title: Enantioseparation of omeprazole--effect of different packing particle size on productivity.
abstract: Enantiomeric separation of omeprazole has been extensively studied regarding both product analysis and preparation using several different chiral stationary phases. In this study, the preparative chiral separation of omeprazole is optimized for productivity using three different columns packed with amylose tris (3,5-dimethyl phenyl carbamate) coated macroporous silica (5, 10 and 25 μm) with a maximum allowed pressure drop ranging from 50 to 400 bar. This pressure range both covers low pressure process systems (50-100 bar) and investigates the potential for allowing higher pressure limits in preparative applications in a future. The process optimization clearly show that the larger 25 μm packing material show higher productivity at low pressure drops whereas with increasing pressure drops the smaller packing materials have substantially higher productivity. Interestingly, at all pressure drops, the smaller packing material result in lower solvent consumption (L solvent/kg product); the higher the accepted pressure drop, the larger the gain in reduced solvent consumption. The experimental adsorption isotherms were not identical for the different packing material sizes; therefore all calculations were recalculated and reevaluated assuming identical adsorption isotherms (with the 10 μm isotherm as reference) which confirmed the trends regarding productivity and solvent consumption.
authors.affiliation: Department of Chemistry and Biomedical Sciences, Karlstad University, SE-651 88 Karlstad, Sweden.
authors.forename: Martin
authors.initials: M
authors.lastname: Enmark
authors.forename: Jörgen
authors.initials: J
authors.lastname: Samuelsson
authors.forename: Patrik
authors.initials: P
authors.lastname: Forssén
authors.forename: Torgny
authors.initials: T
authors.lastname: Fornstedt
mesh_terms: D000327:Adsorption; D000688:Amylose / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods; D005021:Ethylamines / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D017711:Nonlinear Dynamics; D009853:Omeprazole / Q000737:chemistry* / Q000302:isolation & purification; D010316:Particle Size; D048448:Phenylcarbamates / Q000737:chemistry; D011312:Pressure; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005021:Ethylamines; D048448:Phenylcarbamates; C511479:amylose tri(3,5-dimethyl carbamate); D012822:Silicon Dioxide; D000688:Amylose; D009853:Omeprazole; C016162:triethylamine; D000432:Methanol