Microreactors in Chemistry! Christina Moberg!
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1 Microreactors in Chemistry! Christina Moberg!
2 19th century equipment for synthesis 20th centrury equipment for synthesis
3 Today: high throughput and downsizing
4 Microreactors! Threedimensional structures with inner dimensions under 1 mm High surface-to-volume area: m 2 m -3 (compared to about 100 m 2 m -3 for a traditional reactor) Efficient heat transfer - suitable for exothermic and endothermic reactions Temperature induced side reactions suppressed Higher safety (toxic compounds, high temperatures/pressures, explosions) Number of publications Series
5 Reviews T. Fukuyama, M. T. Rahman, M. Sato, I. Ruy, Adventures in Inner Space: Microflow Systems for Practical Organic Synthesis, Synlett, 2008, B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Greener Approaches to Organic Synthesis Using Microreactor Technology, Chem. Rev. 2007, 107, B. Ahmed-Omer, J. C. Brandt, T. Wirth, Advanced organic synthesis using microreactor technology, Org. Biomol. Chem. 2007, 5, P. Watts, C. Wiles, Micro reactors, a new tool for the synthetic chemist, Org. Biomol. Chem. 2007, 5, C. Wiles, P. Watts, Continous Flow Reactors, a Tool for the Modern Synthetic Chemist, Eur. J. Chem. 2007, P. Watts, C. Wiles, Recent advances in synthetic micro reactions technology, Chem.Commun. 2007, K. Geyer, J. D. C. Codée, P. H. Seeberger, Microreactors as Tools for Synthetic Chemists - The Chemists Round-Bottomed Flask of the 21st Century?, Chem. Eur. J. 2006, 12, M. Brivio, W. Verboom, D. N. Reinhoudt, Minituarized continous flow reaction vessels: Influence on chemical reactions, Lab Chip 2006, 6, P. Watts, S. J. Haswell, The application of micro reactors for organic synthesis, Chem. Soc. Rev. 2005, 34, K. Jänisch, V. Hessel, H. Löwe, M. Baerns, Chemistry in Microstructured Reactors, Angew. Chem. Int. Ed. 2004, 43, B. H. Weigl, R. L. Bardell, C. R. Cabrera, Lab-on-a-chip for drug development, Adv. Drug Deliv. Rev. 2003, 55, P. D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong, X. Zhang, Micro reactors: principles and applications in organic synthesis, Tetrahedron 2002, 58,
6 Downsizing Production of chemical compounds Synthesis of new compounds to be evaluated for specific applications Optimization of reactions Biotechnology (e g DNA sequencing) When can MRT be useful? Improved mixing & heat transfer compared to batch process Improved Yields Improved product profiles, higher purity Topmost reproducibility Safe & reliable handling of highly exothermic or hazardous reactions. Easy scale-up from mg to kg scale Easier handling of instable products & intermediates Minimise time frame for process development
7 Scaling up vs Numbering up CYTOS Pilot System P. Watts, C. Wiles, Micro reactors, a new tool for the synthetic chemist, Org. Biomol. Chem. 2007, 5, Capacity: tons/year Commercial microreactors Made of silicon, quartz, metal, polymer, ceramics, glass
8 B. H. Weigl, R. L. Bardell, C. R. Cabrera, Lab-on-a-chip for drug development, Adv. Drug Deliv. Rev. 2003, 55, Efficient mixing B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Greener Approaches to Organic Synthesis Using Microreactor Technology, Chem. Rev. 2007, 107,
9 Control of fluids Hydrodynamic flow (pressure-driven flow) Electrokinetic flow (electroosmotic flow) B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Greener Approaches to Organic Synthesis Using Microreactor Technology, Chem. Rev. 2007, 107, A: 50!l B: 50!l 100 product Applied voltage B Applied voltage A Conversion% Electroosmotic flow Oxidized silicon surface Y v X X X X X X O- O- O- Si Si Si direction of flow for the reacting species 0 v (ground) S Haswell, Hull
10 Synthesis of new compounds There are about stable compounds with mw! 500 (a size of molecules suitable for pharmaceuticals). Around 2-3x10 6 compounds are known today.. New compounds are needed for applications in Life sciences Material sciences There is a need for synthesis of new small organic molecules needed for test against targets Downsizing why? -! Availibility of material: stable compounds with up to 30 atoms of the elements C, O, N and S. If 1 mg of each is synthesized, the total mass of the products is g, to be compared to the mass of the universe, g. - Safety - Environmental aspects - Economy
11 High throughput strategies to identify effective organometallic chiral catalysts! Design Testing Design Synthesis Synthesis Testing Rational design and high throughput evaluation H3 C! OCH3 CH3 N S N HN OCH3 H3 C OCH3 CH3 N S H3 C O OCH3 CH3 N HN N OCH3 O S N HN OCH3
12 Optimization of reactions Reaction conditions: solvent temperature stoichiometry Catalyst structure: ligand metal ion activator Variation of substrate - scope and limitations Importance of temperature control for chemical selectivity B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107,
13 Reactive intermediates: lifetime shorter than generation time
14 Twostep/multistep reactions Synthesis - purification, separation
15 Synthesis - analysis! High throughput strategies to analyze yield and selectivity in catalytic reactions
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