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Prepn process of nitro aromatic amine compound

A technology of nitroarylamine and aminotriphenylamine is applied in the field of preparation of hole transport material intermediates, and can solve the problems of long reaction time, expensive catalyst, high solvent toxicity and the like

Active Publication Date: 2006-03-01
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, to synthesize triarylamine compounds with good hole transport properties, the preparation of amine compounds as one of the raw materials for preparing products is very important. The solvents used in the preparation methods of nitro compounds reported in the data include toluene, di Toluene and nitrobenzene, but the general reaction time is long, the catalyst is expensive, and the solvent is highly toxic

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0010] Example 1: Synthesis of 4-nitrodiphenylamine

[0011] Add 9.3g (0.1mol) aniline, 16.9g (0.12mol) p-fluoronitrobenzene, 4g (0.1mol) 60% sodium hydride and 150mL DMF , stirring and heating to 110°C, maintaining the reaction for 9h, filtering while hot after the reaction, diluting the filtrate with a large amount of ice water, filtering, and recrystallizing the obtained crude product with absolute ethanol to obtain 18.7g of the product, yield: 87.5%.

example 2

[0012] Example 2: Synthesis of 4-methyl-4'-nitrodiphenylamine

[0013] Add 10.7g (0.1mol) p-toluidine, 16.9g (0.12mol) p-fluoronitrobenzene, 4g (0.1mol) 60% sodium hydride in a 250mL four-necked flask equipped with a reflux condenser, thermometer and stirrer and 150mL of DMF, stirred and heated to 110°C, maintained the reaction for 9h, filtered while hot after the reaction, diluted the filtrate with a large amount of ice water, filtered, and recrystallized the obtained crude product with absolute ethanol to obtain 20.1g of the product, yield: 88.1% .

example 3

[0014] Example 3: Synthesis of 4-nitrotriphenylamine

[0015] Add 16.9g (0.1mol) diphenylamine, 16.9g (0.12mol) p-fluoronitrobenzene, 4g (0.1mol) 60% sodium hydride and 150mL of DMF, stirred to raise the temperature to 110°C, and maintained the reaction for 9h. After the reaction was completed, it was filtered while it was hot. The filtrate was diluted with a large amount of ice water and filtered. The obtained crude product was recrystallized with absolute ethanol to obtain 24.7g of the product, with a yield of 85.2%.

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PUM

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Abstract

The present invention belongs to the field of preparation technology of aromatic amine as hole transmission material intermediate. The preparation process of nitro aromatic amine compound includes the following steps: reacting one of phenylamine, diphenylamine and triphenylamine, strong alkali and p-fluoro nitrobenzene or p-chloro nitrobenzene in certain molar proportion in N, N-dimethyl formamide as solvent inside some reactor at 90-130 deg.c for 5-16 hr; filtering in the hot state to eliminate reaction produced impurity; decompression distillation to eliminate DMF and to obtain initial product; and re-crystallization with methanol, ethanol or acetonitrile to obtain the nitro aromatic amine compound. The present invention has the advantages of cheap material, simple post-treatment, high product yield, high product purity and being suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing a hole transport material intermediate nitroarylamine compound, and belongs to the preparation technology of a hole transport material intermediate. Background technique [0002] Aromatic amine hole transport materials are an important part of hole transport materials. Due to their low ionization potential and high hole mobility, aryl amine hole transport materials have become the focus of research in recent years. However, to synthesize triarylamine compounds with good hole transport properties, the preparation of amine compounds as one of the raw materials for preparing products is very important. The solvents used in the preparation methods of nitro compounds reported in the data include toluene, di Toluene and nitrobenzene, but the general reaction time is long, the catalyst is expensive, and the solvent is highly toxic. The invention provides a simple and effective me...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/76
Inventor 王世荣徐国辉张毅李祥高李楠
Owner TIANJIN UNIV
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