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Method for preparing 2-phenyl-4,4'-diamido diphenyl ether

A technology of diaminodiphenyl ether and phenylphenol, applied in the preparation of aminohydroxyl compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of large by-product emissions, low purity, harsh reaction conditions, etc. Achieve the effect of less environmental pollution, high purity and less by-products

Active Publication Date: 2013-12-18
CHANGZHOU SUNLIGHT PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of this method are: (1) It is necessary to use an equivalent amount of aniline as an auxiliary reaction reagent. After the reaction, a large amount of aniline and its by-products are mixed with the target product, which is difficult to completely remove and the purity is very low; (2) Reaction conditions Harsh, large by-product emissions, serious environmental pollution

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0013] The preparation method of 2-phenyl-4,4'-diaminodiphenyl ether of this embodiment has the following steps:

[0014] ①Add 34g of 2-phenylphenol (200mmol), 320mL of glacial acetic acid, and 200mL of water to a 1L three-necked flask and stir, then cool to about -5°C, and slowly drop 70mL of content into the three-necked flask. 15g sodium nitrite (220mmol) of sodium nitrite solution, maintain the temperature at 0℃~5℃ during the dripping process, and react at 0℃ for 12h after dripping. After the completion of the reaction, suction filtration, the filter cake was washed with water and dried in vacuum to obtain 29.4 g of orange solid 5-nitroso-[1,1'-biphenyl]-2-phenol with a yield of 74%.

[0015] ②Add 10g of 5-nitroso-[1,1'-biphenyl]-2-phenol (50mmol), 0.5g of Pd / C catalyst (Pd content of 3wt%) and 300mL of methanol into the autoclave ,Hydrogen was introduced under stirring until the pressure in the reactor was 0.5MPa, and then the temperature was raised to 40°C for 2h. After the...

Embodiment 2）

[0019] Steps ②, ③, and ④ of this embodiment are the same as those of embodiment 1, except that step ①: add 34g of 2-phenylphenol (200mmol), 320mL of glacial acetic acid and 200mL of water into a 1L three-necked flask And stir, then cool to about -7°C, slowly drop 70mL of sodium nitrite solution containing 15g sodium nitrite (220mmol) into the three-necked flask, and maintain the temperature at -3°C~3°C during the dropping process. After completion, react at -2°C for 13h. After the completion of the reaction, suction filtration, the filter cake was washed with water and dried in vacuum to obtain 28.6 g of orange solid 5-nitroso-[1,1'-biphenyl]-2-phenol with a yield of 72%.

Embodiment 3）

[0021] Steps ②, ③, and ④ of this embodiment are the same as those of embodiment 1, except that step ①: add 34g of 2-phenylphenol (200mmol), 300mL of sulfuric acid and 200mL of water into a 1L three-necked flask Stir, then lower the temperature to about -5°C, slowly drop 80mL of sodium nitrite solution containing 18g of sodium nitrite (260mmol) into the three-necked flask, and maintain the temperature at 0°C~5°C during the dropping process. React at 0°C for 12h. After the completion of the reaction, suction filtration, the filter cake was washed with water and dried in vacuum to obtain 29.8 g of orange solid 5-nitroso-[1,1'-biphenyl]-2-phenol with a yield of 75%.

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Abstract

The invention discloses a method for preparing 2-phenyl-4,4'-diamido diphenyl ether. The method comprises the following steps of: 1, performing nitrosation reaction of 2-phenyl phenol, a mixed solvent and sodium nitrite solution to obtain 5-nitroso-[1,1'-biphenyl]-2-phenol; 2, performing hydrogenation reaction of the 5-nitroso-[1,1'-biphenyl]-2-phenol, a Pd / C catalyst and the solvent to obtain 4-amino-[1,1'-biphenyl]-2-phenol; 3, performing condensation reaction of the 4-amino-[1,1'-biphenyl]-2-phenol, parachloronitrobenzene, potassium carbonate and N,N'-dimethylformamide to obtain 3-amino-6-(4-nitrophenoxy) biphenyl; and 4, performing the hydrogenation reaction of the 3-amino-6-(4-nitrophenoxy) biphenyl, the Pd / C catalyst and the solvent to obtain the 2-phenyl-4,4'-diamido diphenyl ether. By the method, pollution is small, byproducts are few and purity is high; and the method is suitable for large-scale industrial production.

Description

Technical field [0001] The invention belongs to the field of fine chemicals, and specifically relates to a preparation method of 2-phenyl-4,4'-diaminodiphenyl ether. Background technique [0002] 2-Phenyl-4,4'-diaminodiphenyl ether is a versatile polymer monomer compound. Japanese Patent Document JP2011001279A discloses a method for preparing 2-(4-aminophenoxy)-5-aminobiphenyl. It uses aniline as a raw material, firstly makes diazonium salt, then reacts with 2-phenylphenol to generate azobenzene, and then condenses with p-chloronitrobenzene to obtain diphenyl ether with azobenzene, and finally catalyzed by Pd / C Hydrogenation yields 2-(4-aminophenoxy)-5-aminobiphenyl. The disadvantages of this method are: (1) It needs to use equivalent aniline as an auxiliary reagent. After the reaction, a large amount of aniline and its by-products are mixed with the target product, which is difficult to completely remove and the purity is very low; (2) reaction conditions It is harsh, with la...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/90C07C213/02
Inventor 游劲松闵雪锋胡国宜兰静波吴建华杨状杨磊
Owner CHANGZHOU SUNLIGHT PHARMA