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Imidazoline ionic liquid and preparation method and application thereof

A technology of ionic liquids and imidazolines, which is applied in the field of imidazolines ionic liquids and their preparation, achieving the effects of low preparation cost, mild synthesis conditions and low price

Inactive Publication Date: 2013-01-09
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no public report about the imidazoline ionic liquid involved in the present invention, and its preparation method also has the present invention mentioning for the first time

Method used

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  • Imidazoline ionic liquid and preparation method and application thereof
  • Imidazoline ionic liquid and preparation method and application thereof
  • Imidazoline ionic liquid and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 11-Butyl-2-methyl-3-ethyl imidazoline hexafluorophosphate

[0043] (1) Synthesis of 1-butyl-2-methylimidazoline

[0044] (a) Add 1.7 moles of acetic acid to a 250mL three-necked round-bottomed flask equipped with a thermometer, a spherical condenser and a constant pressure dropping funnel, slowly add 0.8 moles of N-butylethylenediamine dropwise, and the reaction solution turns light brown . After the dropwise addition, change to a distillation device to steam out the water and excess acetic acid generated by the reaction. Distillation under reduced pressure then obtains colorless viscous liquid 1-butyl-2-methylimidazoline;

[0045] (b) Add 0.4 moles of 1-butyl-2-methylimidazoline and 0.6 moles of finely ground calcium oxide powder in step (a) to a 250mL three-neck round bottom flask, heat to 240°C, and reflux for 12 hours , Distilled and purified to obtain deacidified 1-butyl-2-methylimidazoline.

[0046] (2) Synthesis of 1-butyl-2-methyl-3-ethyl imidazoline...

Embodiment 2

[0052] Example 21-Butyl-2-methyl-3-butylimidazoline tetrafluoroborate

[0053] (1) Synthetic 1-butyl-2-methylimidazoline according to Example 1

[0054] (2) Synthesis of 1-butyl-2-methyl-3-butyl imidazoline chloride salt

[0055] Get 0.3 moles of 1-butyl-2-methylimidazoline and dissolve it in 180 mL of acetonitrile, then add 0.4 moles of chlorobutane, reflux for 36 hours, evaporate the solvent and excess chlorobutane under reduced pressure to obtain 1-butyl- 2-Methyl-3-butylimidazoline chloride;

[0056] (3) Dissolve 0.3 mol of 1-butyl-2-methyl-3-butylimidazoline chloride salt obtained in step (2) in 200 mL of water, and add 0.4 mol of NaBF at a solution temperature of 25°C 4 , reacted for 3 hours, added 300mL chloroform for extraction, dried the organic phase, and removed the chloroform solvent under reduced pressure to obtain ionic liquid 1-butyl-2-methyl-3-butylimidazoline tetrafluoroborate, with a purity of ≥ 98%.

[0057] The structural formula is as follows:

[0058...

Embodiment 3

[0060] Example 31-Butyl-2-methyl-3-butylimidazoline trifluoromethanesulfonamide salt

[0061] (1) Synthetic 1-butyl-2-methylimidazoline according to Example 1

[0062] (2) Synthesis of 1-butyl-2-methyl-3-butyl imidazoline iodide salt

[0063] Dissolve 0.3 mole of 1-butyl-2-methylimidazoline in 50-250 mL of acetonitrile, add 0.4 mole of iodobutane, reflux for 36 hours, evaporate the acetonitrile solvent and excess iodobutane under reduced pressure to obtain 1-butane Base-2-methyl-3-butylimidazolinium iodide salt;

[0064] (3) Dissolve 0.3 mole of 1-butyl-2-methyl-3-butylimidazoline iodide salt obtained in step (2) in 200 mL of water, and add 0.4 mole of Ag(CF 3 SO 3 ), reacted for 3 hours, removed water, added 300mL dichloromethane for extraction, dried the organic phase, and removed the organic solvent under reduced pressure to obtain ionic liquid 1-butyl-2-methyl-3-butylimidazoline trifluoromethylsulfonamide Salt, purity ≥98%.

[0065] The structural formula is as follow...

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Abstract

The invention discloses an imidazoline ionic liquid and a preparation method and application thereof, belonging to the field of ionic liquids and preparation thereof. The structural formula of the ionic liquid is shown in the specification, wherein R, R' and R'' are same or different and respectively, singly or together have the following meanings: (1) H; (2) linear or branched paraffin with 1-20C atoms; and X- is one of the following anions: I-, Br-, Cl-, BF4-, PF6-, CF3SO3-, NO3-, N(CF3SO2)2-, CF3CO2-, C(CF3SO2)3-, CH3(C6H4)SO3-, N(CN)2-, CH3CO2-, CH3OSO3- and C2H5OSO3-. The invention alsodiscloses the preparation method and application of the imidazoline ionic liquid. The imidazoline ionic liquid is easy to synthesize and has the advantages of low melting point, good thermostability and the like.

Description

technical field [0001] The invention relates to an ionic liquid and a preparation method thereof, in particular to an imidazoline-based ionic liquid and a preparation method and application thereof. Background technique [0002] Ionic liquids are green solvents developed in recent years. Ionic liquids refer to salts that are liquid at or near room temperature and are composed entirely of anions and cations, also known as low-temperature molten salts. It has the advantages of non-toxicity, low volatility, high viscosity, etc., and has been widely used in the analysis fields such as extraction and chromatography. With the continuous emergence of various new ionic liquids and their application research in the field of analytical chemistry, a new option is provided for solving the problems faced by liquid phase extraction technology. Ionic liquids are generally liquid substances at room temperature or near room temperature composed of specific relatively large, asymmetrically ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/06C07D233/10C07C309/06C07C303/32C07C311/48C07C303/36C07C53/18C07C51/41C07C309/30C07C53/10C07C305/04C07C303/24B01D11/00
Inventor 高海翔周文峰周志强
Owner CHINA AGRI UNIV
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