2494-89-5

Basic information

• Product Name: 2-[(4-Aminophenyl)sulfonyl]ethyl hydrogen sulfate
• Synonyms: 2-Sulfanilylethanol Hydrogen Sulfate;2-[(p-aminophenyl)sulphonyl]ethyl hydrogensulphate;VinylSulfoneParaBase;4-AMINOPHENYLSULFONYL-BETA-HYDROXYETHYL SULFATE ESTER;VINYLSULPHONEESTER-PARABASE;4-((2-sulfatoethyl)sulfonyl)aniline;4-AMINOPHENYLSULFATOETHYLSULFONE;2-[(4-aminophenyl)sulfonyl]-ethano hydrogen sulfate (ester)
• CAS NO: 2494-89-5
• Molecular Formula: C₈H₁₁NO₆S₂
• Molecular Weight: 281.31
• EINECS: 219-669-7
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 2494-89-5.mol

Chemical Properties

• Appearance: /
• Density: 1.608 g/cm³
• Refractive Index: 1.608
• PKA: -3.88±0.18(Predicted)
• CAS DataBase Reference: 2-[(4-Aminophenyl)sulfonyl]ethyl hydrogen sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-Aminophenyl)sulfonyl]ethyl hydrogen sulfate(2494-89-5)
• EPA Substance Registry System: 2-[(4-Aminophenyl)sulfonyl]ethyl hydrogen sulfate(2494-89-5)

Safety Data

• Hazardous Substances Data: 2494-89-5(Hazardous Substances Data)

Usage

Uses

4-(Ethylsulfurate Sulfonyl)aniline is a disperse dye.

InChI:InChI=1/C8H11NO6S2/c9-7-1-3-8(4-2-7)16(10,11)6-5-15-17(12,13)14/h1-4H,5-6,9H2,(H,12,13,14)

Synthetic route

oxirane (75-21-8) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
Stage #1: p-acetylaminobenzenesulfonyl chloride With sodium metabisulfite; sodium hydroxide at 30℃; pH=7 - 7.5; Stage #2: oxirane at 40℃; pH=7.5 - 8; Stage #3: With sulfuric acid at 150 - 160℃; under 3750.38 Torr;	99.7%

4-(2'-Hydroxyethylsulphonyl)aniline (5246-58-2) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
With sulfuric acid at 160℃; under 525.053 Torr; for 2.5h; Pressure; Temperature;	98%

acetic acid-[4-(2-hydroxy-ethanesulfonyl)-anilide] (27375-52-6) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
With sulfuric acid	96%
With sulfuric acid In 1,2-dichloro-benzene	95%

oxirane (75-21-8) + Acetanilid (103-84-4) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
Stage #1: Acetanilid With chlorosulfonic acid at 30 - 46℃; for 5h; Stage #2: With thionyl chloride at 60℃; for 2h; Stage #3: oxirane Temperature; Further stages;	87%

Remazol Turquoise Blue G 133 → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5) + 3-sulfophthalimide (115953-80-5)

Conditions	Yield
With dihydrogen peroxide; soybean peroxidase at 25℃; pH=3; aq. phosphate buffer; Enzymatic reaction;

oxirane (75-21-8) + N-(4-chlorophenyl)acetamide (539-03-7) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
With sulfuric acid; sodium sulfite Large scale; Green chemistry;	2050 kg

2-(p-nitrophenylthio)ethanol (13287-76-8) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
Stage #1: 2-(p-nitrophenylthio)ethanol With dihydrogen peroxide In water at 70℃; for 4h; Stage #2: With palladium on activated charcoal; hydrogen In water at 40℃; under 22502.3 Torr; for 4h; Stage #3: With sulfuric acid In water at 150℃; for 2h; Temperature; Time;
Multi-step reaction with 3 steps 1: sodium tungstate; dihydrogen peroxide / 5.5 h / 80 °C 2: hydrogen / methanol / 3.5 h / 85 °C / 15001.5 Torr / Autoclave 3: sulfuric acid / 2.5 h / 160 °C / 525.05 Torr View Scheme

aniline (62-53-3) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonium chloride; dicyclohexyl-carbodiimide / N,N-dimethyl acetamide / 3 h / 120 °C 2.1: phosphorus pentoxide; chlorosulfonic acid; thionyl chloride / 0.5 h / 15 °C 3.1: sodium metabisulfite; sodium hydroxide / 30 °C / pH 7 - 7.5 3.2: 40 °C / pH 7.5 - 8 3.3: 150 - 160 °C / 3750.38 Torr View Scheme

