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Preparation method of 4-amino-2-sulfonic benzoic acid

A technology of sulfobenzoic acid and sulfobenzoic acid disodium salt, which is applied in the field of preparation of aromatic sulfonic acid, can solve the problems of waste residue generation, environmental pollution, low yield and the like, and achieves high yield, high purity, High yield and purity effect

Active Publication Date: 2013-11-20
TIANJIN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports about the preparation method of 4-amino-2-sulfonic acid benzoic acid. It has been proposed to use p-nitrotoluene as a raw material to prepare the intermediate, but potassium permanganate is used as the oxidant, which not only has a large amount of waste residue Produced, serious environmental pollution, and low yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0007] Preparation of 4-amino-2sulfobenzoic acid from sodium 2-methyl-5-nitrobenzenesulfonate:

[0008] 23.9g of sodium 2-methyl-5-nitrobenzenesulfonate and 200mL of 1mol / L sodium hydroxide aqueous solution were added to the oxidation reaction kettle, filled with 0.1MPa air, heated to 120°C, reacted for 4h, cooled , adjusted to pH 6.3 with 30% sulfuric acid. Take 22.4g of iron powder, add 100mL of water, add 0.5mL of concentrated sulfuric acid with a mass fraction of 98% and 0.3g of ammonium chloride as a catalyst, heat to boiling, after refluxing for 1h, slowly drop the above solution of pH 6.3 in 2h Reduction was carried out in the reaction kettle, and then stirred at a speed of 1500 rpm and refluxed for 1 h. The reduction solution was cooled to room temperature, the pH of the reduction product was adjusted to 9 with sodium carbonate powder, and the iron sludge was removed by filtration. The obtained filtrate was adjusted to pH 1 with sulfuric acid with a mass fraction of ...

example 2

[0010] Preparation of 4-amino-2sulfobenzoic acid from sodium 2-aldehyde-5-nitrobenzenesulfonate:

[0011] 25.3g of sodium 2-aldehyde-5-nitrobenzenesulfonate and 200mL of 1mol / L sodium hydroxide aqueous solution were added to the oxidation reaction kettle, after stirring and dissolving, filled with 0.1MPa air, heated to 120°C, After 4 hours of reaction, it was cooled. Adjust the pH to 6.3 with 30% dilute sulfuric acid. Take 22.4g of iron powder, add 100mL of water, add 0.5mL of concentrated sulfuric acid with a mass fraction of 98% and 0.3g of ammonium chloride as a catalyst, heat to boiling, after refluxing for 1h, slowly drop the above solution of pH 6.3 into the reaction within 2h Reduction was carried out in the kettle, and then stirred at a speed of 1500 rpm and refluxed for 1 h. Cool the reducing solution to room temperature, adjust the pH to about 9 with sodium carbonate powder, and filter to remove the iron sludge. The obtained filtrate was adjusted to pH 1 with sulf...

example 3

[0013] 4-Amino-2-sulfobenzoic acid was prepared from 4,4'-dinitrodiphenylethane-2,2'-disulfonic acid disodium salt:

[0014] The aqueous solution of 4,4'-dinitrodiphenylethane-2,2'-disulfonic acid double sodium salt 23.8g and 200mL of 1mol / L sodium hydroxide was added to the oxidation reaction kettle, filled with 0.1MPa Air, heated to 120 ° C, and cooled after 4 h of reaction. Adjust to pH 6.3 with 30% sulfuric acid. Take 22.4g of iron powder, add 100mL of water, add 0.5mL of concentrated sulfuric acid with a mass fraction of 98% and 0.3g of ammonium chloride as a catalyst, heat to boiling, after refluxing for 1h, slowly drop the above solution of pH 6.3 in 2h Reduction was carried out in the reaction kettle, and then stirred at a speed of 1500 rpm and refluxed for 1 h. The reducing solution was cooled to room temperature, adjusted to pH 9 with solid sodium carbonate, and the iron sludge was removed by filtration. The obtained filtrate was adjusted to pH 1 with sulfuric aci...

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Abstract

The invention discloses a preparation method of 4-amino-2-sulfonic benzoic acid, and belongs to the preparation technology of aromatic sulfonic acid. The process of the method comprises the following steps: dissolving raw materials of p-nitrotoluene o-sodium sulfonate, 4-nitro-2- sodium sulfonate benzaldehyde, 4,4'-dinitro diphenylethane-2,2'-disodium disulfonate or 4,4'-dinitro diphenylethene-2,2'-disodium disulfonate in a sodium hydroxide solution, performing oxidation with pressurized air, performing reduction with iron powder, performing filtration and crystallization to obtain 4-amino-2-sulfonic benzoic acid. The invention has a simple process, high yield and purity, and the product 4-amino-2-sulfonic benzoic acid can be prepared into p-aminosalicylic acid through simple alkali fusion technology with high yield and high product purity.

Description

technical field [0001] The invention relates to a preparation method of 4-amino-2-sulfonic acid benzoic acid, which belongs to the preparation technology of aromatic sulfonic acid. Background technique [0002] 4-Amino-2-sulfobenzoic acid is an important pharmaceutical and chemical intermediate. Its main purpose is to prepare a common intermediate and drug-p-aminosalicylic acid through a simple alkali fusion process. Para-aminosalicylic acid is mainly used in the preparation of anti-tuberculosis virus drug-sodium para-aminosalicylate, tuberculosis inhibitor-pasniazide and antiemetic drug-bromanthenidine. In addition, p-aminosalicylic acid can also be used to prepare high-polymer polyamine p-aminosalicylic acid and insecticides. There are few reports about the preparation method of 4-amino-2-sulfobenzoic acid. Some people have proposed to prepare this intermediate with p-nitrotoluene as a raw material, but using potassium permanganate as an oxidant, not only has a large amou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/61C07C303/22
Inventor 张凤宝彭文朝张国亮范晓彬戈建华段卫东
Owner TIANJIN UNIV
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