Continuous synthesis method of m-acetamido phenol

A technology of m-acetamide and phenol, which is applied in the field of continuous synthesis of m-acetamidophenol, can solve the problems of poor safety, three wastes, and high technical cost, and achieve improved safety, less by-products, and high safety of the synthesis process Effect

Active Publication Date: 2018-08-03
JIANGSU D I A N CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to overcome the disadvantages of Disperse Yellow 114 intermediate m-acetamidophenol preparation technology

Method used

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  • Continuous synthesis method of m-acetamido phenol
  • Continuous synthesis method of m-acetamido phenol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of embodiment 1 m-acetamidophenol

[0028] 91.5 g (0.61 mol) m-acetamidoaniline, 270 g (2.70 mol) 98% sulfuric acid and 1200 mL water, stirred evenly to make solution A, 42.8 g (0.62 mol) sodium nitrite and 180 mL water, stirred evenly to make solution A Solution B. Solution A and solution B were fed by metering pump A and metering pump B respectively, the flow rate ratio of metering pump A and metering pump B was controlled to be 1:7.1, and the residence time of the reaction liquid in the tubular reactor was controlled to be 25 s. The whole tubular reactor is a copper tube with an inner diameter of 16 mm and a length of 2 m, and the tube is immersed in an oil bath with a constant temperature of 120 °C. The reaction solution flowed out into a four-necked flask with stirring and cooling, extracted with 3x200 mL of methyl isobutyl ketone at an extraction temperature of 20-35°C, washed with water, and dried over anhydrous sodium sulfate. Filtration and prec...

Embodiment 2

[0029] The synthesis of embodiment 2 m-acetamidophenol

[0030] 91.5 g (0.61 mol) m-acetamidoaniline, 180 g (1.80 mol) 98% sulfuric acid and 1000 mL water, stirred evenly to make solution A, 44.2 g (0.64 mol) sodium nitrite and 160 mL water, stirred evenly to make solution A Solution B. Solution A and solution B were fed by metering pump A and metering pump B respectively, the flow rate ratio of metering pump A and metering pump B was controlled to be 1:6.3, and the residence time of the reaction liquid in the tubular reactor was controlled to be 80 s. The tubular reactor consists of two parts. The first part of the reaction section is a copper tube with an inner diameter of 4 mm and a length of 10 m. m, the pipe was submerged in an ice-water bath. The reaction solution was collected, extracted with 4x150 mL of toluene at an extraction temperature of 50-60°C, washed with water, and dried over anhydrous sodium sulfate. Filtration and precipitation yielded 77.7 g of crude m-a...

Embodiment 3

[0031] The synthesis of embodiment 3 m-acetamidophenol

[0032] 91.5 g (0.61 mol) m-acetamidoaniline, 360 g (3.60 mol) 98% sulfuric acid and 800 mL water, stirred evenly to make solution A, 45.0 g (0.65 mol) sodium nitrite and 110 mL water, stirred evenly to make solution A Solution B. Solution A and solution B were fed by metering pump A and metering pump B respectively, the flow rate ratio of metering pump A and metering pump B was controlled to be 1:8.1, and the residence time of the reaction liquid in the tubular reactor was controlled to be 220 s. The whole tubular reactor is a copper tube with an inner diameter of 6 mm and a length of 40 m, and the tube is immersed in an oil bath at a constant temperature of 70 °C. The reaction solution flowed into a four-neck flask with stirring and cooling, extracted with 4x180 mL of cyclohexane at an extraction temperature of 45-55°C, washed with water, and dried over anhydrous magnesium sulfate. Filtration and precipitation yielded...

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Abstract

The invention discloses a continuous synthesis method of m-acetamido phenol. The method comprises the following steps: respectively preparing two solutions from m-aminoacetanilide, sulfuric acid, sodium nitrite and the like, respectively continuously pumping the solutions into a tubular reactor by a metering pump at a preset flow velocity, performing diazotization and hydrolysis reactions, and cooling, extracting, drying and desolventizing the obtained reaction product to obtain the product, wherein the diazotization reaction and the hydrolysis reaction are completed in the same tubular reactor. The method has the characteristics of sufficient sources and low price of raw materials, high safety in the synthesis process, high product yield, less pollution of three wastes, and high industrialization values.

Description

technical field [0001] The invention relates to a continuous synthesis method of m-acetamidophenol, which belongs to the field of fine chemical industry. Background technique [0002] m-acetamidophenol is the key intermediate of pyridone-type heterocyclic disperse dye Disperse Yellow 114. Disperse Yellow 114 has good fastness properties such as sun resistance, sublimation resistance, washing resistance and rubbing resistance, level dyeing and improvement It is one of the most widely used yellow disperse dyes at present. [0003] [0004] The diazo component m-benzenesulfonyloxyaniline of Disperse Yellow 114 is synthesized by using m-aminophenol as raw material at home and abroad, through three-step reaction of acetylation protection of amino group, benzenesulfonate esterification of hydroxyl group and deacetylation deprotection , but the raw material m-aminophenol used in this method is not only expensive, but also the three wastes in the synthesis process are serious ...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/25
CPCC07C231/12C07C233/25
Inventor 胡效奎徐叙明王一键郑土才牟忠岳
Owner JIANGSU D I A N CHEM CO LTD
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