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Process for synthesizing nitroarylamine compounds

A technology of nitroarylamines and compounds, which is applied in the field of synthesis of nitroarylamines to achieve the effects of high reaction selectivity, simple raw materials, and high yield

Inactive Publication Date: 2005-01-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Selenium-Catalyzed Reduction of Aromatic Nitro Compounds to Amines by CO / H2O in the Selenium-Catalyzed Reduction of Aromatic Nitro Compounds to Amines by CO / H2O Presence ofTriethylamine.Angew Chem Int Ed Engl, 1980, 19(12): 1008), the yield is moderate to good, but triethylamine must be used as a cocatalyst

Method used

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  • Process for synthesizing nitroarylamine compounds
  • Process for synthesizing nitroarylamine compounds

Examples

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Effect test

Embodiment 1

[0024] Add m-dinitrobenzene (10mmol), Se (0.4mmol), H in a 100ml stainless steel autoclave 2 O (200mmol), sodium acetate (10mmol) and solvent tetrahydrofuran (15ml), after replacing 3 times with carbon monoxide, raise the pressure of carbon monoxide to 1MPa, put it into an oil bath that has risen to 160°C and stir for 3 hours, cool To room temperature, open the kettle, feed oxygen or stir in the air for 0.5-1 hour, filter out the selenium powder, concentrate the filtrate obtained by filtering, and separate with a chromatographic column to obtain m-nitroaniline. The separation yield is 83.3% ( In terms of m-dinitrobenzene), the purity is 100%.

Embodiment 2

[0026] The aromatic dinitro substance is p-dinitrobenzene, and other experimental methods and conditions are the same as in Example 1. The yield of p-nitroaniline obtained by column separation is 78.3% (calculated as p-dinitrobenzene), and the purity is 100%.

Embodiment 3

[0028] Aromatic dinitro is 2,6-dinitrotoluene, and the reaction time is 6 hours, and other experimental methods and conditions are the same as in Example 1, and the column separation to obtain 2-methyl-4-nitroaniline yield is 90.8% (with 2,6-dinitrotoluene), the purity is 100%.

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Abstract

The synthesis process of nitroarylamine compounds is reaction of aromatic dinitro compound in organic solvent inside a high pressure reactor in the presence of CO and water, Se as catalyst and alkali as cocatalyst. The aromatic dinitro compound may have substitute radical, which may be one or several electron donor and / or electron acceptor radicals, on its benzene radical. The reaction conditions include the molar ratio between aromatic dinitro compound an water of 1 to 1-30, molar amount of Se being 0.5-20 % that of aroamtic dinitro compound, molar amount of alkali being 0-200 % of aromatic dinitro compound, reaction time 0.5-10 hr, reaction temperature 90-200 deg.c and initial pressure of CO being 1-5 MPa.

Description

technical field [0001] The invention relates to a method for synthesizing nitroarylamine compounds, in particular to a method for synthesizing nitroarylamine compounds through selenium catalytic reduction using carbon monoxide and water. Background technique [0002] As a large class of important organic synthesis intermediates and raw materials, nitroarylamines are widely used in medicine, pesticides, dyes and other fields. At present, the reduction of aromatic dinitro compounds is an important method for the preparation of nitroarylamines, but there are not many methods. In general, the selective reduction methods of dinitro compounds used in industrialization mainly include the following: iron filings reduction, alkali sulfide reduction, and tin chloride reduction. Iron filings method and soda sulfide method have wide adaptability, simple process, and high reduction conversion rate, but serious environmental pollution, and poor reduction selectivity to different nitro gr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/36C07C211/52
Inventor 刘晓智彭爱东陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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