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Compound containing morpholine cation radical and its synthesis process and use

A technology of ionic groups and synthetic methods, applied in organic chemistry and other fields, can solve problems such as simple synthetic routes, high cost of raw materials, and restrictions on industrial production and application

Inactive Publication Date: 2007-06-27
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned common types of ionic liquids have limited their industrial production and application due to high raw material costs, complex synthetic routes, and low yields.
[0004] Have not yet seen the report of the liquid compound containing morpholine cationic group with simple synthetic route, higher yield and low cost

Method used

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  • Compound containing morpholine cation radical and its synthesis process and use
  • Compound containing morpholine cation radical and its synthesis process and use

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preparation example Construction

[0019] 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:

[0020] a. Add n-pentane bromide to N-methyl-morpholine (the molar ratio of N-methyl-morpholine and n-pentane bromide is 1: 1.05~6), 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.

[0021] b, after the completion of the reaction (chromatographic detection), add ammonium fluoroborate (the molar ratio of N-pentyl N-methyl-morpholine ammonium bromide to ammonium fluoroborate is 1: 1.05~6) in the above reaction solution, and the reaction temperature The temperature is 30°C, and the reaction time is 10-200 hours. The reaction product was purified to obtain N-pentyl N-methyl-morpholine ammonium fluoroborate.

[0022] Simil...

Embodiment 1

[0025] Preparation of N-isobutyl-N-methyl-morpholine ammonium chloride

[0026] With 101 grams of N-methyl-morpholine, 180 grams of chloroisobutane 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 ( chromatographic detection), the solvent was evaporated. The reaction product is separated by a chromatographic column equipped with 20-200 times its weight of silica gel, and the mixture of cyclohexane and acetone is used as the eluent. After purification, N-isobutyl-N-methyl-morpholine chloride can be obtained Ammonium compound, stable to air, easy to absorb water, yield 94%.

[0027] m.p.: 36°C

[0028] High resolution mass spectrometry: [M-Cl] + =157

[0029] 1 HNMR (D 2 O, δ / ppm relative to TMS): 3.852-3.866(t, 5H), 3.415-3.418(m, 4H), 3.332(s, 3H), 1.714(m, 3H), 1.332(t, 3H), 0.964 (t, 3H).

Embodiment 2

[0031] Preparation of N-octyl-N-ethyl-morpholine ammonium bromide

[0032] With 101 grams of N-ethyl-morpholine, 200 grams of n-octane bromide and 150 grams of solvent acetonitrile in the reaction device, the reaction temperature is 100 ° C, the pressure is 4 atmospheres, and the reaction time is 80 hours. After the reaction is completed ( chromatographic detection), the solvent was evaporated. The reaction product is separated several times with a chromatographic column filled with 40 times its weight of alumina, using a mixture of dichloromethane and ethanol as the eluent, collecting the eluate, and concentrating to obtain N-octyl-N-ethyl -A morpholine ammonium bromide compound, stable to air, easy to absorb water, with a yield of 93%.

[0033] m.p.: 50°C

[0034] High resolution mass spectrometry: [M-Br] + =228

[0035] 1 HNMR (D 2 O, δ / ppm relative to TMS): 3.818(t, 4H), 3.425(t, 6H), 3.281(t, 2H), 1.734(t, 2H), 1.251(t, 13H), 0.961(t, 3H )

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Abstract

The present invention relates to compound containing morpholine cation radical and its synthesis and use. The compound of the present invention is one excellent green solvent with dissolving capacity higher than organic solvent, has low production cost, simple synthesis path and high yield, and is suitable for industrial production. The compound of the present invention is used as ionic liquid and may be used as gas absorbent and liquid extractant in separation engineering, as reaction medium and catalyst in chemical reaction, as electrolyte in electrochemical engineering, etc.

Description

technical field [0001] The present invention relates to the compound containing morpholine cationic group and its synthesis method and application. 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 non-metallic (such as: BF 4 - 、PF 6 - , NO 3 - , SbF 6 - ,...

Claims

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Application Information

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IPC IPC(8): C07D295/037
Inventor 周晓海张海波张高勇
Owner WUHAN UNIV
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