Analytical and preparative enantioseparations in supercritical fluid chromatography using different brands of immobilized cellulose tris (3,5-dichlorophenylcarbamate) columns: Some differences

J Chromatogr A. 2020 Jul 5:1622:461125. doi: 10.1016/j.chroma.2020.461125. Epub 2020 Apr 28.

Abstract

The aim of this study was to determine the impact of the origin and the manufacturing processes of the chiral stationary phases (CSPs) on their chromatographic behaviors. Hence, four chiral stationary phases based on immobilized tris (3,5-dichlorophenylcarbamate) derivative of cellulose supplied by four different manufacturers were evaluated. A set of twenty-nine compounds, including commercially available and in-house synthesized compounds, with a broad range of lipophilicity and polarity was chosen. Three main parameters were evaluated on all stationary phases: retention factor, selectivity and loading capacity. This work highlighted that the retention factor strongly varied according to the manufacturer. Regardless of the characteristic of the tested compounds i.e. neutral, acidic or basic, there was a trend in retention ability of the four chiral stationary phases: retention was increasing from CHIRAL ART Cellulose-SC, REFLECT I-Cellulose C, Chiralpak IC to Lux i-Cellulose-5. On the contrary, selectivity did not follow the same trend as retention. The difference in selectivity between each column towards one compound was quite low while the difference in resolution depended on the nature of the compounds investigated and was significant in certain cases. Finally, the four different columns presented similar and high loading capacity.

Keywords: Cellulose tris (3,5-dichlorophenylcarbamate); Enantiomers; Loadability; Manufacturers; Supercritical fluid chromatography.

MeSH terms

  • Cellulose / analogs & derivatives*
  • Cellulose / chemistry
  • Chromatography, Supercritical Fluid / methods*
  • Omeprazole / isolation & purification
  • Phenylcarbamates / chemistry*
  • Stereoisomerism

Substances

  • Phenylcarbamates
  • cellulose tris(3,5-dichlorophenylcarbamate)
  • Cellulose
  • Omeprazole