SMB-Chromatography. basic principle. Batch Chromatography. salad. True Moving Bed (TMB) salad. Chromatography Workshop 03/06 (Poland)
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1 SMB-Chromatography basic principle Batch Chromatography salad True Moving Bed (TMB) salad Merck KGaA Darmstadt/Germany Page 53
2 SMB-Chromatography basic principle extract (A) feed raffinate (B) fluid solid counter-current flow of solid and liquid feed is injected in the centre of the process stronger retained component is carried with the solid stream less retained component is carried with the fluid stream Merck KGaA Darmstadt/Germany Page 54
3 SMB-Chromatography running processes (enantioseparation) Name: Levetiracetam Tetralon Escitalopram DOLE Keppra Zoloft Cipralex Indication: antiepileptic antidepressant antidepressant CSE-inhibit. H H N CN O N F H Cl OH OH Cl F CO 2 Et SMB-size: * Prod.amount: 145 to/a 45 to/a 160 to/a 10 to/a N Sales: 417 m (2004) 789 m$ (2003) 163 m (1-9/2004) Merck KGaA Darmstadt/Germany Page 56
4 Isolation of Cyclosporine A new process New Process: Batch separation + two SMB-separations SP: Silica MP: ETAT Cyclosporines D,G,A Cyclosporines A,U,L,B,C ELUENT EXTRACT ELUENT EXTRACT elution order RP Liquid Liquid Si RAFFINATE FEED RAFFINATE FEED Raffinate: Cyclosporine A Raffinate: Cyclosporine A
5 SMB-Chromatography equipment (lab scale) NOVASEP France BTS, Germany Merck KGaA Darmstadt/Germany Page 58
6 SMB-Chromatography equipment (production scale) Industrial SMB-systems 5 to 8 columns, up to 1m diameter Merck KGaA Darmstadt/Germany Page 59
7 Recycling chromatography... with peak shaving Recycling of components until sufficient separation is achieved Simulation of a long column Advisable for a low separation factor Substances with a high separation factor (to the target) are withdrawn in the first cycle Improved performance by withdrawal of the product fractions (peak shaving) c feed eluent product A product B Recycle fraction A B A B A B cycle 1 cycle 2 cycle 3 Merck KGaA Darmstadt/Germany Page 41 t
8 26,99 29,25 Intensity(AU) 20,69 24,21 24,56 25,79 25,01 28,75 29,81 30,29 32,88 Intensity(AU) 27,20 8,48 21,39 Intensity(AU) 19,92 20,72 22,24 27,25 29,04 18,03 15,25 28,05 34,08 26,00 24,24 30,37 23,04 14,11 Recycling chromatography Example (Paclitaxel purification) Extraction - Solvent extraction, Sohxlet - SFE (Supercritical CO 2 ) Herbal or animal material 0,08 0,06 0,04 0,02 10,19 11,31 17,23 16,61 18,93 19,57 24,88 25,12 29,4129,73 31,31 32,80 0,0 crude extract 1, RetentionTime(min) Pre-Purification - liquid/liquid-partitioning, solid phase extraction, silica chromatography 1,2 1,0 0,8 0,6 0,4 0,2 0,0 27,47 28,00 29,01 29,52 purified extract RetentionTime(min) 0,4 Polishing - chromatography in batch-, recycling- or SMB-mode pure product 0,3 0,2 0,1 0,0 Merck KGaA Darmstadt/Germany Page RetentionTime(min) 27,25 27,76
9 Recycling chromatography Example (Paclitaxel purification) analytical chromatogram of a prepurified Taxus extract Chromatographic conditions: stationary phase: LiChrospher RP18, 5 µm column dimension: 250 * 4 mm mobile phase: MeOH/water 60/40 Flow rate: 1.0 ml/min Detection: UV, 220 nm Paclitaxel Merck KGaA Darmstadt/Germany Page 43
10 Recycling chromatography Example (Paclitaxel purification) Chromatographic conditions: stationary phase: LiChroprep RP18, µm column dimension: 200 * 50 mm mobile phase: MeOH/water 70/30 Flow rate: ml/min Detection: UV, 210 nm too short retention time for sufficient resolution Merck KGaA Darmstadt/Germany Page 44
11 Recycling chromatography Example (Paclitaxel purification) Chromatographic conditions: stationary phase: LiChroprep RP18, µm column dimension: 200 * 50 mm mobile phase: MeOH/water 70/30 Flow rate: ml/min Detection: UV, 210 nm Maximum fraction purity: 76% Merck KGaA Darmstadt/Germany Page 45
12 Recycling chromatography Example (Paclitaxel purification) Chromatographic conditions: stationary phase: LiChrospher Si60 15 µm column dimension: 250 * 4 mm mobile phase: Heptane/Dioxane 65/35 Flow rate: 1.0 ml/min Detection: UV, 220 nm Merck KGaA Darmstadt/Germany Page 46
13 Recycling chromatography Example (Paclitaxel purification) waste recycle w rec. w rec. w fraction w recycling chromatogram of a prepurified Taxus extract Chromatographic conditions: Stationary phase: LiChrospher Si 60, 10 µm Column type: Selfpacker NW 50 Column dimension: 220 * 50 mm Mobile phase: EtAt/n-heptane 60/40 Flow rate: 80 ml/min Detection: UV, 280 nm Feed concentration: 220 g/l (in Etat) Injection: 20 ml Cycle time: 75 min Run time with eluent consumption: 42.4 min Merck KGaA Darmstadt/Germany Page 47
14 Transposition, example 1 Flush Chromatography In ideal conditions, transposition from TLC to Flash Chromatography should give such results Merck Chimie S.A.S. 25/11/2005 Page 48
15 Particle size comparisons Test silice Si µm Test silice Si µm Test silice Si µm Merck Chimie S.A.S. 25/11/2005 Page 49
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