πάντα ῥεῖ Using Advanced Fluids: Towards Adaptive Catalytic Systems for Asymmetric Catalysis Walter Leitner and Giancarlo Franciò
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1 πάντα ῥεῖ Continuous-Flow Organometallic Catalysis Using Advanced Fluids: Towards Adaptive Catalytic Systems for Asymmetric Catalysis Walter Leitner and Giancarlo Franciò Institut für Technische und Makromolekulare Chemie RSC/ACG Conference: Challenges in Catalysis for Pharmaceuticals and Fine Chemicals V London, UK, November 2, 2016
2 known reactions known processes flexible known reactions new processing windows integrated new reactions new control mechanisms adaptiv PRODUCTION DEVELOPMENT SYNTHESIS MACRO SCALE MOLECULAR SCALE MESO SCALE H. J. Federsel, Green Chemistry 2013, 15, Continous-flow production is on the top priority list of the Pharmaceutical Industry Round Table of the ACS Green Chemistry Institute!
3 Astra Zeneca API JAK2 kinase inhibitor Augustine Method molecular catalyst Metal oxide porous support material (e.g. silica, alumina) Electrostatic anchor (polyoxometallate, POM) Z. Amara, M. Poliakoff, R. Duque, D. Geier, G. Franciò, C. M. Gordon, R. E. Meadows, R. Woodward, W. Leitner Org. Proc. Res. Dev. 2016, 20, (ACS Editor s Choice)
4 ca 8 month development time, kg per day production, no purification necessary Z. Amara, M. Poliakoff, R. Duque, D. Geier, G. Franciò, C. M. Gordon, R. E. Meadows, R. Woodward, W. Leitner Org. Proc. Res. Dev. 2016, 20, (ACS Editor s Choice)
5 scco 2 substrates Upstream separation scco 2 product(s) Catalyst integrated separation Downstream separation. M. Poliakoff, P.Jessop, D. Cole-Hamilton, T. Baker/B. Tumas, T. Ikariya, K. Nozaki, A. Baiker, P. Lodzano, J. Brennecke,.. Handbook of Green Chemistry Volume 4: Supercritical Fluids,, Wiley-VCH, W. Leitner, Acc. Chem. Res. 2002, 35,
6 Gas-like: miscibility mass transfer pressure e p solid liquid gaseous super- critical critical point T c = 31.0 C p c = bar Liquid-like: solvent power heat capacity Unique: temperature T tunability reactivity Nontoxic, nonflammable, no ecotoxicity, cheap and abundant! Handbook of Green Chemistry Volume 4: Supercritical Fluids,, Wiley-VCH, W. Leitner, Acc. Chem. Res. 2002, 35,
7 Extraction Purification super- critical Catalysis Gas-like: miscibility mass transfer pressure e p Foto: Degussa Particle Formation solid liquid Foto: Natex/Prof. Weidner, Ruhr Uni Bochum critical point T c = 31.0 C Analytics p c = bar gaseous temperature T Foto: Thomas Swan Ltd / Prof. Poliakoff, Nottingham Liquid-like: solvent power heat capacity Chromatography Unique: tunability reactivity Foto: Foto: Separex Nontoxic, nonflammable, no ecotoxicity, cheap and abundant! Foto: Handbook of Green Chemistry Volume 4: Supercritical Fluids,, Wiley-VCH, W. Leitner, Technology Acc. Chem. Platform Res. 2002, for 35, scco
8 Downstream Separation OH IL / scco 2 O O CAL B (CH 2 ) 10 CH + O 3 + H 3 C(H 2 C) 10 O OH rac CH 3 CHO R S reaction 200 bar 50 C separation 130 bar 100 bar 70 C 100 C ee > 97 % sel. > 99.5 % recovery = 81 % OH CO 2 + substrates O O (CH 2 ) 11 H enzyme in ionic liquid high CO 2 -density low CO 2-density ee > 97 % sel. > 99.5 % recovery = 97 % M. T. Reetz, W. Wiesenhöfer, G. Franciò, W. Leitner, Adv. Synth. Catal. 2003, 345, 1221
9 Multiphase Catalysis Compressed air I-1 V-16 V-17 PIRA+ I-4 V-15 vent Ionic Liquid scco 2 S P CO2 WIR I-6 Substrate TIRC V-18 V-14 V-12 E-8 I-8 V-20 E-7 vent PIA+ PIRCA+ I-3 I-7 V-19 V-11 V-2 V-3 E-5 HPLC FCR+ I-11 PIRA+ I-2 V-10 V-9 vent V-13 E-3 V-1 V-4 TIRC I-9 E-9 Back pressure Regulator BPR Gas-liquid separator E-12 E-10 CO2/H2 to vent P-33 V-21 E-1 Dry ice ethanol chiral catalyst H2 E-4 V-6 V-7 V-8 I-10 MFC V-5 TIRCA+ I-5 E-2 Window reactor Liq. Product Fraction collector el. K N, i ci ( CO2) c ( IL) i C. Roosen, J.-L. Muller, M. Kaever, H. Kronenberg, R. Thelen, S. Aey, T. Harwardt, W. Leitner, L. Greiner, J. Supercrit. Fluids 2009, 48,
