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2,2'-di-thio-bibenzoyl cholride chemical synthesis method

A technology of dithiobisbenzoyl chloride and dithiobisbenzoic acid, applied in 2 fields, can solve the problems of high sealing requirements of reaction equipment, low product yield and purity, and high production cost, and achieves high implementation value and Social and economic benefits, low production cost, and no three wastes

Inactive Publication Date: 2006-04-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] However, due to thionyl chloride (SOCl 2 ) is an acyl chloride reagent, which is severely corroded and requires high equipment, and the tail gas of the acyl chloride reaction contains a large amount of asphyxiating sulfur dioxide gas (one of the six indicators strictly controlled by the national environmental protection on the atmosphere) which is difficult to handle. Currently, it is mainly prepared by alkali absorption. A mixture of sodium sulfite and sodium chloride, but there are big problems in market sales, and because it is an aqueous solution after being absorbed by alkali, it must be concentrated to obtain a mixture of sodium sulfite and sodium chloride. The production process consumes a lot of energy and the production cost is high.
In addition, thionyl chloride is a strictly controlled chemical weapon stipulated by the United Nations. Therefore, transportation and use must be strictly controlled, and the reaction equipment has high sealing requirements and large investment; at the same time, the original process still has a large amount of three wastes, and post-processing is difficult. Problems such as low product yield and purity

Method used

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  • 2,2'-di-thio-bibenzoyl cholride chemical synthesis method

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Experimental program
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Effect test

Embodiment 1

[0015] The molar ratio of 2,2'-dithiobisbenzoic acid:bis(trichloromethyl)carbonate:catalyst is 1:0.7:0.01, and the catalyst is 1,3-dimethyl-2-imidazolidinone, organic The solvent is toluene, and its consumption is 3 times of the mass of 2,2'-dithiobisbenzoic acid.

[0016] In a 250mL four-necked flask equipped with a thermometer, reflux condenser, constant pressure dropping funnel and mechanical stirring, add 30.6g (100mmol) of 2,2'-dithiobisbenzoic acid, bis(trichloromethyl)carbonic acid 20.8 g (70 mmol) of ester, 92 g of toluene and 0.1 g (1 mmol) of catalyst. After the addition, the temperature was raised to 45°C, and the reaction was carried out at 45-50°C for 8 hours, monitored by TLC (developing solvent: ethyl acetate:methanol=2:1), after the reaction was completed, the solvent was distilled off under reduced pressure to obtain 2,2' The crude product of dithiobisbenzoyl chloride was recrystallized to obtain 32.6 g of light yellow 2,2'-dithiobisbenzoyl chloride crystals,...

Embodiment 2

[0018] Feeding molar ratio 2,2'-dithiobisbenzoic acid: bis(trichloromethyl) carbonate: catalyst is 1: 1.0:0.01, 2,2'-dithiobisbenzoic acid charging capacity is 30.6g ( 100mmol), two (trichloromethyl) carbonate charging capacity is 29.7g (100mmol), catalyzer is 1,3-dimethyl-2-imidazolidinone, and its consumption is 0.1g (1mmol), and organic solvent is toluene , and its dosage is 92g, that is, 3 times the mass of 2,2'-dithiobisbenzoic acid.

[0019] The reaction temperature is 85-90° C., and the reaction time is 4 hours. Other operations are the same as in Example 1. The product yield is 90.0%, the purity is 98.4%, and the melting point is 152-153° C. 1 H NMR (CDCl 3 )δ: 8.4(m, 2H), 7.7(d, 2H), 7.5(m, 2H), 7.3-7.4(m, 2H).

Embodiment 3

[0021] Feeding molar ratio 2,2'-dithiobisbenzoic acid: bis(trichloromethyl) carbonate: catalyst is 1: 1.6:0.01, 2,2'-dithiobisbenzoic acid charging capacity is 30.6g ( 100mmol), two (trichloromethyl) carbonate charging capacity is 47.5g (160mmol), and catalyst is 1,3-dimethyl-2-imidazolidinone, and its consumption is 0.1g (1mmol), and organic solvent is toluene , and its dosage is 92g, that is, 3 times the mass of 2,2'-dithiobisbenzoic acid.

[0022] The reaction temperature is 108°C, the reaction time is 1 hour, other operations are the same as in Example 1, the product yield is 92.5%, the purity is 99.0%, and the melting point is 148-150°C. 1 H NMR (CDCl 3 )δ: 8.4(m, 2H), 7.7(d, 2H), 7.5(m, 2H), 7.3-7.4(m, 2H).

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Abstract

The present invention provides the reaction process of di(trichloromethyl) carbonate and 2, 2'-dithio diphenyl formic acid at 20-150 deg.c inside organic solvent under the action of organic amine catalyst to prepare 2, 2'-dithio diphenyl formyl chloride. The chemical synthesis process eliminates unsafe hidden trouble and environmental pollution radically, and has the advantages of cheap material, high safety and reliability, high reaction yield, low production cost and no waste generated.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 2,2'-dithiobisbenzoyl chloride. (2) Background technology [0002] The chemical synthesis method of prior art 2,2'-dithiobisbenzoyl chloride is synthesized from 2,2'-dithiobisbenzoic acid and thionyl chloride as raw materials. As proposed in US 5,463,122, it is prepared by refluxing 0.082mol of 2,2'-dithiobisbenzoic acid and 350mL of thionyl chloride for 18h. [0003] However, due to thionyl chloride (SOCl 2 ) is an acyl chloride reagent, which is severely corroded and requires high equipment, and the tail gas of the acyl chloride reaction contains a large amount of asphyxiating sulfur dioxide gas (one of the six indicators strictly controlled by the national environmental protection on the atmosphere) which is difficult to handle. Currently, it is mainly prepared by alkali absorption. The mixture of sodium sulfite and sodium chloride, but there is a big problem in market sales, and because ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/62C07C319/20
Inventor 苏为科陈志卫李永曙
Owner ZHEJIANG UNIV OF TECH
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