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Preparation method of 4,4'-[(9-butyl-9H-carbazole-3-)methylene]bis[N-methyl-N-phenyl]aniline

A technology of methylene and carbazole, which is applied in the field of pressure-sensitive dye preparation, can solve the problems of low utilization rate of carbazole and inaccurate single product, and achieve the goal of improving conversion rate and utilization rate, reducing production cost and reasonable design Effect

Active Publication Date: 2013-05-08
连云港珂玫琳科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The defect of this technical scheme is: the utilization rate of carbazole is low, this technology is the rough process of this series of reactions, and it is not accurate to a single product

Method used

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  • Preparation method of 4,4'-[(9-butyl-9H-carbazole-3-)methylene]bis[N-methyl-N-phenyl]aniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1, a kind of preparation method of 4,4'-[(9-butyl-9 hydrogen-carbazole-3-)methylene]bis[N-methyl-N-phenyl]aniline, its steps as follows:

[0016] (1) Add tetrabutylammonium bromide and carbazole to the sodium hydroxide solution, heat up to dissolve, then slowly add chlorobutane dropwise, then keep warm and reflux for 3 hours, add toluene that is 2 times the weight of the reaction material after the reaction is completed or other organic solvents for heat preservation extraction, after stirring and standing for stratification, the lower water layer is separated, and then all the water and part of the toluene are evaporated to obtain the toluene solution of BC; NaOH solution, tetrabutylammonium bromide, carbazole and The weight ratio of chlorobutane is 60:1.5:25:15.

[0017] (2) Add an appropriate amount of N,N-dimethylformamide to the toluene solution of BC, then dropwise add phosphorus oxychloride 1 weight times of N,N-dimethylformamide, and control the rea...

Embodiment 2

[0019] Embodiment 2, a kind of preparation method of 4,4'-[(9-butyl-9 hydrogen-carbazole-3-)methylene]bis[N-methyl-N-phenyl]aniline, its steps as follows:

[0020] (1) Add tetrabutylammonium bromide and carbazole to the sodium hydroxide solution, heat up to dissolve, then slowly add chlorobutane dropwise, and then keep warm and reflux for 10 hours. After the reaction is completed, add toluene that is 5 times the weight of the reaction material or other organic solvents for heat preservation extraction, after stirring and standing for stratification, the lower water layer is separated, and then all the water and part of the toluene are evaporated to obtain the toluene solution of BC; NaOH solution, tetrabutylammonium bromide, carbazole and The weight ratio of chlorobutane is 70: 2.5: 35: 25;

[0021] (2) Add an appropriate amount of N,N-dimethylformamide to the toluene solution of BC, and then dropwise add phosphorus oxychloride 2 times the weight of N,N-dimethylformamide, an...

Embodiment 3

[0023] Embodiment 3, a kind of preparation method of 4,4'-[(9-butyl-9 hydrogen-carbazole-3-)methylene]bis[N-methyl-N-phenyl]aniline, its steps as follows:

[0024] (1) Add tetrabutylammonium bromide and carbazole to the sodium hydroxide solution, heat up to dissolve, then slowly add chlorobutane dropwise, then keep warm and reflux for 6 hours, add toluene 3 times the weight of the reaction material after the reaction is completed or other organic solvents for heat preservation extraction, after stirring and standing for stratification, the lower water layer is separated, and then all the water and part of the toluene are evaporated to obtain the toluene solution of BC; NaOH solution, tetrabutylammonium bromide, carbazole and The weight ratio of chlorobutane is 65:2:30:20;

[0025] (2) Add an appropriate amount of N,N-dimethylformamide to the toluene solution of BC, then dropwise add phosphorus oxychloride 1.5 times the weight of N,N-dimethylformamide, and control the reactio...

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Abstract

The invention relates to a preparation method of 4,4'-[(9-butyl-9H-carbazole-3-)methylene]bis[N-methyl-N-phenyl]aniline, which comprises the following steps: adding tetrabutyl ammonium bromide and carbazole in a sodium hydroxide solution, dissolving while heating, dropwisely adding chlorobutane, extracting while keeping the temperature after the reaction is completed, and stratifying to obtain a BC methylbenzene solution; adding N,N-dimethylformamide and phosphorus oxychloride, and reacting to obtain a BCA intermediate compound; adding a proper amount of process water for washing, stirring, standing, stratifying, removing the underlayer acidic water, and then distilling to remove all the methylbenzene and water; and adding methanol and N-methyl diphenylamine, reacting, and then refining to obtain the finished product. According to the invention, the method is more reasonable in design; and a catalyst is added in the method, so that the conversion rate and use rate of carbazole are increased, the production cost is lowered, the yields of the intermediate compound and the final product are improved, and the quality of the final product is enhanced.

Description

technical field [0001] The invention relates to a preparation method of pressure-sensitive dyes, in particular to 4,4'-[(9-butyl-9hydro-carbazole-3-)methylene]bis[N-methyl-N-benzene Base] the preparation method of aniline. Background technique [0002] In the prior art, the Chinese patent application with application number CN93105523.7 discloses an azo disperse dye containing a carbazole heterocycle and a preparation method thereof. In this method, Ar in the dye structural formula is the parent of arylamine, arylamine is 2,5-dichloroaniline, 5-nitro-7-amino-benzoisothiazole, R is alkyl, hydroxyalkyl, cyano Alkyl or various ester groups. When preparing, first add the prepared nitrosyl sulfuric acid, add aromatic amine to it, diazotize at 0-65°C, adjust the acidity, add the coupling component carbazole and other solutions, and carry out coupling reaction at 0-60°C , then filtered, washed with water until neutral, and dried. The yield of the original dye was 95%. The defec...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09B11/26
Inventor 伊恩罗伊霍胜涛朱奎李涛王启春李洪伟孔凡祜
Owner 连云港珂玫琳科技有限公司
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