4-chlorobenzonitrile (100-00-5) → 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 5.5 h / 20 - 40 °C 2: sodium tungstate; dihydrogen peroxide / 5.5 h / 80 °C 3: hydrogen / methanol / 3.5 h / 85 °C / 15001.5 Torr / Autoclave 4: sulfuric acid / 2.5 h / 160 °C / 525.05 Torr View Scheme

Upstream product

• 27375-52-6 acetic acid-[4-(2-hydroxy-ethanesulfonyl)-anilide] 
• 75-21-8 oxirane 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 13287-76-8 2-(p-nitrophenylthio)ethanol 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 62-53-3 aniline 
• 5246-58-2 4-(2'-Hydroxyethylsulphonyl)aniline 
• 100-00-5 4-chlorobenzonitrile 
• 103-84-4 Acetanilid 

Downstream Products

• 42986-22-1 2-[(3-sulfo-4-aminobenzene)sulfonyl]ethoxysulfonic acid 
• 52610-09-0 C₁₁H₁₀Cl₂N₄O₆S₂ 
• 878540-08-0 C₁₈H₁₇N₃O₁₀S₃ 
• 906623-81-2 C₂₃H₂₄N₆O₁₇S₅ 
• 934049-34-0 C₂₂H₂₄N₆O₁₅S₅ 
• 292827-64-6 C₂₉H₂₈N₈O₁₇S₅ 
• 215674-61-6 C₂₂H₂₄N₆O₁₅S₅ 
• 1082353-52-3 C₂₁H₂₀N₆O₁₁S₃ 
• 1170184-65-2 C₁₉H₂₀N₄O₉S₃ 

Relevant articles and documents

Para-ester synthesis method and para-ester

The invention discloses a para-ester synthesis method which comprises the following steps: S1, adding a set amount of chlorosulfonic acid and acetanilide into a sulfonation reaction kettle, adding thionyl chloride, and carrying out a reaction to prepare a sulfonated product, wherein the molar ratio of acetanilide to chlorosulfonic acid to thionyl chloride is (0.45-0.46):1:(0.46-0.47); S2, dilutingthe sulfonated substance and then carrying out suction filtration; S3, adding pyronitrite, adjusting a stable pH value, and carrying out a reduction reaction to obtain a reduction solution; S4, taking sodium phosphate as a buffer agent, adding sulfuric acid and ethylene oxide, and carrying out condensation reaction to obtain a condensation product; S5, carrying out suction filtration on the condensation product; S6, adding sulfuric acid into a product obtained after suction filtration, and carrying out an esterification reaction; and S7, crushing and packaging the product obtained after the esterification reaction to prepare the para-ester. The invention also discloses the para-ester. According to the synthetic method disclosed by the invention, the dosage of chlorosulfonic acid is reduced, thionyl chloride is used for replacing part of chlorosulfonic acid, and the para-ester yield is improved by optimizing the ratio.

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

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.

Preparing methods of p-aminophenyl-beta-hydroxyethylsulfonyl and p-minophenyl-beta-hydroxyethylsulfonyl sulphonate

The invention relates to preparing methods of p-aminophenyl-beta-hydroxyethylsulfonyl and p-minophenyl-beta-hydroxyethylsulfonyl sulphonate. The preparing methods both comprise the steps that p-aminophenyl-beta-hydroxyethylsulfonyl and hydrogen are used as raw materials, modified framework nickel is used as a hydrogen-adding catalyst, a catalytic hydrogenation reaction is conducted in a solvent toobtain reduction liquid, and modified framework nickel and the solvent in the reduction liquid are separated and removed to obtain p-minophenyl-beta-hydroxyethylsulfonyl sulphonate; according to modified framework nickel, nickel is used as a framework, and modified framework nickel is prepared from, by mass, 75-95 parts of Ni, 3-15 parts of Al and 2-10 parts of metal adjuvant; the metal adjuvantcomprises the combination of any one or at least two of Mo, Cu and Cr. The yield can reach 94% or above; preparation of p-minophenyl-beta-hydroxyethylsulfonyl sulphonate is a continuous production technology, the technology is simplified, the production efficiency is high, the quality is stable, the production cost is low, and the economic benefit and social benefit are obvious.

