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3-acetamino-5-amino-4-hydroxy benzene sulfonic acid and its salts and synthesis method thereof

A technology of hydroxybenzenesulfonate and hydroxybenzenesulfonic acid, which is applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problems of low production efficiency, low reaction yield, environmental pollution and the like

Inactive Publication Date: 2006-10-11
SHANGHAI WORLD PROSPECT INT TRADE +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of this method is that the iron powder reduction method will cause considerable pollution to the environment, and the reaction yield of this method is low, the product quality is not high, and the production efficiency is low

Method used

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  • 3-acetamino-5-amino-4-hydroxy benzene sulfonic acid and its salts and synthesis method thereof
  • 3-acetamino-5-amino-4-hydroxy benzene sulfonic acid and its salts and synthesis method thereof
  • 3-acetamino-5-amino-4-hydroxy benzene sulfonic acid and its salts and synthesis method thereof

Examples

Experimental program
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preparation example Construction

[0017] A synthesis method includes the following steps: (1) acetylation of 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid; (2) reacting the product obtained in step (1) with a reducing agent, thereby Obtain 3-acetamido-5-amino-4-hydroxybenzene sulfonic acid product, the reducing agent is selected from hydrogen, Na with reducing properties x H m S y O z In the formula, x is an integer of 1-10, m is an integer of 0-10, y is an integer of 1-10, and z is an integer of 0-10.

[0018] The synthesis method can be represented by the following reaction scheme:

[0019]

[0020] Another synthesis method includes the following steps: (1) reacting 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid with a reducing agent, the reducing agent is selected from hydrogen and reducing Na x H m S y O z One or more of in the formula, where x is an integer from 1 to 10, m is an integer from 0 to 10, y is an integer from 1 to 10, and z is an integer from 0 to 10; (2) Step (1) The obtained product undergoes a...

Embodiment 1

[0039] Example 1 Preparation of 3-acetylamino-5-amino-4-hydroxybenzenesulfonic acid

[0040] Add 200 g (equivalent to 0.85 mole) of 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid with a concentration of 100% into the reaction vessel filled with 1000 ml of water, and drop it into the reaction vessel at 20-25°C. Add 100 ml of acetic anhydride (equivalent to 1 mol), continue for 2 hours to complete the dropwise addition, proceed to the acetylation reaction until HPLC analysis shows that the reaction solution does not contain the raw material 3-amino-4-hydroxy-5-nitrobenzenesulfonate Acid to obtain the intermediate 3-acetamido-4-hydroxy-5-nitrobenzenesulfonic acid.

[0041] Add NaHSO to the reaction vessel 3 Sodium bisulfite) 300 grams (equivalent to 4.17 moles), reacted at 80-85°C for about 10 hours until HPLC analysis shows that the reaction solution does not contain the intermediate 3-acetamido-4-hydroxy-5-nitro Benzenesulfonic acid is purified and dried to obtain 180.2 grams of 3-a...

Embodiment 2

[0042] Example 2 Preparation of Sodium 3-Acetylamino-5-amino-4-hydroxybenzenesulfonate

[0043] The 3-acetamido-5-amino-4-hydroxybenzenesulfonic acid prepared in Example 1 was reacted with about 88 ml of 30% sodium hydroxide at 25-35°C, purified and dried to obtain the product 3-acetamido Sodium-5-amino-4-hydroxybenzene sulfonate 177.6 g. The appearance of the obtained product is nearly white powder, the chromatographic content (determined by HPLC) is 98%, the chemical content (determined by diazo titration) is 98%, and the product yield is 76% (based on the raw material 3-amino-4-hydroxy-5 -Nitrobenzene sulfonic acid).

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Abstract

The invention discloses a method for preparation of 3-acetamido-5-amidol-4-hydroxyl benzene sulfonic acid, this method comprises steps as follows: (1) acetylating 3-amidol-4- hydroxyl-5-nitrobenzene-sulfonic acids; (2) the product getted by step (1) reacting with reducer and getting the product 3-acetamido-5-amidol-4-hydroxyl benzene sulfonic acid. The preparation can also contains steps as follows: (1) the 3-amidol-4- hydroxyl-5-nitrobenzene-sulfonic acids reacting with reducer;(2) acetylating the product of step (1) and getting the 3-acetamido-5-amidol-4-hydroxyl benzene sulfonic acid product. The mentioned reducer is selected from one or multiple kinds of hydrogen gas and NaxHmSyOz of reduction possessing, x is integer of 1-10, m is integer of 0-10, y is integer of 1-10, z is integer of 1-10. It also discloses preparation of 3-acetamido-5-amidol-4-hydroxyl benzene sulfonic acid salt. The mentioned method avoiding the pollution for enviroment of powdered iron reduction in existence furthermore can acquire high reaction yield, product quality and production yield.

Description

Technical field [0001] The invention relates to a method for synthesizing 3-acetylamino-5-amino-4-hydroxybenzenesulfonic acid and its salts. Background technique [0002] 3-Acetylamino-5-amino-4-hydroxybenzenesulfonic acid is also known as 6-acetamino-2-aminophenol-4-sulfonic acid and has the following structural formula: [0003] [0004] 3-Acetylamino-5-amino-4-hydroxybenzenesulfonic acid and its salts are mainly used as important intermediates in the synthesis of dyes. Their derivative products have been widely used in daily production and life. [0005] In the prior art, the synthesis method of 3-acetamido-5-amino-4-hydroxybenzenesulfonic acid and its salt is roughly as follows: Take 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid and its salt (usually Sodium salt) as a raw material, after acetylation, and then reduced with iron powder. The main disadvantage of this method is that the iron powder reduction method will cause considerable pollution to the environment, and the r...

Claims

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Application Information

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IPC IPC(8): C07C303/22C07C309/55
Inventor 唐会林许晓峻
Owner SHANGHAI WORLD PROSPECT INT TRADE