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Preparation and application of carboxylic acid modified cyclodextrin chiral chromatographic stationary phase material

A technology of chiral chromatography and cyclodextrin, which is applied in the field of high performance liquid chromatography chiral separation and composite materials, can solve the problems of chiral separation limitations, limited racemate types, and complicated preparation methods, so as to avoid complicated preparation , avoid the use of toxic reagents, the effect of high load

Active Publication Date: 2021-07-16
LANZHOU 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, the construction of excellent cyclodextrin CSPs is still a challenge due to their own shortcomings, such as chiral functional groups or poor water solubility.
Although there are currently about ether bond, urea bond, amino group or triazole bond class cyclodextrin derivatives based CSP technology applied to liquid chromatography separation, such as Félix will β -CD and 4-nitrophenyl chloroformate derivatives bound to silica to obtain β - CD bonded stationary phase, but the ability to chiral separations is somewhat limited
The amino bond immobilized stationary phase prepared by Sun et al. is stable and reproducible. Although the separation effect of triazole compounds is good, the types of other racemates are limited, and the preparation method is relatively complicated.

Method used

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  • Preparation and application of carboxylic acid modified cyclodextrin chiral chromatographic stationary phase material
  • Preparation and application of carboxylic acid modified cyclodextrin chiral chromatographic stationary phase material
  • Preparation and application of carboxylic acid modified cyclodextrin chiral chromatographic stationary phase material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] weigh β -CD (0.4~0.6g) and succinic anhydride (0.5~0.6g), dissolved in the deep eutectic solvent formed by choline chloride and ethylene glycol (choline chloride 40~50g, ethylene glycol 50~ 60 mL); heated to 80~85°C and kept stirring for 30 minutes, added aminopropyl silica gel (2.5~3.0g), carbodiimide (0.05~0.1g) and L-phenylalanine (0.5~0.6g ), continue to react for 10~12h; filter after the reaction, and wash the solid product with 50~60mL acetone and 100~120 mL methanol respectively for 2~3 times; then dry it in a vacuum oven at 55~60℃ for 8~10 hours to obtain Pale yellow powdery solid, which is modified by carboxylic acid β - Cyclodextrin chiral material, labeled Sil-SCD.

[0042] Sil-SCD was packed into a column as the stationary phase. In reverse phase mode, using acetonitrile / water as mobile phase, flavanone, α-phenylethanol, 6-methoxyflavanone, benzoin, benzoin methyl ether, benzoin ethyl ether, 1-phenyl-1-propane Alcohol, 1-(4-methylphenyl)ethanol, and tria...

Embodiment 2

[0047] Will β -CD (0.4~0.6 g) and butenedioic anhydride (0.5~0.6g) were dissolved in the deep eutectic solvent formed by choline chloride and ethylene glycol (choline chloride 40~50g, ethylene glycol 50~ 60mL); warm up to 80~85℃ and keep stirring for 30 minutes; add aminopropyl silica gel (2.5~3.0 g), carbodiimide (0.05~0.1g) and L-phenylalanine (0.5~0.6g) , continue to react for 10~12h; filter after the reaction, wash the solid product with 50~60mL acetone and 100~120 mL methanol for 2~3 times, and then dry in a vacuum oven at 60°C for 8~10 hours to obtain a light yellow powder Shaped solid, that is, carboxylic acid modified β-cyclodextrin chiral material, marked as Sil-CCD.

[0048] Packed into a column as a stationary phase. Determination in the reverse phase mode, using acetonitrile / water as mobile phase, with flavanone, α-phenylethanol, 6-methoxyflavanone, benzoin, benzoin methyl ether, benzoin ethyl ether, 1-phenyl-1 -Propanol, 1-(4-methylphenyl)ethanol, and triadimen...

Embodiment 3

[0051] Will β -CD (0.4~0.6 g) and phthalic anhydride (0.5~0.6 g) were dissolved in the deep eutectic solvent formed by choline chloride and ethylene glycol (choline chloride 40~50 g, ethylene glycol 50 ~60mL); warm up to 80~85°C and keep stirring for 30 minutes; add aminopropyl silica gel (2.5~3.0 g), carbodiimide (0.05~0.1g) and L-phenylalanine (0.5~0.6g ), continue to react for 10~12h, filter after the reaction, wash the solid product with 50~60mL acetone and 100~120 mL methanol for 2~3 times, and then dry it in a vacuum oven at 60°C for 8~10 hours to obtain light yellow Powdered solid, that is, carboxylic acid modification β - Cyclodextrin chiral material, labeled as Sil-PCD.

[0052] Packed into a column as a stationary phase. In reverse phase mode, using acetonitrile / water as mobile phase, flavanone, α-phenylethanol, 6-methoxyflavanone, benzoin, benzoin methyl ether, benzoin ethyl ether, 1-phenyl-1-propane Alcohol, 1-(4-methylphenyl)ethanol, and triadimenol were used ...

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Abstract

The invention provides a carboxylic acid derivative modified beta-cyclodextrin chiral chromatographic stationary phase material which is prepared by the following steps: dissolving beta-cyclodextrin and carboxylic acid in a deep eutectic solvent formed by choline chloride and ethylene glycol, and stirring and reacting at 80-85 DEG C for 25-30 minutes; adding aminopropyl silica gel, carbodiimide and L-phenylalanine into the mixed solution, and continuing to stir and react for 10-12 hours; and after the reaction is finished, filtering, washing solid products with acetone and methanol respectively, and drying in vacuum to obtain the product. The carboxylic acid derivative modified beta-cyclodextrin chiral material prepared by the invention shows high selectivity and a wide raceme separation range, and can selectively separate aromatic secondary alcohol, benzoin, flavanone and triazole chiral compounds thereof in a positive and negative phase mode. In addition, the prepared chiral material is large in surface bonding amount, good in repeatability and high in chiral resolution performance, and the preparation process is green and simple.

Description

technical field [0001] The present invention relates to a modified β -Cyclodextrin chiral materials, especially related to modification of a carboxylic acid derivative β -Cyclodextrin chiral material and preparation method thereof, the present invention also relates to the modification of the carboxylic acid derivative β -The application of cyclodextrin chiral material as chromatographic stationary phase in enantiomer chromatographic separation belongs to the field of composite material technology and the field of high performance liquid chromatography chiral separation. Background technique [0002] Chirality is a fundamental property of nature, present in a variety of fundamental building blocks of life, including amino acids, carbohydrates, hormones, and other processes such as biological processes, pharmaceuticals, agricultural chemistry, or anisotropic environments. Enantiomers of chiral drugs have attracted great attention due to their differences in biological activ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/24B01J20/30B01D15/20B01D15/38C08B37/16
CPCB01J20/24B01D15/3833B01D15/20C08B37/0012
Inventor 李辉王晓萍陈佳赵亮邱洪灯
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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