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Method for preparing p-aminophenyl-beta-hydroxyethyl sulfone sulfate

A technology of p-aminophenyl and hydroxyethyl sulfone is applied in the field of preparing p-aminophenyl-β-hydroxyethyl sulfone sulfate, which can solve the problems of affecting the quality of the para-ester, low sulfuric acid concentration, and high price, and achieves improved performance. The effect of high raw material utilization, purity and yield, and low raw material consumption

Inactive Publication Date: 2018-02-27
SUQIAN YUANYANG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis methods of p-aminophenyl-β-hydroxyethyl sulfone sulfate mainly include acetanilide method, mercaptoethanol method and thioether oxidation method, but the acetanilide method has sulfuric acid to generate during the reaction, and the concentration of sulfuric acid is low , not easy to handle; the mercaptoethanol raw material in the mercaptoethanol method is rare and expensive; the color of the sulfone obtained during the oxidation process of the thioether oxidation method is black, which affects the quality of the para-ester

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] A method for preparing p-aminophenyl-β-hydroxyethyl sulfone sulfate, comprising the steps of:

[0018] (1) Using p-nitrochlorobenzene and mercaptoethanol as the basic raw materials, first add the two basic raw materials into the N,N-dimethylformamide solvent at a molar ratio of 1:1 to fully dissolve and mix evenly, and then slowly Add sodium hydroxide, control the addition of sodium hydroxide for 2 hours, filter, and carry out vacuum distillation of the obtained filtrate at 60mmHg and 120°C for 2 hours, distill off water and N,N-dimethylformamide to obtain p-nitrobenzene Base-β-hydroxyethyl sulfide; wherein, the molar ratio of p-nitrochlorobenzene, mercaptoethanol, N,N-dimethylformamide and sodium hydroxide is 1:1:1.5: 1;

[0019] (2) After mixing p-nitrophenyl-β-hydroxyethyl sulfide and tungstate catalyst with water, slowly add hydrogen peroxide under stirring, and drop hydrogen peroxide over a period of 2 hours at 70°C, then keep the temperature After stirring for 2...

Embodiment 2

[0023] A method for preparing p-aminophenyl-β-hydroxyethyl sulfone sulfate, comprising the steps of:

[0024] (1) Using p-nitrochlorobenzene and mercaptoethanol as the basic raw materials, first add the two basic raw materials into the N,N-dimethylformamide solvent at a molar ratio of 1.5:1 to fully dissolve and mix evenly, and then slowly Add sodium hydroxide, control the addition of sodium hydroxide for 2 hours, filter, and carry out vacuum distillation of the obtained filtrate at 150mmHg and 150°C for 2 hours to distill off water and N,N-dimethylformamide to obtain p-nitrobenzene Base-β-hydroxyethyl sulfide; wherein, the molar ratio of p-nitrochlorobenzene, mercaptoethanol, N,N-dimethylformamide and sodium hydroxide is 1:1.2:2: 1;

[0025] (2) After mixing p-nitrophenyl-β-hydroxyethyl sulfide and tungstate catalyst with water, slowly add hydrogen peroxide under stirring, and drop hydrogen peroxide over a period of 2 hours at 100°C, then keep the temperature After stirring...

Embodiment 3

[0029] A method for preparing p-aminophenyl-β-hydroxyethyl sulfone sulfate, comprising the steps of:

[0030] (1) Using p-nitrochlorobenzene and mercaptoethanol as the basic raw materials, first add the two basic raw materials into the N,N-dimethylformamide solvent at a molar ratio of 1.2:1 to fully dissolve, mix evenly, and then slowly Add sodium hydroxide, control the addition of sodium hydroxide for 2 hours, filter, and carry out vacuum distillation of the obtained filtrate at 70mmHg and 130°C for 2 hours, and distill off water and N,N-dimethylformamide to obtain p-nitrobenzene Base-β-hydroxyethyl sulfide; wherein, the molar ratio of p-nitrochlorobenzene, mercaptoethanol, N,N-dimethylformamide and sodium hydroxide is 1:1.1:1.6: 1;

[0031] (2) After mixing p-nitrophenyl-β-hydroxyethyl sulfide and tungstate catalyst with water, slowly add hydrogen peroxide under stirring, and drop hydrogen peroxide over a period of 4 hours at 50°C, then keep the temperature After stirring ...

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PUM

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Abstract

The invention discloses a method for preparing p-aminophenyl-beta-hydroxyethyl sulfone sulfate. The method comprises the following steps: with p-nitrochlorobenzene and mercaptoethanol as basic raw materials, adding into an N,N-dimethylformamide solvent, sufficiently dissolving and uniformly mixing to obtain p-nitrophenyl-beta-hydroxyethyl sulfide, then adding hydrogen peroxide, separating out an oxidization crystallization material, adding solvent water and a palladium-carbon catalyst into the oxidization crystallization material, reacting, filtering to obtain a hydrogenated product and the solvent water, adding the hydrogenated product into an ice-water mixture, diluting, adding pure sulfuric acid, stirring, heating to 150 DEG C, and performing an esterification reaction for 2-3h under avacuum condition to obtain the p-aminophenyl-beta-hydroxyethyl sulfone sulfate after the reaction. The product prepared by the method provided by the invention is high in purity and yield, the raw material consumption is low, the raw material utilization rate is increased, few byproducts are produced and are easy to separate, produced wastewater is easy to treat, and the environmental protection investment is low.

Description

technical field [0001] The invention relates to a method for preparing p-aminophenyl-β-hydroxyethyl sulfone sulfate. Background technique [0002] p-Aminophenyl-β-hydroxyethylsulfone sulfate, referred to as p-ester, is an intermediate for the synthesis of KN and M reactive dyes, and one of the most important intermediates for vinylsulfone reactive dyes. At present, the synthesis methods of p-aminophenyl-β-hydroxyethyl sulfone sulfate mainly include acetanilide method, mercaptoethanol method and thioether oxidation method, but the acetanilide method has sulfuric acid to generate during the reaction process, and the concentration of sulfuric acid is low , not easy to handle; the mercaptoethanol raw material in the mercaptoethanol method is rare and expensive; the color of the sulfone obtained during the oxidation process of the thioether oxidation method is black, which affects the quality of the para-ester. Therefore, researching and developing a kind of preparation method o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/36
CPCC07C315/04C07C315/02C07C319/14C07C317/36C07C323/12C07C317/14
Inventor 袁雪生
Owner SUQIAN YUANYANG BIOTECH
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