New Developments in Flow Chemistry 20 November 2013 Christian Hornung Research Scientist CSIRO Materials Science and Engineering
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1 uture of Chemical Manufacturing: rom Pots to Pipes New Developments in low Chemistry 20 November 2013 Christian Hornung Research Scientist CSIR Materials Science and Engineering
2 utline 1 New Developments in low Chemistry DSM Process ptimization (Ritter Reaction) presented in Munich, June 2013 EPSRC Continuous Crystallization presented in Munich, June 2013 Univ. South Australia Continuous Solvent Extraction of Metals presented in Singapore, Nov NUS Crystallization from Microfluidic Emulsions presented in Singapore, Nov Continuous low Processing of RAT Polymers Synthesis of Homo Polymers ptimization and Scale up Reactor Characterization (Residence Time Distribution) low Synthesis of lock Copolymers RAT End Group Removal / Modification CSIR. Continuous Processing & Microreactor Technology
3 utline 1 New Developments in low Chemistry DSM Process ptimization (Ritter Reaction) presented in Munich, June 2013 EPSRC Continuous Crystallization presented in Munich, June 2013 Univ. South Australia Continuous Solvent Extraction of Metals presented in Singapore, Nov NUS Crystallization from Microfluidic Emulsions presented in Singapore, Nov Continuous low Processing of RAT Polymers Synthesis of Homo Polymers ptimization and Scale up Reactor Characterization (Residence Time Distribution) low Synthesis of lock Copolymers RAT End Group Removal / Modification CSIR. Continuous Processing & Microreactor Technology
4 Continuous low Processing at CSIR CSIR. Continuous Processing & Microreactor Technology
5 Continuous low Processing at CSIR CSIR. Continuous Processing & Microreactor Technology
6 Continuous low Processing at CSIR CSIR. Continuous Processing & Microreactor Technology
7 Continuous low Processing at CSIR CSIR. Continuous Processing & Microreactor Technology
8 Microfluidic Solvent Extraction of Metal Ions and Complexes from Leach Solutions Containing Nanoparticles for Cu and Cr extractions h = 1 refers to complete phase separation Craig Priest Priest, C., Zhou, J., Klink, S., Sedev, R., Ralston, J., Microfluidic solvent extraction of metal ions and complexes from leach solutions containing nanoparticles, Chemical Engineering & Technology, 35, 1312 (2012)
9 Spherical Crystallization of Glycine from Monodisperse Microfluidic Emulsions Saif A. Khan Arpad I. Toldy, Abu Zayed M. adruddoza, Lu Zheng, T. Alan Hatton, Rudiyanto Gunawan, Raj Rajagopalan, and Saif A. Khan; Cryst. Growth Des., 2012, 12 (8), pp
10 utline 1 New Developments in low Chemistry DSM Process ptimization (Ritter Reaction) presented in Munich, June 2013 EPSRC Continuous Crystallization presented in Munich, June 2013 Univ. South Australia Continuous Solvent Extraction of Metals presented in Singapore, Nov NUS Crystallization from Microfluidic Emulsions presented in Singapore, Nov Continuous low Processing of RAT Polymers Synthesis of Homo Polymers ptimization and Scale up Reactor Characterization (Residence Time Distribution) low Synthesis of lock Copolymers RAT End Group Removal / Modification CSIR. Continuous Processing & Microreactor Technology
11 RAT Polymerization RAT: Reversible Addition ragmentation Chain Transfer Controlled radical polymerization Chains continuously re initiated Tailored molecular weight (M n ~ moles RAT agent) Mostly living (dormant) chain ends with fast activation/deactivation n average, all chains grow simultaneously Narrow molecular weight distribution Access to complex architectures (blocks) Conjugation to reactive molecules (drugs, biomolecules, etc.) blocks grafts stars Conventional Polymerization RAT Polymerization dormant chains dead chains Monomer(s) insert here Molecular Weight (g mol -1 ) CSIR. RAT Polymerisation
