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The preparation method of 1,2-diaminoanthraquinone

A technology of diaminoanthraquinone and aminoanthraquinone, applied in 1 field, can solve the problems of many side reactions, low yield, need to be purified, etc., and achieve the effect of improving yield and purity

Inactive Publication Date: 2011-12-14
上海华元实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art (BIOS987,78) is 1-aminoanthraquinone-2-sulfonic acid through pressurized ammoniation to obtain 1,2-diaminoanthraquinone. BIOS is the abbreviation of the special document "British Intelligence Mission Subcommittee Report". Due to the high temperature and pressurized reaction, there are many side reactions, and the purity of the obtained 1,2-diaminoanthraquinone is only 70%, which needs to be purified, and the yield is low

Method used

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  • The preparation method of 1,2-diaminoanthraquinone
  • The preparation method of 1,2-diaminoanthraquinone
  • The preparation method of 1,2-diaminoanthraquinone

Examples

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Effect test

Embodiment 1

[0027] (1) Condensation reaction

[0028] In a 500ml flask, add 56g of potassium acetate and 66.4g of anhydrous sodium acetate, mix well and heat to 110°C, add 1.6g of copper acetate and 30g of benzenesulfonamide while stirring, heat up to 150-155°C, then add 20 grams of 1-chloro-2-aminoanthraquinone, continue to heat up to 180-190 ° C, keep warm for 3 hours, take a sample and observe under a microscope that there are no yellow crystals and all purple crystals are the end of the reaction. After the end point is reached, slowly pour the material into 1000 ml of hot water while stirring, wash the material in the flask into hot water, stir until the material has no lumps, filter, wash with warm water until neutral, and obtain 26 grams of condensation (1-benzenesulfonylamino-2-aminoanthraquinone). The melting point is 193-194°C.

[0029] (2) Hydrolysis reaction

[0030] In a 250ml flask, add 250g of concentrated sulfuric acid, slowly add the condensate under stirring, and keep ...

Embodiment 2

[0032] In a 500ml flask, add 56g of potassium acetate and 66.4g of anhydrous sodium acetate, mix well and heat to 110°C, add 2.5g of copper acetate and 40g of benzenesulfonamide while stirring, heat up to 150-155°C, then add 20 grams of 1-chloro-2-aminoanthraquinone, continue to heat up to 190-195 ° C, and keep warm for 3 hours. Subsequent operations were the same as in Example 1 to obtain 26.5 g of condensate (1-benzenesulfonylamino-2-aminoanthraquinone), with a melting point of 194-195°C. 16.5 g of 1,2-diaminoanthraquinone was obtained. The yield of 1,2-diaminoanthraquinone synthesized from 1-chloro-2-aminoanthraquinone was 93%, and the purity was 94-96%. The melting point is 289-291°C.

Embodiment 3

[0034] In a 500ml flask, add 56g of potassium acetate and 66.4g of anhydrous sodium acetate, mix well and heat to 110°C, add 0.5g of copper acetate and 20g of benzenesulfonamide while stirring, heat up to 150-155°C, then add 20 grams of 1-chloro-2-aminoanthraquinone, continue to heat up to 195-200 ° C, and keep warm for 5 hours. Subsequent operations were the same as in Example 1 to obtain 25.5 g of a condensate (1-benzenesulfonylamino-2-aminoanthraquinone) with a melting point of 193-193.5°C. 15.6 g of 1,2-diaminoanthraquinone was obtained. The yield of 1,2-diaminoanthraquinone synthesized from 1-chloro-2-aminoanthraquinone was 88%, and the purity was 90-91%. The melting point is 286-287°C.

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Abstract

The invention relates to a method for preparing 1,2-diaminanthraquinone, which is characterized in that the method includes the following steps: (1) condensation reaction, after mixing potassium acetate and anhydrous sodium acetate evenly, heating to Melt at 110°C, add benzene sulfonamide and copper acetate while stirring, raise the temperature to 150-155°C, add 1-chloro-2-aminoanthraquinone, while stirring, continue to heat to 180-200°C, from 1-chloro-2- Aminoanthraquinone and benzenesulfonamide undergo a condensation reaction; the condensation product 1-benzenesulfonylamino-2-aminoanthraquinone is obtained; (2) hydrolysis reaction, the condensation product 1-benzenesulfonylamino-2-aminoanthraquinone is added In concentrated sulfuric acid with a concentration of 96-98% by weight, stir and hydrolyze at 20-30°C for 3 hours, pour into water to dilute, filter and dry to obtain the product 1,2-diaminoanthraquinone. The invention provides a method for preparing high-purity 1,2-diaminoanthraquinone with simple technology and reaction under normal pressure, so as to overcome the shortcomings of the existing technology.

Description

1. Technical field [0001] The present invention relates to a preparation method of 1,2-diaminoanthraquinone, more specifically to a method for preparing 1,2-diaminoanthraquinone from 1-chloro-2-aminoanthraquinone. 2. Background technology [0002] 1,2-Diaminoanthraquinone is an important intermediate. In addition to synthesizing fluorescent vat dyes (BASF.FR 1384677; CGY.EP638613) and vat red RK (Vat Red 40), it can also be prepared into multiple yellow to orange imidazole vat dye. In the prior art, there are various preparation methods of 1,2-diaminoanthraquinone. German patent (IG..DE523523), from 2-chloroanthraquinone, 1-aminoanthraquinone or anthraquinone-2-sulfonic acid, ammoniated under pressure, then treated with concentrated sulfuric acid to form a salt, and recovered from the mother liquor to obtain 1 , 2-Diaminoanthraquinone. German patent (BASF.DE1117137), 1,2-diaminoanthraquinone is obtained by condensing and hydrolyzing 1-chloro-2-aminoanthraquinone with p-to...

Claims

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Application Information

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IPC IPC(8): C07C225/34C07C221/00
Inventor 丁国跃何可立
Owner 上海华元实业有限公司
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