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2,2'-dibenzamido-diphenyl disulfide preparation method

A technology of dibenzoylamino diphenyl disulfide and benzoyl chloride, applied in the field of organic compound synthesis, can solve the problems of high production cost, low yield, complex DBD production process and the like, and achieves low production cost and high yield High, green and environmentally friendly production process

Active Publication Date: 2015-03-11
HUANGHUAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] But at present, the production process of DBD is complicated, the yield is low, and the production cost is high. The market price exceeds 100,000 yuan / ton, while the thiophenol products are only between 40,000 and 50,000 yuan / ton, and the price is comparable to that of thiophenol products. There is obvious inferiority in ratio, therefore, develop a kind of production process simple, productive rate is high, the preparation method of DBD with low production cost has great economic significance to the development of rubber industry

Method used

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Experimental program
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Effect test

Embodiment 2

[0034] Present embodiment 2, the preparation method of 2'-dibenzamidodiphenyl disulfide, the specific operation steps are as follows:

[0035] (1) Add 160g of o-nitrochlorobenzene and 75g of ammonium hydrogen sulfide to 300ml of water, then dropwise add 30g of a 30% sodium hydroxide aqueous solution, and after 3 hours of reaction, add 300ml of a 30% hydrogen peroxide solution to the reaction solution , After reacting for 8h, centrifuge. After the supernatant is degraded in the SBR tank, the iron carbon is internally degraded, the biological anaerobic tank, the aerobic tank, and the settling tank are operated, it is discharged up to the standard; the solid product is dried to obtain 2,2'-diphenylamine disulfide with a yield of 60 %;

[0036] (2) Add 260g of 2,2'-diphenylamine disulfide into 1000ml of dichloromethane, add 50g of potassium carbonate as a catalyst, and dropwise add 850ml of dichloromethane solution with a mass concentration of 20% benzoyl chloride to carry out ac...

Embodiment 3

[0044] Present embodiment 2, the preparation method of 2'-dibenzamidodiphenyl disulfide, the specific operation steps are as follows:

[0045] (1) Add 38g of o-nitroiodobenzene and 14g of sodium sulfide to 80ml of ether, then add 15ml of potassium tert-butoxide tetrahydrofuran solution with a mass concentration of 20%, and react for 12 minutes, then add 20g of potassium peroxide to the reaction solution , After reacting for 3h, centrifuge. The supernatant solvent is diethyl ether, which is recycled after distillation; the solid product is dried to obtain 2,2'-diphenylamine disulfide with a yield of 66%;

[0046] (2) Add 15g of 2,2'-diphenylamine disulfide to 100ml of ethyl acetate, add 3ml of triethylamine as a catalyst, and dropwise add 50ml of acetonitrile solution with a mass concentration of 20% benzoyl chloride for acylation reaction, the reaction After 30 minutes, the ethyl acetate was evaporated for recycling, and the residue was recrystallized with dichloromethane, fi...

Embodiment 4

[0049] Present embodiment 2, the preparation method of 2'-dibenzamidodiphenyl disulfide, the specific operation steps are as follows:

[0050] (1) Add 30g of o-nitrofluorobenzene and 10g of ammonium sulfide to 100ml of ethanol, then add 3g of lithium hydroxide, and react for 3 hours, add 10ml of hydrogen peroxide solution with a mass concentration of 30% to the reaction solution, react for 10 hours, and centrifuge separate. The supernatant solvent is ethanol, which is recycled after distillation; the solid product is dried to obtain 2,2'-diphenylamine disulfide with a yield of 62%;

[0051] (2) Add 10 g of 2,2'-diphenylamine disulfide to 50 ml of chloroform, add 1 ml of triethylamine as a catalyst, and dropwise add 35 ml of acetonitrile solution with a mass concentration of 20% benzoyl chloride for acylation reaction. After 30 minutes of reaction , the chloroform was evaporated for recycling, the residue was recrystallized with chloroform, filtered, dried and granulated, and ...

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Abstract

The invention discloses a 2,2'-dibenzamido-diphenyl disulfide preparation method, and belongs to the technical field of synthesis of organic compounds. The preparation method comprises the following steps: preparing a 2,2'-diphenylamine disulfide from a sulfide and o-nitro halobenzene as raw materials by adopting a one-pot method, and performing acylation on the 2,2'-diphenylamine disulfide to obtain a 2,2'-dibenzamido-diphenyl disulfide. The process step that an intermediate product, namely 2-amino-4-chloro thiophenol, is separated and purified by adopting the processes of steam distillation, organic solvent extraction and the like in the prior art is omitted, the technological process is simplified, meanwhile, the yield of the intermediate product, namely the 2,2'-diphenylamine disulfide, is improved, and the yield of the 2,2'-dibenzamido-diphenyl disulfide is further improved. The preparation method has the advantages of being short in technological process, simple in operation, less in three wastes emission, environmental-friendly in the production process, high in yield, low in production cost, simple in equipment and small in investment, and facilitates industrial popularization and application.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a preparation method of 2,2'-dibenzamidodiphenyl disulfide. Background technique [0002] Since 2002, my country's total rubber consumption has been ranking first in the world. In 2013, the total rubber consumption has reached 8.3 million tons. It is estimated that the rubber consumption in 2014 will reach 9 million tons. Rubber additives improve various performances, and my country has become the largest market for rubber additives, reaching a production scale of 1 million tons in 2012. [0003] Adding peptizer during rubber mastication can reduce the molecular weight of rubber faster, increase plasticity, and improve processability. According to the dosage of 0.2%~3%, the current domestic market demand is about 100,000 tons per year. At present, domestic rubber companies often use sulfur phenolic compounds such as pentachlorothiophenol and pentachlorothiophen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/42C07C319/22
Inventor 喻淼柳准张宁王文豪史娱菲
Owner HUANGHUAI UNIV
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