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X-Cube Flash Presentation

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Information about X-Cube Flash Presentation
Science-Technology

Published on March 24, 2009

Author: ThalesNano

Source: authorstream.com

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Slide 1: The application of X-Cube Flash™ for organic synthesis X-Cube Flash™ Overview : X-Cube Flash™ Overview Coil based flow reactor Pressure: 50-200 bar Temperature: RT to 350°C Flow rate: 0.1-9.99 mL/min Touch screen control using UMPC Changeable Reaction Coil sizes: 4, 8, 16 mL X-Cube Flash™ : X-Cube Flash™ Dual Pump and Injection System Changeable Heater Block UMPC – Operation System Back Pressure Regulator Outlet Tube X-Cube Flash™ Schematic : X-Cube Flash™ Schematic Schematic Diagram Stainless steel coil (1000 mm i.d.) www.thalesnano.com Razzaq, T.; Glasnov, T. N.; Kappe, C. O. Eur. J. Org. Chem. 2009,1321-1325 Advantages : Advantages Perform reactions temperatures and pressures never before available. Reduce reaction times from hours or days to minutes. Scale up reactions quickly using larger coils High pressure capability allows low boiling solvents to be used at high temperatures for increased solubility and short work up time. Reactions are performed on a small scale continuously, so reaction temperature is easier to control and more precise. Reactions using the X-Cube Flash™ System : Reactions using the X-Cube Flash™ System Diels-Alder Reaction : Diels-Alder Reaction Diels-Alder reactions usually require long reaction times This reaction time could be reduced to 5 minutes at 250°C using toluene. Product isolated in near quantitative yield Reaction also possible using lower boiling solvents (MeCN, THF, DME) with same result using higher pressures (200 bar) Cf. MW conditions (toluene, 250°C, 10 min) Kremsner, J.M., Kappe, C.O.; J. Org. Chem., 2006, 51, 4651 Razzaq, T.; Glasnov, T. N.; Kappe, C. O. Eur. J. Org. Chem. 2009,1321-1325 Reaction conditions: 250°C, 60 bar toluene (0.2 M) 0.8 mL/min Slide 8: Newmann-Kwart Rearrangement – MW vs. Flow Experiments “Difficult” Case Moseley, J. D. et al. Tetrahedron, 2006, 62, 4685; Moseley, J. D.; Lenden, P. Tetrahedron, 2007, 63, 4120 Razzaq, T.; Glasnov, T. N.; Kappe, C. O. Eur. J. Org. Chem. 2009,1321-1325 Product, DME HPLC, 215 nm Kinetic Analysis (HPLC) sc. DME critical point: 263 °C; 39 bar Slide 9: Heck Chemistry (MW / Flow) – Homogeneous Catalysis with Pd(OAc)2 Aryl Bromide Glasnov, T.N.; Findenig, S.; Kappe, O.C., Chem. Eur. J., 2009, 15, 1001-1010 Fischer Indole Synthesis: Scale Out : Fischer Indole Synthesis: Scale Out In AcOH/2-propanol (3:1) (0.5M) 150 °C, 60 bar, 1.0 mL min-1 (4 min res. time) 88% isolated yield Continuous Flow Results (4 mL or 16 mL Coil) Scale-up 200 °C, 75 bar, 5.0 mL min-1 (~3 min res. time) 96% isolated yield 25 g indole/hour cf. MW reaction: Bagley, M. C.; et al. J. Org. Chem. 2005, 70 , 7003 Razzaq, T.;, Glasnov, T.N.; Kappe, O. C., Eur. J. Org. Chem., 2009, 9, 1321-1325 Slide 11: sc MeOH (0.05 M) Reaction conditions: 350°C, 150 bar 0.5 mL/min MeOH Tc = 239°C, pc = 81 bar sc EtOH (0.33 M) Reaction conditions: 240°C, 100 bar 1.0 mL/min (3 passes) EtOH Tc = 268°C, pc = 61 bar 88% 91% Cf. Socher, G. et al, J. Anal. Chem., 2001, 371, 369 Razzaq, T.;, Glasnov, T.N.; Kappe, O. C., Eur. J. Org. Chem., 2009, 9, 1321-1325 Reactions in supercritical alcohol Claisen Rearrangement : Claisen Rearrangement Results Difficult reaction. Requires 1-2 hours reaction times in microwave. Reaction proceeded in high yield after only 4 minutes residence time. High temperature control needed: <230°C gave incomplete conversion >250°C gives numerous side products. Reaction optimized “on the fly” for quick results. Cf. MW conditions (toluene, 250°C), Kremsner, J.M.; Kappe, C. O.; J. Org. Chem., 2006, 71, 4651 Razzaq, T.; Kremsner, J.M., Kappe, C.O.; J. Org. Chem., 2008, 73, 6321 Razzaq, T.;, Glasnov, T.N.; Kappe, O. C., Eur. J. Org. Chem., 2009, 9, 1321-1325 Reaction conditions: 240°C, 100 bar 1.0 mL/min toluene (0.1 M) 95% Conclusions : Conclusions High Temperature and Pressure helps reactions progress in minutes. Temperature control ensures high selectivity Reactions easily optimized. Reactions can be scaled out easily. Reactions can be performed under super critical conditions. Many thanks to the ThalesNano chemistry team and Oliver Kappe and his group at the University of Graz for their ground breaking work on the X-Cube Flash™

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