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Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

Zhao, Lu and Xie, Jingqian and Guo, Fangjie and Liu, Kai (2018) Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism. Chirality, 30 (5). pp. 661-669. ISSN 0899-0042. https://resolver.caltech.edu/CaltechAUTHORS:20180423-075156390

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Abstract

Supercritical fluid chromatography (SFC) is already used for enantioseparation in the pharmaceutical industry, but it is rarely used for the separation of chiral pesticides. Comparing with high performence liquid chromatography, SFC uses much more environmnetal friendly and economic mobile phase, supercritical CO2. In our work, the enantioseparation of an amide herbicide, napropamide, using three different polysaccharide‐type chiral stationary phases (CSPs) in SFC was investigated. By studying the effect of different CSPs, organic modifiers, temperature, back‐pressure regulator pressures, and flow rates for the enantioseparation of napropamide, we established a rapid and green method for enantioseparation that takes less than 2 minutes: The column was CEL2, the mobile phase was CO2 with 20% 2‐propanol, and the flow rate was 2.0 mL/min. We found that CEL2 demonstrated the strongest resolution capability. Acetonitrile was favored over alcoholic solvents when the CSP was amylose and 2‐propanol was the best choice when using cellulose. When the concentration of the modifiers or the flow rate was decreased, resolutions and analysis times increased concurrently. The temperature and back‐pressure regulator pressure exhibited only minor influences on the resolution and analysis time of the napropamide enantioseparations with these chiral columns. The molecular docking analysis provided a deeper insight into the interactions between the enantiomers and the CSPs at the atomic level and partly explained the reason for the different elution orders using the different chiral columns.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/chir.22836DOIArticle
https://onlinelibrary.wiley.com/doi/abs/10.1002/chir.22836PublisherArticle
ORCID:
AuthorORCID
Liu, Kai0000-0002-2109-8196
Additional Information:© 2018 Wiley Periodicals, Inc. Issue Online 19 April 2018; Version of Record online: 28 February 2018; Manuscript accepted: 26 January 2018; Manuscript revised: 05 January 2018; Manuscript received: 27 October 2017. Funding: National Natural Science Foundation of China. Grant Numbers: 21320102007, 21427815, 21621005.
Funders:
Funding AgencyGrant Number
National Natural Science Foundation of China21320102007
National Natural Science Foundation of China21427815
National Natural Science Foundation of China21621005
Subject Keywords:chirality; enantioseparation; napropamide; separation mechanism; supercritical fluid chromatography
Issue or Number:5
Record Number:CaltechAUTHORS:20180423-075156390
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180423-075156390
Official Citation:Zhao L, Xie J, Guo F, Liu K. Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism. Chirality. 2018;30:661–669. https://doi.org/10.1002/chir.22836
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:85994
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:25 Apr 2018 18:33
Last Modified:03 Oct 2019 19:38

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