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Method for the synthesis of anthraquinone dye or chromophore by aryl amination of bromoacid

A bromamic acid arylamine, anthraquinone type technology, applied in the field of dyes, can solve the problems of reducing the amount of catalyst used and converting bromamic acid to COD, etc.

Active Publication Date: 2016-06-15
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The object of the present invention is to propose an anthraquinone-type dye by aryl amination of bromic acid for the problems of incomplete conversion of bromic acid, many by-products and high COD in waste water in the production process of the above-mentioned anthraquinone-type dyes or chromophores. Dye or chromophore method to achieve nearly 100% conversion of bromine, no hydrolysis of bromine (purple by-product) and debromination by-products, significantly reduce the generation of by-products, significantly increase the yield of condensation products, and reduce acid-containing And the discharge of deep-color wastewater; at the same time, copper powder is not used, the amount of catalyst used is reduced, the content of heavy metals in condensation products is reduced, the content of heavy metals in wastewater is reduced, environmental pollution is reduced, and production costs are reduced

Method used

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  • Method for the synthesis of anthraquinone dye or chromophore by aryl amination of bromoacid
  • Method for the synthesis of anthraquinone dye or chromophore by aryl amination of bromoacid
  • Method for the synthesis of anthraquinone dye or chromophore by aryl amination of bromoacid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Weigh 8.4 g of sodium 2,4-diaminobenzenesulfonate, 8.4 g of sodium bicarbonate, and 20 ml of water, add them into a container equipped with a stirrer, condenser, and thermometer, and heat to 80°C while stirring. Weigh respectively 8.08 grams of bromine, 15% mol (based on bromine) of monovalent copper and 1,4,7,10-tetraazacyclododecane-1,3-diene (C 8 h 18 N 4 ) complex aqueous solution. Alternately add solid bromine and monovalent copper complexes into the container within 1 hour, keep the reaction temperature at 80-82°C, the pH of the reaction system at 9, and stir for 3 hours; raise the reaction temperature to 85-90°C, stir Reaction, sampling for thin-layer chromatography and liquid chromatography analysis, no bromidine as the reaction end point. In the reaction liquid mixture, there are no hydrolyzed products of bromoacidic acid (purple side) and bicondensates, but there are traces of debrominated products.

[0051] The above materials were cooled to 40°C, slowly ...

Embodiment 2

[0053] Weigh 21 grams of 2,4-diaminobenzenesulfonic acid, 26.5 grams of sodium carbonate, and 50 milliliters of water, add them into a container equipped with a stirrer, a condenser, and a thermometer, and heat to 80°C while stirring. Weigh respectively 20.2 grams of bromine, 10% mol (based on bromine) of monovalent copper and 1,4,7,10-tetraazacyclododecane-1,3-diene (C 8 h 18 N 4 ) complex aqueous solution. Alternately add solid bromine and monovalent copper complexes into the container within 2.5 hours, keep the reaction temperature at 80-82°C, the pH of the reaction system at 9, and stir for 3 hours; raise the reaction temperature to 85-90°C, stir Reaction, sampling for thin-layer chromatography and liquid chromatography analysis, no bromidine as the reaction end point. In the reaction liquid mixture, there are no hydrolyzed products of bromoacidic acid (purple side) and bicondensates, but there are traces of debrominated products.

[0054] The above materials were cool...

Embodiment 3

[0056] Weigh 8.4 g of 2,4-diaminobenzenesulfonic acid, 8.4 g of sodium bicarbonate, and 20 ml of water, add them into a container equipped with a stirrer, a condenser, and a thermometer, and heat to 80°C while stirring. Weigh respectively 8.08 grams of bromine, 10% mol (based on bromine) of monovalent copper and 1,4,7,10-tetraazacyclododecane-1,3-diene (C 8 h 18 N 4 ) complex ethanol solution. Alternately add solid bromine and monovalent copper complexes into the container within 1 hour, keep the reaction temperature at 80-82°C, the pH of the reaction system at 9, and stir for 2 hours; raise the reaction temperature to 80-90°C, stir Reaction, sampling for thin-layer chromatography and liquid chromatography analysis, no bromidine as the reaction end point. In the reaction liquid mixture, there are no hydrolyzed products of bromoacidic acid (purple side) and bicondensates, but there are traces of debrominated products.

[0057] The above materials were cooled to 40°C, slowly...

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Abstract

The invention provides a method for synthesizing anthraquinone type dye or chromophore by aromatic amination of bromamine acid. The method comprises the following steps: catalyzing a condensation reaction of bromamine and arylamine in a solvent by adopting a catalyst system containing cuprous complex. According to the method, the cuprous complex is used as the catalyst system, nearly 100% conversion of the bromaine acid can be realize, no bromamine acid hydrolyzed (purple byproduct) or debrominated byproduct is generated, generation of by products is remarkably reduced, the yield of condensation products is remarkably increased, emission of acid-containing wastewater with deep chromaticity is reduced; and copper powder is not used, the usage of catalyst can be reduced, the content of heavy metals in the condensation products can be reduced, the content of heavy metals in wastewater can be reduced, environmental pollution can be reduced, and production cost can be reduced.

Description

technical field [0001] The invention relates to dye technology, in particular to a method for synthesizing anthraquinone dyes or chromophores by aryl amination of bromic acid. Background technique [0002] Anthraquinone dyes or chromophores are mainly used in the production of acid dyes and reactive dyes, such as C.I. Acid Violet 48, C.I. Acid Blue 25, C.I. Reactive Blue 19, C.I. Reactive Blue 49, C.I. Reactive Green 6, etc. These dyes have good solubility, excellent light fastness and soaping fastness, and are widely used in fiber and paper dyeing and printing, as well as inkjet printing. [0003] Anthraquinone-type dyes or chromophores are compounds of the general formula I: [0004] [0005] Aromatic amination of bromic acid is one of the important reactions in the synthesis of dyes, which is used in industry to synthesize a series of anthraquinone-type acidic and reactive dyes. At present, cuprous chloride is used as a catalyst in the industry to carry out the aroma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B1/34C09B1/30C09B62/505C09B62/467C09B62/525C09B56/12
Inventor 吕荣文高崑玉
Owner DALIAN UNIV OF TECH
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