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

A technology of methylimidazolium ion and mercaptobutyl group, which is applied in separation methods, chemical instruments and methods, material separation, etc., can solve the problems of low utilization value, fluorescence quenching effect, poor luminescence performance, etc., and achieve improved fluorescence sensitivity , Strong fluorescence sensitization effect, strong fluorescence effect

Inactive Publication Date: 2017-12-22
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the research on the luminescent properties of ionic liquids has aroused the interest of scientific researchers, and the focus of the research is on the synthesis of dialkylimidazolium cations and anions BF 4 - 、PF 6 - On the imidazole-based ionic liquids, the effects of different alkyl chain lengths and solvents on the luminescent properties of ionic liquids were explored. However, the luminescent properties of imidazole-based ionic liquids are relatively poor, and they often have negative effects on some weak fluorescent pollutants such as bisphenol A. fluorescence quenching effect, and the anion BF 4 - 、PF 6 - Poor stability, easy hydrolysis in aqueous solution to release hydrogen fluoride, so it is of little value in the fluorescent sensitive detection of trace pollutants

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0052] The bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of this embodiment has a structural formula as shown in formula II:

[0053]

[0054] The preparation method of bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of the present embodiment adopts the following steps:

[0055] A) Add 7.93g (36.72mmol) of 1,4-dibromobutane to a single-necked flask, add dichloromethane to dissolve, then weigh 3.49g (30.6mmol) of potassium thioacetate, add it, and react at 35°C for 8 hours , the system gradually turns yellow; the white solid is removed by suction filtration, the solvent is evaporated to dryness, and the mixed solvent of petroleum ether and dichloromethane is used as the mobile phase for column chromatography separation with a volume ratio of 3:1 to obtain 4-bromobutyl-sulfur Substituted acetate 3.76g, productive rate is 58.2%;

[0056] B) Weigh 2.05g (9.72mmol) of 4-bromobutyl-thioacetate into a single-necked flask, add methanol to dissolve, then...

Embodiment 2

[0059] The bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of this example has the same structural formula as that of Example 1.

[0060] The preparation method of bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of the present embodiment adopts the following steps:

[0061] A) Add 5.15g (23.84mmol) of 1,4-dibromobutane to a single-necked flask, add dichloromethane to dissolve, then weigh 2.27g (19.87mmol) of potassium thioacetate, add it, and react at 60°C for 8 hours , the system gradually turns yellow; the white solid is removed by suction filtration, the solvent is evaporated to dryness, and the mixed solvent of petroleum ether and dichloromethane is used as the mobile phase for column chromatography separation with a volume ratio of 3:1 to obtain 4-bromobutyl-sulfur Acetate 1.43g, productive rate is 34.2%;

[0062] B) Weigh 1.5g (7.11mmol) of 4-bromobutyl-thioacetate into a single-necked flask, add methanol to dissolve, then add HBr to adjust pH=...

Embodiment 3

[0065] The bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of this example has the same structural formula as that of Example 1.

[0066] The preparation method of bromide-1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid of the present embodiment adopts the following steps:

[0067] A) Add 4.55g (21.05mmol) of 1,4-dibromobutane to a single-necked flask, add dichloromethane to dissolve, then weigh 2.0 g (17.54mmol) of potassium thioacetate, add it, and react at 10°C for 8 hours , the system gradually turns yellow; the white solid is removed by suction filtration, the solvent is evaporated to dryness, and the mixed solvent of petroleum ether and dichloromethane is used as the mobile phase for column chromatography separation with a volume ratio of 3:1 to obtain 4-bromobutyl-sulfur Acetate 1.13g, productive rate is 30.6%;

[0068] B) Weigh 1.0g (4.74mmol) of 4-bromobutyl-thioacetate into a single-necked flask, add methanol to dissolve, then add HBr to adjust pH=...

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Abstract

The invention discloses a halogenated-1-(4-mercaptobutyl)-3-methylimidazole ionic liquid and its preparation method and application. The invention uses N-methylimidazole, potassium thioacetate, 1,4- Dihalobutane is used as a raw material, and the target product is synthesized through a three-step reaction; the reaction cycle of the present invention is short, the reaction conditions of each step are mild, the post-treatment process is simple, the repeatability and stability are good, and it is suitable for popularization and application; the ionic liquid prepared by the present invention It can be applied to the micro-extraction system of ionic liquid and used as an extractant or dispersant; the ionic liquid prepared by the present invention can greatly improve the fluorescence sensitivity of detection in the fluorescence detection of biological macromolecules, and can also be used as a fluorescent probe for pesticide residue detection , has good analytical application value.

Description

technical field [0001] The invention belongs to the field of ionic liquids, in particular to a halogenated 1-(4-mercaptobutyl)-3-methylimidazolium ionic liquid and its preparation method and application. Background technique [0002] Ionic liquids are ionic compounds that are liquid at or near room temperature and are composed of organic cations and inorganic or organic anions. This type of liquid is completely composed of anions and cations, and there are no electrically neutral molecules. Ionic liquids are evolved from traditional high-temperature molten salts, but have significantly different properties and behaviors from general molten salts. Generally known ionic compounds are generally solid at room temperature, with high melting point, viscosity and strong corrosiveness. The main difference between ionic liquid and traditional molten salt is that its melting point is low, generally lower than 150 ° C, so it can be It is used to replace traditional organic solvents an...

Claims

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Application Information

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IPC IPC(8): C07D233/60C09K11/06B01D11/04G01N21/64G01N30/74G01N30/02G01N30/06
CPCC07D233/60B01D11/0492C09K11/06C09K2211/1044G01N21/64G01N21/6428G01N30/02G01N30/06G01N30/74G01N2021/6417G01N2030/062
Inventor 谭成侠谭悦王学东曲劲刚
Owner ZHEJIANG UNIV OF TECH
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