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Method for preparing diaryl ketone by means of spontaneously oxidizing diaryl alkane under promotion effect of alkali

A technology of diaryl alkanes and methoxy groups, which is applied in the field of alkali-promoted autoxidation of diaryl alkanes to prepare diaryl ketones, which can solve the problems of poor recyclability, by-products, and low catalyst activity

Inactive Publication Date: 2017-02-22
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some progress has been made in this type of research, there are still many problems in the process, such as low catalyst activity, poor recyclability, cumbersome preparation process, and by-products, etc.

Method used

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  • Method for preparing diaryl ketone by means of spontaneously oxidizing diaryl alkane under promotion effect of alkali
  • Method for preparing diaryl ketone by means of spontaneously oxidizing diaryl alkane under promotion effect of alkali
  • Method for preparing diaryl ketone by means of spontaneously oxidizing diaryl alkane under promotion effect of alkali

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1, using diphenylmethane to prepare diphenyl ketone as an example to illustrate the reaction operation and detect the influence of different solvents on the autoxidation reaction (taking the I-1 compound shown in the formula as an example)

[0016] Diphenylmethane (0.2 mmol), different reaction solvents (0.5 mL) (dimethylsulfoxide, N,N-dimethylformamide, tetrahydrofuran, ethyl acetate, acetonitrile, dichloromethane) and sodium tert-butoxide (0.4 mmol) into the reaction flask in turn, hang an oxygen balloon at 50 o C was reacted for 0.5 hours. Add water, dilute hydrochloric acid successively to the reaction solution, extract with ethyl acetate, and separate the oxidation product by silica gel column chromatography. The calculated separation yield is shown in Table 1, wherein, the yield of the target product ketone in dimethyl sulfoxide The highest value was obtained, which was 92%, and the best solvent was determined as dimethyl sulfoxide.

[0017]

[0018] ...

Embodiment 2

[0022] Embodiment 2, the influence of temperature of reaction on autooxidation reaction of the present invention

[0023] In addition to the different reaction temperatures (25 o C. 30 o C. 40 o C, 50 o C. 60 o C. 70 o C. 80 o C), other reaction conditions were the same as in Example 1, and the influence of reaction temperature on oxidation reaction yield was detected. After the reaction finishes, the separation yield measurement result of target ketone is as shown in table 2, shows that along with the change of reaction temperature, there is an optimum value in the yield of oxidation reaction, and optimum reaction temperature is determined as 50 oC .

[0024] temperature reflex( o c)

Embodiment 3

[0025] Embodiment 3, the influence of different bases on the autoxidation reaction of the present invention

[0026] Except that the reaction base is different (sodium tert-butoxide, potassium tert-butoxide, sodium hydride, potassium hydroxide, sodium hydroxide, potassium carbonate, DBU), other reaction conditions are the same as in Example 1. Yield impact. After the reaction finishes, the separation yield measurement result of target ketone is as shown in table 3, shows that stronger base can all promote oxidation reaction, and tert-butanol base and hydroxide base are the best among the bases tested, especially tert-butanol Sodium is optimal.

[0027] alkali Sodium tert-butoxide Potassium tert-butoxide sodium hydride Potassium hydroxide sodium hydroxide Potassium Carbonate or DBU Separation yield (%) 92 84 77 79 80 N.R.

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Abstract

The invention discloses a method for preparing diaryl ketone by means of spontaneously oxidizing diaryl alkane under the promotion effect of alkali. The method includes dissolving diaryl alkane compounds in dry organic solvents; adding the alkali into the organic solvents; carrying out reaction in air or oxygen atmosphere at the temperature of 25-80 DEG C for 0.5-5 hours to obtain the diaryl ketone. A molar ratio of the diaryl alkane compounds to the alkali is 1:1-1.3. The method has the advantages that the shortcoming of required strong acid or expensive metal reagents or strong oxidizing agents or the like in the prior art can be overcome by the aid of the method; oxygen is used as an oxidizing agent, and accordingly strong or expensive chemical oxidizing agents can be omitted; transition metal catalysts are omitted, and accordingly heavy metal ion residues in products can be prevented; the method includes simple processes, is low in cost and is environmentally friendly, and substrates are wide in application range; important effects can be realized for diaryl ketone preparation industrial production by the method for synthesizing the diaryl ketone.

Description

technical field [0001] The present invention relates to a method for preparing diaryl ketones by alkali-promoted autoxidation of diaryl alkanes, in particular, it relates to the preparation of diaryl ketones by autoxidation of diaryl alkane compounds in air or oxygen atmosphere under the action of alkali method. Background technique [0002] Diaryl ketones are a class of important additives and chemical intermediates. Mainly used in plastics, photosensitive, medicine, spices and other chemical fields. The reported preparation methods of aryl ketones mainly include carbonylation method (Shen, et al, Tetrahedron, 2015, 71, 6733-6739 and cited literature), acylation method (G. A. Olah, Friedel-Crafts Chemistry, Wiley, New York, 1973; G. Sartori, R. Maggi, Advances in Friedel-Crafts Acylation Reactions, CRC Press, Boca Raton, FL, 2010), carbon monoxide intercalation method (László Kollár, Modern Carbonylation Methods, Wiley, Weinheim, 2008; H.M. Colquhoun, D. J. Thompson an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/36C07C49/784C07C49/786C07C49/813C07C201/12C07C205/45C07C49/84
CPCC07C45/36C07C201/12C07C49/784C07C49/786C07C49/813C07C49/84C07C205/45
Inventor 李江胜杨帆杨倩陈郭芹达玉栋
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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