Preparation method for 2,2-di[3-amino-4-(4-cyanophenoxy)phenyl]propane

A technology of cyanophenoxy and hydroxyphenyl, applied in 2 fields, can solve problems such as no published literature or patent reports, and achieve the effects of good quality, simple operation steps and less three wastes

Inactive Publication Date: 2008-01-09
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The preparation method of 2,2-bis[3-amino-4-(4-cyanophenoxy)phenyl]propane involved in the present invention has not yet seen any published literature or patent reports

Method used

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  • Preparation method for 2,2-di[3-amino-4-(4-cyanophenoxy)phenyl]propane

Examples

Experimental program
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Effect test

Embodiment 1

[0020] 25.8 grams (0.1 moles) of 2,2-bis(3-amino-4-hydroxyphenyl) propane (BAHPP), 33.0 grams (0.24 moles) of 4-chlorobenzonitrile (CBN), 44.2 grams (0.32 moles) Potassium carbonate, 252 ml of N,N-dimethylformamide (DMF) and 84 ml of toluene were added to a round-bottomed flask with a thermometer, nitrogen tube, oil-water separator, reflux condenser and mechanical stirrer, and nitrogen was passed at room temperature After stirring for 0.5 hours, heat up to 120°C and react for 3 hours, gradually increase the reaction temperature, and finally rise to 150°C for 1 hour, and maintain the reaction at 150°C for 26 hours, cool to 80°C, and filter while it is hot. Remove the filter residue, concentrate the mother liquor under reduced pressure, cool, crystallize, filter, and dry to obtain 2,2-bis[3-amino-4-(4-cyanophenoxy)phenyl]propane, according to 2,2-bis (3-Amino-4-hydroxyphenyl)propane was measured for the amount of feed and product, and the yield was 96% (purity 99%).

Embodiment 2

[0022] 25.8 g (0.1 mol) of 2,2-bis(3-amino-4-hydroxyphenyl)propane (BAHPP), 0.12 mol of potassium hydroxide, 100 ml of N-methylpyrrolidone (NMP) and 100 ml of xylene were added Put it into a round-bottomed flask equipped with a thermometer, nitrogen tube, oil-water separator, reflux condenser and mechanical stirrer. After stirring with nitrogen at room temperature for 0.5 hours, heat and reflux until no water is analyzed, and cool the reaction system to 90 ° C. Add 27.5 grams (0.2 moles) of 4-chlorobenzonitrile (CBN), heat and stir, and react at 120°C for 3 hours, gradually increase the reaction temperature, and finally rise to 150°C for 1 hour, and maintain the reaction at 150°C for 16 Hours later, cool to 80°C, filter while it is hot, remove the filter residue, concentrate the mother liquor under reduced pressure, cool, crystallize, filter, and dry to obtain 2,2-bis[3-amino-4-(4-cyanophenoxy ) phenyl] propane, according to 2,2-bis(3-amino-4-hydroxyl phenyl) propane charging ...

Embodiment 3

[0024] 25.8 g (0.1 mol) of 2,2-bis(3-amino-4-hydroxyphenyl)propane (BAHPP), 0.22 mol of 4-chlorobenzonitrile (CBN), 0.2 mol of potassium carbonate, 120 ml of N,N -Dimethylformamide (DMF) and 200 milliliters of toluene are added in the round-bottomed flask with thermometer, nitrogen pipe, oil-water separator, reflux condenser and mechanical stirrer. After reacting at 120°C for 3 hours, gradually increase the reaction temperature, and finally rise to 150°C for 1 hour, and maintain the reaction at 150°C for 26 hours, then cool to 80°C, filter while it is hot, remove the filter residue, concentrate the mother liquor under reduced pressure, Cooling, crystallization, filtration, and drying to obtain 2,2-bis[3-amino-4-(4-cyanophenoxy)phenyl]propane, according to 2,2-bis(3-amino-4-hydroxy The feeding amount and product amount of phenyl)propane were measured, and the yield was 82%.

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Abstract

Production of 2,2-di(3-amino-4-(4-cyano-phenoxy)phenyl)propane is carried out by taking 2,2-di(3-amino-4-hydroxy-phenyl)propane and 4-chloroformonitrile in proportion of 1:2.0-2.4 mol, reacting at 120-200 deg. C for 10-30 hrs under nitrogen protection in solvents of salting agent, azeotropic agent and indifferent polar, filtering, removing filter residue, decompressing while concentrating for mother liquor, cooling, crystallizing, filtering and drying. The proportion of salting agent and 2,2-di(3-amino-4-hydroxy-phenyl)propane is 1.2-3.2:1 mol, the proportion of azeotropic agent and indifferent polar solvent is 1:0.6-3.0 volume; the proportion of 4-chloroformonitrile and indifferent agent is 1 mol: 350-700 / ml. It's simple and efficient, has circulation utilization, less waste discharge, excellent operation environment, easy reactive solvent recovery and higher purity.

Description

technical field [0001] The invention relates to a preparation method of an aromatic dibasic primary amine compound containing an aromatic cyano group, in particular to a 2,2-bis[3-amino-4-(4-cyanophenoxy)phenyl]propane method of preparation. Background technique [0002] Aromatic dibasic primary amine compounds containing aromatic cyano groups in their molecular structure are used to prepare high-temperature resistant polyimide resins, liquid crystal alignment agents, carbon fiber reinforced advanced composite material matrix resins, high-impact epoxy resin curing agents, and polyurethane chain extenders. It is an important raw material for VLSI passivation coating and α-particle barrier coating material, as well as substrate matrix resin or adhesive for printed electronic circuit boards. [0003] Aromatic polyimide has excellent thermal stability, nuclear radiation resistance, excellent mechanical properties, electrical properties and resistance to organic solvents, and ha...

Claims

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Application Information

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IPC IPC(8): C07C255/54C07C253/30
Inventor 虞鑫海徐永芬赵炯心
Owner DONGHUA UNIV
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