Bronsted acidic compound of containing L- proline radical, preparation method, and application

A Bronsted acid and acidic compound technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., to achieve reduced synthesis costs, high yield, and complete conversion Effect

Inactive Publication Date: 2007-10-10
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no synthesis of Brönsted acidic ionic liquids using L-proline groups as cationic groups has been found.

Method used

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  • Bronsted acidic compound of containing L- proline radical, preparation method, and application
  • Bronsted acidic compound of containing L- proline radical, preparation method, and application
  • Bronsted acidic compound of containing L- proline radical, preparation method, and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 11.5 grams (0.1 mol) of L-proline, slowly add 21.95 grams of 40wt% tetrafluoroboric acid aqueous solution (containing 0.1 mol tetrafluoroboric acid) dropwise under stirring at 0°C, drop it in 30 minutes, and continue to stir the reaction at room temperature After 2 hours, heat and remove water under vacuum to obtain the product L-proline fluoroboric acid ionic liquid. Stable to water and air, the yield is 98%. Density 1.156 g / ml, conductivity 1.43×10 -3 S / cm, the melting point is -68°C.

[0024] High resolution mass spectrometry: [M-BF 4 ] + =116

[0025] 1 HNMR (CDCl 3 , δ / ppm relative to TMS): 15.60 (t, 2H), 12.37 (m, 1H), 4.415-4.418 (m, 1H), 3.332 (t, 2H), 1.974 (t, 4H).

Embodiment 2

[0027]Weigh 11.5 grams (0.1mol) of L-proline and dissolve it in water, slowly add 6.3 grams (0.1mol) of 65wt% concentrated nitric acid dropwise under stirring at room temperature, drop it in 30 minutes, continue stirring and reacting for 6 hours at room temperature, heat Water was removed in a vacuum to obtain the product L-proline nitrate ionic liquid. Stable to water and air, the yield is 97.7%. Density 1.323 g / ml, conductivity 2.5×10 -3 S / cm, the melting point is -57°C.

[0028] High resolution mass spectrometry: [M-NO 3 ] + =116

[0029] 1 HNMR (D 2 O, δ / ppm relative to TMS): 4.415-4.418 (m, 1H), 3.332 (t, 2H), 1.974 (t, 4H).

Embodiment 3

[0031] Weigh 11.5 g (0.1 mol) of L-proline and dissolve it in water, slowly add 11.40 g (0.1 mol) of chloroacetic acid dropwise under stirring at room temperature, and finish dropping in 50 minutes, continue to stir and react at room temperature for 6 hours, heat and vacuum to remove water , that is, a brown viscous liquid is obtained, which is the product L-proline chloroacetic acid ionic liquid. Stable to water and air, the yield is 96%. Density 1.134 g / ml, conductivity 2.3×10 -3 S / cm, the melting point is -68°C.

[0032] High resolution mass spectrometry: [M-ClCH 2 COO] + =116

[0033] 1 HNMR (D 2 O, δ / ppm relative to TMS): 4.415-4.418 (t, 3H), 3.332 (t, 2H), 1.974 (t, 4H).

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Abstract

This invention relates to a method for preparing L-proline-containing Bronsted acidic compound and its application. The L-proline-containing Bronsted acidic compound is prepared from L-proline and Bronsted acid by one-step neutralization in a mild condition. The L-proline-containing Bronsted acidic compound has strong acidity and high stability to water and air, thus can be used as ionic liquid, and can replace inorganic acid as both catalyst and reaction medium in acid catalytic reaction. The method has such advantages as simple reaction system, no pollution, saved resources, and is suitable for industrialization.

Description

technical field [0001] The invention relates to a Brönsted acidic compound containing L-proline as a cationic group, a preparation method and application thereof. Background technique [0002] Ionic liquids (ionic liquids) are also called room temperature ionic liquids (room temperature ionic liquids), room temperature molten salts (room temperature molten salts), organic ionic liquids, etc., referred to as RTILs. for liquid salt. There are only anions and cations in ionic liquids, and there are no neutral molecules. Its main feature is that the cations are large and asymmetric, and the anions are small. The ionic liquids currently studied can be divided into cations: alkyl quaternary ammonium ions [NR x h 4-x ] + ; Alkyl quaternary phosphorus ion [PR x h 4-x ] + ; 1,3-dialkyl substituted imidazolium ions or N, N'-dialkyl substituted imidazolium ions, abbreviated as [R 1 R 3 I m ] + , if there is a substituent R on the 2-position 2 , it is abbreviated as [R 1 R ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16B01J31/04
Inventor 周晓海张海波
Owner WUHAN UNIV
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