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Am imidazole dicationic ionic liquid hydrophilic interaction chromatography stationary phase, and preparation and applications thereof

A chromatographic stationary phase and double cation technology, applied in the field of high performance liquid chromatography stationary phase

Inactive Publication Date: 2015-06-10
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far there are no reports on the use of dicationic liquids as stationary phases in HPLC

Method used

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  • Am imidazole dicationic ionic liquid hydrophilic interaction chromatography stationary phase, and preparation and applications thereof
  • Am imidazole dicationic ionic liquid hydrophilic interaction chromatography stationary phase, and preparation and applications thereof
  • Am imidazole dicationic ionic liquid hydrophilic interaction chromatography stationary phase, and preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of Dicationic Liquid

[0028] Dissolve 1-allylimidazole and 1,4-dibromobutane in methanol solvent at a molar ratio of 3.5:1, stir and heat to 65°C under argon protection for about five days under reflux reaction, after cooling, vacuum rotary evaporation removes Methanol, the remaining mixture was washed five times with ethyl acetate to remove unreacted raw materials to obtain a light yellow viscous liquid, that is, a dicationic liquid 1,4-bis(3-allylimidazole)butane dibromide (C4DIL-Br ), dried under vacuum at 60°C. Then, 1,4-bis(3-allylimidazole) butane bis(bis-trifluoromethylsulfonimide) salt (C4DIL-NTf 2 ), the steps are as follows: 3.5g C4DIL-Br is dissolved in water, and the bis-trifluoromethylsulfonylimide lithium salt (LiNTf 2 ) solution, after adding dichloromethane with the same volume as water, stir at 35°C for 40 hours, and remove the upper water layer after standing for stratification, and continue to wash the dichloromethane layer w...

Embodiment 2

[0031] Example 2: Preparation of Dicationic Liquid Bonded Silica Gel Stationary Phase

[0032] Silica balls (particle size 3μm, specific surface area 310m 2 g -1 ) at 100°C for 24 hours in vacuum, after cooling, disperse in anhydrous toluene and stir evenly. Reflux at 110°C for 24 hours, centrifuge, wash with methanol five times to obtain silica spheres with 3-mercaptopropyl groups bonded to the surface, and dry at 60°C in vacuum.

[0033] Through the click chemical reaction of thiol and double bond, the prepared dianionic liquid C4DIL-Br, C4DIL-NTf 2 and C8DIL-NTf 2 Bonded to the surface of silica spheres with 3-mercaptopropyl groups bonded to the surface. Disperse the silicon spheres with 3-mercaptopropyl groups bonded on the surface in methanol, add the cation liquid (the molar number of double bond groups is 2-3 times that of the mercapto groups on the surface of the silicon spheres) and 1%-2% mass ratio of the two The initiator AIBN was reacted at reflux at 60°C for ...

Embodiment 3

[0036] Example 3: Evaluation of Dicationic Liquid Bonded Silica Gel Stationary Phase

[0037] First, the elemental analysis was carried out on the ionic liquid bonded silica gel stationary phase, and Table 1 lists the elemental characterization results. At the same time, the column efficiency of the dicationic liquid-bonded silica gel stationary phase is listed, the column efficiency uses cytosine as the probe, and the mobile phase is 95% ACN (10mM NH 4 FA) / H 2 O (10mM NH 4 FA)=95 / 5(v / v), isocratic elution, DAD254nm detection, flow rate 0.2mL / min.

[0038] Table 1 Properties of ionic liquid bonded silica gel stationary phase

[0039]

[0040] Secondly, nucleoside mixtures, nucleic acid base mixtures and substituted benzoic acid mixtures were used to evaluate the retention behavior and selectivity of dianionic liquid-bonded silica stationary phases under hydrophilic interaction chromatography conditions. Figure 4 and Figure 5 The separation chromatograms of the nucleo...

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Abstract

The invention relates to an imidazole dicationic ionic liquid-bonded silica gel hydrophilic interaction chromatography stationary phase, and provides a preparing method of the stationary phase. Firstly, imidazole dicationic ionic liquid with N-terminal alkenyl is prepared, 3-mercaptopropyl is grafted to surfaces of silicon spheres, and the imidazole dicationic ionic liquid with the N-terminal alkenyl is boned to the surfaces of the silicon spheres modified with the 3-mercaptopropyl by utilization of a mercapto-alkenyl click chemical reaction. The stationary phase has good retention and separation selectivity for typical hydrophilic compounds such as nucleosides, nucleic acid bases and organic acids, is ideal in column efficiency which can reach 130000 / m, and shows a good application prospect as a hydrophilic interaction chromatography stationary phase.

Description

technical field [0001] The invention belongs to high-performance liquid chromatography stationary phase, in particular to imidazole dication liquid-bonded silica gel hydrophilic interaction chromatography stationary phase, its preparation method and its application to the separation of polar and hydrophilic substances. Background technique [0002] As a modern separation and analysis technique, high performance liquid chromatography has played an important role in many fields such as food safety, environment and drug detection. Among them, the stationary phase plays a pivotal role in the chromatographic separation process, and its development and research has always been a hot spot in the field of chromatography. Hydrophilic Interaction Chromatography (HILIC) was first proposed by Alpert in 1990. It uses a polar stationary phase, which can well retain polar and hydrophilic compounds that are not retained or are weakly retained in reversed-phase chromatography. Chromatograph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/286B01J20/30B01D15/36
Inventor 许国旺乔利珍石先哲路鑫
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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