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Method for one-step synthesis of diphenylenediamine derivatives through oxidative coupling reaction of phenylamine derivatives

A technology of aniline derivatives and benzphenyl diamine, which is applied in the field of synthesis of benzphenyl diamine derivatives, can solve the problems of pneumoconiosis and harm to human health in contacts, and achieve good product quality, low cost and mild reaction conditions Effect

Inactive Publication Date: 2010-10-20
CHONGQING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Long-term exposure of workers to rare earth dust will not only cause occupational diseases such as bronchioles, alveoli and pulmonary interstitial histological reactions, but also cause pneumoconiosis in the contacts, seriously endangering human health

Method used

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  • Method for one-step synthesis of diphenylenediamine derivatives through oxidative coupling reaction of phenylamine derivatives

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Embodiment 1

[0029] A method for synthesizing biphenyldiamine derivatives in one step through oxidative coupling of aniline derivatives, the specific steps are as follows:

[0030] (1) With N, N-dibenzylaniline as raw material, ferric chloride hexahydrate as oxidant, and toluene as solvent, according to N, N-dibenzylaniline (mmol): ferric chloride hexahydrate (mmol): toluene (milliliter) ratio is the ratio of 1: 2.5: 5, in reactor, add iron trichloride hexahydrate (0.2703g, 1mmol) oxidant and toluene solvent (2mL) earlier, add N under stirring , N-dibenzylaniline (0.1093g, 0.4mmol), after the addition was completed, the temperature was raised to 85°C, and the coupling reaction was carried out with continuous stirring for 2 hours.

[0031] (2) After step (1) is completed, the reaction solution of the biphenylenediamine derivative prepared in step (1) was cooled naturally in air, and ammonia water (10 mL) was added to completely terminate the reaction. Extract with 10mL of dichloromethane e...

Embodiment 2

[0034] A method for synthesizing biphenyldiamine derivatives in one step through oxidative coupling of aniline derivatives, the specific steps are the same as in Example 1, wherein:

[0035] In step (1), N, N-dimethylaniline is used as raw material, ferric chloride hexahydrate is used as oxidant, and toluene is used as solvent, according to N, N-dimethylaniline (mmol): three Ferric chloride (mmol): toluene (milliliter) ratio is the ratio of 1: 2.5: 5, in reactor, add iron trichloride hexahydrate (0.2703g, 1mmol) oxidant and toluene solvent (2mL) earlier, stir Additional N,N-dimethylaniline (50.7 μL, 0.4 mmol) was added.

[0036] In step (2), 10 mL of saturated potassium carbonate solution was added to quench the reaction, and the eluent was a mixture of ethyl acetate: petroleum ether with a volume ratio of 1:70 to obtain a light yellow needle-like solid product N, N, N' , N'-tetramethyl-4,4'-diaminobiphenyl (37.0 mg, yield 77%).

Embodiment 3

[0038] A method for synthesizing biphenyldiamine derivatives in one step through oxidative coupling of aniline derivatives, the specific steps are the same as in Example 1, wherein:

[0039] In step (1), N, N-diethylaniline is used as raw material, iron trichloride hexahydrate is used as oxidant, and toluene is used as solvent, according to N, N-diethylaniline (mmol): trihydrate hexahydrate Ferric chloride (mmol): toluene (milliliter) ratio is the ratio of 1: 2.5: 1, in reactor, add ferric chloride hexahydrate (1.3515g, 5mmol) and toluene (2mL) earlier, add under stirring N,N-Diethylaniline (320.9 μL, 2 mmol).

[0040] In step (2), 20 mL of saturated potassium carbonate solution was added to quench the reaction, and the eluent was ethyl acetate: petroleum ether with a volume ratio of 1: 100 mixed solution to obtain white solid product N, N, N', N' - Tetraethyl-4,4'-diaminobiphenyl (65.7 mg, yield 22%).

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Abstract

The invention relates to a method for synthesizing diphenylenediamine derivatives, in particular to a method for the one-step synthesis of diphenylenediamine derivatives through the oxidative coupling reaction of phenylamine derivatives. The finished product of diphenylenediamine derivatives is prepared from various phenylamine derivatives through the following steps in the presence of ferric chloride or hexahydrated ferric chloride as oxidizing agent: conducting one-step coupling reaction in solvent; and carrying out the processes of cancellation, extraction, concentration and purification. The invention has the characteristics of simple method, convenient operation, energy conservation, low production cost, environment friendliness and convenient popularization and application; and the method of the invention is capable of preparing the product of diphenylenediamine derivatives having the advantages of high yield, good quality and structural diversity. Therefore, the method of the invention is widely applicable to the industrialized product of diphenylenediamine derivatives; and the product prepared by the method of the invention is widely applicable to the dyeing industry, in particular to the manufacture of direct dye, acidic dye, vat dye, azoic dye, sulfur dye, reactive dye and organic pigment. Meanwhile, the product has the property of conductivity adjustability. Therefore, the product is widely applicable to LEDs (light-emitting diode), FETs (field-effect tube), OPCs (organic photoconductor) and organic solar cells, thus meeting the requirements of the market for extensive range and huge demand.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a synthesis method of biphenyl diamine derivatives. Background technique [0002] Biphenylenediamine derivatives are an important class of nitrogen-containing organic compounds, widely used in the dye industry to manufacture direct dyes, acid dyes, vat dyes, ice dyes, sulfur dyes, reactive dyes and organic pigments, etc. With the property of adjustable conductivity, it is widely used in light-emitting diodes, field effect transistors, organic photoconductor devices, organic solar cells, etc. [0003] Existing methods for synthesizing biphenyldiamine derivatives, such as the patent "A Method for Synthesizing Diaminobiphenyl Derivatives" published on November 30, 2005 with the publication number CN1702063A. The method disclosed in the patent is to add aniline derivatives into water or methanol solution of ammonium cerium nitrate and react at 5-30° C....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/50
Inventor 熊燕秦莉晓张学强凌学戈周明李赛
Owner CHONGQING UNIV
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