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A kind of preparation method of disperse yellow dye n-(2,4-dinitrophenyl) p-phenylenediamine

A technology of dinitrophenyl and p-phenylenediamine, applied in the preparation of amino compounds, organic compounds, azo dyes, etc., can solve the problems of low product purity and poor product quality, and achieve the effect of high reactivity

Active Publication Date: 2018-08-28
DALIAN JOIN KING FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this route only needs one step, the product has low purity, contains more double-substituted impurities, and the product quality is poor

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] In a 2L four-necked flask, add 54.8g (506.8mmol, 1.2eq) of p-phenylenediamine, 85.6g (422.6 mmol, 1.0eq) of 2,4-dinitrochlorobenzene and 300g of acetonitrile, and then place the four-necked flask Heat to 50°C in an oil bath with mechanical stirring. A solution prepared by adding 24.7g (592.8mmol, 1.4eq) of sodium hydroxide and 1000.0g of water into a 500mL constant-pressure dropping funnel in batches, and then began to add dropwise. After 3.0-3.5h, the dropping temperature was controlled at 50-55°C. After dripping, continue to keep stirring for 1.0h. The reaction solution was stirred and cooled to 30°C for 20-30 minutes, then neutralized by adding 145g of 20% sulfuric acid, filtered with suction, and the filter cake was beaten with water / acetonitrile (500g / 200g) at room temperature for 1.0h. After filtration, the filter cake was dried at 30°C to obtain 101.2 g of red powder (external standard content: 98.1%, HPLC purity: 99.2%, simple impurity: 0.35%), with a yield of ...

Embodiment 2

[0020] In a 2L four-neck flask, add 54.8g (506.8mmol, 1.2eq) of p-phenylenediamine, 85.6g (422.6 mmol, 1.0eq) of 2,4-dinitrochlorobenzene and 300g of ethylene glycol dimethyl ether, and then Place the four-neck flask in an oil bath and heat it to 50°C with mechanical stirring. A solution prepared by adding 24.7g (592.8mmol, 1.4eq) of sodium hydroxide and 1000.0g of water into a 500mL constant-pressure dropping funnel in batches, and then began to add dropwise. After 3.0-3.5h, the dropping temperature was controlled at 50-55°C. After dripping, continue to keep stirring for 1.0h. The reaction solution was stirred and cooled to 30°C for 20-30 minutes, then neutralized by adding 145g of 20% sulfuric acid, filtered with suction, and the filter cake was beaten with water / acetonitrile (500g / 200g) at room temperature for 1.0h. After filtration, the filter cake was dried at 30°C to obtain 98.2 g of red powder (external standard content: 98.2%, HPLC purity: 99.1%, simple hetero: 0.29%)...

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PUM

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Abstract

The invention discloses a preparation method of disperse yellow dye N-(2,4-dinitrophenyl)p-phenylenediamine, and belongs to the field of organic synthesis. The method comprises the steps that p-phenylenediamine and 2,4-dinitrochlorobenzene are added into a solvent, an aqueous sodium hydroxide solution is dropwise added at the temperature of 50 DEG C to 55 DEG C, reacting liquid is cooled and neutralized with 20 wt% of sulfuric acid, and filtering is conducted; beating is conducted on an obtained filter cake through a mixed solvent of water and acetonitrile, filtering and drying are conducted in sequence, and then the disperse yellow dye N-(2,4-dinitrophenyl)p-phenylenediamine is obtained, wherein the external standard content is higher than 98.0%, the HPLC purity is higher than 99.0%, and the single impurity content is lower than 0.5%. The method has the advantages that few steps are needed, the time is short, few by-products are generated, the activity is high, and post-processing is easy.

Description

technical field [0001] The invention relates to a preparation method of disperse yellow dye N-(2,4-dinitrophenyl)-p-phenylenediamine, which belongs to the field of synthesis of fine chemical intermediates. Background technique [0002] Disperse yellow dye N-(2,4-dinitrophenyl) p-phenylenediamine is an important disperse yellow dye and an important intermediate for the synthesis of azodiphenylamine yellow disperse dyes. There are two main synthetic routes, both of which use 2,4-dinitrochlorobenzene and p-phenylenediamine as raw materials: (1) p-phenylenediamine is protected with acetic anhydride to generate p-aminoacetanilide, and 2,4-dinitrochlorobenzene Chlorobenzene is condensed, and then the condensate is hydrolyzed to obtain N-(2,4-dinitrophenyl)-p-phenylenediamine (see: CN87100778, 1987). Although the product obtained in this route has high purity, it needs to be protected , condensation, and deprotection three-step reaction, the cycle is long, and the cost is high. (...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B51/00C07C209/10C07C211/56
CPCC07C209/10C09B51/00C07C211/56
Inventor 戴耀刘玲玲梁全德王荣良
Owner DALIAN JOIN KING FINE CHEM CO LTD