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Novel method for synthesizing 2-chloro-5-aminophenol

The technology of an aminophenol and a new method is applied in the directions of chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., and can solve the problems of high comprehensive cost, complicated process, and many kinds of raw materials, etc., and achieves easy separation and purification of products, The effect of simple post-treatment process and high product yield

Pending Publication Date: 2022-01-25
郭峰
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] It is not difficult to see that the above synthetic methods have long synthetic routes, many types of raw materials required, large consumption of raw materials, high overall cost, complicated process, difficult reaction control and difficult guarantee of product quality due to the involvement of diazotization reaction and substitution reaction, waste water and Disadvantages such as large amount of waste residue and difficult to handle

Method used

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  • Novel method for synthesizing 2-chloro-5-aminophenol
  • Novel method for synthesizing 2-chloro-5-aminophenol
  • Novel method for synthesizing 2-chloro-5-aminophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 110 kg of m-aminophenol in a 5000 liter reactor, pump 1000 liters of water, stir and dissolve; add 135 kg of N-chlorosuccinimide in another 2000 liter reactor, pump 1000 liters of ethanol, stir Make it dissolve; slowly pump the ethanol solution of N-chlorosuccinimide into the above-mentioned 5000-liter reaction kettle through a metering pump, and control the temperature at 45-50 ° C. When the ethanol solution of N-chlorosuccinimide The solution is added, and the liquid chromatography monitors the reaction process. When the m-aminophenol content is lower than 0.1%, the reaction is stopped, and the ethanol and most of the water are evaporated under reduced pressure. The residue is cooled to room temperature, and 200 liters of ice water are slowly added under stirring. Immediately a large amount of yellow precipitate was produced, continued to stir for 1 hour, centrifuged, the solid filter cake was washed with 100 liters of cold water, and dried to obtain 71.5 kg of 2-c...

Embodiment 2

[0033] Add 110 kg of m-aminophenol in a 5000 liter reactor, pump 1000 liters of N, N-dimethylformamide, stir and dissolve; add 160 kg of N-chlorosuccinyl in another 2000 liter reactor Amine, pump 1000 liters of N, N-dimethylformamide, stir to dissolve it; slowly pump the N, N-dimethylformamide solution of N-chlorosuccinimide into the above 5000 In a liter reaction kettle, under stirring, the temperature is controlled at 55-65°C. When the N,N-dimethylformamide solution of N-chlorosuccinimide is added, the reaction process is monitored by liquid chromatography. When the phenol content is lower than 0.1%, stop the reaction, distill out N,N-dimethylformamide under reduced pressure, cool the residue to room temperature, slowly add 300 liters of ice water under stirring, immediately a large amount of yellow precipitate is produced, continue stirring Centrifuge for 1 hour, wash the solid filter cake with 100 liters of cold water, and dry to obtain 93 kg of 2-chloro-5-aminophenol with...

Embodiment 3

[0035] Add 110 kilograms of m-aminophenol in 5000 liters of reactor, pump into 1000 liters of tetrahydrofuran, stir and dissolve; add 160 kilograms of N-chlorosuccinimide in another 2000 liters of reactor, pump into 1000 liters of tetrahydrofuran, Stir to dissolve it, and control the temperature at 50°C-60°C; slowly pump the tetrahydrofuran solution of N-chlorosuccinimide into the above-mentioned 5000-liter reaction kettle through a metering pump, when N-chlorosuccinimide Add the tetrahydrofuran solution of the amine, finish adding, reflux for 2 hours, monitor the reaction process by liquid chromatography, stop the reaction when the content of m-aminophenol is lower than 0.1%, distill off the tetrahydrofuran under reduced pressure, cool the residue to room temperature, and slowly Add 300 liters of ice water, a large amount of yellow precipitate is produced immediately, continue to stir for 1 hour, centrifuge, the solid filter cake is washed with 100 liters of cold water, dried ...

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Abstract

The invention discloses a novel method for synthesizing 2-chloro-5-aminophenol, which takes m-aminophenol or m-nitrophenol as a raw material and takes a microreactor or a common reactor as reaction equipment. A selective chlorinating agent N-chloro succinimide (or N-chloro polymaleimide) or chlorine gas quantitatively synthesized on site is used for performing micro-region selective chlorination to obtain the 2-chloro-5-aminophenol. The method has the advantages of cheap and easily available raw materials, simple reaction operation, simple post-treatment, environmental protection, and realization of continuous production.

Description

Technical field: [0001] The invention belongs to the field of fine chemicals and relates to the synthesis of organic chemical intermediates, in particular to the industrial synthesis of 2-chloro-5-aminophenol. Background technique: [0002] Regarding the synthetic technique of 2-chloro-5-aminophenol, the synthetic routes reported in the open literature are as follows: [0003] 1. In the U.S. patent US3918896A applied by Gregoire Kalopissis in June 1974, 2-amino-5-nitroanisole was used as the raw material, and it went through steps such as diazotization, chlorination, nitro reduction, and demethylation. , to obtain 2-chloro-5-nitrophenol, the reaction formula is as follows: [0004] [0005] 2. In the European patent EP0313160A1 filed in October 1988, inventors Sopher.David Willlam and Vietje Gerrit used m-nitrophenol as a raw material and electrolyzed it in a mixed solution of hydrochloric acid and sulfuric acid to obtain 2-chloro-5-aminophenol , yield 37%, the reaction...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C215/76
CPCC07C213/08C07C215/76
Inventor 郭峰
Owner 郭峰
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