Micro-Reactors from Laboratories to Production
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1 Micro-Reactors from Laboratories to Production Michael Grund, Michael Häberl, Dirk Schmalz, Hanns Wurziger Merck KGaA, Darmstadt, Germany CPAC Satellite Workshop, Rome, Page 1
2 Outline 1 Introduction 2 Nitration 3 Micro-reaction System Microtauros 4 Automated Reaction Optimisation 5 Upscale in Larger Laboratory Scale 6 Upscale in Pilot Plant 7 Conclusion CPAC Satellite Workshop, Rome, Page 2
3 What is a Microreactor? A microreactor is generally defined as a series of interconnecting channels ( microns in diameter) formed in a planar surface in which small quantities of reagents are manipulated. S.J. Haswell et al., Chem. Commun. 2001,391 CPAC Satellite Workshop, Rome, Page 3
4 Why Microreaction Technology? Why do we invest in Microreaction Technology? In microsystems the surface / volume ratio is increased ( m 2 /m 3 vs m 2 /m 3 ) heat transfer is very efficient improved control increased selectivity increased yields the stationary volume is small safety is increased defined flow characteristics CPAC Satellite Workshop, Rome, Page 4
5 Opportunities and Risks Isothermal processing of exothermal reactions Chemical processing within explosive regimens New process regimens possible Waste reduction and saving of resources Point-of-use synthesis of harmful chemicals Integrated systems Numbering-up instead of scaling-up Smaller production units and distributed production Accelerated development Potential for higher productivity Not realising the potential of the technology (early enough) Investing too much and too early in a technology that might not work CPAC Satellite Workshop, Rome, Page 5
6 The Reynolds Number Re = v l / v = flow rate [m/sec] l = diameter of channel [m] = density of fluid [kg /m 3 ] = viscosity [kg / m sec] Passau Re krit ~ 2300 in microchannels the Reynold numbers are far below 10! the flow is laminar CPAC Satellite Workshop, Rome, Page 6
7 The Merck-Ilmenau System The Merck-Patent CPAC Satellite Workshop, Rome, Page 7
8 Fluidic Handling System CPAC Satellite Workshop, Rome, Page 8
9 New Design of Micromixer CPAC Satellite Workshop, Rome, Page 9
10 Micro-Reaction System CPAC Satellite Workshop, Rome, Page 10
11 Nitration O N O O N O O N O O N + O H 2 N CPAC Satellite Workshop, Rome, Page 11
12 HPLC-chromatogram of the crude reaction mixture ortho-isomer meta-isomer para-isomer starting material higher nitrated products CPAC Satellite Workshop, Rome, Page 12
13 HPLC-chromatogram of the recrystallised product CPAC Satellite Workshop, Rome, Page 13
14 HPLC-chromatogram of the mother liquor para-isomer depleted CPAC Satellite Workshop, Rome, Page 14
15 Orienting Laboratory Nitrations Nitration with 65% nitric acid in acetic acid at room temperature Min Educt (%) Ortho (%) Meta/Para (%) 4,0 79,6 4,5 14,9 8,0 49,4 11,7 36,9 16,0 46,1 13,4 38,4 32,0 37,7 19,9 43,4 Nitration with 65% nitric acid in acetic acid at 52 C Min Educt (%) Ortho (%) Meta/Para (%) 8,0 25,6 29,6 42,3 16,0 8,8 34,6 53,1 Nitration with fuming nitric acid in acetic acid. Min Educt (%) Ortho (%) Meta/Para (%) 8,0 9,4 48,4 40,5 10,6 5,7 48,0 44,8 15,0 0,6 50,6 47,4 Nitration with 65% nitric acid in concentrated sulphuric acid Min Educt (%) Ortho (%) Meta/Para (%) 3,0 4,2 9,7 83,8 4,0 1,4 8,8 87,7 5,3 0,0 9,1 89,8 6,4 0,0 8,5 89,8 CPAC Satellite Workshop, Rome, Page 15
16 Nitration in a larger laboratory scale stoich. educt meta ortho para by-product selectivity Exp. C min ratio (%) (%) (%) (%) (%) (%) ,6 10,5 15,8 70,5 1,8 71, ,3 10,3 15,5 70,0 2,5 71, ,3 11,1 15,1 70,4 2,0 71, ,2 11,2 15,2 61,2 9,1 63, ,3 12,0 15,4 62,3 7,4 64, ,2 10,6 15,6 64,9 6,6 66, ,2 12,3 17,7 68,4 0,7 69, ,2 11,0 16,1 70,9 1,2 71, ,2 10,6 16,5 71,3 0,7 72, ,2 11,5 16,6 69,6 1,7 70, ,2 10,1 14,3 70,2 4,0 71,2 CPAC Satellite Workshop, Rome, Page 16
17 Nitration with neat 65% Nitric Acid Temperature Residence time Concentration of 4-(Phenyl)- morpholin-3-one in conc. Sulphuric Acid Excess of Nitric acid vs.4- (Phenyl)-morpholin-3-one Starting Material Ortho Product Meta Product Para Product Open Chain By-Product Conversion Selectivity Yield [mol/kg [mol/m [Area- [Area- [Area- [Area- [Area- [ C] [min] ] ol] %] %] %] %] %] [%] [%] [%] 10 2,5 0,53 1,00 0,250 12,550 14,420 69,800 0,900 99,74 71,28 71, ,5 0,53 2,00 0,000 13,100 14,250 69,500 1, ,00 70,95 70, ,5 0,83 1,00 2,100 14,000 12,800 68,600 0,700 97,86 69,86 68, ,5 0,83 2,00 0,500 15,300 12,100 69,500 0,800 99,49 70,77 70,41 CPAC Satellite Workshop, Rome, Page 17
18 Setup of the automatic reaction optimiser MICROTAUROS* Chemicals Controller Pumps Mixer HPLC re l. Y ie ld [ % ] re l. Y ie ld [ % ] Friedel-Crafts Friedel-Crafts Acylation, Acylation, 5 l/min 5 l/min Thermostatic bath Residence time loop Waste Temperature Temperature [ C] [ C] Plot * MICROreacTor for AUtomatic Reaction OptimiSation CPAC Satellite Workshop, Rome, Page 18
19 Microtauros Ancient coin from Knossos, Crete, featuring the Minotaur and on the enlarged back apparently a fluidic microreaction system with trenches and micropump rather than a labyrinth CPAC Satellite Workshop, Rome, Page 19
20 First Prototype of MICROTAUROS CPAC Satellite Workshop, Rome, Page 20
21 Second Prototype CPAC Satellite Workshop, Rome, Page 21
22 Contamination-free Sampling Device CPAC Satellite Workshop, Rome, Page 22
23 Flow-scheme and Modules for Process Development CPAC Satellite Workshop, Rome, Page 23
24 Conclusion We have described the evolution of the Merck Micro- Reaction System leading to the automatic reactionoptimiser Microtauros. Using the nitration of N-Phenylmorpholone the optimal parameters of the lab-scale were finally verified in the largescale process of 200 kg within 50 hours. For the first time it was shown that in principle the laboratory parameters can be used directly for a production process. CPAC Satellite Workshop, Rome, Page 24
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