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Method for preparing 3, 4'-diaminodiphenyl ether

A technology of diaminodiphenyl ether and p-nitrochlorobenzene is applied in chemical instruments and methods, preparation of organic compounds, preparation of amino hydroxy compounds, etc., and can solve the problems of many solid-liquid separation steps, serious environmental pollution, and reaction steps. It can achieve the effect of less process waste water, simple management and low production cost.

Pending Publication Date: 2020-04-28
南通汇顺化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The whole reaction steps are long, there are many solid-liquid separation steps, three kinds of solvents are used, the operation is complicated, difficult to control, and there are many by-products, which seriously pollutes the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Put 458g of N,N-dimethylformamide, 152.6g (1.4mol) of m-aminophenol, 0.15g of antioxidant sodium bisulfite, and 106.9g of acid-binding agent potassium carbonate into a 2000ml reaction bottle, stir, and protect with nitrogen; Raise the temperature to 100-120°C; keep the temperature and add 220g of p-nitrochlorobenzene dropwise, after 5h dropwise addition, keep warm for 3h to continue the reaction; sampling, HPLC central control detection, the content of m-aminophenol is 0.27%, stop the reaction; heat filtration, filtrate Transfer to a 2L autoclave; put in 1.6g of 5% palladium carbon, 0.32g of ferric chloride as a promoter, and replace with nitrogen; keep at 60-80°C, feed hydrogen for catalytic hydrogenation, and the pressure of hydrogen does not exceed 0.5MPa; until no longer Inhale hydrogen, continue to maintain the temperature for 2 hours, and the reaction ends. Filter out the catalyst, and simply distill the filtrate to recover N,N-dimethylformamide; change to high va...

Embodiment 2

[0030] Put 610g of N,N-dimethylformamide, 152.6g (1.4mol) of m-aminophenol, 0.3g of antioxidant sodium bisulfite, and 111.5g of acid-binding agent potassium carbonate into a 2000ml reaction bottle, stir, and protect with nitrogen; Raise the temperature to 100-120°C; maintain the temperature and add 222g of p-nitrochlorobenzene dropwise, after 6h, the dropwise addition is completed, and keep warm for 3h to continue the reaction; sampling, HPLC central control detection, the content of m-aminophenol is 0.19%, and the reaction is stopped; hot filtration, filtrate Transfer to a 2L autoclave; put in 4.5g of 5% palladium carbon, 0.92g of ferric chloride as a promoter, and replace with nitrogen; keep at 60-80°C, feed hydrogen for catalytic hydrogenation, and the pressure of hydrogen does not exceed 0.5MPa; until no longer Inhale hydrogen, continue to maintain the temperature for 2 hours, and the reaction ends. Filter out the catalyst, and simply distill the filtrate to recover N,N-di...

Embodiment 3

[0032] Put 763g of N,N-dimethylformamide, 152.6g (1.4mol) of m-aminophenol, 0.46g of antioxidant sodium bisulfite, and 117.5g of acid-binding agent potassium carbonate into a 2000ml reaction bottle, stir, and protect with nitrogen Raise the temperature to 100-120°C; keep the temperature and add 224g of p-nitrochlorobenzene dropwise, after 7h dropwise addition, keep warm for 3h to continue the reaction; sampling, HPLC central control detection, the content of m-aminophenol is 0.15%, stop the reaction; heat filtration, The filtrate was transferred to a 2L autoclave; 7.6g of 5% palladium carbon and 1.53g of cocatalyst ferric chloride were put into it, and replaced with nitrogen; at 60-80°C, hydrogen was fed into catalytic hydrogenation, and the hydrogen pressure did not exceed 0.5MPa; Inhale hydrogen again, continue to maintain the temperature for 2 hours, and the reaction ends. Filter out the catalyst, and simply distill the filtrate to recover N,N-dimethylformamide; change to h...

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Abstract

The invention discloses a method for preparing 3, 4'-diaminodiphenyl ether, which mainly comprises the following steps: adding m-aminophenol, an acid-binding agent and a solvent into a condensation reaction kettle, stirring, heating under the protection of inert gas, keeping the temperature at 100-120 DEG C, dropwisely adding p-nitrochlorobenzene, keeping the temperature for 2-4 hours after 5-7 hours, and continuing the reaction; after the reaction is finished, filtering to remove inorganic salt, transferring a filtrate into a hydrogenation kettle, adding a noble metal catalyst and a cocatalyst, performing nitrogen replacement, maintaining the temperature at 60-80 DEG C, and introducing hydrogen for catalytic hydrogenation under the hydrogen pressure of not more than 0.5 MPa; after the reaction is finished, filtering out the catalyst, distilling the filtrate, removing the solvent, rectifying, collecting 206-210 DEG C (2-3 mmHg) fraction which is white 3, 4'-diaminodiphenyl ether, and packaging under the protection of nitrogen. The method is short in process step, low in energy consumption and low in production cost, the content of the obtained 3, 4'-diaminodiphenyl ether is largerthan 99.5%, and the total molar yield is larger than 93%.

Description

technical field [0001] The invention relates to a method for preparing fine chemical organic materials, in particular to a method for preparing 3,4'-diaminodiphenyl ether. Background technique [0002] 3,4'-diaminodiphenyl ether is an important monomer for the synthesis of special polyimides. It can be polymerized with various dianhydrides to form polyimides. The synthesized polyimides have excellent hydrolysis resistance, mechanical It can be widely used in the production of heat-resistant resin moldings, electrical insulation films, etc. [0003] At present, the main preparation method of 3,4'-diaminodiphenyl ether is to conduct condensation reaction between m-aminophenol and p-nitrochlorobenzene, separate and obtain 3,4'-dinitrodiphenyl ether, and then add solvent for iron powder or Catalytic hydrogenation reduction to produce 3,4'-diaminodiphenyl ether product. [0004] Prior art CN200410025151, first prepare sodium m-aminophenolate in toluene solution, then add N,N-di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/06C07C217/90C07C213/08C07C213/02C07C213/10
CPCC07C213/06C07C213/08C07C213/02C07C213/10C07C217/90
Inventor 郭君华郑玉龙
Owner 南通汇顺化工有限公司
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