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Preparation method of N-phenyl-tetrahydro-2-naphthylamine

A technology of naphthylamine and phenyl, which is applied in the field of preparation of N-phenyltetrahydro-2-naphthylamine, can solve the problems of unsuitable purchase of raw materials, long reaction time, complicated operation, etc., and achieves less generation of three wastes and easy reaction. Control, the effect of high reaction yield

Active Publication Date: 2013-11-27
天津均凯农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this route are not suitable for purchase, the reaction time is long, the operation is complicated, and the yield is low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0015] In the industrial field, the preparation method of N-phenyltetrahydro-2-naphthylamine can be according to the method that the inventor develops, preferably utilizes N-phenyl-2-naphthylamine in polar protic solvent-methanol or ethanol, The crude product of N-phenyltetrahydro-2-naphthylamine was obtained by heating and reducing hydrogenation under catalysis. To describe the method in detail, methanol or ethanol is preferably used as the reaction solvent, and the catalyst is preferably metal nickel or palladium carbon. In addition, the reaction temperature ranges from 95°C to 105°C, preferably from 95°C to 100°C.

[0016] In addition, the present invention can also be used for the hydrogenation reduction reaction of similar compounds containing methyl, methoxy, amino and other groups.

Embodiment 1

[0020] Add 1kg of N-phenyl-2-naphthylamine, 0.12kg of RaneyNi, 1.6kg of methanol into a 5L autoclave, seal the autoclave, evacuate it twice with hydrogen, let it stand for 30min, then inject 6MPa, heat up to 100℃ for reaction Until the hydrogen pressure no longer changes. The supernatant was taken from the reaction solution, and the nickel in the lower layer continued to be applied mechanically and filtered. Evaporate 50% of the filtrate, stir and cool at room temperature, crystallize, cool to below 10°C, filter, rinse the filter cake with a small amount of methanol and drain to obtain 0.58 kg of crude product, liquid phase content 97.5%, yield: 57%.

Embodiment 2

[0022] Add 1 kg of N-phenyl-2-naphthylamine and 0.12 kg of RaneyNi (recycled) and 1.6 kg of methanol to a 5L autoclave, seal the autoclave, and evacuate it twice with hydrogen. React at 100°C until the hydrogen pressure no longer changes. Cool down, release pressure. The supernatant was taken from the reaction solution, and the nickel in the lower layer continued to be applied mechanically and filtered. The filtrate was evaporated to 50%, stirred and cooled at room temperature, and crystallized. Cool down to below 10°C, filter, rinse the filter cake with a small amount of methanol and drain to obtain 0.56 kg of crude product, liquid phase content 97.1%, yield: 55%.

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PUM

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Abstract

The invention relates to a new preparation method of N-phenyl-tetrahydro-2-naphthylamine. In the preparation method, N-phenyl-2-naphthylamine is taken as a raw material, and reaction is performed in a polar protic solvent under the heating condition; the polar protic solvent is methanol or ethanol; the range of the reaction temperature is 90 DEG C-120 DEG C; RaneyNi is taken as a catalyst for performing catalytic hydrogenation reaction; a refining solvent is methanol preferably, and the refining content is greater than 99%. The new preparation method has the following characteristics and advantages: by adopting the method provided by the invention, the reaction yield is relatively higher, the catalyst can be recycled, the product purity is high, few three wastes are generated, the reaction is easy to control, the refining is simple, the cost of the raw materials is low and the like.

Description

technical field [0001] The invention relates to a preparation method of N-phenyltetrahydro-2-naphthylamine which can be used as medicine, pesticide intermediate and electronic photosensitive material. Background technique [0002] N-phenyltetrahydro-2-naphthylamine can be used to manufacture electrophotographic photoreceptors, electroluminescent devices, charge transfer reagents, and is mostly used in the field of electronic imaging; it can also be used as a monomer for synthesizing polymeric nitrosation reagents, due to its high It is widely used in pesticide, pharmaceutical and other industries due to its high activity. [0003] The preparation method of N-phenyltetrahydro-2-naphthylamine is currently: use 2-(benzenesulfonyl)cyclohexanone and butenone with dichloromethane as solvent to generate intermediate 2-(3- Ketobutyl)-2-(benzenesulfonyl)cyclohexanone, and then react with aniline under reflux conditions under the catalysis of p-toluenesulfonic acid, toluene as solven...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/48C07C209/72
CPCY02P20/584
Inventor 尚振华栗晓东张慧丽
Owner 天津均凯农业科技有限公司