Alkyl imidazole-L-proline salt chiral ionic liquid and preparation method thereof

A chiral ionic liquid, proline salt technology, applied in the direction of organic chemistry, etc., can solve the problem of many reaction steps, and achieve the effect of good optical activity

Inactive Publication Date: 2010-11-24
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Amino acids are a class of natural chiral sources. Guillen et al. used (S)-histidine as a starting material to prepare a series of chiral ionic liquids in which imidazole amino acids are cations. The reaction is from histidine methyl ester and carbonyldiimidazole At the beginning, but there are many reaction steps; patent document 200410009958.3 describes a series of chiral ionic liquids with amino acids as cations and various strong acids as anions, but many strong acids are highly corrosive
The present invention takes L-proline as anion and prepares the alkylimidazole chiral ionic liquid that there is no report yet

Method used

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  • Alkyl imidazole-L-proline salt chiral ionic liquid and preparation method thereof
  • Alkyl imidazole-L-proline salt chiral ionic liquid and preparation method thereof
  • Alkyl imidazole-L-proline salt chiral ionic liquid and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Example 1: 1,3-Dibutylimidazole-L-proline salt chiral ionic liquid

[0020] Raw materials: imidazole analytical reagent

[0021] Bromobutane Analytical grade reagent

[0022] L-Proline Analytical Reagent

[0023] Potassium hydroxide Analytical grade reagent.

[0024] DMSO Analytical Grade Reagents

[0025] Anhydrous ethanol analytical reagent

[0026] 1. Synthesis of N-butylimidazole

[0027] Add 4.136g (61mmol) of imidazole into a 100mL three-necked flask, add 4.099g (73mmol) of potassium hydroxide, add 30mL of DMSO, stir and dissolve, measure 73mmol of bromoalkane after 5h, add dropwise with a dropping funnel under ice bath, and react A large number of white solids appeared in the solution, and the reaction was stopped after stirring at room temperature for 11 h. The reaction solution was separated with distilled water and chloroform, and the chloroform layer was washed with (4×20 mL) distilled water, and the anhydrous MgSO 4 Drying overnight, filtering, and ro...

Embodiment 2

[0043] Example 2: 1,2-Dimethyl-3-butylimidazole-L-proline salt chiral ionic liquid

[0044] Raw material: 1,2-Dimethylimidazole Analytical reagent

[0045] Bromobutane Analytical grade reagent

[0046] L-Proline Analytical Reagent

[0047] Potassium hydroxide Analytical grade reagent.

[0048] DMSO Analytical Grade Reagents

[0049] Absolute ethanol Analytical grade reagent

[0050] 1. Synthesis of 1,2-dimethyl-3-butylimidazole bromide

[0051]

[0052] 1,2-Dimethylimidazole N-Butane Bromide 1,2-Dimethyl-3-Butylimidazole Bromide

[0053] Add 45mmol of 1,2-dimethylimidazole and 50mmol of n-butane bromide into a 100mL three-necked flask. The preparation method is the same as that of 1,2-dibutylimidazole bromide in Example 1.

[0054] 2. Synthesis of 1,2-dimethyl-3-butylimidazolium proline salt chiral ionic liquid

[0055]

[0056] 1,2-Dimethyl L-proline bromide 1,2-Dimethyl-3-butyl

[0057] -3-Butylimidazole imidazole-L-proline salt

[0058] In a 100mL three-necke...

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Abstract

The invention relates to an alkyl imidazole-L-proline salt chiral ionic liquid and a preparation method thereof. The structural formula of the alkyl imidazole-L-proline salt chiral ionic liquid is shown in formula (I), and the preparation method thereof comprises the following steps: enabling alkyl imnidazole bromide and potassium hydroxide to react in ethanol solution for 4h; removing generated salt; stirring with L- L-proline at the temperature of 0 DEG C and reacting for 12h; and carrying out vacuum drying on products for 24h. The optical rotation and optical purity OP%ee of the alkyl imidazole-L-proline salt chiral ionic liquid prepared by the invention are measured at the temperature of 25 DEG C; according to the method provided by the invention, the preparation process is green and environmental friendly, and no secondary pollution is generated; and the alkyl imidazole-L-proline salt chiral ionic liquid synthesized in the invention has favorable optical activity. The formula (I) is shown in the specification, wherein R1 is CH3 or (CH2)n-CH3, and n is from 1 to 5; R2 is H, CH3 or (CH2)n-CH3, and n is from 1 to 5; and R3 is (CH2)n-CH3, and n is from 1 to 5.

Description

technical field [0001] The invention relates to an ionic liquid and a preparation method, in particular a chiral alkylimidazole-L-proline salt ionic liquid and a preparation method thereof. technical background [0002] Ionic liquids are completely composed of anions and cations, and have many unique properties such as good solubility, good chemical stability, good thermal stability, wide temperature range, low vapor pressure, good conductivity, fast ion migration and diffusion, non-combustible, and odorless. nature. Ionic liquids have attracted people's attention as a green alternative solvent technology in many fields such as electrochemistry, organic synthesis, catalysis, biochemistry, physical chemistry, materials and separation. There are many research reports on ionic liquids at home and abroad, but there are relatively few studies on chiral ionic liquids (C IL). Ionic liquids containing chiral fragments have both the characteristics of ionic liquids and chiral featu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58C07D207/16
Inventor 刘红霞徐群代剑飞
Owner QIQIHAR UNIVERSITY
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