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Synthesis method of 1-phenyl-5-mercaptotetrazole

A technology of mercaptotetrazolium and synthesis method, which is applied in the field of synthesis of 1-phenyl-5-mercaptotetrazolium, can solve the problems of complex production method, poor operation safety and high production cost, and achieves simple and easy after-treatment , Low water solubility, and the effect of avoiding biodegradation

Active Publication Date: 2020-12-11
河北凯力昂生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the production method of phenylmercaptotetrazolium is complicated, the production cost is high and the yield is low, and the purification is difficult. Phenyl ester reacts with hydrazine hydrate, then undergoes cyclization with nitrous acid, and finally rearranges under the action of sodium carbonate to obtain the final product with a yield of 33%.
Chinese patent CN104098522A reports that carbon disulfide and aniline are used as starting materials, and the product is synthesized through steps such as addition, methylation, and synthetic acidolysis. The total yield of the product is 90%, but carbon disulfide is used in production, which is a highly toxic substance. Poor operational security

Method used

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  • Synthesis method of 1-phenyl-5-mercaptotetrazole
  • Synthesis method of 1-phenyl-5-mercaptotetrazole
  • Synthesis method of 1-phenyl-5-mercaptotetrazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 290kg of sodium anilinodithiocarboxylate and 1167kg of water to the 5000L reaction kettle in turn, mix and start stirring, slowly add the catalyst, that is, 404kg of sodium hydroxide solution with a mass fraction of 30%, and add azide to the reaction system under stirring. Sodium 103.6kg, heat up to 90°C and keep it warm for 11 hours, cool down to 8°C after sampling and testing is qualified, filter with suction, heat up the filtrate to 35°C, stir for 30min, neutralize with 149kg of concentrated sulfuric acid solution until the pH of the solution is 2, stir for 30min evenly Afterwards, re-test the PH no longer changed, lower the temperature to 9°C, and suction filter to obtain the crude product of filter cake 1-phenyl-5-mercaptotetrazolium, and the obtained crude product of 1-phenyl-5-mercaptotetrazolium was fully dissolved Carry out recrystallization in the recrystallization solution that 510L mass fraction is 85% toluene / 15% water, the mass fraction of toluene is 85...

Embodiment 2

[0028] Add 290kg of sodium anilinodithiocarboxylate and 1557kg of water to the 5000L reaction kettle in turn, mix them, start stirring, slowly add the catalyst, that is, 303kg of sodium hydroxide solution with a mass fraction of 40%, and add azide to the reaction system under stirring. Sodium 108.6kg, heat up to 95°C and keep it warm for 10 hours, cool down to 10°C after sampling and testing is qualified, filter with suction, heat up the filtrate to 30°C, stir for 30min, neutralize with 149kg of concentrated sulfuric acid solution until the pH of the solution is 3, stir for 60min After mixing evenly, re-test the PH no longer changes, lower the temperature to 10°C, and filter with suction to obtain the crude product of filter cake 1-phenyl-5-mercaptotetrazolium, and the obtained 1-phenyl-5-mercaptotetrazolium The crude azole product was fully dissolved in 758L of 90% toluene / 10% water for recrystallization, separated and dried to obtain 253 kg of finished product, with a product...

Embodiment 3

[0030] Add 290kg of sodium anilinodithiocarboxylate and 1847kg of water in turn to the 5000L reactor, mix and start stirring, slowly add the catalyst dropwise, that is, 242.4kg of sodium hydroxide solution with a mass fraction of 50%, and add azide to the reaction system under stirring Sodium chloride 113.5kg, heat up to 85°C and keep it warm for 12 hours. After the sampling test is qualified, cool down to below 9°C, filter with suction, heat the filtrate to 30°C, stir for 30 minutes, and mix the solution evenly. Retest the pH without changing. Use 149kg concentrated Sulfuric acid solution was neutralized until the pH of the solution was 2, stirred for 30-60min, then cooled to 8°C, suction filtered, and the crude product of filter cake 1-phenyl-5-mercaptotetrazolium was obtained by suction filtration, and the obtained 1-phenyl-5- - The crude product of mercaptotetrazolium fully dissolved in 510L with a mass fraction of 95% toluene / 5% water recrystallized, separated and dried to...

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Abstract

The invention relates to a synthesis method of 1-phenyl-5-mercaptotetrazole, which comprises the steps of (1) by using sodium anilino dithiocarboxylate and sodium azide as raw materials, water as a reaction solvent and an alkaline solution as a catalyst, carrying out heating reflux reaction, and neutralizing the reaction solution with an acid after the reaction is ended to obtain a 1-phenyl-5-mercaptotetrazole crude product; and (2) recrystallizing the 1-phenyl-5-mercaptotetrazole crude product obtained in the step (1) by using a recrystallization solution to obtain a 1-phenyl-5-mercaptotetrazole finished product, wherein the recrystallization solution is a mixed solution of toluene and water. The 1-phenyl-5-mercaptotetrazole prepared by the method is high in purity, safer in reaction process and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular, the invention relates to a synthesis method of 1-phenyl-5-mercaptotetrazolium. Background technique [0002] 1-Phenyl-5-mercaptotetrazolium is mainly used in electroplating additives and chemical reagents, photographic anti-fogging agents, photosensitive materials and stabilizers of electronic chemicals. Because of its benzene ring and nitrogen heterocyclic structure, it can form a thin and dense protective film on the surface of electronic materials, which enhances the photosensitivity and corrosion resistance of photosensitive materials. At present, the production method of phenylmercaptotetrazolium is complicated, the production cost is high and the yield is low, and the purification is difficult. The phenyl ester was reacted with hydrazine hydrate, then cyclized by nitrous acid, and finally rearranged under the action of sodium carbonate to obtain the final product with a yiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/04
CPCC07D257/04
Inventor 孙佳伟杜照磊李石磊张琛
Owner 河北凯力昂生物科技有限公司
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