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Halogenated-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid and preparation method and application thereof

A technology of methylimidazolium ion and mercaptobutyl group, which is applied in chemical instruments and methods, organic chemistry, instruments, etc., can solve the problems of weak fluorescence effect, long reaction cycle, complicated post-processing process, etc., and achieve repeatability and stability Good, short reaction cycle, and the effect of improving fluorescence sensitivity

Inactive Publication Date: 2018-08-07
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Its reaction cycle is longer, and the aftertreatment process of step (1), step (2) is complicated, and the fluorescence effect of the obtained target product bromide-1-(2-mercaptoethyl)-3-methylimidazole is also weak

Method used

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  • Halogenated-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid and preparation method and application thereof
  • Halogenated-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid and preparation method and application thereof
  • Halogenated-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0049] The bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of this embodiment has a structural formula as shown in formula II:

[0050]

[0051] The preparation method of bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of the present embodiment adopts the following steps:

[0052] 1) Add 3.21g (15.0mmol) of 1,4-dibromobutane to a single-necked flask, add dichloromethane to dissolve, then weigh 2.05g (18.0mmol) of potassium thioacetate, add it to the system, and react at 35°C 8h, the system gradually turned yellow; the white solid was removed by suction filtration, the solvent was evaporated to dryness, and the mixed solvent of petroleum ether and dichloromethane with a volume ratio of 3:1 was used as the mobile phase for column chromatography separation to obtain 4-bromobutyl- Thioacetate 1.64g, yield rate is 52.1%;

[0053] 2) Weigh 0.52g (6.3mmol) of N-methylimidazole into a single-necked flask, add dichloromethane to dissolve, then add 1.2g (5....

Embodiment 2

[0056] The bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of this embodiment has the same structural formula as that of Embodiment 1.

[0057] The preparation method of bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of the present embodiment adopts the following steps:

[0058] 1) Add 3.05g (14.2mmol) of 1,4-dibromobutane to a single-necked flask, add dichloromethane to dissolve, then weigh 1.94g (17.0mmol) of potassium thioacetate and add it to the system, and react at 60°C 8h, the system gradually turned yellow; the white solid was removed by suction filtration, the solvent was evaporated to dryness, and the mixed solvent of petroleum ether and dichloromethane with a volume ratio of 3:1 was used as the mobile phase for column chromatography separation to obtain 4-bromobutyl- Thioacetate 1.01g, yield rate is 33.9%;

[0059] 2) Weigh 0.34g (4.2mmol) of N-methylimidazole into a single-necked flask, add dichloromethane to dissolve, then add 0.81g (3....

Embodiment 3

[0062] The bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of this embodiment has the same structural formula as that of Embodiment 1.

[0063] The preparation method of bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of the present embodiment adopts the following steps:

[0064] 1) Add 2.51g (11.7mmol) of 1,4-dibromobutane to a single-necked flask, add dichloromethane to dissolve, then weigh 1.60g (14.0mmol) of potassium thioacetate and add it to the system, and react at 10°C 8h, the system gradually turned yellow; the white solid was removed by suction filtration, the solvent was evaporated to dryness, and the mixed solvent of petroleum ether and dichloromethane with a volume ratio of 3:1 was used as the mobile phase for column chromatography separation to obtain 4-bromobutyl- Thioacetate 0.76g, yield rate is 31.0%;

[0065] 2) Weigh 0.26g (3.2mmol) of N-methylimidazole into a single-necked flask, add dichloromethane to dissolve, then add 0.61g (2....

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Abstract

The invention discloses halogenated-1-(4-sulfydryl butyl)-3-methylimidazole ionic liquid, and a preparation method and application thereof. The ionic liquid has a structural formula shown as the formula I. According to the halogenated-1-(4-sulfydryl butyl)-3-methylimidazole ionic liquid, sulfydryl butyl is used as a substituent group; lone pair electrons of sulfydryl can generate p-Pi conjugation with large Pi bonds on an imidazole ring; the distance from the sulfydryl to the imidazole ring is proper through the butyl; the conditions of repulsion force increase when the distance is too small and sulfydryl coating when the distance is too great are avoided; the microenvironment effect of the ionic liquid is combined, so that the fluorescence property of the ionic liquid can reach the optimum. The ionic liquid can be applied to an ionic liquid microextraction system, is used as an extracting agent or a dispersing agent, and is suitable for being popularized and applied to an organic solvent-free microextraction technology. When the ionic liquid is used in weak fluorescence compound or biomacromolecule fluorescence detection, the detection fluorescence sensitivity can be greatly improved; the analysis and application values are high.

Description

technical field [0001] The invention belongs to the field of ionic liquids, and in particular relates to a halogenated 1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid and a preparation method and application thereof. Background technique [0002] Ionic liquid is an organic liquid substance composed entirely of ions at room temperature, composed of organic cations and inorganic anions or organic anions, and is a liquid salt at room temperature or near room temperature; due to the weak electrostatic attraction between ions, it has a smaller crystal Glenn, ionic liquids are liquid at room temperature. Ionic liquids have the characteristics of good chemical stability, low volatility, low melting point and wide liquid range, and have the advantages of high electrical conductivity and wide electrochemical window. They have unique properties, wide application fields, and less environmental pollution. Therefore, in recent years, ionic liquids have been widely used as a new typ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/60C09K11/06G01N21/64
CPCC07D233/60C09K11/06C09K2211/1044G01N21/643G01N2021/6432
Inventor 王学东曲晋刚谭成侠王慧利
Owner WENZHOU MEDICAL UNIV
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