12 Continuous low Processing at CSIR Vapourtec R2/R4 system Uniqsis lowsyn AMT Coflore CRD gas liquid reactor module tubular reactor modules Liquid / Gas Liquid and Slurry Reactions: organic synthesis of small molecules synthesis of new materials: e.g. polymers, ionic liquids CRD tubular scale up reactor CSIR. Continuous Processing & Microreactor Technology
13 RAT Polymerisation in Continuous low two different operation modes: RAT agents: monomers: conversion [%] pdma batch segmented flow continuous flow time [h] C.H. Hornung, C. Guerrero-Sanchez, M. rasholz, S. Saubern, J. Chiefari, G. Moad, E. Rizzardo, S.H. Thang, rg. Process Res. Dev., 2011, 15(3),
14 RAT Polymerisation in Continuous low polydispersity index [-] conversion [%] ) ) 92 2) ) ) 3) ) ) C 80 C 90 C 100 C 80 C 80 C 100 C NIPAM 1 NIPAM 2 NIPAM 3 NIPAM 4 DMA 5 na 6 VAc 7 5) 85 7) C 80 C 90 C 100 C 80 C 80 C 100 C NIPAM 1 NIPAM 2 NIPAM 3 NIPAM 4 DMA 5 na 6 VAc 7 5) 7) 81 8) 8) Mn [g/mol] 5 x10 ml ) ) ) ) C 80 C 90 C 100 C 80 C 80 C 100 C NIPAM 1 NIPAM 2 NIPAM 3 NIPAM 4 DMA 5 na 6 VAc 7 HN NIPAM SCALE UP: 50 ml flow reactor capable of producing 1.36 kg polymer (pdma) per day. N DMA 5) na 7) VAc 8) C.H. Hornung, C. Guerrero-Sanchez, M. rasholz, S. Saubern, J. Chiefari, G. Moad, E. Rizzardo, S.H. Thang, rg. Process Res. Dev., 2011, 15(3),
15 Scale-up of the RAT Process Synthesis of Acid unctional Polymers in Water: H H S n S S H H HN S n S S H S 3 H DI water Inline degasser Tubular low Reactor: tubing ID 6 mm static mixers reactor volume 108 ml min 0.5 L stock sol. per run N 2 Supply ml/min Polymer Monomer Solution CSIR. Microreactor Technology submitted to Processes, 2013
16 Scale-up of the RAT Process Synthesis of polyacrylic acid in water: Tubular continuous flow reactor (6 mm ID, V R = 108 ml) 0.5 L monomer solution per run / experiment RAT agent: trithiocarbonate containing carboxylic acid groups average conversion at steady state: 95% Problems with scale up in batch: temperature gradients concentration gradients dead zones inefficient mixing small scale batch comparison at identical conditions: 95% small ideal system Laboratory large non ideal system Industry CSIR. Microreactor Technology submitted to Processes, 2013
17 Scale-up of the RAT Process Temperature Profiles: paac 2 5 ml MW paac 3 20 ml MW paac ml R paac ml R paac ml flow T [ C] t [min] Problems with scale up in batch: temperature gradients concentration gradients dead zones inefficient mixing small ideal system Laboratory large non ideal system Industry CSIR. Microreactor Technology submitted to Processes, 2013
18 Reaction Profiling Axial dispersion in tubular reactors 1 3 : at reactor inlet: ideal plug Reaction Profiles taken on Vapourtec SS tubular reactor modules (1 2.2 mm ID): 4 multiple NMR samples in 2 to 7 min intervals conversion profile Pe crit = 100 laminar flow profile at reactor outlet: dispersed plug well defined fluid segment (e.g. monomer solution or tracer dye) dispersed fluid segment different flow rate Pe = 503 Pe = mm ID 2.2 mm ID different reactor tube diameter 10 or 20 ml PLUG LW CRITERIA 1 2 : Pe v l D ax d 2 2 v D ax D 192 D Pe 100 reactor behaves plug flow like different sample size Pe 100 axial dispersion is significant (1) G.I. Taylor, Proc. R. Soc. London, Ser. A, 1953, 219, /// (2). Levenspiel, Chemical Reaction Engineering, Wiley: New York, (3) C.H. Hornung and M.R. Mackley, Chem. Eng. Sci., 2009, 64, /// (4) C. H. Hornung, X. Nguyen, G. Dumsday, S. Saubern, Macromol. React. Eng., 2012, 6,
