Synthesis method of environmental-friendly p-(beta-sulfatoethylsulfonyl) aniline

Abstract

The invention discloses a synthesis method of environmental-friendly p-(beta-sulfatoethylsulfonyl) aniline. The synthesis method comprises the following steps: (1) in the presence of a chlorination inhibitor, carrying out sulfonation reaction on acetanilide and chlorosulfonic acid, and then carrying out chlorination reaction on the obtained product and thionyl chloride, so that a chlorosulfonation substance is obtained; and (2) sequentially carrying out condensation reaction, sulfonating reaction and hydrolysis reaction on the chlorosulfonation substance obtained in the step (1), so that environmental-friendly p-(beta-sulfatoethylsulfonyl) aniline is obtained. According to the preparation method, by changing a production formula, introducing the chlorination inhibitor, and changing the reaction reactivity of reaction raw materials, p-chloroacetanilide byproducts are greatly reduced, so that an effect that a para-ester product parachloroaniline meets the standard is finally achieved.

Description

technical field

[0001] The invention belongs to the field of synthesis of dye intermediates, and in particular relates to a synthesis method of environment-friendly p-(β-hydroxyethylsulfone sulfate) aniline. Background technique

[0002] p-(β-hydroxyethylsulfone sulfate) aniline, whose structure is shown in formula (I), also known as p-ester, is an important intermediate in the synthesis of reactive dyes. With the improvement of the country's environmental protection requirements for printing and dyeing textile products, the requirements for the prohibition of aromatic amines in textile products are becoming more and more stringent, so the most direct impact is the textile printing and dyeing industry's control over the relevant indicators of dyeing dyes used At the same time, the country has also formulated the standard for prohibiting aromatic amines in dyes and dye intermediates.

[0003]

[0004] Among p-(β-hydroxyethyl sulfone sulfate) aniline, the most direct natio...

Examples

Embodiment 1

[0025] After adding 2500kg of chlorosulfonic acid into the sulfonation reaction pot, cool down to below 30 degrees, add 300kg of sulfur trioxide, stir and react for 2 hours, when the temperature is below 25 degrees, start feeding 1100kg of acetanilide, and keep the temperature below 30 degrees during the feeding process , feed intake finishes, insulation reaction 2 hours, reaction finishes, logical dry air is blown off redundant sulfur trioxide in the system, enters in the reactor containing hydrogen chloride, carries out chlorosulfonic acid synthesis, obtains reclaiming chlorosulfonic acid 280kg (for next a sulfonation reaction). Then the material for removing sulfur trioxide is heated up to about 45 degrees, and 1000 kg of thionyl chloride is added dropwise, and the temperature is kept at about 45 degrees during the dropping process. After the feeding is completed, the heat preservation reaction is carried out for 4 hours, and the content of p-chloroacetanilide is measured by...

Embodiment 2

[0027] After adding 2500kg of chlorosulfonic acid into the sulfonation reaction pot, cool down to below 30 degrees, add 500kg of oleum (the mass percentage of sulfur trioxide is 40%), stir and react for 2 hours, when the temperature is below 25 degrees, start to throw acetyl Aniline 1100kg, the feeding process keeps the temperature below 30 degrees, the feeding is completed, and the heat preservation reaction is carried out for 2 hours, then the redundant sulfur trioxide in the system is blown out by logical dry air, enters in the reactor containing hydrogen chloride, and synthesizes chlorosulfonic acid to obtain Reclaim 150kg of chlorosulfonic acid (for the next sulfonation reaction). Then the temperature of the material stripped of sulfur trioxide is raised to about 45 degrees, and 1000 kg of thionyl chloride is added dropwise, and the temperature is kept at about 45 degrees during the dropping process. The result was 220 ppm / kg. Then further add 820kg of sodium sulfite for...

