Method of utilizing micro channel reactor to prepare fluorine containing chalcone derivatives

A technology of microchannel reactor and fluorine-containing chalcone, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve problems such as low product quality, shorten reaction time, and increase safety. Achieve the effect of improving reaction efficiency, shortening reaction time and increasing safety

Inactive Publication Date: 2018-07-20
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to provide a method for preparing fluorine-containing chalcone derivatives by using a microchannel reactor, the reaction efficiency is significantly improved, the reaction time is greatly shortened, the possible phenomenon of runaway temperature in the kettle reaction is avoided, and by-products are reduced The production increases safety, the production process is easy to control, reduces production costs, and overcomes the shortcomings of traditional production such as high labor intensity, long production cycle, low product quality, and more three wastes.

Method used

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  • Method of utilizing micro channel reactor to prepare fluorine containing chalcone derivatives
  • Method of utilizing micro channel reactor to prepare fluorine containing chalcone derivatives
  • Method of utilizing micro channel reactor to prepare fluorine containing chalcone derivatives

Examples

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Effect test

Embodiment 1

[0031] Example 1 Synthesis of 4'-fluorochalcone by reaction of 4-fluorobenzaldehyde and acetophenone

[0032] 4-fluorobenzaldehyde is formulated with ethanol into a 0.5mol / L solution, acetophenone is formulated with ethanol into a 0.5mol / L solution, sodium hydroxide is formulated into a 0.2mol / L aqueous solution, 4-fluorobenzaldehyde / ethanol solution, benzene Ethanone / ethanol solution and sodium hydroxide aqueous solution were pumped into the microchannel reactor at flow rates of 15ml / min, 18ml / min, and 3ml / min respectively, the temperature in the first temperature zone was set to 35°C, the residence time was 30s, and the second temperature zone was set at 35°C. The zone temperature is 60°C and the residence time is 60s. The product flows out from the outlet, and after acidification, it is refined to obtain 4'-fluorochalcone. The selectivity of 4-fluorobenzaldehyde is 98.7%, the conversion rate is 98.1%, and the yield is 96.8%.

Embodiment 2

[0033] Example 2 Synthesis of 4-trifluoromethyl-4'-fluorochalcone by reaction of 4-fluorobenzaldehyde and 4-trifluoromethylacetophenone

[0034] 4-fluorobenzaldehyde is formulated with isopropanol into a 0.6mol / L solution, 4-trifluoromethylacetophenone is formulated with a 0.5mol / L solution with isopropanol, and sodium hydroxide is formulated with a 0.1mol / L aqueous solution, 4-fluorobenzaldehyde / ethanol solution, 4-trifluoromethylacetophenone / ethanol solution, sodium hydroxide aqueous solution are pumped into the microchannel reactor with the flow velocity of 10ml / min, 10ml / min, 2ml / min respectively, the first The temperature in the temperature zone is set at 40°C, and the residence time is 40s. The temperature in the second temperature zone is 60°C, and the residence time is 70s. The product flows out from the outlet, and after acidification, it is refined to obtain 4-trifluoromethyl-4'-fluorochalcone , The selectivity of 4-fluorobenzaldehyde was 98.2%, the conversion rate w...

Embodiment 3

[0035] Embodiment 3 benzaldehyde reacts with 3-fluoroacetophenone to synthesize 3-fluorochalcone

[0036]Benzaldehyde is formulated with methanol into a 1.0mol / L solution, 3-fluoroacetophenone is formulated with methanol into a 0.5mol / L solution, sodium hydroxide is formulated into a 0.4mol / L aqueous solution, benzaldehyde / methanol solution, 3-fluorobenzene Acetone / ethanol solution and sodium hydroxide aqueous solution were pumped into the microchannel reactor at flow rates of 20ml / min, 48ml / min, and 5ml / min respectively, the temperature in the first temperature zone was set to 25°C, and the residence time was 30s. The zone temperature is 45°C, the residence time is 90s, and the product flows out from the outlet, and is acidified and refined to obtain 3-fluorochalcone. The selectivity of benzaldehyde is 98.9%, the conversion rate is 98.2%, and the yield is 97.1%.

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Abstract

The invention discloses a method of utilizing a micro channel reactor to prepare fluorine containing chalcone derivatives. The method comprises following steps: individually dissolving a compound represented by a formula I and a compound represented by a formula II into a solvent to prepare solutions; introducing the solutions and a catalyst water solution into a micro channel reactor, mixing, heating the mixture to a temperature of 20-50 DEG C, maintaining the temperature for 10 to 40 seconds, then heating the temperature to 50-180 DEG C, carrying out condensation reactions for 15 to 70 seconds, and acidifying the reaction product to obtain fluorine containing chalcone derivatives. The method obviously improves the reaction efficiency, largely shortens the reaction time, avoids the temperature runaway phenomenon of kettle reactions, reduces the generation of byproducts, and improves the safety. The production process is convenient to control. The production cost is reduced. The shortages such as large labor strength, long production period, low product quality, large amount of wastes, and the like, are overcome.

Description

technical field [0001] The invention belongs to the field of chalcone preparation, and in particular relates to a method for preparing fluorine-containing chalcone derivatives using a microchannel reactor. Background technique [0002] Chalcone is a product of cross-aldol condensation of aromatic aldehydes and ketones. Its chemical name is 1,3-diphenylpropenone. Compounds based on chalcone are widely distributed in plants and exist in licorice, safflower, etc. Among many kinds of natural plants, it is the precursor of flavonoids synthesized in plants, and it is a kind of natural drug without toxic and side effects. This kind of compound belongs to one of the flavonoids, which itself has important pharmacological effects. [0003] In addition, since the molecular structure of chalcone contains α, β-enone moiety, it has greater flexibility, can bind to various targets (different receptors), and has a wide range of biological activities, such as anti-cancer, anti- Physiologica...

Claims

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Application Information

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IPC IPC(8): C07C45/74C07C49/813
CPCC07C45/74
Inventor 张传好詹家荣周励
Owner SHANGHAI CHEM REAGENT RES INST
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