Download PDF
Jamison, T. F. et al.: 2018 Science of Synthesis, 2018/5: Flow Chemistry in Organic Synthesis DOI: 10.1055/sos-SD-228-00262
Flow Chemistry in Organic Synthesis

15.3 Flow Chemistry in the Pharmaceutical Industry: Part 3

More Information

Book

Editors: Jamison, T. F.; Koch, G.

Authors: Beeler, A. B.; Beingessner, R. L.; Bottecchia, C.; Browne, D. L.; Coley, C. W.; Ferguson, S.; Folgueiras-Amador, A. A.; Gilmore, K.; Hicklin, R. W.; Imbrogno, J.; Itsuno, S.; Jamison, T. F.; Jensen, K. F.; Kelly, L. P.; Kerr, M. S.; Kiesman, W. F.; Kim, H.; Kwok, D.-I. A.; Ley, S. V.; Longstreet, A. R.; May, S. A. ; McTeague, T. A.; Mijalis, A. J.; Mo, Y.; Moon, S.; Myerson, A.; Noël, T.; O’Brien, A. G.; O’Brien, M.; O’Mahony, M.; Opalka, S. M.; Pentelute, B. L.; Polyzos, A. ; Schepartz, A.; Seeberger, P. H.; Seo, H.; Steinauer, A.; Stelzer, T.; Stephenson, C. R. J.; Strom, A. E.; Styduhar, E. D.; Sun, A. C.; Telmesani, R.; Thomas, D. A.; Tran, T. H.; Ullah, M. S.; Wicker, A. C.; Wirth, T.; Yoshida, J.

Title: Flow Chemistry in Organic Synthesis

Print ISBN: 9783132423312; Online ISBN: 9783132423350; Book DOI: 10.1055/b-006-161272

1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner (Editor-in-Chief), A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

When considering whether to develop a flow-chemistry approach to a particular synthetic route, the criteria of safety, quality, cost, sustainability, scalability, and speed are all considered. This chapter presents a case study of a single reaction, the formylation of an aryl bromide, being performed in a batch reactor, a microreactor, a plug-flow reactor, and a spinning-disk reactor. An assessment of the various technologies is made with respect to the abovementioned criteria.

Key words

Keywords: - flow chemistry - scale-up - batch reactions - microreactors - plug-flow reactors - spinning-disk reactors - process development - optimization
 
