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Functional ino liquid containing bidentate nitrogen ligands and synthesis method thereof

A technology of ionic liquid and bidentate nitrogen, which is applied in the field of new materials and its preparation, achieves the effects of high yield, simple synthesis steps, and reduced loss

Inactive Publication Date: 2009-02-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been no patent reports in the domestic and foreign literature on functionalized ionic liquids containing 2,2'-dipyridylamine (bidentate nitrogen ligand)

Method used

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  • Functional ino liquid containing bidentate nitrogen ligands and synthesis method thereof
  • Functional ino liquid containing bidentate nitrogen ligands and synthesis method thereof
  • Functional ino liquid containing bidentate nitrogen ligands and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Under a nitrogen atmosphere, add 2.92 mmol of 2,2'-dipyridylamine and equimolar triethylamine into a three-necked flask containing 15 ml of dichloromethane, cool to -20°C in an ice-salt bath, and then gradually 11.68 mmol of 3-chloropropionyl chloride was added dropwise, the temperature was gradually raised to room temperature, and stirred overnight. Transfer to a 60ml separatory funnel, add 8ml of cooled saturated sodium carbonate solution, wash with water (2×4ml) twice, separate the organic phase, dry over sodium sulfate, filter, and drain the solvent under reduced pressure to obtain 3-chloro-N,N - Bis(2-pyridine)propionamide. Synthetic chemical formula:

[0032]

[0033] (2) Under a nitrogen atmosphere, 2.56 mmol of 3-chloro-N, N-di(2-pyridine) propionamide and 2.81 mmol of 1-methylimidazole were dissolved in 15 ml of acetonitrile, refluxed for 8 hours, and the acetonitrile was drained, and then Dissolve in 20ml of deionized water, wash with toluene (3×5ml),...

Embodiment 2

[0036] (1) Under a nitrogen atmosphere, add 2.92 mmol of 2,2'-dipyridylamine and equimolar triethylamine into a three-necked flask containing 15 ml of dichloromethane, cool to -20°C in an ice-salt bath, and then gradually 11.68 mmol of 3-chloropropionyl chloride was added dropwise, the temperature was gradually raised to room temperature, and stirred overnight. Transfer to a 60ml separatory funnel, add 8ml of cooled saturated sodium carbonate solution, wash with water (2×4ml) twice, separate the organic phase, dry over sodium sulfate, filter, and drain the solvent under reduced pressure to obtain 3-chloro-N,N - Bis(2-pyridine)propionamide. Synthesis reaction formula:

[0037]

[0038] (2) Under a nitrogen atmosphere, dissolve 2.56mmol of 3-chloro-N,N-bis(2-pyridine)propionamide and 2.81mmol of 1,2-dimethylimidazole in 15ml of acetonitrile, reflux for 8 hours, and drain Acetonitrile was redissolved in 20ml deionized water, washed with toluene (3×5ml), and the solvent was d...

Embodiment 3

[0041] (1) Under a nitrogen atmosphere, add 2.92 mmol of 2,2'-dipyridylamine and equimolar triethylamine into a three-necked flask containing 15 ml of dichloromethane, cool to -20°C in an ice-salt bath, and then gradually 11.68 mmol of 3-chloropropionyl chloride was added dropwise, the temperature was gradually raised to room temperature, and stirred overnight. Transfer to a 60ml separatory funnel, add 8ml of cooled saturated sodium carbonate solution, wash with water (2×4ml) twice, separate the organic phase, dry over sodium sulfate, filter, and drain the solvent under reduced pressure to obtain 3-chloro-N,N - Bis(2-pyridine)propionamide. Synthesis reaction formula:

[0042]

[0043] (2) Under a nitrogen atmosphere, dissolve 1-ethylimidazole containing 2.56mmol and 2.81mmol of bidentate nitrogen ligand 3-chloroamide in 1 in 15ml of acetonitrile, reflux for 8 hours, drain the acetonitrile, and then dissolve in 20ml Wash with deionized water and toluene (3×5ml), and dry th...

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Abstract

The invention provides a novel functionalized ionic liquid based on bidentate nitrogen ligands and a synthetic method of the ionic liquid, pertaining to the field of novel chemical materials and a preparation technique thereof. The synthetic method comprises the following steps: chloro-acyl chloride of terminal position and 2, 2'-bipyridine amine are taken as raw materials and react under the function of triethylamine that acts as an acid binding agent, so as to generate amide intermediate containing bidentate nitrogen ligands; the intermediate reacts with 1-alkyl-2-methyl (or hydrogen) imidazole to generate imidazole cation containing the bidentate nitrogen ligands and the cation is the functionalized ionic liquid of chlorine and then exchanges anion with various inorganic salts to obtain the anion required and as well as the functionalized ionic liquid containing 2, 2'-bipyridine amine. The method first combines bidentate nitrogen ligands and the ionic liquid, lays a foundation for the research and development of the novel functionalized ionic liquid, has wide application, simple operation and high yield and provides a new path for the development and application of the novel functionalized ionic liquid in future.

Description

technical field [0001] The invention relates to an ionic liquid and a preparation method thereof, in particular to a novel bidentate nitrogen ligand functionalized ionic liquid and a preparation method thereof, belonging to the technical field of new materials and their preparation. Background technique [0002] Ionic liquids are molten salt systems composed of cations and anions that are liquid at or near room temperature. With the continuous upgrading of ionic liquids, from the initial synthesis of ionic liquids with aluminum trichloride as anion and applied to various organic synthesis catalysts, in the 1980s, people developed a more effective solution for air and water. For stable 1-alkyl-3-methyl-imidazolium tetrafluoroborates (hexafluorophosphates), these ionic liquids were subsequently found to be good solvents and novel catalytic materials, with organic solvents and conventional catalysts Some special properties that it does not have, such as a wide range of liquid ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14
Inventor 侯震山胡玉冯博李欢
Owner EAST CHINA UNIV OF SCI & TECH
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