IES86996B2

IES86996B2 - Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method

Info

Publication number: IES86996B2
Application number: IES20180096A
Authority: IE
Inventors: Peng Xiangliang
Original assignee: Chengdu Zhong Heng Hua Tie Tech Co Ltd
Priority date: 2018-04-03
Filing date: 2018-04-03
Publication date: 2019-05-01
Also published as: IES20180096A2

Abstract

Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method, comprises the following steps: adding 2 mol 3-methylaniline, 3-4 mol sulfuric acid solution and 10-13g alumina powder in the reaction vessel, raising the temperature of the solution to 40-45 °C, controlling the stirring speed at 90-110 rpm, stirring for 90-110 min , raising the solution temperature to 70-80 °C, refluxing for30-40min, washed with potassium bromide solution, washed with cyclohexane solution, washed with ketone solution, dehydrated with dehydrating agent, recrystallized in isopropanol solution, finally get the crystal m-aminobenzenesulfonic acid.

Description

Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method FIELD OF THE INVENTION The present invention relates to organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method.

GENERAL BACKGROUND M-aminobenzenesulfonic acid is mainly used for the production of anti-cancer drugs, pesticides, and contrast agent. However, most of the existing synthetic methods are complicated and the final yield is not very high. Therefore, it is necessary to propose a new synthetic method for further improving the quality and yield of the product and reducing the byproduct content, it has important economic significance.

SUMMARY The purpose of the present invention is to provide organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method, comprises the following steps: (i) adding 2 mol 3-methylaniline, 3-4 mol sulfuric acid solution and 10-13g alumina powder in the reaction vessel, raising the temperature of the solution to 40-45 °C, controlling the stirring speed at 90-110 rpm, stirring for 90-110 min , raising the solution temperature to 70-80 °C, refluxing for30-40min, washed with potassium bromide solution, washed with cyclohexane solution, washed with ketone solution, dehydrated with dehydrating agent, recrystallized in isopropanol solution, finally get the crystal m-aminobenzenesulfonic acid; wherein the sulfuric acid solution in the step (i) has a mass fraction of 30-40%, the mass fraction of the potassium bromide solution in the step (i) is 15-20%, the mass fraction of the hexane solution in the step (i) is 35-40%, the mass fraction of the butanone solution in the step (i) is 45-50%, the dehydrating agent in the step (i) is any one of phosphorus pentoxide and anhydrous potassium carbonate, and the mass fraction of the isopropyl alcohol solution in the step (i) is 70 to 80%.

Throughout the reaction process can be the following reaction formula: CIO,OB Advantage of the present invention is that: reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS The following examples with reference to specific embodiments of the present invention are further illustrated: organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method.

Embodiment .1 mol 3-methylaniline, 3 mol sulfuric acid solution with a mass fraction of 30% and 10 g alumina powder were added to the reaction vessel, the temperature of the solution was raised to 40°C and the stirring speed was controlled at 90 rpm, stirring for 90min, raised the temperature to 70°C, refluxing for 30 min, washed with potassium bromide solution with a mass fraction of 15%, washed with cyclohexane solution with a mass fraction of 35%, washed with butanone solution with a mass fraction of 45%, dehydrated with phosphorus pentoxide dehydration, recrystallized in isopropanol solution with a mass fraction of 70%, finally get the crystal m-aminobenzenesulfonic acid 306.24g, yield 88%.

Embodiment 2 mol 3-methylaniline, 3.5 mol sulfuric acid solution with a mass fraction of 35% and 11 g alumina powder were added to the reaction vessel, the temperature of the solution was raised to 42 °C and the stirring speed was controlled to 100 rpm, after stirring for 95 min, the solution temperature was increased to 75 °C , refluxing for 35 min, washed with potassium bromide solution with a mass fraction of 17%, washed with cyclohexane solution with a mass fraction of 37%, washed with butanone solution with a mass fraction of 47%, dehydrated with anhydrous potassium carbonate dehydrating agent, recrystallized in isopropanol solution with a mass fraction 75%, finally get the crystal m-aminobenzenesulfonic acid 316.68g, yield 91%.

Embodiment 3 2mol 3-methylaniline, 4mol sulfuric acid solution with a mass fraction of 40% and 13g alumina powder were added to the reaction vessel, the temperature of the solution was raised to 45 C and the stirring speed was controlled at llOrpm, after 0 stirring for I lOmin, the solution temperature was raised to 80°C, refluxing for 40 min, washed with potassium bromide solution with a mass fraction of 20%, washed with cyclohexane solution with a mass fraction of 40%, washed with butanone solution with a mass fraction was 50%, dehydrated with phosphorus pentahydrate dehydrating agent, recrystallized in isopropanol solution with a mass fraction of 80%, finally get 5 the crystal m-aminobenzenesulfonic acid 323.64g, yield 93%.

Claims

1. Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method, comprises the following steps: (i) adding 2 mol 3-methylaniline, 3-4 mol sulfuric acid solution and 10-13g 5 alumina powder in the reaction vessel, raising the temperature of the solution to 40-45 °C, controlling the stirring speed at 90-110 rpm, stirring for 90-110 min , raising the solution temperature to 70-80 °C, refluxing for30-40min, washed with potassium bromide solution, washed with cyclohexane solution, washed with ketone solution, dehydrated with dehydrating agent, recrystallized in isopropanol solution, 10 finally get the crystal m-aminobenzenesulfonic acid; wherein the sulfuric acid solution in the step (i) has a mass fraction of 30-40%, the mass fraction of the potassium bromide solution in the step (i) is 15-20%, the mass fraction of the hexane solution in the step (i) is 35-40%, the mass fraction of the butanone solution in the step (i) is 45-50%.

2. Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method according to claim 1 wherein the dehydrating agent in the step (i) is any one of phosphorus pentoxide and anhydrous potassium carbonate. 20

3. Organic synthesis intermediates m-aminobenzenesulfonic acid synthesis method according to claim 1 wherein the mass fraction of the isopropyl alcohol solution in the step (i) is 70 to 80%.