Preparation method of para-ester

The invention provides a preparation method of para-ester. The preparation method of para-ester comprises the following steps: under the existence of phosphorus pentoxide, carrying out chlorosulfonation on N-phenylacetamide and chlorosulfonic acid as well as thionyl chloride, thus obtaining a chlorosulfonation composition; and sequentially carrying out reduction reaction, condensation reaction andesterification reaction on the chlorosulfonation composition, thus obtaining para-ester. Compared with the prior art, the preparation method has the advantages that phosphorus pentoxide is added in chlorosulfonation, a balance state is broken, the balance moves to the direction in which 4-acetamidobenzenesulfonyl azide is generated, the conversion rate of N-phenylacetamide is increased, namely the yield of chlorosulfonation is increased, and meanwhile, excessive chlorosulfonic acid is avoided, so that wastewater pollution is alleviated.

An environment-friendly to-(β-hydroxyethyl sulphone sulfate) method for the synthesis of aniline

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.

Oxidative degradation of Remazol Turquoise Blue G 133 by soybean peroxidase

Reactive dyes are widely employed in textile industries and their removal from wastewaters is a relevant environmental problem. In addition to chemical and physical methods, several bioremediation approaches, involving intact micro-organisms or isolated enzymes, have been proposed to decolorize dye solutions. In this paper, we report the complete and fast decolourization of a Cu(II)-phthalocyanine based reactive dye (Remazol Turquoise Blue G 133) by means of the soybean peroxidase/H2O2 system. The oxidative degradation of the dye in aqueous solution at 25 °C was studied as function of pH, revealing a quantitative decolourization yield at acidic pH values with a maximum of activity at pH 3.3. The reaction products were identified and characterized by HPLC-diode array detector (DAD)-mass spectrometry (MS), ionic chromatography and EPR techniques. This analysis showed that the enzyme catalyses the breaking of the phthalocyanine ring producing sulfophthalimide as the main degradation product, and the release of stoichiometric amount of ammonium and Cu(II) ions.

Reactive polysaccharide derivatives, their preparation and their use

A reactive polysaccharide derivative of formula (1a) or (1b), in which A is —O—, —S— or (1c), Q1 is hydrogen, the radical —B—A—Z, C1-C10aryl which is unsubstituted or substituted, C1-C12alkyl which may be interrupted by oxygen and is unsubstituted or substituted, Q2 and Q3 are each independently of the other hydrogen, C1-C12aryl which is unsubstituted or substituted, C1-C12alkyl which may be interrupted by oxygen and is unsubstituted or substituted, B is an aliphatic or aromatic bridge member, Z1 and Z2 are each independently of the other a reactive radical of the vinylsulfonyl series, the haloacryloyl series or the heterocyclic series, PS is a polysaccharide radical, m is 0, 1 or an integer greater than 1, n is 1 or an integer greater than 1, and the sum of n+m corresponds to the original number of hydroxy groups in the polysaccharide molecule, is useful as a finishing agent for textile fibers and for other applications.

Asymmetric dioxazine compounds and method for dyeing or printing fiber materials using the same

An asymmetric dioxazine compound represented by the following formula (I) in the free acid form: STR1 wherein A1 and A2 independently of one another are each sulfo, halo, alkyl or alkoxy, W is an unsubstituted or substituted aliphatic or aromatic bridging group, X1 and X2 independently of one another are each hydrogen, halo, alkyl, alkoxy or phenoxy, R1 and R2 independently of one another are each hydrogen or unsubstituted or substituted alkyl, R3 and R4 independently of one another are each hydrogen, halo, alkyl, alkoxy or unsubstituted or substituted amino, Z is a fiber-reactive group, m and n independently of one another are each 0 or 1, provided that m≠n, and l is 1 or 2. This compound is suitable for dyeing and printing cellulose fiber, natural and synthetic polyamide fibers, polyrethane fiber, leather and the like and mixed yarns thereof, to obtain dyed or printed products of a color fast to light, wetness and chlorine with superior build-up and level dyeing properties.

Process for producing aminoaryl-β-sulfatoethylsulfone

An improved process for producing sulfuric acid semiesters of the formula: wherein A is a substituted or unsubstituted aromatic group, and n is an integer of 1 or 2, which are important as intermediates of the vinylsulfonic reactive dyes, said process comprising reacting a compound of the formula: wherein A and n are as defined above, and B is hydrogen or a group capable of being hydrolyzed by an acid, with an acid.

Process for producing aminoaryl-β-sulfatoethylsulfone

An improved process for producing sulfuric acid semiesters of the formula: wherein A is a substituted or unsubstituted aromatic or heterocyclic group, and n is an integer of 1 or 2, which are important as intermediate of the vinylsulfonic reactive dyes, said process comprising reacting a compound of the formula: or wherein A and n are as defined above, and B is hydrogen or a group capable of being hydrolyzed by an acid, with an acid.