Method for synthesizing 1-aminoanthraquinone

A technique for the synthesis of aminoanthraquinones, which is applied in chemical instruments and methods, preparation of nitro compounds, preparation of organic compounds, etc., can solve the problems of large amount of solvent, low level of total yield, large energy consumption, etc., and achieve production The effect of low cost and high product purity

Inactive Publication Date: 2014-10-08
中国人民解放军防化学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, patent CN101391963B and patent CN102320979B disclose methods for post-treatment of waste residues. Although useful components such as 1-nitroanthraquinone can be extracted, the amount of solvent used is large, the recovery process is cumbersome and complicated, and the energy consumption is large. High difficulty
[0009] Although the solvent process of 1-nitroanthraquinone has made great achievements, nearly 20% of isomers are produced in the production process, and these isomers are removed through repeated refining. The overall yield level is low, and efforts should be made to seek better process to solve this problem

Method used

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  • Method for synthesizing 1-aminoanthraquinone
  • Method for synthesizing 1-aminoanthraquinone
  • Method for synthesizing 1-aminoanthraquinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) In a 500ml four-necked flask, add 130ml of dichloroethane, 20ml of DMF, add 120g of anthraquinone, 1.2g of p-toluenesulfonic acid, and 24.08g of 98% nitric acid under stirring, and maintain the reaction temperature at 30°C ± 5°C, Slowly add 56g of oleum dropwise within 10 hours. After adding oleum, keep the temperature at 40°C for 6 hours, then add 80ml of water and adjust the pH to 5 with ammonia water, evaporate the solvent under reduced pressure, and recover dichloroethane and DMF. 140.26 g of the solid mixture was obtained. The 1-nitroanthraquinone content is 83.04%, and the anthraquinone content is 17.01%.

[0034] (2) Add the solid mixture obtained in the above (1) into a solution of 33.6g sodium hydrosulfide and 120g water in batches, keep it at 25°C for 3 hours, then raise the temperature to 90°C to 95°C and continue the reaction for 2 hours, filter and wash with water , to obtain 126.91 g of a solid mixture. The 1-aminoanthraquinone content is 81.09%, and...

Embodiment 2

[0037] (1) In a 500ml four-neck flask, add 80ml of xylene and 10ml of DMF, add 60g of anthraquinone, 0.5g of sodium p-toluenesulfonate under stirring, add 7.41g of 98% nitric acid, and maintain the reaction temperature at 30°C ± 5°C, 10 Slowly add 30g of oleum dropwise within 1 hour, after adding oleum, keep the temperature at 40°C for 8 hours, then add 50ml of water and adjust the pH to 5 with ammonia water, evaporate the solvent under reduced pressure, recover xylene and DMF, and obtain a solid mixture 70.37g. The 1-nitroanthraquinone content is 83.54%, and the anthraquinone content is 16.51%.

[0038] (2) Add the solid mixture obtained in the above (1) in batches to a solution of 25 g of sodium hydrosulfide and 100 g of water, maintain 25° C. for 2 hours, then raise the temperature to 90° C. to 95° C. and continue the reaction for 3 hours, filter, wash with water, 63.46 g of a solid mixture was obtained. The 1-aminoanthraquinone content is 81.10%, and the anthraquinone co...

Embodiment 3

[0041] (1) In a 500ml four-neck flask, add 120ml of chlorobenzene, 20ml of DMF, add 120g of anthraquinone, 0.6g of p-toluenesulfonate sodium, 0.5g of p-toluenesulfonic acid, add 33.34g of 98% nitric acid, and maintain the reaction temperature 30°C±5°C, slowly add 60g of oleum dropwise within 10 hours, after adding the oleum, keep the temperature at 40°C for 6 hours, then add 80ml of water and adjust the pH to 5 with 15% NaOH, evaporate the solvent under reduced pressure, Chlorobenzene and DMF were recovered to obtain 139.93 g of a solid mixture. The 1-nitroanthraquinone content is 83.98%, and the anthraquinone content is 16.01%.

[0042] (2) Add the solid mixture obtained in the above (1) in batches to a solution of 35.0 g of sodium hydrosulfide and 120 g of water, maintain 25 ° C for 2 hours, then raise the temperature to 90 ° C to 95 ° C and continue the reaction for 3 hours, filter and wash with water , to obtain 126.95 g of a solid mixture. The 1-aminoanthraquinone conte...

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Abstract

The invention relates to a method for synthesizing 1-aminoanthraquinone. According to the method, the dosage of anthraquinone and nitric acid is adjusted in a mixed solvent in the presence of a catalyst, the depth of nitrification is controlled, anthraquinone is subjected to partial nitrification by using a mixed-acid nitrification method, so as to produce 1-nitroanthraquinone, and then, 1-aminoanthraquinone is synthesized through reduction reaction; the solvent used is one or more of dichloroethane, dimethyl formamide, xylene, chlorobenzene and toluene; mixed acid used means a mixture prepared from fuming nitric acid and fuming sulfuric acid; the catalyst used is para-toluenesulfonic acid and salt thereof; during the nitrification of the method, 1-nitroanthraquinone is mainly produced, and 1,8-dinitroanthraquinone, 1,5-dinitroanthraquinone, 1,7-dinitroanthraquinone, 1,6-dinitroanthraquinone and 2-nitroanthraquinone are not produced; the yield of the product, namely 1-aminoanthraquinone, is 95-99%, the purity is high (over 99%), refining is not required, the production cost is low, the operation is simple and convenient, and the industrial production is convenient to realize.

Description

technical field [0001] The invention relates to a synthesis method for significantly reducing by-products in the process of synthesizing 1-aminoanthraquinone from anthraquinone, and belongs to the technical field of chemical synthesis. Background technique [0002] With the development of the printing and dyeing industry, in addition to azos, the application of anthraquinone and its homologues in this field is increasing. [0003] 1-Aminoanthraquinone is an important dye intermediate, which can be used to prepare vat dyes, acid dyes, disperse dyes, reactive dyes and direct dyes. There are many ways to produce 1-aminoanthraquinone, but the main method of production today is the reduction of 1-nitroanthraquinone. [0004] At present, the main methods for synthesizing 1-nitroanthraquinone in the world are divided into three categories: pure nitric acid nitration, mixed acid (nitric acid+sulfuric acid) nitration and solvent nitration. The pure nitric acid nitration method and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/08C07C205/47C07C221/00C07C225/34
Inventor 王相承李丹段圣亮李德斌齐秀丽
Owner 中国人民解放军防化学院
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