Synthesis method of aza-crown ether functionalized ionic liquid

An azacrown ether, ionic liquid technology, applied in the fields of organic synthesis and supramolecules, to achieve the effect of improving stability, optimizing synthesis process and good stability

Pending Publication Date: 2019-11-01
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention aims at the synthesis problem of existing crown ether functionalized ioni

Method used

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  • Synthesis method of aza-crown ether functionalized ionic liquid
  • Synthesis method of aza-crown ether functionalized ionic liquid
  • Synthesis method of aza-crown ether functionalized ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Step 1: In a 100 mL single-necked round bottom flask, add 6-bromohexanoic acid (0.290 g, 1.5 mmol), 1-methylimidazole (0.123 g, 1.5 mmol), and 30 mL of acetone, and install Spherical condenser, stirred and refluxed for 36 h, after the reaction was completed, the acetone was removed by rotary evaporation to generate 1-carboxy-3-methylimidazolium bromide;

[0023] Step 2: Dissolve 1-carboxy-3-methylimidazolium bromide obtained in the previous step in an appropriate amount of N,N-dimethylformamide, add 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride (0.287 g, 1.5 mmol) and 1-hydroxybenzotriazole (0.202 g, 1.5 mmol) were stirred at 0 °C for 0.5 h to activate the carboxyl group, and then aza 12-crown-4 ether ( 0.263 g, 1.5 mmol) and triethylamine (0.152 g, 1.5 mmol) were stirred at room temperature for 24 h. After the reaction, the reactants were poured into 100 mL of water, extracted with dichloromethane (20 mL×3), the organic phases were combined, and washe...

Embodiment 2

[0026] Step 1: In a 100 mL single-necked round bottom flask, add 6-bromohexanoic acid (0.290 g, 1.5 mmol), 1-methylimidazole (0.123 g, 1.5 mmol), and 30 mL of acetone, and install Spherical condenser, stirred and refluxed for 36 h, after the reaction was completed, the acetone was removed by rotary evaporation to generate 1-carboxy-3-methylimidazolium bromide;

[0027] Step 2: Dissolve 1-carboxy-3-methylimidazolium bromide obtained in the previous step in an appropriate amount of N,N-dimethylformamide, add 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride (0.287 g, 1.5 mmol) and 1-hydroxybenzotriazole (0.202 g, 1.5 mmol) were stirred at 0 °C for 0.5 h to activate the carboxyl group, and then aza-15-crown-5 ether ( 0.328 g, 1.5 mmol) and triethylamine (0.152 g, 1.5 mmol) were stirred at room temperature for 24 h. After the reaction, the reactants were poured into 100 mL of water, extracted with dichloromethane (20 mL×3), the organic phases were combined, and washe...

Embodiment 3

[0030] Step 1: In a 100 mL single-necked round bottom flask, add 6-bromohexanoic acid (0.290 g, 1.5 mmol), 1-methylimidazole (0.123 g, 1.5 mmol), and 30 mL of acetone, and install Spherical condenser, stirred and refluxed for 36 h, after the reaction was completed, the acetone was removed by rotary evaporation to generate 1-carboxy-3-methylimidazolium bromide;

[0031] Step 2: Dissolve 1-carboxy-3-methylimidazolium bromide obtained in the previous step in an appropriate amount of N,N-dimethylformamide, add 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride (0.287 g, 1.5 mmol) and 1-hydroxybenzotriazole (0.202 g, 1.5 mmol) were stirred at 0 °C for 0.5 h to activate the carboxyl group, and then aza-18-crown-6 ether ( 0.395 g, 1.5 mmol) and triethylamine (0.152 g, 1.5 mmol) were stirred at room temperature for 24 h. After the reaction, the reactants were poured into 100 mL of water, extracted with dichloromethane (20 mL×3), the organic phases were combined, and washe...

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Abstract

The invention discloses a synthesis method of aza-crown ether functionalized ionic liquid, and belongs to the technical field of organic synthesis and supermolecules. The invention aims to provide a synthetic method of hydrophobic crown ether functionalized ionic liquid. The method comprises the following steps of: 1) performing a reaction on 1-methylimidazole and bromoalkyl acid serving as raw materials to obtain 1-carboxyl-3-methylimidazole bromide; 2) carrying out a reaction with aza-crown ether to obtain 1-alkanoyl-aza-crown ether-3-methylimidazole bromide; and 3) dissolving the 1-alkanoyl-aza-crown ether-3-methylimidazole bromide and lithium/sodium/potassium bistrifluoromethanesulfonimide (or lithium/sodium/potassium hexafluorophosphate) in water for anion exchange, and finally washing and drying the products to obtain 1-alkanoyl-aza-crown ether-3-methylimidazole bistrifluoromethanesulfonimide/hexafluorophosphate ionic liquid. The synthesis method can effectively avoid the loss ofcrown ether molecules and improve the stability of the chelate. In addition, the anionic bistrifluoromethanesulfonimide salt of the ionic liquid is hydrophobic, so that the ionic liquid can be used for recycling metal ions in a water phase.

Description

technical field [0001] The invention belongs to the field of organic synthesis and supramolecular technology, in particular to a method for synthesizing an azacrown ether functionalized ionic liquid. Background technique [0002] The advantage of azacrown ethers is that the electron-donating ability of nitrogen atoms is stronger than that of oxygen, which makes azacrown ethers more active. It has good coordination ability for a variety of metal ions and organic ions. N provides the active site of the substituent, which can be further functionalized, thereby greatly improving the coordination ability and selectivity of the crown ether ring, thereby further broadening the range of azacrown ethers. field of application. [0003] As a new type of green solvent, ionic liquid has great application potential in the separation of metal ions. It is composed of anions and cations and is a liquid organic salt at room temperature or near room temperature. It has low vapor pressure and ...

Claims

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Application Information

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IPC IPC(8): C07D405/06
CPCC07D405/06
Inventor 康锦李恩泽崔莉阴彩霞程芳琴
Owner SHANXI UNIV
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