83-62-5

Usage

Uses

Used in Textile Industry:
1-amino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acid is used as a dyeing agent for textiles, providing vibrant and long-lasting colors to fabrics.
Used in Paper Industry:
In the paper industry, 1-amino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acid is used as a coloring agent to impart desired shades to paper products.
Used in Plastics Industry:
1-amino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acid is used as a pigment in the production of colored plastics, enhancing their visual appeal and durability.
Used in Pharmaceutical Manufacturing:
1-amino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acid may have applications in the manufacturing of pharmaceuticals, potentially serving as an active ingredient or a component in drug formulations.
Used as a Chemical Intermediate:
1-amino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acid can also be used as a chemical intermediate in the synthesis of other compounds, contributing to the development of new products and materials across various industries.

InChI:InChI=1/C14H9NO5S/c15-12-10(21(18,19)20)6-5-9-11(12)14(17)8-4-2-1-3-7(8)13(9)16/h1-6H,15H2,(H,18,19,20)

Upstream product

• 82-45-1 1-amino-9,10-anthracenedione 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 88-63-1 2,4-Diaminobenzenesulfonic acid 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 
• 76382-39-3 1-amino-2-mercapto-anthraquinone 
• 14380-61-1 hypochlorite 
• 75-44-5 phosgene 
• 861600-75-1 2-(3-amino-4-sulfo-benzoyl)-benzoic acid 
• 7664-93-9 sulfuric acid 

Downstream Products

• 81-49-2 1-amino-2, 4-dibromoanthraquinone 
• 1758-68-5 1,2-diamino-9,10-anthraquinone 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 117-07-7 1-amino-2-chloro-9,10-anthraquinone 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 

Relevant academic research and scientific papers

1-amino anthraquinone sulfonation process for bromamine acid production

The invention relates to the technical field of organic synthesis, and discloses a 1-amino anthraquinone sulfonation process for bromamine acid production, which has the advantages of mild reaction conditions, no pollution, meeting of the concept of green chemistry, simplicity and convenience in operation, and high-efficiency synthesis of a precursor 1-amino anthraquinone-2-sulfonic acid product of bromamine acid by regulating and controlling a recrystallized benign solvent and a poor solvent. The purity is high and the yield is high.

Sulfonation method for preparing bromamine acid by solvent method

The invention discloses a sulfonation method for preparing bromamine acid by a solvent method, which comprises the following steps: (1) adding an inert solvent which is 9-13 times of the weight of 1-amino-anthraquinone into a sulfonation reactor, stirring and heating to 75-85 DEG C to completely dissolve the 1-amino-anthraquinone; (2) starting a vacuum system, continuously heating to 70-100 DEG C, and completing dehydration under the vacuum degree of-0.008 Mpa; (3) cooling to 70-75 DEG C, slowly adding chlorosulfonic acid which is 1.2-1.5 times of the mole number of 1-aminoanthraquinone at a uniform speed within 6-10 hours, starting to heat to 75-85 DEG C, and preserving heat after heating; (4) continuously raising the temperature to 110-130 DEG C, and keeping the temperature after raising the temperature; (5) adding 98% concentrated sulfuric acid of which the mole number is 2.75-3.15 times that of the 1-aminoanthraquinone at 110-130 DEG C, and finishing at a uniform speed within 4-6 hours; and (6) cooling to 60-75 DEG C, preserving heat after cooling, and standing for layering separation. The method has the advantages of thorough conversion, high yield, simple operation, clear control process, low energy consumption, low cost, continuous treatment and automatic operation.

Process for synthesizing 1-amino-anthraquinone-2-sulfonic acid through solid-phase method

The invention provides a method for synthesizing 1-amino-anthraquinone-2-sulfonic acid from 1-amino-anthraquinone. The method comprises the following steps: generating a sulfate solid of 1-amino-anthraquinone through reaction of the 1-amino-anthraquinone and sulfuric acid, and then performing transposition on the sulfate solid of the 1-amino-anthraquinone to generate the 1-amino-anthraquinone-2-sulfonic acid. A process of synthesizing the 1-amino-anthraquinone-2-sulfonic acid by a sulfuric acid method is fundamentally improved; the sulfate of the 1-amino-anthraquinone is efficiently subjectedto transposition reaction under a solid-phase condition without a solvent after generated water is removed, so that the reaction yield is high, and no side effects are caused; furthermore, no 1-amino-4-chloroant-2-sulfonic acid is generated, and no wastewater, waste gas and waste residues are generated; an obtained product is further synthesized into bromamine acid, and the purity of the obtainedbromamine acid is close to 100 percent; the quality and the yield of the bromamine acid are both higher than the quality and the yield of bromamine acid synthesized by a chlorosulfonic acid method, afuming sulfuric acid method and a conventional sulfuric acid method.

Preparation process for sodium 1-amino-4-bromoanthraquinone-2-sulfonate

The invention discloses a preparation process for sodium 1-amino-4-bromoanthraquinone-2-sulfonate. The preparation process comprises the following steps: (1) sulfonation: with 1-aminoanthraquinone as a raw material, copper sulfate as a catalyst and dichloroethane as a solvent, carrying out dehydration, then adding chlorosulfonic acid drop by drop for a sulfonation reaction, adding 98% concentrated sulfuric acid after completion of the reaction, extracting 1-aminoanthraquinone-2-sulfonic acid out, allowing 1-aminoanthraquinone-2-sulfonic acid to enter the concentrated sulfuric acid, separating out an acid phase at a lower layer and subjecting the acid phase to a subsequent reaction; (2) bromination: adding bromine into the concentrated sulfuric acid solution of 1-aminoanthraquinone-2-sulfonic acid drop by drop for a reaction so as to obtain the concentrated sulfuric acid solution of bromoamine acid; (3) dilution: adding water into the concentrated sulfuric acid solution of bromoamine acid for dilution and successively carrying out cooling, crystallization and filtering so as to obtain bromoamine acid; and (4) salt formation: adding water to dissolve bromoamine acid and adding sodium sulfite to obtain bromoamine acid sodium salt. The preparation process provided by the invention can reduce energy consumption during solvent recovery; the utilization rate of bromine in bromination is high; sodium sulfite is used for salt formation, so the amount of impurities is reduced; and product quality is high.

OPTIMIZATION OF THE OXIDATIVE BROMINATION OF 1-AMINOANTHRAQUINONE-2-SULFONIC ACID

An efficient method of synthesis of 1-amino-4-bromoanthraquinone-2-sulfonic acid using bromination of the corresponding aminoathraquinonesulfonic acid with bromine in the presence of hydrogen peroxide has been proposed.The optimum conditions of synthesis, with a yield of the target product of 68percent, have been found.

MECHANISM OF THE ULLMANN CONDENSATION

It has been found that the condensation rate of 1-amino-4-bromoanthraquinone-2-sulphonic acid (I) with 1,3-diaminobenzene-4-sulphonic acid (II)giving 1-amino-4-(3'-amino-4'-sulphoanilino)anthraquinone-2-sulphonic acid (III) in media of NaHCO3 - CO2 and NaHCO3 - Na2CO3 with catalysis by CuI obeys the kinetic relation v = k, being controlled by the kinetic relation v = k2 in media of NaH2PO4 - Na2HPO4 buffers.The suggested reaction mechanism presumes formation of a bifunctional catalyst CuCO3 or Cu2PO4(1-) which splits off the proton and bromide anion from the reaction intermediate in the rate-limiting step.