Method for preparing carbazole and vinyl carbazole

A technology of carbazole and carbazole derivatives is applied in the field of preparation of carbazole and its derivatives, and can solve the problems of high production cost and low purity of carbazole

Inactive Publication Date: 2014-02-12
上海永鸿实业集团化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Aiming at the current problems of high cost and low purity of carbazole production, the prese

Method used

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  • Method for preparing carbazole and vinyl carbazole
  • Method for preparing carbazole and vinyl carbazole
  • Method for preparing carbazole and vinyl carbazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Mix 150g of cyclohexanone and 550g of acetic acid, heat to reflux state (external temperature 160°C, internal temperature 122°C), add dropwise 180g of phenylhydrazine, complete the dropwise addition within 2 hours, and proceed to the reaction.

[0052] After 1.5h, the reaction was completed, and solids were precipitated after cooling, filtered, and the filter cake was washed with water and 70% ethanol to obtain 195g of intermediate A-H (R 1 and R 2 Both are H).

[0053] Add 100g of intermediate A-H, 2g of Pd / C (water content 54%, catalyst content 10%) into 300ml n-octanol, and suspend. Heating to 164~174°C (external temperature 180°C) for reaction, after 28 hours the reaction was completed, cooled to 0°C, filtered, washed with methanol, and dried to obtain 71.7g of carbazole.

Embodiment 2

[0055] Mix 300g of cyclohexanone and 1100g of acetic acid, heat to reflux state (external temperature 130°C, internal temperature 120°C), add dropwise 350g of phenylhydrazine, complete the dropwise addition within 3 hours, and proceed to the reaction.

[0056] After 1 h, the reaction was completed, and solid precipitated after cooling, filtered, washed the filter cake with water and 75% ethanol, and recrystallized from methanol to obtain 408 g of intermediate A-H.

[0057] 408g of intermediate A-H, 17g of Pd / C (54% water content, 10% catalyst content) were added to 1100ml n-octanol, and suspended. Heat to 145~177°C (external temperature 180°C) for reaction, after 24 hours the reaction is complete, cool to 0°C, filter, wash with acetone, and dry to obtain 330g of carbazole.

[0058] The products obtained in the above examples were detected by nuclear magnetic resonance and infrared spectroscopy, and all of them obtained the target products.

Embodiment 3

[0060] The carbazole prepared in the foregoing examples is a raw material, and the method for preparing vinyl carbazole is as follows:

[0061] 20g carbazole, 100ml N-methylpyrrolidone, 1.2g potassium hydroxide, pass through acetylene to 0.2Mpa, hold the pressure for 30min, raise the temperature to 140°C, react for 3.5h, cool down and sample for LC analysis, the reaction is complete, methanol recrystallized to get Vinyl carbazole, LCMS 99.5% purity by liquid chromatography mass spectrometry analysis.

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Abstract

The invention relates to a preparation method for carbazole and a derivative thereof. The preparation method comprises the following steps of: taking a phenylhydrazine derivative shown in structural formula (I) and a cyclohexanone derivative shown in structural formula (II) as raw materials, reacting in organic carboxylic acid to prepare an intermediate A, and then performing a dehydrogenation reaction to prepare carbazole or a derivative thereof. A carbazole derivative containing an olefin group can be obtained after reacting the carbazole or the derivative thereof with a compound.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a preparation method of carbazole and derivatives thereof. Background technique [0002] Carbazole, also known as iminodiphenylene, dibenzopyrrole, and 9-azafluorene, can be used to prepare dyes, lubricants, antioxidants, explosives, insecticides, plant auxins, luminescent materials, anti-inflammatory drugs, and treat tumors It is one of the most economically valuable components in coal tar, and 90% of the world's carbazole is extracted from coal tar. [0003] Coal tar contains a large amount of aromatic hydrocarbons such as anthracene and phenanthrene and their derivatives. At present, the methods for separating anthracene and carbazole in foreign countries mainly include: 1) rectification method, which uses the characteristics of large differences in boiling points of anthracene, phenanthrene and carbazole to separate , but anthracene, phenanthrene and carbazole are all high-boil...

Claims

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Application Information

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IPC IPC(8): C07D209/86
CPCC07D209/86
Inventor 金伊男
Owner 上海永鸿实业集团化学科技有限公司
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