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A kind of synthetic method and application of substituted phenyldiazenes

A technology of substituted phenyldiazene and phenyldiazene, which is applied in the field of intermediate synthesis, can solve the problems of great environmental hazards, increased environmental protection and process equipment costs, and material mixing.

Active Publication Date: 2018-05-08
PAPANNA BEIJING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The above process requires freshly prepared potassium sulfite to obtain azosulfonate in the preparation process, which will lead to a substantial increase in production costs; and the sulfur dioxide gas required for the preparation of potassium sulfite is very harmful to the human body and the environment. It has high requirements for workers' protective equipment and operation in the production process, and also puts forward high requirements for the sealing and corrosion resistance of production equipment, which will undoubtedly greatly increase the cost of environmental protection and process equipment; in addition, the process A large amount of reducing agent is used in the process, which produces more acidic and saline wastewater, and a variety of salts and coke sulfur substances are mixed, the treatment cost is high, and it is difficult to recycle.

Method used

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  • A kind of synthetic method and application of substituted phenyldiazenes
  • A kind of synthetic method and application of substituted phenyldiazenes
  • A kind of synthetic method and application of substituted phenyldiazenes

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Example 1: Synthesis of 2-methoxy-5-phenylphenyldiazenes and 2-methoxy-5-phenylphenylhydrazine hydrochloride

[0049] 5-Phenyl-o-anisidine (0.50mol, 106g, 1eq, 94%) was mixed with 416g of 18% H 2 O-HCl (2.0mol, 213g, 4eq) solution was mixed evenly, and the temperature was lowered to 0~-5°C. Weigh sodium nitrite (0.51mol, 35.2g, 1.02eq) and 84g water to prepare a 30% aqueous solution, slowly add the solution dropwise to the system, and detect no raw materials after 1h, and obtain the diazonium salt system, Massspectrum: (ES-API) m / z 211 (M+, 40), 183 (100), 154 (10).

[0050] Dissolve potassium sulfite (0.9mol, 142g, 1.8eq) in 800g of water, add dilute hydrochloric acid to adjust the pH to 6-8, and cool down to 0°C. Add the diazonium salt system dropwise to potassium sulfite, and at the same time add 15% potassium hydroxide aqueous solution dropwise to control the pH between 6 and 8. After the dropwise addition, keep it warm at 0°C for 2h, then heat the system at 60°C ...

Embodiment 2

[0053] Example 2: Synthesis of 2-methoxy-5-phenylphenyldiazenes and 2-methoxy-5-phenylphenylhydrazine hydrochloride

[0054] 5-Phenyl o-anisidine (0.5mol, 106g, 1eq, 94%) was mixed with 416g of 18% H 2 O-HCl (2.0mol, 213g, 4eq) solution was mixed evenly, and the temperature was lowered to 0~-5°C. Weigh sodium nitrite (0.51mol, 35g, 1.02eq) and 84g water to prepare a 30% aqueous solution, slowly add the solution dropwise to the system, and detect no raw materials after 1h, and obtain the diazonium salt system, Massspectrum: (ES-API)m / z 211 (M+, 40), 183 (100), 154 (10).

[0055] Dissolve sodium sulfite (1mol, 126g, 2eq) in 1000g water, add dilute hydrochloric acid to adjust the pH to 4-6, and cool down to 0°C. Add the diazonium salt system dropwise to sodium sulfite, and at the same time add dropwise 15% sodium hydroxide aqueous solution to maintain the pH of the system between 4-6, and keep it warm for 2 hours after the dropwise addition; then heat the system at 80°C for 1 ...

Embodiment 3

[0058] Example 3: Synthesis of 2-methoxy-5-phenylphenyldiazenes and 2-methoxy-5-phenylphenylhydrazine hydrochloride

[0059]5-Phenyl o-anisidine (0.5mol, 106g, 1eq, 94%) was mixed with 416g of 18% H 2 O-HCl (2.0mol, 213g, 4eq) solution was mixed evenly, and the temperature was lowered to 0~-5°C. Weigh sodium nitrite (0.51mol, 35g, 1.02eq) and 84g water to prepare a 30% aqueous solution, slowly add the solution dropwise to the system, and detect no raw materials after 1h, and obtain the diazonium salt system, Mass spectrum: (ES-API) m / z 211 (M+, 40), 183 (100), 154 (10).

[0060] Dissolve potassium sulfite (0.9mol, 144g, 1.8eq) in 800g of water, add dilute hydrochloric acid to adjust the pH to 6-7, and lower the temperature to 0°C. Add the diazonium salt system dropwise to potassium sulfite, and at the same time add 15% potassium hydroxide aqueous solution dropwise to control the pH between 6-7. After the dropwise addition, keep it warm at 0°C for 1h, then heat the system at ...

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Abstract

The invention relates to a novel synthetic method of a substituted phenyl diazene compound and an application of the synthetic method. The substituted phenyl diazene compound is obtained through reduction of substituted phenyl diazonium salt; a reducing agent A is prepared into a reducing agent A aqueous solution, then substituted phenyl is dropwise added to the reducing agent A aqueous solution, the pH and temperature of a reaction system are controlled in a dropwise adding process, then heating is carried out, and the substituted phenyl diazene compound is produced after reaction. The synthetic method can adopt a market product as the reducing agent, so that the production cost is lowered substantially; in addition, technological operation and post treatment are simple, waste water, waste gas and solid waste are little, the produced waste water is single in component, convenient to recover, and low in treatment cost, and corresponds with the green chemistry requirement. In general, the synthetic method of the substituted phenyl diazene compound is more suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a synthesis method and application of a substituted phenyldiazene compound, belonging to the technical field of intermediate synthesis. Background technique [0002] Substituted phenyldiazene compounds are a class of very important intermediates widely used in the fields of medicine, pesticides and dyes. At present, the synthesis of substituted phenyldiazene compounds is based on substituted aniline as raw material, and carries out diazotization reaction with sodium nitrite at low temperature in acidic medium to generate diazonium salt, and then reduces it with potassium sulfite to generate azosulfonic acid Salt. [0003] The above process requires freshly prepared potassium sulfite to obtain azosulfonate in the preparation process, which will lead to a substantial increase in production costs; and the sulfur dioxide gas required for the preparation of potassium sulfite is very harmful to the human body and the environment. I...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C241/02C07C243/22
CPCC07C241/02C07C243/22
Inventor 陈安军杨文龙孙飞徐格邹晨
Owner PAPANNA BEIJING TECH