Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Capillary gas chromatography chiral column based on chiral organic molecular cage material

An organic molecule and gas chromatography technology, which is applied in the field of capillary gas chromatography chiral columns based on chiral organic molecular cage materials, can solve the complex preparation process of cyclodextrin derivatives, the high price of gas chromatography chiral columns, and racemization. The problem of not being able to resolve the body is achieved, and the effect of good chiral separation effect, low cost of column preparation and simple preparation method is achieved.

Active Publication Date: 2020-04-17
YUNNAN NORMAL UNIV
View PDF3 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, gas chromatography columns prepared with cyclodextrin derivatives as chiral stationary phases are the most widely used, but there are still some racemates that cannot be resolved well on such chiral columns
In addition, the eluting time of some enantiomers of this type of chiral column is often relatively long, the maximum use temperature is generally lower than 230 °C, and the preparation process of many cyclodextrin derivatives is relatively complicated, and the preparation process is relatively complicated. GC chiral columns are also more expensive

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Capillary gas chromatography chiral column based on chiral organic molecular cage material
  • Capillary gas chromatography chiral column based on chiral organic molecular cage material
  • Capillary gas chromatography chiral column based on chiral organic molecular cage material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Synthesis of chiral organic molecular cage materials: Take 0.318g (1.5mmol) (1R,2R)-1,2-diphenyl-1,2-ethylenediamine in a 100mL round bottom flask, add 45mL di Methyl sulfoxide and 5mL water, stir to dissolve; 5 minutes later, add 0.178g (1mmol) 2-hydroxy-1,3,5-triscarbaldehyde to the above solution, seal the entire reaction solution, and stir the reaction at room temperature 2 weeks; during the reaction process, a yellow solid is gradually produced. After 2 weeks of reaction, the reaction solution is filtered, and the obtained solid is washed 3 times with chloroform and water to obtain the chiral organic molecular cage material;

[0024] (2) Roughening treatment of the inner wall of the capillary: Fill the quartz capillary column (30m×0.25mm i.d.) with 1mol / L NaOH solution and keep it for 2 hours to make the inner wall roughened by NaOH reaction corrosion, then rinse the capillary with distilled water The inner wall was washed for 1 hour, then washed with 0.1mol / L ...

Embodiment 2

[0027] The capillary column obtained in Example 1 was used to test its resolution effect on chiral compounds. For the split chromatogram see image 3 . image 3 The chiral compounds resolved in and the optimized chromatographic conditions are as follows: (A) 1-phenylethanol, column temperature 157°C, nitrogen linear velocity 15.0cm s -1 ; (B) 2-octanol, column temperature 145°C, nitrogen linear velocity 15.6cm s -1 ; (C) 1,2-butanediol, column temperature 170°C, nitrogen linear velocity 16.7cm s -1 ; (D) 1,2-dichlorobutane, column temperature 120°C, nitrogen linear velocity 15.2cm s -1 ; (E) Epibromopropane, column temperature 120°C, nitrogen linear velocity 16.1cm s -1 ; (F) 1,2-epoxyhexane, column temperature 125°C, nitrogen linear velocity 16.4cm s -1 ; (G) ethyl 3-hydroxybutyrate, column temperature 150°C, nitrogen linear velocity 16.7cm s -1 ; (H) γ-decalactone, column temperature 205 ℃, nitrogen linear velocity 14.3cm s -1 ; (I) 3-hydroxy-2-butanone, column temper...

Embodiment 3

[0030] Some chiral compounds (such as 2-octanol, 1,2-dichlorobutane, epoxybromohydrin, 3-hydroxybutyrate) are treated with the capillary column obtained in Example 1 and the existing commercial product β-DEX 120 capillary gas chromatography column Acetate methyl ester, 3-hydroxybutyrate ethyl ester, γ-decalactone, propylene glycol monomethyl ether and sec-butyl methyl ether) for resolution research, and compare their chiral resolution effects. See the attached chromatogram for the comparison resolution effect Figure 4 .

[0031] Depend on Figure 4 Known: 2-octanol, 1,2-dichlorobutane, epibromohydrin, methyl 3-hydroxybutyrate, ethyl 3-hydroxybutyrate, γ-decalactone, propylene glycol monomethyl ether and sec-butyl methyl Ether is not resolved on the existing commercial β-DEX 120 capillary column, but the chromatographic column of the present invention can better resolve the above-mentioned chiral compounds, showing that the chromatographic column of the present invention is b...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a capillary gas chromatography chiral column based on a chiral organic molecular cage material, which is prepared by the following steps: firstly, synthesizing the chiral organic molecular cage material, dissolving the chiral organic molecular cage material in a volatile organic solvent to prepare a solution, mixing the solution with a polysiloxane solution to obtain a stationary phase, and preparing the capillary gas chromatography chiral column by adopting a static column preparation method. The prepared chromatographic column shows excellent chiral resolution performance on a plurality of chiral compounds including alcohol, dihydric alcohol, halogenated hydrocarbon, epoxy compounds, esters, lactones, ketones, ethers, organic acids and the like. The chromatographic column disclosed by the invention is applied to gas chromatography resolution of the chiral compounds, has the remarkable characteristics of simple preparation method, cheap raw materials, good stability, reusability, excellent chiral resolution performance and the like, and has a very good application prospect.

Description

technical field [0001] The invention belongs to the technical field of capillary gas chromatography chiral separation, and in particular relates to a capillary gas chromatography chiral column based on a chiral organic molecular cage material. The capillary gas chromatographic chiral column is applied to gas chromatographic separation of chiral compounds. Background technique [0002] Different enantiomers of chiral compounds, especially chiral drugs, will exhibit different biological activities or pharmacological effects. Under normal circumstances, only one enantiomer of the racemic chiral drug has medicinal effect, and the other enantiomers have no medicinal effect, or have opposite medicinal effects, and even have toxic and side effects. For example, the left-handed enantiomer in the broad-spectrum antibacterial antibiotic drug chloramphenicol has a bactericidal effect, while the right-handed enantiomer has no drug effect at all; the barbiturate enantiomer of the S-(-)-...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): B01D15/20B01D15/38G01N30/60
CPCB01D15/206B01D15/3833G01N30/6052
Inventor 章俊辉李红兴
Owner YUNNAN NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com