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Preparation method of 1-(acetyl bromide)pyrene

A technology of bromoacetyl and bromoacetyl bromide, which is applied in the field of preparation of 1-(bromoacetyl)pyrene, can solve the problems of high price, increased energy consumption, and high production cost, and achieves production cost reduction, color improvement, and simple operation Effect

Inactive Publication Date: 2015-05-20
XUCHANG HAOFENG CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, anhydrous AlBr 3 The price is expensive, which makes the production cost of the enterprise too high. In addition, with anhydrous AlBr 3 The color of the product obtained by the Lewis acid catalyst is red, which affects the color of the product, and usually requires distillation or multiple recrystallization for further purification, which invisibly greatly increases the energy consumption of the production of this product
This is not in line with the development trend of energy saving and green chemistry, and also limits the development of AlBr 3 Applications as Lewis Acid Catalysts

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] At room temperature, in a 5L four-necked reaction flask equipped with mechanical stirring, add 115.4g of pyrene, 1.8L of dichloromethane, 1.73g of tetrabutylammonium bromide and 5.19g of tetraethylammonium bromide respectively, and the reaction flask Put it into an ice-salt bath with temperature control -5°C to 0°C and stir until it is completely dissolved; add 115g of bromoacetyl bromide at one time, stir evenly and the solution turns brownish black; then add 87.4g of anhydrous aluminum trichloride and 1.2L of Dichloromethane, stirring, the color of the solution turns purple and black, and gradually viscous. Keep the above temperature and stir for 4 hours. After the reaction is completed, the reaction solution is slowly poured into 10kg of crushed ice to quench, and then adjusted with 10% sodium bicarbonate solution. PH≈8, separate the liquid to collect the organic phase, wash the organic phase with water for 2 to 3 times, spin dry the solvent with a rotary evaporator, ...

Embodiment 2

[0019] At room temperature, in a 5L four-necked reaction flask equipped with mechanical stirring, add 101.1g pyrene, 1.5L dichloromethane, 1.44g tetrabutylammonium bromide and 4.33g tetraethylammonium bromide respectively, put the reaction flask Put it into an ice-salt bath and control the temperature at -5°C to 0°C and stir until it is completely dissolved; add 100.1g of bromoacetyl bromide at one time, stir evenly, and the solution turns brownish black; then add 76.1g of anhydrous aluminum trichloride and 1 L of Dichloromethane, stirring, the solution color turns purple black, and gradually viscous, keep the above temperature stirring reaction for 4.5 hours, after the reaction is completed, the reaction solution is slowly poured into 10kg of crushed ice to quench, and then adjusted with 10% sodium bicarbonate solution PH≈8, separate the liquid to collect the organic phase, wash the organic phase with water for 2 to 3 times, spin dry the solvent with a rotary evaporator, and c...

Embodiment 3

[0021] At room temperature, in a 5L four-necked reaction flask equipped with mechanical stirring, add 121.4g pyrene, 2.1L dichloromethane, 1.97g tetrabutylammonium bromide and 5.90g tetraethylammonium bromide respectively, put the reaction flask Put it into an ice-salt bath and control the temperature at -5°C to 0°C and stir until it is completely dissolved; add 121.1g of bromoacetyl bromide at one time, stir evenly, and the solution turns brownish black; then add 76.1g of anhydrous aluminum trichloride and 1.4 L of Dichloromethane, stirring, the solution color turns purple black, and gradually viscous, keep the above temperature stirring reaction for 4.5 hours, after the reaction is completed, the reaction solution is slowly poured into 10kg of crushed ice to quench, and then adjusted with 10% sodium bicarbonate solution PH≈8, separate the liquid to collect the organic phase, wash the organic phase with water for 2 to 3 times, spin dry the solvent with a rotary evaporator, and...

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PUM

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Abstract

The invention discloses a preparation method of 1-(acetyl bromide)pyrene, belonging to the field of organic chemical synthesis. The preparation method disclosed by the invention aims at solving the technical problems that the raw materials of a traditional synthesis method are expensive and the cost is high and the treatment after reaction is complicated and the product is red; according to the preparation method disclosed by the invention, a proper phase transfer catalyst is added in the reaction and a buffer solution control quenching system is added in a reaction quenching process, the expensive AlBr3 is successfully replaced by cheap anhydrous AlCl3, and the product can be obtained directly through once recrystallization after the reaction; and therefore, the preparation method disclosed by the invention has the advantages of low cost, little pollution, simple and convenient treatment after reaction, good product color and adaptability to industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a preparation method of 1-(bromoacetyl)pyrene. Background technique [0002] 1-(Bromoacetyl)pyrene is an important organic intermediate compound, which is an intermediate of many spices, dyes and fluorescent materials. The preparation of 1-(bromoacetyl)pyrene is mainly through the bromoacetylation reaction of aromatic compounds, which is a type of Friedel-Crafts acylation reaction. Anhydrous AlCl is mainly used in the Friedel-Crafts acylation reaction 3 It is a Lewis acid catalyst, but it is worth noting that the bromine atom in the bromoacetyl group in this reaction product is easily replaced by a chlorine atom, and the substitution product is very similar in nature to 1-(bromoacetyl)pyrene, resulting in low reaction conversion and difficult purification. In order to prevent this phenomenon in the reaction, this product generally uses anhydrous AlBr 3 Pr...

Claims

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Application Information

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IPC IPC(8): C07C63/44C07C51/62
CPCC07C51/62C07C2603/50C07C63/44
Inventor 孙光辉刘成张满良王豪征陶韬骆俊邢远杨廷飞陈震宇张佩云
Owner XUCHANG HAOFENG CHEM TECH
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