19 Inline Degassing / Integrated low Process inline degasser 2 concentration [mg/l] 7 6 nitrogen 0.2 l/min nitrogen 0.5 l/min 5 nitrogen 0.7 l/min in line degasser 1 loop degassing time [min] measurement of dissolved oxygen in aqueous systems: % 2 Deoxygenating time for 40 ml of monomer stock solution: atch freeze pump thaw min atch nitrogen purging 5 20 min low inline degassing continuous C. H. Hornung, X. Nguyen, G. Dumsday, S. Saubern, Macromol. React. Eng., 2012, 6,
20 Synthesis of lock Copolymers in low HM PLYMER DI LCK Reactor system: Vapourtec R2/R4 SS 10 ml coils Method Ratio M:R:I Solvent Reaction Temp. [ C] Reaction TIme [min] Conv. [%] M n theo [g/mol] M n GPC [g/mol] M w /M n [ ] batch 100 : 1.0 : 0.2 MeCN 70 / / / cont 100 : 1.0 : 0.2 MeCN 70 / / 60 / batch 100 : 0.5 : 0.1 MeCN 80 / / / batch 100 : 0.5 : 0.1 Acetone 75 / / / cont 100 : 0.5 : 0.1 Acetone 75 / / 40 / DMA / ta DMA / ta DMA / ta C.H. Hornung, X. Nguyen, S. Kyi, J. Chiefari, S. Saubern, Aust. J. Chem., 2013, 66,
21 RAT End Group Removal / Modification block copolymers X X "click" R n-1 SH block conjugates copolymers RAT Y Y X ATRP nucleophiles X Cu I R n-1 thermolysis Y Y S X X R' X X X X R n-1 S Z R n-1 H [H] R Y Y radical-induced n-1 S Z [4+2] R' Y Y reduction Y Y S 2 X X Co II R' R' R n-1 R' 2 R' M Y Y hetero Diels Alder [H] N addition-fragmentationcoupling X X X X R X X R n-1 N n-1 Y Y R n-1 H Y Y Y Y NMP radical-induced oxidation X R n-1 Y X Y H block copolymers G. Moad, E. Rizzardo, S.H. Thang, End-functional polymers, thiocarbonylthio group removal/transformation and reversible addition-fragmentation-chain transfer (RAT) polymerization, Polymer International, 2011, 60(1), 9-25.
22 Radical Induced End Group Removal - complete desulfurization unreactive end group - organic solvents or water - comparison: batch v flow process pdma flow batch before g/mol / g/mol / g/mol / 1.03 steel reactor coil time [min] example: pdma Reaction conditions: SS reactor coil 10 ml Reaction time: 120 min Reaction temperature: 100 C before after ~ 100% conversion for pdma, ps, pnipam C. H. Hornung, A. Postma, S. Saubern, J. Chiefari, Macromol. React. Eng. 2012, 6,
23 low Thermolysis Two Step Process Reaction conditions: SS reactor coil 10 ml Reaction time: 60 min Reaction temperature: C pmma before thermolysis after thermolysis polymer reactor 1 (polymerisation) reactor 2 (thermolysis) molar ratio M/R/I T [ C] t [h] conversion [%] M n [g/mol] Ð [-] pma 10 ml 5 ml 100/1.2/ / / 1 97 / pma batch batch 100/1.2/ / / 1 97 / pmma 10 ml 5 ml 100/1.2/ / / 1 46 / ~ pmma 10 ml 5 ml 100/1.2/ / / 1 59 / ~ pmma 2 10 ml 5 ml 100/1.2/ / / 1 84 / ~ polymerisation thermolysis (1) J. Chiefari, C.H. Hornung, A. Postma, S. Saubern, RAT Polymers, 2011, W , /// (2) to be submitted to Polymer, 2013
24 Conclusions ully Integrated low Process Continuous low Processing bridges the gap from laboratory / discovery scale to preparation / small production scale: mg to kg Integrated Processing allows for combination of several processing steps to form one continuous production line, e.g. purification, block co polymers, Efficient Processing is achieved by using micro and millimetre scale flow geometries enhanced heat and mass transfer, large surface to volume ratio CSIR. Continuous Processing & Microreactor Technology
25 Thank you Acknowledgements Ivan Martinez Thomas Kohl Xuan Nguyen Julien Rosselgong Nenad Micic Alan Young Paul Savage John Tsanaktsidis John Chiefari Ezio Rizzardo San Thang Graeme Moad Simon Saubern Tash Polyzos Almar Postma Stella Kyi Maria Espiritu Carlos Guerrero Sanchez CSIR Material Science and Engineering Christian Hornung Research Scientist t e christian.hornung@csiro.au w mail: ag 10, Clayton South Victoria 3169 Australia
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