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Method for preparing 4-nitroso-substituted aromatic amine

A technology of nitroaromatic and aromatic amines, which is applied in the field of preparing 4-nitroso-substituted aromatic amines, and can solve the problems of not preparing aromatic amines

Inactive Publication Date: 2005-02-02
KOREA KUMHO PETROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no relevant literature on the preparation of 4-nitroso-substituted aromatic amines

Method used

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  • Method for preparing 4-nitroso-substituted aromatic amine
  • Method for preparing 4-nitroso-substituted aromatic amine
  • Method for preparing 4-nitroso-substituted aromatic amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 2.0 g (34 mmol) of acetamide, 4.1 g (68 mmol) of potassium hydroxide, 10 g of anhydrous potassium carbonate, 200 mg of pyrene and 15 ml of DMSO into a 100 ml reactor equipped with a condenser and a thermometer , and the mixture was heated with stirring in an oxygen atmosphere. When the reaction temperature reached 85° C., 1.4 g (11 mmol) of nitrobenzene was added dropwise through the dropping funnel for about 10 minutes. An extreme caution was employed in case the temperature inside the reactor might exceed 85±4°C. The time point at which nitrobenzene disappeared was determined as the end point of the reaction using HPLC. After reacting for 2 hours, DMSO was added to a predetermined amount of reactant, diluted with ethyl acetate, and then analyzed by HPLC.

[0049] The conversion of nitrobenzene was 100%. According to quantitative analysis, the product yield based on internal standard pyrene was 61 mole % for 4-nitrosoaniline and 8 mole % for 4-nitrosoaniline.

...

Embodiment 2

[0056] This example illustrates the results using different amides. The same procedure was carried out as described in Example 1, except that various amides as listed in Table 2 were used instead of acetamide. The results are listed in Table 2.

[0057] Amide

Embodiment 3

[0059] Operate in the same manner as described in Example 1, except that the amount of nitrobenzene based on acetamide is variable as listed in Table 3. The results are listed in Table 3.

[0060] Nitrobenzene / B

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PUM

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Abstract

Disclosed is a method for preparing a 4-nitroso-substituted aromatic amine that includes contacting an amide compound with a nitroaromatic compound in the presence of a base and a solvent to directly prepare 4-nitroso-substituted aromatic amine as a main product and 4-nitro-substituted aromatic amine as a by-product without producing 4-nitroso- or 4-nitro-substituted amide as an intermediate.

Description

technical field [0001] The present invention relates to a process for the preparation of 4-nitroso-substituted aromatic amines, more particularly to the selective preparation by contacting an amide compound with a nitroaromatic compound in a polar organic solvent in the presence of a base A method for 4-nitroso-substituted aromatic amines. technical background [0002] In general, 4-nitroso-substituted aromatic amines, which are partially used as intermediates and light stabilizers of dyes or hair dyes, have not been studied much on their applications due to their complicated preparation methods. Among the 4-nitroso-substituted aromatic amines, 4-nitrosoaniline is used as an intermediate for dyes or hair dyes and is often reduced as a starting material for the preparation of p-phenylenediamine (USP 6,245,943). [0003] Conventionally, 4-nitrosoaniline is obtained by reacting aniline with sodium nitrite (NaNO 2 ) contact to generate N-nitrosoaniline, and then N-nitrosoanili...

Claims

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Application Information

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IPC IPC(8): C07C209/68C07C209/00C07C211/52C07C213/02C07C217/84C07C231/08C07C233/66
CPCC07C213/02C07C231/08C07C209/00C07C209/68
Inventor 朱泳悌金镇亿元贞妊
Owner KOREA KUMHO PETROCHEMICAL CO LTD
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