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Preparation method of 2,2'-bis(trifluoromethyl)-4,4'-diaminodiphenyl

A technology of diaminobiphenyl and trifluoromethyl is applied in the field of preparation of 2,2'-bis-4,4'-diaminobiphenyl, and can solve the problems of low product quality, complicated process, unfavorable environmental protection and the like, Achieve the effect of less discharge of three wastes, simple process and low cost

Inactive Publication Date: 2019-01-18
烟台海川化学制品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention aims at the problems existing in the prior art that the process is cumbersome, the three wastes are serious, not conducive to environmental protection, the product quality is low, the cost is high, and it is not conducive to industrial production, and provides a simple process, less three wastes, mild reaction conditions, product quality and yield High-efficiency, low-cost, environmentally friendly synthesis of 2,2'-bis(trifluoromethyl)-4,4'-dinitrobiphenyl

Method used

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  • Preparation method of 2,2'-bis(trifluoromethyl)-4,4'-diaminodiphenyl
  • Preparation method of 2,2'-bis(trifluoromethyl)-4,4'-diaminodiphenyl

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Under nitrogen protection, with 300g m-nitrobenzotrifluoride as raw material, add 3g Pd / C, 3g sodium dodecylbenzenesulfonate, 1.5g 2,3-dichloro-1,4-naphthoquinone, 150g 25 % sodium hydroxide aqueous solution, 900g toluene, pressure 3-5 atm, temperature 55-65°C, keep warm for 5-8 hours, cool down to 20-30°C, take out the material, and obtain 1150g 3,3'-bis (Trifluoromethyl)diphenylhydrazine in toluene, the purity is 95.1%.

[0031] Under the protection of nitrogen, add 960g of 80% sulfuric acid to the reaction flask equipped with a stirrer and dropping funnel, and slowly add one step of 3,3'-bis(trifluoromethyl) Diphenylhydrazine toluene solution, add dropwise for 2-3 hours, keep warm for 1 hour, add 350g of water, heat up to 70-75°C, separate the liquids, neutralize the water phase with lye to pH=7, a off-white solid precipitates, add 500g of toluene to extract , washed with water, and recrystallized to obtain 130.6g of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl as...

Embodiment 2

[0033]Under nitrogen protection, with 300g m-nitrobenzotrifluoride as raw material, add 1.5g Pd / C, 1.5g sodium dodecylbenzenesulfonate, 0.75g 2,3-dichloro-1,4-naphthoquinone, 120g 25% sodium hydroxide aqueous solution, 800g toluene, pressure 3-5atm, temperature 55-65°C, keep warm for 5-8 hours, cool down to 20-30°C, take out the material, and obtain 1050g 3,3' after liquid separation - Bis(trifluoromethyl)diphenylhydrazine in toluene with a purity of 94.5%.

[0034] Under the protection of nitrogen, add 800 g of 80% sulfuric acid to the reaction flask equipped with a stirrer and dropping funnel, and slowly add one step of 3,3'-bis(trifluoromethyl) di Phenylhydrazine toluene solution, after 2-3 hours of dropwise addition, keep warm for 1 hour, add 350g of water, heat up to 70-75°C, separate the liquids, neutralize the water phase with lye to pH=7, a off-white solid precipitates, add 500g of toluene to extract, Washing with water and recrystallization gave 125.7 g of 2,2'-bis(t...

Embodiment 3

[0036] Under nitrogen protection, with 300g m-nitrobenzotrifluoride as raw material, add 4.5g Pd / C, 5.0g sodium dodecylbenzenesulfonate, 2.5g 2,3-dichloro-1,4-naphthoquinone, 160g of 25% sodium hydroxide aqueous solution, 900g of toluene, pressure of 3-5 atm, temperature of 55-65°C, heat preservation reaction for 5-8 hours, cooling to 20-30°C, taking out the materials, and obtaining 1150g of 3,3' after liquid separation - Bis(trifluoromethyl)diphenylhydrazine in toluene with a purity of 96.1%.

[0037] Under the protection of nitrogen, add 85% 760g sulfuric acid to the reaction flask equipped with a stirrer and dropping funnel, and slowly add 3,3'-bis(trifluoromethyl) di Phenylhydrazine toluene solution, after 2-3 hours of dropwise addition, keep warm for 2 hours, add 350g of water, heat up to 70-75°C, separate the liquids, neutralize the water phase with lye to pH=7, a off-white solid precipitates, add 600g of toluene to extract, Washed with water and recrystallized to obtai...

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Abstract

The invention relates to a preparation method of 2,2'-bis(trifluoromethyl)-4,4'-diaminodiphenyl. The preparation method comprises the following steps: synthesizing 3,3'-bis(trifluoromethyl)hydrazo-benzene in an inorganic alkaline aqueous solution by adopting nitrobenzotrifluoride as a raw material, adopting a phase transfer catalyst, a co-catalyst and Pd / C as a catalytic system and adopting aromatic hydrocarbon as a solvent, and performing the re-arrangement reaction on the 3,3'-bis(trifluoromethyl)hydrazo-benzene in an inorganic acid aqueous solution, thus obtaining 2,2'-bis(trifluoromethyl)-4,4'-diaminodiphenyl, wherein the phase transfer catalyst is one or a mixture of more of sodium dodecyl benzene sulfonate, sodium dodecyl sulfate and cetyl trimethyl ammonium bromide, and the co-catalyst is one or a mixture of more of 2,3-dichloro-1,4-naphthoquinone, 2-hydroxyanthraquinone and 2,6-dioxyanthraquinone. The preparation method has the advantages of mild reaction condition, simple process, high product quality and yield, low production cost, environmental friendliness, suitability for continuous production and the like.

Description

technical field [0001] The invention relates to a preparation method of 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, belonging to the technical field of fine chemicals. Background technique [0002] 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl is a material chemical intermediate product with excellent performance and one of the important raw materials for the synthesis of soluble polyimide. Imine is a high temperature resistant polymer with excellent oxidation stability, chemical resistance, radiation resistance, good toughness and flexibility, and is widely used in aviation / aerospace, electronics / electrical, glass , automobiles, ships, electrical, precision machinery and automatic office machinery and other fields. [0003] 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl is one of the important raw materials for the synthesis of polyimide resin, and it can also be used for high temperature resistant polyimide carbon fiber reinforced composite materials, It is also an ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/54C07C211/52C07C241/02C07C243/22
CPCC07C209/54C07C241/02C07C211/52C07C243/22
Inventor 张钊冯绍全李树国赵峰赵青山李军
Owner 烟台海川化学制品有限公司
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