  • 1 Burcham CL, Florence AJ, Johnson MD. Annu. Rev. Chem. Biomol. Eng 2018; 9: 253
  • 2 Nepveux K, Sherlock J.-P, Futran M, Thien M, Krumme M. J. Pharm. Sci 2015; 104: 850
  • 3 Cole KP, Johnson MD. Expert Rev. Clin. Pharmacol 2018; 11: 5
  • 4 Laue S, Haverkamp V, Mleczko L. Org. Process Res. Dev 2016; 20: 480
  • 5 Thaisrivongs DA, Naber JR, Rogus NJ, Spencer G. Org. Process Res. Dev 2018; 22: 403
  • 6 Feng R, Ramchandani S, Ramalingam B, Tan SWB, Li C, Teoh SK, Boodhoo K, Sharratt P. Org. Process Res. Dev 2017; 21: 1259
  • 7 Kopach ME, Cole KP, Pollock PM, Johnson MD, Braden TM, Webster LP, McClary Groh J, McFarland AD, Schafer JP, Adler JJ, Rosemeyer M. Org. Process Res. Dev 2016; 20: 1581
  • 8 Nagaki A, Yoshida J.-I. Top. Organomet. Chem 2016; 57: 137
  • 9 Throughout this chapter, the terms butyllithium and BuLi refer to the unbranched alkyllithium, n-butyllithium.
  • 10 Tai O, Hopson R, Williard PG. Org. Lett 2017; 19: 3966
  • 11 Collum DB. Acc. Chem. Res 1992; 25: 448
  • 12 Usutani H, Tomida Y, Nagaki A, Okamoto H, Nokami T, Yoshida J.-I. J. Am. Chem. Soc 2007; 129: 3046
  • 13 Nagaki A, Tomida Y, Usutani H, Kim H, Takabayashi N, Nokami T, Okamoto H, Yoshida J.-I. Chem.–Asian J 2007; 2: 1513
  • 14 Jensen KF. AIChE J 2017; 63: 858
  • 15 Mielke E, Plouffe P, Koushik N, Eyholzer M, Gottsponer M, Kockmann N, Macchi A, Roberge DM. React. Chem. Eng 2017; 2: 763
  • 16 Holvey CP, Roberge DM, Gottsponer M, Kockmann N, Macchi A. Chem. Eng. Process 2011; 50: 1069
  • 17 Mielke E, Roberge DM, Macchi A. J. Flow Chem 2016; 6: 279
  • 18 Tu NP, Hochlowski JE, Djuric SW. Mol. Diversity 2012; 16: 53
  • 19 Vaxelaire S, Gonze E, Merlin G, Gonthier Y. Environ. Technol 2008; 29: 1307
  • 20 Cintas P, Tagliapietra S, Caporaso M, Tabasso S, Cravotto G. Ultrason. Sonochem 2015; 25: 8
  • 21 Roberge D, Rainone F, Quittmann W, Gottsponer M, Eyholzer M. WO 2011023761, 2011
  • 22 Britton J, Jamison TF. Nat. Protoc 2017; 12: 2423
  • 23 Slocum DW, Reinscheld TK, Austin ND, Kusmic D, Whitley PE. Synthesis 2012; 44: 2531
  • 24 Jacobsen NC, Hinrichsen O. Ind. Eng. Chem. Res 2012; 51: 11643
  • 25 Boodhoo K, In Process Intensification for Green Chemistry: Engineering Solutions for Sustainable Chemical Processing. Boodhoo K, Harvey A. Wiley; Hoboken, NJ 2013
    Google Scholar
  • 26 Oxley P, Brechtelsbauer C, Ricard F, Lewis N, Ramshaw C. Ind. Eng. Chem. Res 2000; 39: 2175
  • 27 A newer model can now operate at pressures of up to 10 bar.
  • 28 Kern S, Meyer K, Guhl S, Gräßer P, Paul A, King R, Maiwald M. Anal. Bioanal. Chem 2018; 410: 3349
  • 29 Sheldon RA. Chem. Soc. Rev 2012; 41: 1437
  • 30 Fanelli F, Parisi G, Degennaro L, Luisi R. Beilstein J. Org. Chem 2017; 13: 520
  • 31 Dallinger D, Kappe CO. Curr. Opin. Green. Sustainable Chem 2017; 7: 6
  • 32 Poechlauer P, Colberg J, Fisher E, Jansen M, Johnson MD, Koenig SG, Lawler M, Laporte T, Manley J, Martin B, OʼKearney-McMullan A. Org. Process Res. Dev 2013; 17: 1472
  • 33 Roschangar F, Sheldon RA, Senanayake CH. Green Chem 2015; 17: 752
  • 34 Sheldon RA. Green Chem 2007; 9: 1273
  • 35 Sheldon RA. Green Chem 2017; 19: 18
  • 36 May SA, Johnson MD, Braden TM, Calvin JR, Haeberle BD, Jines AR, Miller RD, Plocharczyk EF, Rener GA, Richey RN, Schmid CR, Vaid RK, Yu H. Org. Process Res. Dev 2012; 16: 982
  • 37 Wang T, Lu H, Wang J, Xiao Y, Zhou Y, Bao Y, Hao H. J. Ind. Eng. Chem 2017; 54: 14
  • 38 Zhang D, Xu S, Du S, Wang J, Gong J. Engineering 2017; 3: 354
  • 39 Hohmann L, Löbnitz L, Menke C, Santhirakumaran B, Stier P, Stenger F, Dufour F, Wiese G, zur Horst-Meyer S, Kusserow B, Zang W, Nirschl H, Kockmann N. Chem. Eng. Technol 2018; 41: 1152
  • 40 Cole KP, McClary Groh J, Johnson MD, Burcham CL, Campbell BM, Diseroad WD, Heller MR, Howell JR, Kallman NJ, Koenig TM, May SA, Miller RD, Mitchell D, Myers DP, Myers SS, Phillips JL, Polster CS, White TD, Cashman J, Hurley D, Moylan R, Sheehan P, Spencer RD, Desmond K, Desmond P, Gowran O. Science (Washington, D. C.) 2017; 356: 1144
  • 41 Britton J, Raston CL. Chem. Soc. Rev 2017; 46: 1250
  • 42 Shukla CA, Kulkarni AA. Beilstein J. Org. Chem 2017; 13: 960
  • 43 May SA. J. Flow Chem 2017; 7: 137
  • 44 Srai JS, Badman C, Krumme M, Futran M, Johnston C. J. Pharm. Sci 2015; 104: 840
  • 45 McWilliams JC, Allian AD, Opalka SM, May SA, Journet M, Braden TM. Org. Process Res. Dev 2018; 22