Embodiment 3

[0029] After adding 2500kg chlorosulfonic acid in the sulfonation reactor, cool down to below 30 degrees, add 500kg fuming sulfuric acid (the mass percentage of sulfur trioxide is 25%) and 100kg phosphorus pentoxide, stir and react for 4 hours, reduce the temperature to Below 25 degrees, start to feed 1100kg of acetanilide, keep the temperature below 30 degrees during the feeding process, after feeding, keep warm for 2 hours, then blow dry air to blow out the excess sulfur trioxide in the system, and enter the reactor containing hydrogen chloride. Carry out chlorosulfonic acid synthesis, obtain and reclaim chlorosulfonic acid 200kg (for next sulfonation reaction). Then the temperature of the material stripped of sulfur trioxide is raised to about 45 degrees, and 1000 kg of thionyl chloride is added dropwise, and the temperature is kept at about 45 degrees during the dropping process. The result was 180 ppm / kg. Then further add 830kg of sodium sulfite for reduction, then add 6...

technical field

[0001] The invention belongs to the field of synthesis of dye intermediates, and in particular relates to a synthesis method of environment-friendly p-(β-hydroxyethylsulfone sulfate) aniline. Background technique

[0002] p-(β-hydroxyethylsulfone sulfate) aniline, whose structure is shown in formula (I), also known as p-ester, is an important intermediate in the synthesis of reactive dyes. With the improvement of the country's environmental protection requirements for printing and dyeing textile products, the requirements for the prohibition of aromatic amines in textile products are becoming more and more stringent, so the most direct impact is the textile printing and dyeing industry's control over the relevant indicators of dyeing dyes used At the same time, the country has also formulated the standard for prohibiting aromatic amines in dyes and dye intermediates.

[0003]

[0004] Among p-(β-hydroxyethyl sulfone sulfate) aniline, the most direct natio...

Examples

Embodiment 1

[0025] After adding 2500kg of chlorosulfonic acid into the sulfonation reaction pot, cool down to below 30 degrees, add 300kg of sulfur trioxide, stir and react for 2 hours, when the temperature is below 25 degrees, start feeding 1100kg of acetanilide, and keep the temperature below 30 degrees during the feeding process , feed intake finishes, insulation reaction 2 hours, reaction finishes, logical dry air is blown off redundant sulfur trioxide in the system, enters in the reactor containing hydrogen chloride, carries out chlorosulfonic acid synthesis, obtains reclaiming chlorosulfonic acid 280kg (for next a sulfonation reaction). Then the material for removing sulfur trioxide is heated up to about 45 degrees, and 1000 kg of thionyl chloride is added dropwise, and the temperature is kept at about 45 degrees during the dropping process. After the feeding is completed, the heat preservation reaction is carried out for 4 hours, and the content of p-chloroacetanilide is measured by...

Embodiment 2

[0027] After adding 2500kg of chlorosulfonic acid into the sulfonation reaction pot, cool down to below 30 degrees, add 500kg of oleum (the mass percentage of sulfur trioxide is 40%), stir and react for 2 hours, when the temperature is below 25 degrees, start to throw acetyl Aniline 1100kg, the feeding process keeps the temperature below 30 degrees, the feeding is completed, and the heat preservation reaction is carried out for 2 hours, then the redundant sulfur trioxide in the system is blown out by logical dry air, enters in the reactor containing hydrogen chloride, and synthesizes chlorosulfonic acid to obtain Reclaim 150kg of chlorosulfonic acid (for the next sulfonation reaction). Then the temperature of the material stripped of sulfur trioxide is raised to about 45 degrees, and 1000 kg of thionyl chloride is added dropwise, and the temperature is kept at about 45 degrees during the dropping process. The result was 220 ppm / kg. Then further add 820kg of sodium sulfite for...

Embodiment 3

[0029] After adding 2500kg chlorosulfonic acid in the sulfonation reactor, cool down to below 30 degrees, add 500kg fuming sulfuric acid (the mass percentage of sulfur trioxide is 25%) and 100kg phosphorus pentoxide, stir and react for 4 hours, reduce the temperature to Below 25 degrees, start to feed 1100kg of acetanilide, keep the temperature below 30 degrees during the feeding process, after feeding, keep warm for 2 hours, then blow dry air to blow out the excess sulfur trioxide in the system, and enter the reactor containing hydrogen chloride. Carry out chlorosulfonic acid synthesis, obtain and reclaim chlorosulfonic acid 200kg (for next sulfonation reaction). Then the temperature of the material stripped of sulfur trioxide is raised to about 45 degrees, and 1000 kg of thionyl chloride is added dropwise, and the temperature is kept at about 45 degrees during the dropping process. The result was 180 ppm / kg. Then further add 830kg of sodium sulfite for reduction, then add 6...

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