Synthetic method of 2-aminophenol-4-sulfonamide

A synthesis method and technology of aminophenol, applied in the preparation of sulfonic acid amide, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of large amount of chlorosulfonic acid, waste, and low yield, so as to reduce waste and reduce Dosage, the effect of increasing the yield

Inactive Publication Date: 2015-05-06
QINGDAO DOUBLE PEACH SPECIALTY CHEM GRP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In sum, the consumption of chlorosulfonic acid is big in the meth

Method used

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  • Synthetic method of 2-aminophenol-4-sulfonamide
  • Synthetic method of 2-aminophenol-4-sulfonamide
  • Synthetic method of 2-aminophenol-4-sulfonamide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of embodiment 1,2-aminophenol-4-sulfonamide

[0041] (1) Chlorosulfonation reaction

[0042] a) Add 109g of chlorosulfonic acid into the reaction kettle, add 50g of o-nitrochlorobenzene within 1.5 hours, keep warm at 110°C after the addition, and obtain 4-chloro-3-nitrobenzenesulfonic acid through sulfonation reaction for 4 hours solution;

[0043] b) Cool down the solution obtained in step a) to 70° C., add 49.2 g of thionyl chloride and undergo chlorination for 2 hours to obtain 4-chloro-3-nitrobenzenesulfonyl chloride; the product yield is 96.88%.

[0044] (2) Amination reaction

[0045] Dissolve 79.3 g of 4-chloro-3-nitrobenzenesulfonyl chloride obtained in step b) in 120 mL of water, add 120 ml of concentrated ammonia water (16%) at 19°C within 4 hours, then raise the temperature to 36°C, and react for 3.5 hours to obtain 2-Nitrochlorobenzene-4-sulfonamide. The product yield is 90%.

[0046] (3) Hydrolysis and acidification reaction

[0047]Rais...

Embodiment 2

[0050] The synthesis of embodiment 2,2-aminophenol-4-sulfonamide

[0051] (1) Chlorosulfonation reaction

[0052] a) Add chlorosulfonic acid to the reaction kettle, add o-nitrochlorobenzene within 1 hour, keep warm at 100°C after the addition, and obtain 4-chloro-3-nitrobenzenesulfonic acid solution through sulfonation reaction for 3 hours; Wherein the mol ratio of chlorosulfonic acid and o-nitrochlorobenzene is 3:1;

[0053] b) Cool the solution obtained in step a) to 60° C., add thionyl chloride and undergo a chlorination reaction for 1.5 hours to obtain 4-chloro-3-nitrobenzenesulfonyl chloride; the product yield is 96.87%; wherein thionyl chloride and The molar ratio of o-nitrochlorobenzene is 1.3:1.

[0054] (2) Amination reaction

[0055] Dissolve the 4-chloro-3-nitrobenzenesulfonyl chloride obtained in step b) in 120 mL of water, add 120 ml of concentrated ammonia water (16%) at 16°C within 4 hours, then raise the temperature to 37°C, and react for 4.5 hours to obtain...

Embodiment 3

[0060] The synthesis of embodiment 3,2-aminophenol-4-sulfonamide

[0061] (1) Chlorosulfonation reaction

[0062] a) Add chlorosulfonic acid to the reaction kettle, add o-nitrochlorobenzene within 5 hours, keep warm at 120°C after the addition, and obtain 4-chloro-3-nitrobenzenesulfonic acid solution through sulfonation reaction for 5 hours; Wherein the mol ratio of chlorosulfonic acid and o-nitrochlorobenzene is 2.5:1;

[0063] b) Cool the solution obtained in step a) to 65°C, add thionyl chloride and undergo a chlorination reaction for 3.5 hours to obtain 4-chloro-3-nitrobenzenesulfonyl chloride; the product yield is 96.82%; wherein thionyl chloride and The molar ratio of o-nitrochlorobenzene is 1.2:1.

[0064] (2) Amination reaction

[0065] Dissolve the 4-chloro-3-nitrobenzenesulfonyl chloride obtained in step b) in 120 mL of water, add 120 ml of concentrated ammonia water (16%) at 18°C ​​within 4 hours, then raise the temperature to 36°C, and react for 4 hours to obtai...

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Abstract

The invention relates to a synthetic method of 2-aminophenol-4-sulfonamide. The synthetic method comprises the steps of chlorosulfonation, ammoniation, hydrolysis, acidification and reduction, wherein the chlorosulfonation comprises the following two steps: (a) adding chlorosulfonic acid into p-nitrochlorobenzene which serves as a raw material, and carrying out sulfonation reaction to obtain 4-chloro-3-nitrobenzene sulfonic acid; and (b) adding sulfoxide chloride into 4-chloro-3-nitrobenzene sulfonic acid obtained in the step (a), and carrying out chlorination to obtain 4-chloro-3-nitrobenzenesulfonyl chloride. According to the synthetic method, a chlorosulfonation process is improved, and the chlorosulfonation is carried out in two steps, namely p-nitrochlorobenzene is taken as the raw material, is firstly sulfonated by chlorosulfonic acid and is then chloridized by sulfoxide chloride, so that the consumption of chlorosulfonic acid is reduced, the unnecessary wasting is reduced, the production cost is saved, and the yield of products is increased to reach up to 96.88%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2-aminophenol-4-sulfonamide. Background technique [0002] Dye intermediates are important substances for the synthesis of various dyes. Various and colorful dyes can be made from it, giving people a sense of beauty. 2-aminophenol-4-sulfonamide, Chinese alias: 3-amino-4-hydroxybenzenesulfonamide, molecular formula: C 6 h 8 N 2 o 3 S, having the chemical structural formula shown in formula (I), off-white or light brown feathery crystal, is an important reactive dye intermediate, which can be made into many kinds of neutral and acid dyes, such as neutral orange RL, neutral Purple BL, etc., have a wide range of applications. [0003] [0004] The current production process of 2-aminophenol-4-sulfonamide is to use o-nitrochlorobenzene as raw material, obtain 4-chloro-3-nitrobenzenesulfonyl chloride by chlorosulfonation with chloros...

Claims

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Application Information

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IPC IPC(8): C07C311/39C07C303/40C07C309/88C07C303/12
Inventor 卢克磊王永康杨伦花
Owner QINGDAO DOUBLE PEACH SPECIALTY CHEM GRP
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