Process of preparing 4-amino-3-nitro phenol

A technology for nitrophenol and p-aminophenol, applied in the field of fine chemical intermediate synthesis, can solve the problems of difficulty in selective reduction, low yield, explosion danger of azide compounds, etc., and achieves high acylation activity, cost reduction, The effect of mild reaction conditions

Active Publication Date: 2007-11-07
溧阳常大技术转移中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route uses azide compounds, azide compounds are explosive, and selective reduction is difficult, and the yield is very low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0017] In a 250 ml four-neck flask equipped with a thermometer and a stirring device, add 21.0 grams (0.1927 mol) of p-aminophenol, 40 grams (0.3854 mol) of acetic anhydride (refined anhydrous) and a small amount of glacial acetic acid, and heat to reflux at 128 ° C. After reacting for about 2 hours, the reaction solution was cooled to 25° C., then 30.0 ml (0.7142 mol) of 98% nitric acid was added dropwise and the temperature was kept constant, and stirred for 1.0 hour under strong acid condition. Then 20 milliliters (0.4444 mol) of 65% nitric acid was added, the temperature was controlled at 20° C., and the reaction was stirred for 1.5 hours. Then the reaction solution was poured into ice water, and yellow crystals were precipitated, washed with water 2 to 3 times until neutral, filtered with suction, and the filter cake was dried to obtain yellow 4-acetoxy-2-acetamido nitro 34.6 grams of benzene, the yield is 75.5%. Melting point: 144℃~146℃.

example 2

[0019] In a 250 ml four-necked flask equipped with a thermometer and a stirring device, add 21.0 grams (0.1927 mol) of p-aminophenol, 59 grams (0.5781 mol) of acetic anhydride (refined anhydrous) and a small amount of glacial acetic acid, and heat to reflux at 128 ° C. After reacting for about 2 hours, the reaction liquid was cooled to 25° C., then 40.0 ml (0.9541 mol) of 98% nitric acid was added dropwise and the temperature was kept constant, and stirred for 1.0 hour under strong acid condition. Then 22 milliliters (0.4889 mol) of 65% nitric acid was added, the temperature was controlled at 20° C., and the reaction was stirred for 1.0 hour. Then the reaction solution was poured into ice water, and yellow crystals were precipitated, washed with water 2 to 3 times until neutral, filtered with suction, and the filter cake was dried to obtain yellow 4-acetoxy-2-acetamido nitro 32.8 grams of benzene, the yield is 71.6%. Melting point: 144℃~146℃.

[0020] Synthesis of 4-amino-3-...

example 3

[0022] Add 5.4 (0.0227mol) gram of 4-acetoxy-2-acetamidonitrobenzene and 30.0 milliliters of 3mol / L NaOH solution prepared in 150 milliliters of four-necked flasks with a thermometer and a stirring device, Heat to 60°C and control the stirring reaction at 50-55°C for 4 hours. After the reaction is finished, the reaction solution is cooled to below 10°C, and then the pH value of the reaction solution is adjusted to 3-4 with a hydrochloric acid solution with a mass ratio of 1:1 to water. Red crystals precipitated. Suction filtration, drying the filter cake to obtain 2.7 g of brown-red 4-amino-3-nitrophenol. The yield was 77.1%. Melting point: 149℃~150℃.

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Abstract

The present invention belongs to the field of fined chemical intermediate synthesizing technology, and is process of preparing 4-amino-3-nitro phenol. The process of preparing 4-amino-3-nitro phenol includes the following three steps: acetylation of p-aminophenol as material with acetic anhydride, the subsequent nitration with nitric acid, and final hydrolysis of 4-acetoxy-2-acetamino nitrobenzene with sodium hydroxide. The present invention has simple operation and low cost.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fine chemical intermediates, and 4-amino-3-nitrophenol involves three reaction steps of acetylation, nitration and hydrolysis. Background technique [0002] 4-Amino-3-nitrophenol is mainly used as an intermediate of medicine and organic dyes, and also as a dyeing agent for cotton, linen, and viscose fabrics and hair dyes. At present, there is no domestic production enterprise. [0003] Abroad, only Kehrmann, F et al. reported the synthesis route of 4-amino-3-nitrophenol by using o-azidonitrobenzene as raw material through hydroxylation reaction and selective reduction. This route uses the azide compound, and the azide compound has the danger of explosion, and the selective reduction is relatively difficult, and the yield is very low. Contents of the invention [0004] Based on the innovative research of the existing synthetic route, the present invention completes acetylation and nitratio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/76C07C213/08
Inventor 邱滔张丽吕新宇
Owner 溧阳常大技术转移中心有限公司
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