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Method for preparing 4,4'-disubstituted-2,2'-diaminodiphenyl and hydrochloride thereof by continuous flow oxidative coupling method

A technology of diaminobiphenyl hydrochloride and diaminobiphenyl, which is applied in the field of downhole operations in oil and gas fields, can solve the problems of many reaction steps, unfavorable mass production, high cost, etc., and achieves mild reaction conditions, few synthetic precursors, and controlled production. Warm and precise effect

Active Publication Date: 2020-06-12
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But above-mentioned synthesis method all adopts precious metal catalyst, and used raw material is the derivative of aniline, and reaction step is more, and cost is bigger, is unfavorable for mass production

Method used

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  • Method for preparing 4,4'-disubstituted-2,2'-diaminodiphenyl and hydrochloride thereof by continuous flow oxidative coupling method
  • Method for preparing 4,4'-disubstituted-2,2'-diaminodiphenyl and hydrochloride thereof by continuous flow oxidative coupling method
  • Method for preparing 4,4'-disubstituted-2,2'-diaminodiphenyl and hydrochloride thereof by continuous flow oxidative coupling method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] S1, dissolving 0.1g of copper chloride in 400g of glacial acetic acid to form a glacial acetic acid solution of copper chloride, and then dissolving 200g of p-methoxyaniline in the glacial acetic acid solution of copper chloride to form a reaction solution;

[0033] S2. After the reaction solution prepared in step S1 is preheated to 50°C in the preheating module of the microchannel reactor, it enters the reaction module at a liquid flow rate of 100 mL / min through a metering pump; Pure oxygen is passed into the reaction module of the microchannel reactor through a metering pump at a gas flow rate of 2400mL / min, so that p-methoxyaniline and pure oxygen are mixed in the reaction module according to the molar ratio of 1:4, and the gas flow rate is 1.2MPa. React for 45s, then the oxidative coupling product generated by the reaction is transferred to the receiving tank after cooling;

[0034] S3. Add 6g of sodium bisulfite to the receiving kettle and stir the reaction for 1h to...

Embodiment 2

[0037] S1, ferrous chloride 1g is dissolved in 350g glacial acetic acid, forms the glacial acetic acid solution of ferrous chloride, then 200g p-methoxyaniline is dissolved in the glacial acetic acid solution of ferrous chloride, forms reaction solution;

[0038] S2. After the reaction solution prepared in step S1 is preheated to 80° C. in the preheating module of the microchannel reactor, it enters the reaction module at a liquid flow rate of 200 mL / min through a metering pump; Pure oxygen is passed into the reaction module of the microchannel reactor through a metering pump at a gas flow rate of 5600mL / min, so that p-methoxyaniline and pure oxygen are mixed in the reaction module according to the molar ratio of 1:5, and the gas is mixed under the condition of 1.5MPa Reaction 75s, then the oxidative coupling product that reaction generates is transferred in the receiving kettle after cooling;

[0039] S3. Add 10g of sodium bisulfite to the receiving kettle and stir for 1h to ...

Embodiment 3

[0042] S1, ferrous ammonium sulfate 2g is dissolved in 380g glacial acetic acid, forms the glacial acetic acid solution of ferrous ammonium sulfate, then 200g p-methoxyaniline is dissolved in the glacial acetic acid solution of ferrous ammonium sulfate, forms reaction solution;

[0043] S2. After the reaction solution prepared in step S1 is preheated to 75°C in the preheating module of the microchannel reactor, it enters the reaction module at a liquid flow rate of 100 mL / min through a metering pump; Pure oxygen is passed into the reaction module of the microchannel reactor through a metering pump at a gas flow rate of 2000mL / min, and pure oxygen is passed into the reaction module of the microchannel reactor at the same time, so that p-methoxyaniline and pure oxygen are in a molar ratio of 1 : 5 mixed in the reaction module, and reacted for 50s under the condition of 2MPa, then the oxidative coupling product generated by the reaction was cooled and then transferred to the recei...

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Abstract

The invention discloses a method for preparing 4,4'-disubstituted-2,2'-diaminodiphenyl and hydrochloride thereof on the basis of 4-substituted nitrobenzene by a reductive coupling method. The method comprises the following steps: in the presence of an organic solvent, a noble metal catalyst and strong alkali, carrying out catalytic hydrogenation by using hydrogen, generating corresponding 1,2-diphenyl hydrazine from the 4-substituted nitrobenzene, then carrying out rearrangement in a hydrochloric acid-ammonium salt mixed solution, and sequentially carrying out pH adjustment, ethyl acetate precipitation, toluene recrystallization, and acidification and acid precipitation treatment to obtain the 4,4'-disubstituted-2,2'-diaminodiphenyl and hydrochloride thereof; the method has the advantagesof cheap and accessible raw materials, simple and convenient operation process, recyclable catalyst, mild reaction conditions and higher yield, and has wide industrial prospects.

Description

technical field [0001] The invention relates to the technical field of downhole operations in oil and gas fields, in particular to a method for preparing 4,4'-disubstituted-2,2'-diaminobenzidine and its hydrochloride by a continuous flow oxidation coupling method. Background technique [0002] Benzidine compounds are important chemical raw materials, widely used in the synthesis of pigments and dyes, the preparation of polyimide materials, and chain extenders in the production of polyurethane rubber and fibers. At present, the most widely used benzidine is 4,4'-diaminobiphenyl and its derivatives, but the synthesis and functional research of its corresponding isomer 2,2'-diaminobenzidine is relatively lacking. About 4,4 The synthesis methods of '-disubstituted-2,2'-diaminobiphenyl mainly include Suzuki coupling method, Pd catalyzed dehalogenation coupling method, and amide oxidative coupling-hydrolysis method, wherein the amide precursor of oxidative coupling method Relativ...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C213/10C07C217/84C07C209/68C07C209/84C07C211/50C07C211/52
CPCC07C213/08C07C213/10C07C209/68C07C209/84C07C217/84C07C211/50C07C211/52Y02P20/584
Inventor 郭敏杰朱笛程博闻李盛华周迅樊志赵金
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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