Method for synthesizing N-[4-[(4-hydroxyanthraquinone-1-yl) amino] benzyl] acetamide

A technology of hydroxyanthraquinone and dihydroxyanthraquinone, which is applied in the field of solvent dye synthesis, can solve the problems of difficult synthesis of high-purity products, no industrial production value, no large-scale production, etc., and achieve bright and stable color, good filtration performance, low cost effect

Active Publication Date: 2011-05-11
宁波龙欣精细化工有限公司
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

The shortcoming of this synthesis method is: the raw material 1-hydroxyl-4-chloroanthraquinone is a product without large-scale production, it is difficult to synthesize a high-purity produc...

Method used

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  • Method for synthesizing N-[4-[(4-hydroxyanthraquinone-1-yl) amino] benzyl] acetamide
  • Method for synthesizing N-[4-[(4-hydroxyanthraquinone-1-yl) amino] benzyl] acetamide

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Experimental program
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Effect test

Embodiment 1

[0024] Condensation: In a 1000 ml three-necked flask, add 405 grams of n-butanol and 100 grams of water, add 40.8 grams of 95% 1,4-dihydroxyanthraquinone and 95% 1,4-dihydroxyanthraquinone leuco 12 under stirring gram, 8 grams of 30% industrial hydrochloric acid, 35 grams of 99% p-phenylenediamine, in about half an hour, the temperature is raised until a fraction is distilled, and the temperature is about 95° C. As the amount of water decreases, the temperature rises slowly, and the reaction is kept at 98-100°C for 12 hours. Add 150 ml of water to distill and recover butanol, and when no oil is evaporated, filter and wash the filter cake with hot water at 70°C until it becomes neutral. Add 400 ml of water to the filter cake for beating, add 40 ml of 30% liquid caustic soda, stir at 90-95°C for 1 hour, filter, wash with hot water at 80°C until nearly neutral, and dry at 105°C to obtain 63.9 grams of condensation material. 96.7%, the condensation yield is 89.6%.

[0025] Acyla...

Embodiment 2

[0027] Condensation: In a 1000 ml three-necked flask, add 400 grams of n-butanol and 100 grams of water, and add 40.8 grams of 97.0% 1,4-dihydroxyanthraquinone and 96% 1,4-dihydroxyanthraquinone leuco 12 under stirring gram, 8 grams of 30% industrial hydrochloric acid, 35 grams of p-phenylenediamine, in about half an hour, the temperature is raised to have distillate, about 95 ℃ of temperature. As the amount of water decreases, the temperature rises slowly, and the reaction is kept at 99-102°C for 15 hours. Add 150 ml of water to distill and recover butanol, and when no oil is evaporated, filter and wash the filter cake with hot water at 70°C until it becomes neutral. Add 400 ml of water to the filter cake for beating, add 40 ml of liquid caustic soda, stir at 90-95°C for 1 hour, filter, wash with hot water at 80°C until nearly neutral, and dry at 105°C to obtain 64.5 grams of condensed material with a purity of 98.7% by liquid phase analysis , The condensation yield is 90.6%...

Embodiment 3

[0030] Condensation: In a 1000 ml three-necked flask, add 420 grams of n-butanol and 80 grams of water, and add 40.8 grams of 96.5% 1,4-dihydroxyanthraquinone and 96% 1,4-dihydroxyanthraquinone leuco 12 under stirring gram, 8 grams of 30% industrial hydrochloric acid, 40 grams of p-phenylenediamine, in about half an hour, the temperature is raised until a fraction is distilled, and the temperature is about 95° C. As the amount of water decreases, the temperature rises slowly, and the reaction is kept at 95-98°C for 16 hours. Add 150 ml of water to distill and recover butanol, and when no oil is evaporated, filter and wash the filter cake with hot water at 70°C until it becomes neutral. Add 400 ml of water to the filter cake for beating, add 40 ml of liquid caustic soda, stir at 90-95°C for 1 hour, filter, wash with hot water at 80°C until nearly neutral, and dry at 105°C to obtain 64.0 grams of condensed material with a liquid phase analysis purity of 96.2% , The condensation...

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Abstract

The invention relates to a method for synthesizing N-[4-[(4-hydroxy anthraquinone-1-yl) amino] benzyl] acetamide. The method comprises the steps of: with hydrochloric acid as a catalyst, carrying out condensation reaction on 1,4-dihydroxy anthraquinone, a 1,4-dihydroxy anthraquinone leuco body and p-phenylenediamine for 10-16h at 95-105 DEG C in a butanol-water solution medium; after the condensation reaction is completed, sequentially carrying out water adding and distilling, filtering, heating treatment with dilute alkali liquor, water washing till reaching a neutral state and drying to obtain a condensation material; and carrying out acylation reaction on the condensation material and acetic anhydride for 2h at 110-112 DEG C in a acetic acid medium, cooling to normal temperature, filtering, washing and drying to obtain a product of N-[4-[(4-hydroxy anthraquinone-1-yl) amino] benzyl] acetamide. The N-[4-[(4-hydroxy anthraquinone-1-yl) amino] benzyl] acetamide product synthesized with the method has high purity, controllable content, fewer 1,4-dihydroxy anthraquinone residues, and low byproduct content and product ash content, and is suitable for polyester spinning and dying.

Description

technical field [0001] The invention relates to the technical field of solvent dye synthesis methods, in particular to a method for synthesizing N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide. Background technique [0002] N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide (CAS No.: 67905-17-3), commonly known as solvent blue 122, is a solvent dye with excellent performance. The shade is dark blue, mainly used for engineering plastics and polyester spinning coloring, it can be used in single color or color matching. [0003] There are two main methods for the synthesis of N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]acetamide in the traditional way: one is to use 1,4-dihydroxyanthraquinone and 1,4- Dihydroxyanthraquinone leuco as raw material, in 95% ethanol or butanol-water solution, use boric acid as catalyst to carry out condensation reaction with p-aminoacetanilide, and obtain N-[4- [(4-Hydroxyanthraquinone-1-yl)amino]phenyl]acetamide. The shortco...

Claims

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Application Information

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IPC IPC(8): C07C233/43C07C231/02C09B1/514
Inventor 刘晓梅刘华杰
Owner 宁波龙欣精细化工有限公司
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