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Compound of containing cation radical of L ¿C proline, preparation method, and application

A technology of ionic groups and proline cations, which is applied in the field of compounds containing L-proline cation groups and their synthesis and application, and can solve problems such as simple synthetic routes

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

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Problems solved by technology

[0005] Have not yet seen the report of the liquid compound containing L-proline cationic group with simple synthetic route, higher yield and low cost

Method used

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  • Compound of containing cation radical of L ¿C proline, preparation method, and application
  • Compound of containing cation radical of L ¿C proline, preparation method, and application

Examples

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preparation example Construction

[0020] R in the above formula (1) 1 is methyl, R 2 is pentyl, X - The synthetic method that is the example compound of the present invention of fluoroborate anion comprises the following steps:

[0021]a. Add n-pentane bromide to L-proline (the molar ratio of L-proline and n-pentane bromide is 1:2~6), the solvent can be methanol, ethanol, propanol, isopropanol , N, N-dimethylformamide, etc., react by heating, the reaction temperature is 80°C, the pressure is 1-10 atmospheres, and the reaction time is 10-200 hours.

[0022] b. After the reaction is completed (chromatographic detection), add ammonium fluoroborate (the molar ratio of N, N-dipentyl-L-proline ammonium bromide to ammonium fluoroborate is 1: 2~6) in the above reaction solution, The reaction temperature is 30°C, and the reaction time is 10-200 hours. The reaction product is purified to obtain N, N-dipentyl-L-proline ammonium fluoroborate.

[0023] Similarly, R 1 , R 2 for C 2 ~C 8 Alkyl, X - For bromine or c...

Embodiment 1

[0026] Preparation of N, N-diethyl-L-proline ammonium bromide

[0027] Put 11.5 grams of L-proline, 100 grams of bromoethane and 150 grams of solvent ethanol in the reaction device, the reaction temperature is 80° C., the pressure is 1 atmosphere, and the reaction time is 10 hours. After the reaction is completed (chromatographic detection), The solvent was evaporated. The reaction product can be purified to obtain N, N-diethyl-L-proline ammonium bromide compound, which is stable to air, and the yield is 94%.

[0028] m.p.: 30°C

[0029] High resolution mass spectrometry: [M-Br] + =172

[0030] 1 HNMR (D 2 O, δ / ppm relative to TMS): 4.415-4.418 (m, 1H), 3.332 (t, 6H), 1.974 (t, 4H), 1.332 (m, 6H).

Embodiment 2

[0032] Preparation of N, N-dibutyl-L-proline ammonium chloride

[0033] With 11.5 grams of L-proline, 100 grams of n-chlorobutane and 150 grams of solvent acetonitrile in the reaction device, the reaction temperature is 100 DEG C, the pressure is 4 atmospheres, and the reaction time is 80 hours. After the completion of the reaction (chromatographic detection ), and the solvent was evaporated. After the reaction product is purified, N,N-dibutyl-L-proline ammonium chloride compound can be obtained, which is stable to air and absorbs water, and the yield is 93%.

[0034] m.p.: 40°C

[0035] High resolution mass spectrometry: [M-Br] + =228

[0036] 1 HNMR (D 2 O, δ / ppm relative to TMS): 4.425(t, 1H), 3.281(t, 6H), 1.974(t, 2H), 1.734(t, 6H), 1.251(t, 4H), 0.961(t, 6H ).

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Abstract

This invention relates to a method for synthesizing compounds containing L-proline cations and their application. The structural formula of the compounds is shown in formula 1, wherein, R1 and R2 are C2-C8 alkyl; X- is Br-, Cl-, BF4-, or PF6-. The compounds are environmentally friendly ionic liquids with higher solvency than common organic solvents, and can be used as gas absorbents and liquid extraction phases in separation process, both reaction media and catalysts in chemical reaction, electrolytes in electrochemical process, solvents for cellulose, lubricants, matrices in mass spectrometry, or stationary phases in chromatography. The method has such advantages as simple process and high yield, and is suitable for industrialization.

Description

technical field [0001] The invention relates to a compound containing L-proline cationic groups, a synthesis method and application thereof, and belongs to the technical field of organic chemical reaction methods. 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. According to the cations, the currently researched ionic liquids can be divided into: alkyl quaternary ammonium ions; alkyl quaternary phosphorus ions; 1,3-dialkyl substituted imidazolium ions; N-alkyl substituted pyridinium ions. According to anion, it can be divided into: metals (such as: AlCl 4 - 、CuC 2 - etc.) and ...

Claims

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Application Information

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IPC IPC(8): C07D207/16
CPCC10N2220/04C10N2020/077
Inventor 周晓海张海波
Owner WUHAN UNIV
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