction, does not carry out without DDQ reaction, sodium nitrite and acetic acid are very important, do not add the bad product yield that reaction carries out only 7-12%. When DDQ, sodium nitrite, and acetic acid are added in a matching ratio, the product can obtain a yield greater than 90%. Of course oxygen is also very important, it is th...

Embodiment 11

[0023] The impact of the amount of embodiment 11-acetic acid on reaction

[0024]

[0025] Note: The dosage of cinnamyl alcohol is 0.1mol. Dichloromethane was used as solvent 100mL. The reaction temperature is 35°C, and the reaction time is 25h. DDQ, NaNO 2 The amount of HOAc used is relative to the amount of cinnamyl alcohol, respectively. As seen from Table 2, the amount of acetic acid has a great impact on the reaction, and it is better when the mol ratio of acetic acid and substrate is greater than 1: 10. Oxygen as oxidant reacts faster than air as oxidant.

[0026] 18. Oxidation of cinnamyl alcohol

[0027] In a 500mL round bottom flask, add 134.18g cinnamyl alcohol, 11.35g DDQ, 69.0g sodium nitrite, 280mL toluene, 10mL acetic acid, 0.1MPaO 2 , Stir at 25°C for 36h. After the reaction was completed, the solvent was removed under reduced pressure, and the resulting mixture was dissolved in dichloromethane, washed with water, and dried to remove the dichlorometha...

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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 organic solvent in the presence of an acid additive and under a liquid phase condition to generate aldehyde and ketone. The method is mild in reaction condition, simple in operation, and less in metal 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 a method for the oxidation of alcohols to aldehydes or ketones. 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 2009-2010Aldrich 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, the oxidant is used to oxidize the reduction product DDQH of DDQ to D...

Claims

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Application Information

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IPC IPC(8): C07B41/06C07C47/232C07C45/29C07C47/54C07C47/565C07C49/786C07C49/675C07C49/603C07C49/84C07C47/575C07C49/796C07C49/794
Inventor 李军高爽张恒耘赵公大张毅吕迎
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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