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Radical benzene sulfonamide ethyl sulfuryl hydroxyethyl sulfate aniline compound and preparation method thereof

A technology of ethylsulfone-based hydroxyethylsulfate and hydroxyethylsulfate, applied in the fields of sulfonamide preparation, chemical instruments and methods, organic chemistry, etc., can solve the problem of light fastness and soaping fastness The rubbing fastness is only 1-2 grades, which cannot meet the requirements of users and environmental protection, and the absolute color fixation rate is low, so as to achieve the effects of excellent fastness, bright color and good environmental benefits

Active Publication Date: 2015-02-25
TAIXING JINYUN DYESTUFF
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AI Technical Summary

Problems solved by technology

The reactive dyes synthesized by 4-(2-hydroxyethyl sulfone sulfate) aniline have high directness and easy to cause heavy color on the cloth surface, and the absolute color fixation rate is low, only 60-70%; and the light fastness, The soaping fastness and rubbing fastness are only 1-2 grades, which cannot meet the requirements of the majority of users and environmental protection.

Method used

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  • Radical benzene sulfonamide ethyl sulfuryl hydroxyethyl sulfate aniline compound and preparation method thereof
  • Radical benzene sulfonamide ethyl sulfuryl hydroxyethyl sulfate aniline compound and preparation method thereof
  • Radical benzene sulfonamide ethyl sulfuryl hydroxyethyl sulfate aniline compound and preparation method thereof

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preparation example Construction

[0038] Such as image 3 Shown, the preparation method of the benzenesulfonamide ethyl sulfone base hydroxyethyl sulfate aniline compound of the embodiment of the present invention comprises:

[0039] S101: Acetanilide reacts with chlorosulfonic acid and thionyl chloride to generate p-acetamidobenzenesulfonyl chloride;

[0040] S102: Condensation of 2-chloroethylamine hydrochloride and mercaptoethanol to generate 2-hydroxyethyl sulfide ethylamine;

[0041] S103: Condensation of p-acetamidobenzenesulfonyl chloride and β-hydroxyethyl sulfide ethylamine to generate p-acetamidobenzenesulfonamide ethyl-2-hydroxyethyl sulfide;

[0042] S104: P-acetamidobenzenesulfonamide ethyl-2-hydroxyethyl sulfide is oxidized to sulfone by hydrogen peroxide under the conditions of catalyst sodium tungstate and pH=5-7;

[0043] S105: Hydrolysis and esterification of 2-[2-(4-aminobenzenesulfonamido)ethylsulfone]hydroxyethyl with sulfuric acid to obtain the compound of formula (III).

Embodiment 1

[0045] 1. Sulfonation reaction

[0046] Add 135 parts of acetanilide to 1154 parts of chlorosulfonic acid and control the temperature at 20-30°C. After the addition, slowly raise the temperature to 50°C for 2 hours, add 236.8 parts of thionyl chloride dropwise for 2 hours, cool down to 25°C and add ice water Diluted and filtered to obtain 513 parts (40.9%) of p-acetaminobenzenesulfonyl chloride.

[0047] 2. Condensation of mercaptoethanol

[0048] Add 119 parts of 2-chloroethylamine hydrochloride to 78 parts of mercaptoethanol solution under stirring, while adjusting the pH to 4.5 with baking soda, react at 45°C for 4 hours to generate 115.3 parts of 2-hydroxyethyl sulfide ethyl base amine.

[0049] 3. Condensation of acetaminobenzenesulfonyl chloride

[0050] After the end point is reached, the mercaptoethanol condensation liquid is cooled to 0°C, and 513 parts (40.9%) of the tide product p-acetaminobenzenesulfonyl chloride is slowly added, after the addition is completed,...

Embodiment 2

[0056] 1. Sulfonation reaction

[0057] Add 135 parts of acetanilide to 1154 parts of chlorosulfonic acid and control the temperature at 20-30°C. After the addition, slowly raise the temperature to 62°C for 2 hours, add 240 parts of thionyl chloride dropwise for 2 hours, cool down to 25°C and add ice water After dilution and filtration, 524 parts (41.2%) of p-acetaminobenzenesulfonyl chloride were obtained.

[0058] 2. Condensation of mercaptoethanol

[0059] Add 118.5 parts of 2-chloroethylamine hydrochloride to 78 parts of mercaptoethanol solution under stirring, and at the same time adjust pH=5 with baking soda, and react at 52°C for 4 hours to generate 116.5 parts of 2-hydroxyethyl sulfide ethyl base amine.

[0060] 3. Condensation of acetaminobenzenesulfonyl chloride

[0061] After the end point is reached, the mercaptoethanol condensation liquid is cooled to 0°C, and 524 parts (41.2%) of the tide product p-acetaminobenzenesulfonyl chloride is slowly added. After the a...

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Abstract

The invention discloses a radical benzene sulfonamide ethyl sulfuryl hydroxyethyl sulfate aniline compound and a preparation method thereof. The preparation method comprises the following steps: reacting acetanilide with chlorosulfonic acid and sulfoxide chloride to generate p-acetamido benzene sulfonyl chloride, and then condensing with sulfide generated through reaction between 2-chlorethamin hydrochloride and mercaptoethanol to obtain sulfur ether, re-oxidizing, etherifying or sulfonating the sulfur ether to obtain 2-[2-(4-amonibenzenesulfonamido)ethyl sulfuryl]hydroxyethyl sulfate or 2-[2-(4-amonibenzenesulfonamido)ethyl sulfuryl] hydroxyethyl sulfate-3-sulfonic acid. Comparing the active radical benzene sulfonamide ethyl sulfuryl hydroxyethyl sulfate aniline compound with 4-(2-sulfonylethanol sulfate)aniline; the synthesized reactive dye has bright colored light, and is low in substantivity, high in dye-uptake rate and fixation rate, less in hydrolysis dye, and excellent in various fastness indexes; especially, the light fastness, the soaping resistant fastness, and rubbing fastness are 0.5-1 level higher than ordinary variety.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a benzenesulfonamide ethyl sulfone hydroxyethyl sulfate aniline compound and a preparation method thereof. Background technique [0002] At present, the commonly used intermediates for the synthesis of M-type, ME-type, and KN-type traditional reactive dyes are 4-(2-hydroxyethylsulfone sulfate) aniline (the industrial name is para-ester) or 3-(2-hydroxyethylsulfone Sulfate) aniline (industrial name is meta-ester), this kind of dye has high directness, low dyeing rate and color fixation rate, more hydrolyzed dyes, fastness to light, soaping fastness, friction resistance The fastness performance is poor. In order to solve many defects of commonly used dyes, the present invention aims to disclose a compound of active group benzenesulfonamide ethyl sulfone hydroxyethyl sulfate aniline, compared with 4-(2-hydroxyethyl sulfone sulfate) aniline; The synthetic reactive dyes have ...

Claims

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Application Information

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IPC IPC(8): C07C311/39C07C303/40C09B62/523
Inventor 肖卫国奚进唐炬吴新荣李华美丁骏黄红英
Owner TAIXING JINYUN DYESTUFF
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