10 CO 2 [Ru( 6 -benzene)cl 2 ] 2 Ionic Liquid J. Theuerkauf, G. Franciò, W. Leitner, Adv. Synth. Catal., 2013, 355,
11 Cv, ee [% %] ee: 90% TOF: 122 h STY = 0.15 kg/l h productivity: 30 kg / g (Ru) conv. ee 5000 TON t [h] TON J. Theuerkauf, G. Franciò, W. Leitner, Adv. Synth. Catal., 2013, 355,
12 Processing profile for 100 kg of product Batch Cont. Flow Number of batches 4 1 Reaction unit [L] 50 5,4 Reaction solvent [L] ,7 Catalyst [g] Reaction time [h] 4x6 96 Processing time [weeks] 1-2 <1 Pressure [bar] Temperature [ C] J. Theuerkauf, G. Francio, W. Leitner, Adv. Synth. Catal., 2013, 355,
13 solubility: product > substrate acid co-catalyst [Ru( 6 -benzene)cl 2 ] 2 solubility: product < substrate base co-catalyst t J. Theuerkauf, G. Franciò, W. Leitner, Adv. Synth. Catal., 2013, 355,
14 T. M. Konrad, P. Schmitz, W. Leitner, G. Franciò, Chem. Eur. J. 2013, 19,
15 C. Schmitz, K. Holthusen, W. Leitner, G. Franciò, ACS Catal. 2016, 6, (ACS Editor s choice). For asymmeric hydroformylation in scco 2 flow, see: K. Nozaki et al., J. Am. Chem. Soc. 2003, 125,
16 Comparison of Immobilization Strategies: Modular Set-Up Z. Zhang, G. Franciò, W. Leitner, ChemCatChem, 2015, 7,
![Cv v, ee [%] 100 90 80 70 60 50 40 30 20 10 0 90000](/docs-images/87/97063423/images/17-0.jpg "80000 70000 60000 50000 40000 30000 conv.")
![20000 ee TON 10000 0 0 50 100 150 200 250 t[h] TON Z.](/docs-images/87/97063423/images/17-1.jpg "Zhang, G. Franciò, W.")
17 Cv v, ee [%] conv ee TON t[h] TON Z. Zhang, G. Franciò, W. Leitner, ChemCatChem 2015, 7,
18 Cole-Hamilton Wasserscheid, Ferhmann/Rijsager, Hölderich,.. Supported Ionic Liquid Phase For gas phase C4-hydroformylation y see: S. Walter, M. Haumann, P. Wasserscheid, H. Hahn, R. Franke, AIChE J. 2015, 61, 893. G. Francò, U. Hintermair, W. Leitner, Phil. Trans. R. Soc. A 2015, 373,
19 scco 2 scco 2 H 2 water scavenger SILP catalyst ee > 99% lab scale: > 1 kg/week STY = 0.3 kg/l x h productivity: > 100 kg / g (Rh) U. Hintermair, G. Franciò, W. Leitner, Chem. Eur. J. 2013, 19,
20 MFC (CO 2 ) MFC (H 2 ) Pump Reactor Sampling Analytics labscale 80 ml N /min 20 ml N /min 0.04 ml/min 10 ml manual offline upscaled 4 L N /min 1 L N /min 2.12 ml/min 170 ml automated online SYNFLOW Demonstrator Unit: An Adaptive Reactor System
21 Possible interactions of catalyst complex and IL matrix Ion Pairing - Ligand Conformation + Coordination Early Examples for External chirality transfer: Seebach, Anderson, Brown, Faller, Mikami,.. Angew. Chem Int. Ed. 2006, 45, ; Chem. Commun. 2007, ; Angew. Chem. Int. Ed. 2008, 47, ; ChemCatChem. 2010, 2,
22 ee = 69 % (S) racemic catalyst chiral ionic liquid rac-binap (R)-BINAP ppm 31 P{ 1 H}-NMR D. Chen, M. Schmitkamp, G. Franciò, J. Klankermayer, W. Leitner, Angew. Chem. Int. Ed. 2008, 47,
23 Ph 2 P O Rh P O Ph 2 chiral IL CH 2 Cl 2, -10 C, 10 min Ph 2 P N Rh H O P Ph 2 NTf 2 - OMe + Ph - 2 NTf 2 P N diastereomerisation Rh H O OMe CH 2 Cl 2, P Ph 50 C, 20 h 2 Ph 2 P N Rh H O P Ph 2 OMe NTf 2 - (S a S c ) (R a S c ) (R a S c ) chiral ionic liquid P. Oczipka, D. Müller, W. Leitner, G. Franciò, Chem. Sci. 2016, 7,
24 P. Oczipka, D. Müller, W. Leitner, G. Franciò, Chem. Sci. 2016, 7,
25 scco 2 substrates scco 2 product(s) Catalyst in supported liquid phase matrix For Review, see: E. García-Verdugo, B. Altava, M. I. Burguete, P. Lozano, S. V. Luis, Green Chem. 2015, 17, For Review, see: K. L. Luska, P. Migowski, W. Leitner, Green Chem. 2015, 17; Review (gold open access): G. Franciò, U. Hintermair, W. Leitner, Phil. Trans. R. Soc. A. 2015, 373,
26 DFG Thomas Müller* Marcus Rose Marcel Liauw Regina Palkovits Walter Leitner Jürgen Klankermayer Giancarlo Franciò Markus Hölscher Nils Theyssen* * affiliated members Technical RWTH Aachen University
27 πάντα ῥεῖ panta rhei Ἡράκλειτος Heraclitus ca BC all flows
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