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Morpholine quaternary ammonium salt ion liquid and preparation method thereof

A technology of ionic liquid and quaternary ammonium salt, applied in the direction of organic chemistry, can solve the problems of high cost, difficult industrial production and application, and achieve the effects of less equipment, easy promotion and use, and increased yield

Inactive Publication Date: 2008-04-09
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, the cost of preparing the ionic liquid is relatively high, and it is difficult to achieve industrial production and application.

Method used

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  • Morpholine quaternary ammonium salt ion liquid and preparation method thereof
  • Morpholine quaternary ammonium salt ion liquid and preparation method thereof
  • Morpholine quaternary ammonium salt ion liquid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Preparation of N-methyl-N-butylmorpholine hydrochloride ionic liquid.

[0061] Weigh 10.1g (0.1mol) of N-methylmorpholine and 11.25g (0.12mol) of 1-chlorobutane, add 20ml of acetonitrile as solvent, mix them in a 100ml three-necked flask, heat for 20h under vigorous stirring, and control the temperature At 85°C, a small amount of white crystals were produced after 20 hours, and the solvent was evaporated with a rotary evaporator, and a large amount of crystals were produced after cooling. After suction filtration, washed with 20ml of acetone, and dried, 8.10g of white solids were obtained, namely N- Methyl-N-butylmorpholine hydrochloride ionic liquid.

[0062] The calculated yield was 42%. Adopt nuclear magnetic resonance instrument to detect, the parameter of gained product is: 1 H NMR (300MHz, CDCl 3 ), δ: 1.00ppm (t, 3H, CH 3 ), 1.47ppm (m, 2H, CH 2 ), 1.79ppm (m, 2H, CH 2 ), 3.53ppm (s, 3H, NCH 3 ), 3.62-4.12ppm (m, 10H).

Embodiment 2

[0064] Preparation of N-methyl-N-hydroxyethylmorpholine hydrochloride ionic liquid.

[0065] Weigh 10.1g (0.1mol) of N-methylmorpholine and 9.66g (0.12mol) of 2-chloroethanol, add 20ml of acetonitrile as solvent, mix them in a 100ml three-necked flask, heat for 35h under vigorous stirring, and control the temperature at After 35 hours at 85°C, a colorless transparent liquid was obtained, and the solvent was evaporated by a rotary evaporator to obtain a white transparent solid. After drying, 11.80 g of the product was obtained, which was N-methyl-N-hydroxyethyl morpholine salt salt ionic liquid.

[0066] The calculated yield was 65.2%. Adopt nuclear magnetic resonance instrument to detect, the parameter of gained product is:

[0067] 1 H NMR (300MHz, CDCl 3 ), δ: 1.65ppm (s, 1H, OH), 2.02ppm (s, 3H, CH 3 ), 2.11(t, 2H, CH 2 ), 3.69ppm (t, 6H, CH 2 , CH 2 NCH 2 ), 4.90ppm (t, 4H, CH 2 OCH 2 ).

Embodiment 3

[0069] Preparation of N-methyl-N-allylmorpholine hydrochloride ionic liquid.

[0070] Weigh 20.2g (0.2mol) of N-methylmorpholine, 14.3g (0.2mol) of allyl chloride, and 40ml of acetonitrile as a solvent, mix them into a 100ml three-necked flask, control the temperature at 45°C and stir for about 0.5h. The mixture becomes turbid. A white solid appeared, and there were more and more solids. After 2 hours, the reaction was basically completed, and the solvent was evaporated with a rotary evaporator to obtain a large amount of white solid. Add a small amount of acetone (10ml) to wash off the solvent, filter with suction and dry to obtain 15.02g of the product , which is N-methyl-N-allyl morpholine hydrochloride ionic liquid.

[0071] After calculation, the yield is 85%. Adopt nuclear magnetic resonance instrument to detect, the parameter of gained product is:

[0072] 1 H NMR (300MHz, CDCl 3 ), δ: 3.53ppm (s, 3H, CH 3 ), 3.74ppm (s, 4H, CH 2 NCH 2 ); 4.06ppm (s, 4H, CH 2 OC...

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PUM

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Abstract

The invention relates to a morpholine quaternary ammonium salt ionic liquid and a preparation method. The ionic liquid has the following structural general formula: A +B-, wherein, the A+ has the structural general formula as the right, in the general formula: R1 is the saturated or unsaturated alkyl containing 1 to 4 carbon atoms, and the R2 is in line with the following rules: a) at least 2 carbon atoms are contained; b) not more than 20 carbon atoms are contained; the B- is selected from one the following anions: chlorine, bromine, iodine, acetate, sulfate, nitrate, tetrafluoroborate, thiocyanate, hexafluorophosphate, p-toluenesulfonic and trifluoromethanesulfonic.

Description

technical field [0001] The invention relates to a chemical product and its preparation technology, in particular to a morpholine quaternary ammonium salt type ionic liquid and its preparation method. The international patent classification number is proposed to be Int.Cl.C07C 68 / 00 (2006.01). Background technique [0002] Ionic liquids mainly refer to organic salts that can be dissolved at around room temperature or lower temperatures, or their mixtures. As a new type of green material, ionic liquid has been successfully used for Organic synthesis, electrochemistry, separation and extraction and materials science and other fields. In recent years, people have carried out extensive research on ionic liquids. Among the currently synthesized ionic liquids, the most common cations are N-alkylpyridine, N,N,-dialkylimidazolium cations, alkyl quaternary ammonium ions and alkyl quaternary phosphine ions, and the anions are mostly Cl - , Br - , BF 4 - , PF 6 - Wait. Various ...

Claims

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Application Information

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IPC IPC(8): C07D295/037C07D295/088
Inventor 臧洪俊王美玲程博闻殷友利郑伟
Owner TIANJIN POLYTECHNIC UNIV
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