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
4 Cites 1 Cited by

AI-Extracted 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 multipl...
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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.

Application Domain

Organic compound preparationCarboxylic compound preparation

Technology Topic

QuenchingPhase-transfer catalyst +7

Examples

  • Experimental program(4)

Example Embodiment

[0016] Example 1
[0017] At room temperature, in a 5L four-necked reaction flask equipped with mechanical stirring, add 115.4g pyrene, 1.8L dichloromethane, 1.73g tetrabutylammonium bromide and 5.19g tetraethylammonium bromide. Put it in an ice-salt bath to control the temperature at -5℃~0℃ and stir until it is completely dissolved; add 115g bromoacetyl bromide at one time, the solution becomes brownish black after stirring; then add 87.4g anhydrous aluminum trichloride and 1.2L Dichloromethane, stir, the color of the solution turns purple and black, and gradually viscous, keep the above temperature and stir for 4 hours, after the reaction, slowly pour the reaction solution into 10kg of crushed ice to quench, then adjust with 10% sodium bicarbonate solution PH≈8, separate and collect the organic phase, wash the organic phase with water for 2 to 3 times, spin-dry the solvent with a rotary evaporator, and collect the solid to be the crude product. The crude product is dissolved in dichloromethane, decolorized by adding activated carbon, filtered, and then recrystallized once with a mixture solvent of dichloromethane and petroleum ether in a volume ratio of 2:1, and a bright yellow product is obtained after drying.

Example Embodiment

[0018] Example 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, and place the reaction flask Put it in an ice-salt bath and stir at -5℃~0℃ to dissolve it completely; add 100.1g bromoacetyl bromide at one time, and the solution will be brown and black after stirring; then add 76.1g anhydrous aluminum trichloride and 1 L Dichloromethane, stir, the color of the solution turns purple and black, and gradually viscous, keep the above temperature and stir for 4.5 hours, after the reaction, slowly pour the reaction solution into 10kg of crushed ice to quench, and then adjust with 10% sodium bicarbonate solution PH≈8, separate and collect the organic phase, wash the organic phase with water for 2 to 3 times, spin-dry the solvent with a rotary evaporator, and collect the solid to be the crude product. The crude product is dissolved in dichloromethane, decolorized by adding activated carbon, filtered, and then recrystallized once with a mixture solvent of dichloromethane and petroleum ether in a volume ratio of 2:1, and a bright yellow product is obtained after drying.

Example Embodiment

[0020] Example 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, and place the reaction flask Put it in an ice-salt bath and stir at -5℃~0℃ to dissolve it completely; add 121.1g bromoacetyl bromide at one time, and the solution will be brown-black after stirring; then add 76.1g anhydrous aluminum trichloride and 1.4 L Dichloromethane, stir, the color of the solution turns purple and black, and gradually viscous, keep the above temperature and stir for 4.5 hours, after the reaction, slowly pour the reaction solution into 10kg of crushed ice to quench, and then adjust with 10% sodium bicarbonate solution PH≈8, separate and collect the organic phase, wash the organic phase with water for 2 to 3 times, spin-dry the solvent with a rotary evaporator, and collect the solid to be the crude product. The crude product is dissolved in dichloromethane, decolorized by adding activated carbon, filtered, and then recrystallized once with a mixture solvent of dichloromethane and petroleum ether in a volume ratio of 2:1, and a bright yellow product is obtained after drying.

PUM

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