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Advisor(s)
Abstract(s)
The separation of the four nadolol stereoisomers on ChiralpakW AD by chiral
liquid chromatography was carried out at both analytical and preparative scales. A screening
of possible mobile-phase compositions was performed using different alcohol–hydrocarbon
mixtures. The results obtained confirm the use of 20:80:0.3 ethanol-hexane-diethylamine
reported by McCarthy (1994) but introduce other possibilities for the complete resolution of
the four nadolol stereoisomers at analytical scale, namely, the mixtures 30–40:70–60:0.3
ethanol-heptane-diethylamine. Additionally, this work describes how retention and resolution
depend on the ethanol content in hexane and heptane mixtures. The separation of nadolol
stereoisomers is also carried out at preparative scale and different alcohol–hydrocarbon compositions
are proposed, depending on the target component to be obtained. Particularly, this work
presents the experimental separation of the more retained nadolol stereoisomer (RSR-nadolol)
by simulated moving bed (SMB) chromatography using an 80:20:0.3 ethanol-heptane-diethylamine
mobile phase. For a 2 g/l feed concentration, RSR-nadolol is 100% recovered at the extract outlet
stream, 100% pure, and with a system productivity of 0.65 gRSR-nadolol/(lbed
. h) and a solvent
consumption of 9.6 lsolvent/gRSR-nadolol.
Description
Keywords
Multicomponent chiral separations Pharmaceutical intermediate; Nadolol stereoisomers Preparative chiral separation Simulated moving bed chromatography
Citation
Ribeiro, A. E.; Rodrigues, A. E.; Pais, L. S. (2013). Separation of nadolol stereoisomers by chiral liquid chromatography at analytical and preparative scales. Chirality. ISSN 1520-636X. 25:3, p. 197-205
Publisher
Wiley