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Method for continuously and quickly preparing propiolic acid and derivatives thereof by using microreactor

A kind of microreactor, technology of propynoic acid, applied in the field of synthesis of propynoic acid and its derivatives

Inactive Publication Date: 2020-10-09
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report on the method of using microreactor to prepare propiolic acid

Method used

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  • Method for continuously and quickly preparing propiolic acid and derivatives thereof by using microreactor
  • Method for continuously and quickly preparing propiolic acid and derivatives thereof by using microreactor

Examples

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Embodiment 1

[0026] A method for continuously and rapidly preparing propiolic acid and derivatives thereof by using a microreactor, the main steps of which are as follows:

[0027] First, under anhydrous and oxygen-free conditions, add 20.0 g metallic magnesium, 6.0 g elemental iodine and 200 mL anhydrous ether into the reactor and stir evenly. After the elemental iodine is dissolved, slowly add 1.0 mol ethyl bromide dropwise at It is advisable to keep the liquid boiling, and then heat to 60 after the dropwise addition o C was refluxed for 180 min to obtain ethyl magnesium bromide and ether mixed solution; then as figure 1 As shown, the ether solution containing ethylmagnesium bromide and acetylene gas are respectively injected into the micro-mixer D1 (T-type tee, inner diameter: 0.021 mm) by the pump A1 and the flow controller C1 according to the molar ratio of 1:1. After mixing in the medium, enter the microchannel reactor E1 (inner diameter: 0.01mm) at -20 o Under the condition of C,...

Embodiment 2

[0029] A method for continuously and rapidly preparing propiolic acid and derivatives thereof by using a microreactor, the main steps of which are as follows:

[0030] First, under anhydrous and oxygen-free conditions, add 20.0 g metallic magnesium, 6.0 g elemental iodine and 200 mL anhydrous ether into the reactor and stir evenly. After the elemental iodine dissolves, slowly add 1 mol of vinyl chloride dropwise at a rate of It is advisable to keep the liquid boiling, and then heat to 100 o C was refluxed for 120 min to obtain vinylmagnesium chloride and ether mixed solution; then as figure 2 As shown, the ether solution containing vinylmagnesium chloride and phenylacetylene were respectively injected into the micro-mixer D1 (T-type tee, inner diameter: 1 mm) by the pumps A1 and A2 according to the molar ratio of 1:0.8. Channel reactor E1 (inner diameter: 1 mm), at 40 o Under the condition of C for 10 s, a Grignard exchange reaction occurred to obtain phenylethynylmagnesium...

Embodiment 3

[0032] A method for continuously and rapidly preparing propiolic acid and derivatives thereof by using a microreactor, the main steps of which are as follows:

[0033] First, under anhydrous and oxygen-free conditions, add 20.0 g metallic magnesium, 6.0 g iodine element and 200 mL anhydrous ether into the reactor and stir evenly. After the iodine element dissolves, slowly add 1 mol of bromobenzene dropwise at a rate of It is advisable to keep the liquid boiling, and then heat to 100 o C was refluxed for 60 min to obtain phenylmagnesium bromide and ether mixed solution; then as figure 2As shown, the diethyl ether solution containing phenylmagnesium bromide and 4-methylphenylacetylene were injected into the micro-mixer D1 (T-type tee, inner diameter: 10 mm) by the pumps A1 and A2 according to the molar ratio of 1:1.5. After mixing in the medium, enter the microchannel reactor E1 (inner diameter: 10 mm) at 40 o Under the condition of C, the reaction was carried out for 5 min, ...

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Abstract

The invention discloses a method for continuously and rapidly preparing propiolic acid and derivatives thereof by using a microreactor. The preparation method comprises the following steps: firstly, under anhydrous and anaerobic conditions, adding magnesium metal, elemental iodine and a solvent into a reactor, uniformly stirring, and then dropwise adding halogenated hydrocarbon to react to generate a hydrocarbyl magnesium halide Grignard reagent; in a microreactor, with the prepared alkyl magnesium halide and terminal alkyne as raw materials, performing a Grignard exchange reaction under a continuous flowing condition to obtain alkynyl magnesium halide; and by using the alkynyl magnesium halide and CO2 as raw materials, carrying out nucleophilic addition reaction under continuous flow to prepare the propiolic acid compound. The method provided by the invention has the characteristics of rapid and continuous preparation of propiolic acid, continuous and controllable process and mild conditions, and can achieve industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of propiolic acid and its derivatives. Background technique [0002] Propiolic acid compounds are a very important class of organic intermediates. It is widely used in organic synthesis and is often used to prepare functional materials [Zhang et al., Angew.Chem.Int.Ed.2015,55,236-239]. In addition, propiolic acid allows the synthesis of many heterocyclic compounds such as coumarins, flavones and indoles [Bararjanian et al., J. Org. Chem. 2010, 75, 2806-2812.]. Also used for decarboxylation cross-coupling to synthesize alkynyl arenes or aminoalkynes [Jia et al., Org. Lett. 2010, 12, 2000-2003.]. Therefore, it is of great significance to develop efficient methods for the synthesis of propiolic acid compounds. [0003] In the prior art, the method for synthesizing propiolic acid compounds is mainly the oxidative carboxylation reaction of alkynes, us...

Claims

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Application Information

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IPC IPC(8): C07C57/20C07C57/42C07C59/48C07C51/15C07D333/24
CPCC07C51/15C07D333/24C07F3/02C07C57/20C07C57/42C07C59/48
Inventor 邓秋林黄晓枫
Owner SOUTHWEAT UNIV OF SCI & TECH
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