Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF5 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at the synthesis problem of existing crown ether functionalized ionic liquids, and provides a method for synthesizing hydrophobic crown ether functionalized ionic liquids

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D405/06
CPCC07D405/06
Inventor 康锦李恩泽崔莉阴彩霞程芳琴
Owner SHANXI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com