Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Process of preparing 4-amino-3-nitro phenol

A technology for nitrophenol and p-aminophenol, which is applied in the field of fine chemical intermediate synthesis, can solve the problems of azide compounds such as explosion danger, low yield, difficulty in selective reduction, etc., and achieves high acylation activity, cost reduction, The effect of reducing the amount of production

Active Publication Date: 2010-04-21
溧阳常大技术转移中心有限公司
View PDF2 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Process of preparing 4-amino-3-nitro phenol

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0018] 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 conditions. 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 to precipitate yellow crystals, which were washed 2 to 3 times with water until neutral, filtered with suction, and the filter cake was dried to obtain yellow 2-acetamido-5-acetoxynitro 34.6 grams of benzene, the yield is 75.5%. Melting point: 144℃~146℃.

example 2

[0020] 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 to precipitate yellow crystals, which were washed 2 to 3 times with water until neutral, filtered with suction, and the filter cake was dried to obtain yellow 2-acetamido-5-acetoxynitro 32.8 grams of benzene, the yield is 71.6%. Melting point: 144℃~146℃.

[0021] Synthesis of 4-amino-...

example 3

[0023] Add 5.4 (0.0227mol) gram of 2-acetamido-5-acetoxynitrobenzene prepared in Example 1 and 30.0 milliliters of 3mol / L NaOH solution in a 150 milliliter four-necked flask 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℃.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

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 nitrobenzenewith 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com