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Ionic liquid of N-methyl piperazine salt and preparation method thereof

A methylpiperazine and salt ion technology is applied in the field of N-methylpiperazine salt ionic liquid and its preparation, and achieves the effects of high yield, mild reaction conditions and good product quality

Inactive Publication Date: 2011-11-23
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many kinds of ionic liquids, but N-methylpiperazine salt ionic liquids and their preparation have not been reported yet

Method used

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  • Ionic liquid of N-methyl piperazine salt and preparation method thereof
  • Ionic liquid of N-methyl piperazine salt and preparation method thereof
  • Ionic liquid of N-methyl piperazine salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The propionate ionic liquid of embodiment 1N-methylpiperazine

[0018] A solution of propionic acid (7.41 g, 0.1 mol) in ethanol (50 mL) was slowly added dropwise to a solution of N-methylpiperazine (10.02 g, 0.1 mol) in ethanol (100 mL) under an ice-water bath, and reacted for 1 hour. Then the temperature was raised to 30° C., and the reaction was carried out for 3 hours. After the reaction was completed, the solvent was removed by rotary evaporation to obtain a light yellow solid. Recrystallized with ethanol / ether mixed solvent at 40°C to obtain white needle-like crystals. After vacuum drying at 40°C, 15.67 g of pure N-methylpiperazine propionate was obtained with a yield of 90% and a melting point of 71.7°C.

[0019] 1 H NMR (500MHz, CDCl 3 ): δ8.90(s, 2H), 3.04(t, 4H), 2.57(m, 4H), 2.33(s, 3H), 2.25(q, 2H), 1.11(t, 3H)

[0020] The reaction formula is:

[0021]

Embodiment 2

[0022] The lactate ionic liquid of embodiment 2N-methylpiperazine

[0023] N-methylpiperazine (10.02 g, 0.1 mol) in ethanol (30 mL) was slowly added dropwise to lactic acid (9.01 g, 0.1 mol) in ethanol (100 mL), and stirred at 40°C for 4 hours. After the reaction, the solvent was removed by rotary evaporation. Impurities and unreacted raw materials were evaporated under low pressure at 80°C to obtain lactate ionic liquid of light yellow viscous N-methylpiperazine with a yield of 85% and a melting point below -20°C.

[0024] 1 H NMR (500MHz, CDCl 3 ): δ6.02(broad, 3H), 4.05(q, H), 3.12(t, 4H), 2.63(m, 4H), 2.34(s, 3H), 1.36(d, 3H)

[0025] The reaction formula is:

[0026]

Embodiment 3

[0027] The methanesulfonate ionic liquid of embodiment 3N-methylpiperazine

[0028] The ethanol solution (30mL) of methanesulfonic acid (4.81g, 0.05mol) was slowly added dropwise to the ethanol (50mL) solution of N-methylpiperazine (5.01g, 0.05mol) under ice-water bath, and the methanesulfonic acid After the solution was added dropwise, the temperature was raised to 30° C., and the reaction was carried out for 5 hours. After the reaction, part of the solvent was removed by rotary evaporation under low pressure, and then a certain amount of diethyl ether was added, crystals were formed at 0°C, the white solid was obtained by filtration, and vacuum-dried at 30°C for 8 hours to obtain methanesulfonic acid of pure N-methylpiperazine Salt ionic liquid, the yield is 95%. The melting point is 42.1°C, 1 H NMR (500MHz, CDCl 3 ): δ3.25(s, 2H), 3.16(t, 4H), 2.79(s, 3H), 2.68(m, 4H), 2.35(s, 3H).

[0029] The reaction formula is:

[0030]

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Abstract

The invention discloses ionic liquid of N-methyl piperazine salt. The ionic liquid has the structural general formula shown as the specifications. The invention also discloses a preparation method for the ionic liquid. N-methyl piperazine and Y acid are subjected to one-step reaction to directly form the ionic liquid of N-methyl piperazine salt. The method has the advantages of simple operation, wild reaction condition, high yield and product purity, simple storage and transportation, and suitability for industrial production; and in the produced ionic liquid of N-methyl piperazine salt, anions have plenty of selection spaces and structure and performance design spaces, and the ionic liquid can be applied to multiple fields.

Description

technical field [0001] The invention belongs to the technical field of ionic liquids, in particular to a class of N-methylpiperazine salt ionic liquids and a preparation method thereof. Background technique [0002] Ionic Liquid (Ionic Liquid) refers to a salt with a melting point below 100°C, which is composed entirely of cations and anions. Ionic liquids in which the melting point is equal to or lower than room temperature are called room temperature ionic liquids (RTIL). The cation end of most ionic liquids is generally an organic compound, such as imidazole, N-picoline, tetramethylammonium or tetramethylphosphonium ion; the anion end can be organic or inorganic, including some halides, nitrates, ethyl salt, hexafluorophosphate [PF 6 ], Tetrafluoroborate [BF 4 ], trifluoromethanesulfonate [OTf] and bis(trifluoromethylsulfonyl)imide salt [NTf 2 ]. [0003] Ionic liquids have unique physical and chemical properties. Room temperature ionic liquids have a wide liquid ra...

Claims

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Application Information

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IPC IPC(8): C07D295/03C07C53/122C07C59/08C07C59/06C07C53/16C07C51/41C07C309/04C07C309/29C07C303/32C10G29/20
Inventor 方文军邵东贝童威陆晓星郭永胜
Owner ZHEJIANG UNIV
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