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Method for preparing 4-nitrosoaniline and 4-nitroaniline

A technology of nitrosoaniline and nitroaniline, which is applied in disproportionation to prepare amino compounds, amino substitution of hydrogen atoms, organic chemistry, etc., can solve the problem of low yield of 4-nitrosoaniline, achieve high selectivity, Effect of reducing pollution and low price

Pending Publication Date: 2021-01-08
江苏方圆芳纶研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the yield of 4-nitrosoaniline is too low

Method used

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  • Method for preparing 4-nitrosoaniline and 4-nitroaniline
  • Method for preparing 4-nitrosoaniline and 4-nitroaniline
  • Method for preparing 4-nitrosoaniline and 4-nitroaniline

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Experimental program
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Effect test

Embodiment 1

[0045] First purging the empty autoclave with compressed air, then adding 7.44 grams of nitrobenzene, 120 grams of dimethyl sulfoxide, 2.2 grams of tetramethylammonium hydroxide pentahydrate, 10.6 grams of desiccant calcium oxide, and Trimethyl ammonium chloride 1.2 grams, then airtight autoclave, be filled with 1.63 grams of liquid ammonia, the pressure in the still reaches 1.6 MPa, and stirs 10 minutes under this pressure, records the volumetric concentration of ammonia in the gaseous phase in the still is 12%. The reaction mixture was heated to 80°C with stirring, and reacted at this temperature for 7 hours. After the reaction, the pressure still was released, cooled, the reaction mixture was weighed, and sampling was carried out by gas chromatography, and the calculated yield of 4-nitrosoaniline in terms of nitrobenzene was 56.4%, 4-nitroaniline The yield was 42.3%.

Embodiment 2

[0047] First purging the empty autoclave with compressed oxygen, then adding 7.44 grams of nitrobenzene, 240 grams of N,N-dimethylformamide, 1.94 grams of sodium methylate, and 50 grams of desiccant anhydrous magnesium sulfate into the autoclave, and then Airtight autoclave is filled with 4 grams of liquid ammonia, the pressure in the autoclave reaches 2 MPa, and it is stirred under this pressure for 10 minutes, and the volume concentration of ammonia in the gas phase in the autoclave is measured to be 85%. The reaction mixture was heated to 96°C with stirring, and reacted at this temperature for 7 hours. After the reaction, the autoclave was depressurized, cooled, and the reaction mixture was weighed and sampled for gas chromatographic analysis. Calculated in terms of nitrobenzene, the yield of 4-nitrosoaniline was 54.7%, 4-nitroaniline The yield was 43.7%.

Embodiment 3

[0049] First purging the empty autoclave with compressed oxygen, then adding 7.44 grams of nitrobenzene, 51 grams of N-methylpyrrolidone, 3.36 grams of potassium hydroxide, 63.6 grams of desiccant anhydrous sodium carbonate, tetramethyl bromide Ammonium chloride 3.5 grams, then airtight autoclave, be charged with 2.45 grams of liquid ammonia, the pressure in the still reaches 1.7 MPa, and stirs 10 minutes under this pressure, records the volume concentration of ammonia in the gas phase in the still and is 67%. The reaction mixture was heated to 100°C with stirring, and reacted at this temperature for 7 hours. After the reaction, the autoclave was depressurized, cooled, and the reaction mixture was weighed and sampled for gas chromatographic analysis. Calculated in terms of nitrobenzene, the yield of 4-nitrosoaniline was 54.7%, 4-nitroaniline The yield was 43.7%.

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Abstract

The invention discloses a method for preparing 4-nitrosoaniline and 4-nitroaniline by reacting nitrobenzene with ammonia under the action of a catalyst. The method is high in conversion rate, good inselectivity and environment-friendly. In addition, the invention further provides a method for preparing p-phenylenediamine by reducing 4-nitrosoaniline and 4-nitroaniline, the yield is high, and separation and purification are not needed.

Description

[0001] field of invention [0002] The invention relates to the field of chemical synthesis, in particular to a method for preparing 4-nitrosoaniline and 4-nitroaniline by reacting nitrobenzene and ammonia under the action of a catalyst. Background technique [0003] 4-Nitrosoaniline is mainly used in the preparation of p-phenylenediamine, a widely used chemical intermediate, which can be used in the preparation of azo dyes, fur dyes, antioxidants and photographic developers, especially It is used as raw material for aramid fiber and rubber additives. [0004] There are two main methods for preparing 4-nitrosoaniline at present. The first is the synthesis of N-nitrosoaniline from aniline and sodium nitrite, followed by the preparation of 4-nitrosoaniline by Fischer-Hepp rearrangement. The disadvantage of this method is that denitrosation occurs during the Fischer-Hepp rearrangement process, and nitroso-containing compounds that are harmful to the environment are produced in ...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/02C07C209/64
CPCC07C209/02C07C209/64C07C211/52Y02P20/584
Inventor 王农跃张启俊沙艳松陈莉李斌
Owner 江苏方圆芳纶研究院有限公司
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