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Method for preparing aromatic diamine containing adamantane structure

A technology of aromatic diamine and adamantane, which is applied in the field of synthesis of adamantane derivatives, can solve the problems of high cost and low yield, and achieve the effect of low cost, high yield and stable process

Inactive Publication Date: 2018-02-09
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In short, the disadvantage of this method is that the yield is low and the cost is high

Method used

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  • Method for preparing aromatic diamine containing adamantane structure

Examples

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preparation example Construction

[0025] In one embodiment, the present invention provides a method for preparing an aromatic diamine containing an adamantane structure, the method may include the following steps:

[0026] (1) Under the protection of an inert gas and the presence of a catalyst, react a dihaloadamantane with an anilide to obtain an adamantane containing a diacylaminophenyl group; and

[0027] (2) Hydrolyzing the diacylaminophenyl-containing adamantane to obtain an aromatic diamine containing an adamantane structure.

Embodiment 1

[0029] This example involves the synthesis of 1,3-bis(4-aniline)adamantane using 1,3-dibromoadamantane and acetanilide as main raw materials.

[0030] The synthetic route of this embodiment is as figure 1 shown. Specifically, the synthesis method of this embodiment mainly includes the following two steps.

[0031] 1. Under nitrogen protection, add 440g of 1,3-dibromoadamantane into a 10L four-neck flask, then add 2.0L of dichloroethane, stir well, add 500g of acetanilide and stir well. Slowly add zinc dichloride and stir evenly, then heat up to reflux (internal temperature 80-85°C), first use a water separator to divide part of the water, and then use a reflux device. Reflux at this temperature for 24 hours. At this time, the lower layer is viscous solid, and the upper layer is dichloroethane solvent. Cool to room temperature, pour out the upper solvent, add 1.0LDMF (N,N-dimethylformamide) to raise the temperature to make the solid a fluid slurry, slowly pour the slurry int...

Embodiment 2

[0035] This example involves the synthesis of 1,3-bis(4-aniline)adamantane using 1,3-dichloroadamantane and acetanilide as main raw materials.

[0036] The synthesis method of this embodiment mainly includes the following two steps.

[0037] 1. Under nitrogen protection, add 420g of 1,3-dichloroadamantane into a 10L four-necked flask, then add 2.0L of dichloroethane, stir well, add 500g of acetanilide and stir well. Slowly add aluminum trichloride and stir evenly, then raise the temperature to reflux (internal temperature 80-85°C), first use a water separator to separate part of the water, and then use a reflux device. Reflux at this temperature for 24 hours. At this time, the lower layer is viscous solid, and the upper layer is dichloroethane solvent. Cool to room temperature, pour out the upper solvent, add 1.0LDMF to raise the temperature to make the solid a mobile slurry, slowly pour the slurry into 4.0L of stirred water, filter after stirring for 30 minutes, and obtain a...

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Abstract

The invention relates to a method for preparing aromatic diamine containing an adamantane structure. The method includes a step (1) of causing dihalogenated adamantane and anilide to react under the protection of inert gas in the presence of a catalyst, to obtain adamantane containing diacyl amino phenyl; and a step (2) of hydrolyzing the adamantane containing diacyl amino phenyl to obtain aromatic diamine containing the adamantane structure. The adamantane containing diacyl amino phenyl includes 1,3-bis(4-acetyl amino phenyl) adamantane. The method has the advantages that the synthetic methodis high in yield and low in cost.

Description

technical field [0001] The invention relates to the technical field of synthesis of adamantane derivatives. Specifically, the present invention relates to a method for preparing aromatic diamines containing adamantane structure with high yield and low cost. Background technique [0002] Adamantane is a highly symmetrical and very stable cage hydrocarbon, and it is easy to synthesize various adamantane derivatives. The disubstituted derivatives of adamantane are important intermediates of polymer materials and are widely used. For example, 1,3-bis(4-aniline)adamantane can be reacted with various aryl diacid anhydrides to synthesize polymer material polyimide, which has low dielectric constant, high thermal stability and excellent mechanical properties. The organic polymer material with the best comprehensive performance. Therefore, the application prospect of 1,3-bis(4-aniline)adamantane in the field of polymer materials is very promising. [0003] The yields of the two m...

Claims

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Application Information

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IPC IPC(8): C07C209/00C07C211/50
CPCC07C209/00C07C231/12C07C211/50C07C233/43
Inventor 傅志伟贺宝元潘新刚余文卿李永立陆伟
Owner XUZHOU B&C CHEM CO LTD