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Method for preparing 2,6-di(4-amino-benzene oxygen) cyanobenzene

A technology of aminophenoxy and benzonitrile, which is applied in two fields, can solve the problems of unsatisfactory industrial production, target product yield and low melting point, etc., and achieve the effects of low production cost, simple and feasible preparation method, and good working environment

Inactive Publication Date: 2010-05-19
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above preparation methods need to be improved in terms of environmental protection and production cost control, and the yield and melting point of the target product are relatively low, so they cannot meet the needs of industrial production

Method used

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  • Method for preparing 2,6-di(4-amino-benzene oxygen) cyanobenzene
  • Method for preparing 2,6-di(4-amino-benzene oxygen) cyanobenzene
  • Method for preparing 2,6-di(4-amino-benzene oxygen) cyanobenzene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add 21.8 grams (0.2 moles) of 4-aminophenol (4AP), 27.6 grams (0.2 moles) of potassium carbonate, 200 milliliters of N-methyl-2-pyrrolidone (NMP) and 200 milliliters of xylene into the reaction flask, blow nitrogen After 2 hours of reflux and water separation reaction, cool the reaction solution to 80 ° C, add 17.2 grams (0.1 mole) of 2,6-dichlorobenzonitrile (26DCBN), heat and reflux reaction, and separate part to all xylene , to increase the reaction temperature, react at a temperature range of 170°C to 200°C for 12 hours, cool the reaction solution to 80°C, filter while it is hot, remove inorganic salts, keep the mother liquor, cool to room temperature, add water dropwise, precipitate the product, filter (collect the mother liquor to reclaim the organic solvent), wash the filter cake, and dry in vacuo to obtain 28.9 grams of brown 2,6-bis(4-aminophenoxy)benzonitrile (26B4APBN) solid product, according to the theoretical yield (31.7 grams ) and the actual amount obtai...

Embodiment 2

[0040] Add 21.8 grams (0.2 moles) of 4-aminophenol (4AP), 2.76 grams (0.02 moles) of potassium carbonate, and 90 milliliters of anhydrous N-methyl-2-pyrrolidone (NMP) into the reaction flask, argon, and reflux After reacting for 0.5 hours, cool the reaction solution to 80°C, add 26.1 grams (0.1 moles) of 2,6-dibromobenzonitrile (26DBBN), heat up, react at a temperature range of 170°C to 200°C for 3 hours, and cool The reaction solution was heated to 80°C, filtered while it was hot, and the inorganic salts were removed, the mother liquor was retained, cooled to room temperature, water was added dropwise, the product was precipitated, filtered (the mother liquor was collected to recover the organic solvent), the filter cake was washed, and vacuum dried to obtain 12.1 g The brown solid product of 2,6-bis(4-aminophenoxy)benzonitrile (26B4APBN) was calculated to yield 38.2% based on the theoretical yield (31.7 g) and the actual yield.

Embodiment 3

[0042]24.0 grams (0.22 moles) of 4-aminophenol (4AP), 26.5 grams (0.25 moles) of sodium carbonate, 200 milliliters of anhydrous N-methyl-2-pyrrolidone (NMP) and 40 milliliters of anhydrous N, N-di Methyl acetamide (DMAc) was added to the reaction flask, nitrogen was passed, and after 5 hours of reflux reaction, the reaction solution was cooled to 80°C, 13.9 grams (0.1 moles) of 2,6-difluorobenzonitrile (26DFBN) was added, and heated Raise the temperature, react in the temperature range of 170°C to 200°C for 7 hours, cool the reaction solution to 80°C, filter while it is hot, remove the inorganic salt, keep the mother liquor, cool to room temperature, add water dropwise, precipitate the product, filter (collect the mother liquor, to reclaim the organic solvent), wash the filter cake, and dry in vacuo to obtain 25.9 grams of brown 2,6-bis(4-aminophenoxy)benzonitrile (26B4APBN) solid product, according to the theoretical yield (31.7 grams) and the actual obtained amount, the calc...

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Abstract

The invention relates to a preparation process for 2, 6-bis(4-diaminophenoxy) benzonitrile. The invention comprises the following procedures: the p-aminophenol with mole ratios of 1.0:0.1 to 2.5 and the halogen agent are made a refluence reaction for 0.5 to 5 hours in organic solvent system under inertia atmosphere, and 2, 6-dihalogenated benzonitrile is added to react together for 3 to 12 hours at 170 to 200 DEG C, then the mixing solution are filtered and cleaned as well as dried in vacuum to obtain the brown 2, 6-bis(4-diaminophenoxy) benzonitrile solid product. The preparation process of the invention has simple process, low cost, environment-friendly feature, less energy consumption work hours, high yields and purity, and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of preparation of organic compounds, in particular to a preparation method of 2,6-bis(4-aminophenoxy)benzonitrile. Background technique [0002] 2,6-bis(4-aminophenoxy)benzonitrile belongs to the aromatic dibasic primary amines containing ether bonds in the molecular structure. As we all know, primary aromatic diamines are one of the important raw materials for synthesizing polyimide materials, and aromatic primary diamines containing ether bonds are important raw materials for synthesizing thermoplastic polyimides. [0003] Aromatic polyimide has excellent thermal stability, nuclear radiation resistance, excellent mechanical properties, electrical properties and resistance to organic solvents, and has been widely used in aerospace, electronic microelectronics, electrical and other fields. [0004] With the development of high-performance, lightweight, thin, and refined information electronic products, higher require...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/54C07C253/30
Inventor 虞鑫海徐永芬赵炯心
Owner DONGHUA UNIV
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