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Preparation method and application of multi-mode and multifunctional molecular cage high performance liquid chromatography stationary phase

A technology of high performance liquid chromatography and molecular cage, which is applied in the field of molecular cage high performance liquid chromatography stationary phase to achieve the effect of good chiral separation performance and wide application range

Pending Publication Date: 2022-05-13
JINING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As far as we know, so far, there is no research on the use of RCC3-R as the HPLC stationary phase for the separation of enantiomers and the analysis of complex mixtures with a wide polarity range. The new HPLC stationary phase lays the foundation for

Method used

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  • Preparation method and application of multi-mode and multifunctional molecular cage high performance liquid chromatography stationary phase
  • Preparation method and application of multi-mode and multifunctional molecular cage high performance liquid chromatography stationary phase
  • Preparation method and application of multi-mode and multifunctional molecular cage high performance liquid chromatography stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of molecular cage high performance liquid chromatography stationary phase with a loading capacity of 5%-30%, see the preparation process figure 1 ;

[0026] (1) Preparation of molecular cage HPLC stationary phase with a loading capacity of 5%: dissolve 0.05 g RCC3-R reduced cyclohexanediamine molecular cage in 20 mL toluene, and then add 0.3 g epoxyalkyltrimethyl Silane, react at 60°C for 24 h, continue to add 1 g of hydrochloric acid-activated silica gel, react at 110°C for 24 h, filter through a sand core funnel, wash with toluene and absolute ethanol, and dry at 60°C to prepare a molecular cage with a loading capacity of 5%. RCC3-R bonded silica gel stationary phase;

[0027] (2) Prepare a molecular cage HPLC stationary phase with a loading capacity of 15%: dissolve 0.3 g RCC3-R reduced cyclohexanediamine molecular cage in 50 mL toluene, and then add 0.3 g epoxyalkyltrimethyl Silane, react at 60°C for 24 h, continue to add 1.7 g of hydrochloric acid-act...

Embodiment 2

[0031] Using the molecular cage RCC3-R bonded silica gel stationary phase with a loading capacity of 15% obtained in Example 1 to test the resolution effect of chiral compounds, the chromatogram of the resolution is shown in image 3 , 4; image 3 It is the stationary phase of the present invention under normal phase chromatographic conditions for chiral compounds (a) 1-phenylethanol, (b) p-methyl-1-phenylethanol, (c) 1,1'-2-naphthol, ( d) Chromatographic separation of dibromo-binaphthol, (e) 8H-1,1′-binaphthol, and (f) 6-methoxyflavanone. Mobile phase: (a, b) ethanol / n-hexane (5 / 95, v / v); (c, d) ethanol / n-hexane (20 / 80, v / v); (e) ethanol / n-hexane (5 / 95 , v / v); (f) ethanol / n-hexane (2 / 98, v / v); flow rate: 1.0 mL / min; detection wavelength: 254 nm; temperature: 25 ℃; image 3 It can be proved that the complex interaction between the RCC3-R bonded silica chiral stationary phase and the chiral compounds of alcohols, naphthols and flavanones makes the stationary phase suitable f...

Embodiment 3

[0034] Using the molecular cage RCC3-R bonded silica gel stationary phase with a loading capacity of 15% obtained in Example 1, the separation effect of p-alkylbenzene compounds in the normal phase and reverse phase chromatography separation modes, the separation effect is shown in Figure 5 ; Figure 5 The chromatographic conditions and separated compounds are: mobile phase: methanol / water (40:60, v / v); flow rate: 1.0 mL / min; detection wavelength: 254 nm; analyte: 1. toluene; 2. ethylbenzene ; 3. Propylbenzene; 4. Butylbenzene; 5. Pentylbenzene.

[0035] It can be seen from Example 3 that the good separation of five benzenecycloalkyl homologues shows that the RCC3-R bonded silica gel stationary phase has better reversed-phase chromatographic separation mode performance and methylene selectivity.

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Abstract

The invention discloses a preparation method and application of a multi-mode and multifunctional molecular cage high performance liquid chromatography stationary phase. The novel molecular cage RCC3-R bonded silica gel stationary phase is prepared by covalently bonding RCC3-R to the surface of silica gel through a ring-opening chemical reaction of a secondary amino group of RCC3-R and an epoxy group of 3-(2, 3-epoxypropoxy) propyltrimethoxysilane under an alkaline condition. The prepared stationary phase has four separation modes of normal phase, reverse phase, ion exchange and hydrophilic chromatography; the compound shows excellent separation and analysis performance for resolution of chiral compounds (alcohols, naphthol and flavanone) and separation of achiral compounds (benzene naphthenic base homologues, polybenzene rings, phenols, aromatic amines, sulfonamides, acids and nucleosides) with a wide polarity range, and can make up for the defects of single-mode chromatography in complex sample analysis. The method has the remarkable advantages of simple and environment-friendly preparation process, high separation selectivity, good repeatability and the like, and has good popularization and application prospects.

Description

technical field [0001] The invention belongs to the technical field of high performance liquid chromatography separation, and in particular relates to a molecular cage high performance liquid chromatography stationary phase which can be used for multimode and multifunctional separation. The high-performance liquid chromatography stationary phase is used for resolution of chiral compounds and separation of non-chiral compounds. Background technique [0002] The stationary phase of high performance liquid chromatography (HPLC) is a key part of the separation. The traditional HPLC separation mode is usually a single mode, which is mainly divided into normal phase liquid chromatography (NPLC), reversed phase liquid chromatography (RPLC), and ion exchange chromatography. (IEC), Hydrophilic Interaction Chromatography (HILIC). Due to the separation and analysis of multiple compounds in complex samples, a single chromatographic mode with only one retention effect is difficult to me...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/281B01J20/287G01N30/02
CPCB01J20/29B01J20/281B01J20/287G01N30/02
Inventor 王利涛吕美于清华丁瑞芳张敏娜
Owner JINING MEDICAL UNIV
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