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Method for chemical synthesizing compound in symmetric bi-aromatic base ketone group

A technology for diaryl ketones and aromatic compounds, which is applied in the field of chemical synthesis of symmetrical diaryl ketone compounds, can solve the problems of difficult post-processing, large amount of three wastes, low product yield and purity, etc., and achieves mild reaction conditions, The effect of advanced process route and low production cost

Inactive Publication Date: 2005-11-16
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional Lewis acids such as aluminum trichloride can be used as catalysts to improve reaction efficiency under mild conditions, and have been widely used in organic synthesis. However, the disadvantage of this production process is that the amount of catalyst aluminum trichloride is large
Because most of the traditional Lewis acids are decomposed with water and become ineffective, the reaction must be strictly controlled under anhydrous conditions, and for nitrogen-containing or imine compounds, nitrogen atoms will inhibit the catalytic activity of Lewis acids, and a large amount is required to meet the reaction. At the same time, this method also has the disadvantages of large amount of three wastes, difficult post-treatment, low product yield and purity, etc.
In addition, highly toxic phosgene is not suitable for industrial production due to its difficult operation and troublesome post-processing.

Method used

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  • Method for chemical synthesizing compound in symmetric bi-aromatic base ketone group

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The molar ratio of benzene, BTC, and ytterbium trifluoromethanesulfonate is 6:1:0.05, and dichloromethane is used as an organic solvent, and its consumption is 10 times the mass of BTC.

[0029] In a 50ml four-necked flask equipped with a thermometer, a reflux condenser and mechanical stirring, 4.68g (60mmol) of benzene was added and dissolved with 15g of dichloromethane. In addition, 2.97g of BTC and 0.31g of ytterbium trifluoromethanesulfonate were dissolved in 15g of dichloromethane, and the above solution was slowly added into a four-neck flask. Reacted at 40°C for 4 hours, evaporated the solvent, and slowly added 20ml of ice water under ice cooling, stirred continuously for 10min, and filtered.

[0030] The filtrate was concentrated under reduced pressure, washed, heated and dehydrated under vacuum at 190° C. for 4 hours to obtain 0.30 g of white ytterbium trifluoromethanesulfonate crystals, with a recovery rate of 95%.

[0031] The white filter cake was the produ...

Embodiment 2

[0033] The molar ratio of aromatic compounds, BTC, and ytterbium trifluoromethanesulfonate is 6:1:0.1, and the aromatic compound is benzene, and the consumption is 4.68g; the consumption of ytterbium trifluoromethanesulfonate is 0.62g, and the consumption of BTC is 2.97g; two Chloromethane is used as organic solvent, and its consumption is 10 times of BTC quality, and other operations are with embodiment 1.

[0034] As a result, 4.8 g of benzophenone was obtained, with a yield of 88%, a purity of 99.6%, and a melting point of 45.5° C.; 0.58 g of ytterbium trifluoromethanesulfonate was recovered, with a recovery of 94%.

Embodiment 3

[0036] The molar ratio of aromatic compound, BTC, and ytterbium trifluoromethanesulfonate is 6:1:0.2, the aromatic compound is benzene, and the consumption is 4.68g; the BTC consumption is 2.97g; dichloromethane is used as the organic solvent, and its consumption is the mass of BTC 10 times of ytterbium trifluoromethanesulfonate consumption is 1.24g, and other operations are with embodiment 1.

[0037] As a result, 4.86 g of benzophenone was obtained, with a yield of 89%, a purity of 99.1%, and a melting point of 46° C.; 1.14 g of ytterbium trifluoromethanesulfonate was recovered, with a recovery of 92%.

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Abstract

A process for chemically synthesizing symmetrical diarylketone compound includes reaction between aromatic compound and bis-trichloromethyl carbonate in organic solvent under the action of yttarbium trifluoromethane sulfonate, filtering, separating filtered cake, and purifying.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of a symmetrical diaryl ketone compound. (2) Technical background [0002] Symmetrical diaryl ketones are widely used in the synthesis of pesticides, medicines and dyes, and have high practical value. [0003] In the prior art, the chemical synthesis method of symmetrical diaryl ketones is prepared by using traditional Lewis acid as a catalyst and using highly toxic phosgene. Traditional Lewis acids such as aluminum trichloride can be used as catalysts to improve reaction efficiency under mild conditions, and have been widely used in organic synthesis. However, the disadvantage of this production process is that the amount of catalyst aluminum trichloride is large. Because most of the traditional Lewis acids are decomposed with water and become ineffective, the reaction must be strictly controlled under anhydrous conditions, and for nitrogen-containing or imine compounds, nitrogen atoms will inh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/786
Inventor 苏为科金灿
Owner ZHEJIANG UNIV OF TECH
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