Flow Process Development and Optimization of A Suzuki-Miyaura Cross Coupling Reaction using Response Surface Methodology

*Girish Basavaraju  -  Department of Chemical Engineering, Dayanand Sagar College of Engineering, India
Ravishankar Rajanna  -  Department of Chemical Engineering, Dayanand Sagar College of Engineering, India
Received: 22 Jun 2020; Revised: 24 Jul 2020; Accepted: 25 Jul 2020; Published: 1 Dec 2020; Available online: 15 Aug 2020.
Open Access Copyright (c) 2020 Bulletin of Chemical Reaction Engineering & Catalysis
License URL: http://creativecommons.org/licenses/by-sa/4.0

Citation Format:
Cover Image
Article Info
Section: Original Research Articles
Language: EN
In 2020: BCREC Volume 15 Issue 3 Year 2020 (Issue in Progress, December 2020)
Statistics: 92 10
Abstract

A custom-made tubular flow reactor was utilized to develop a mathematical model and optimize the Suzuki-Miyaura cross coupling reaction. In this study, the experimentation was designed and executed through the statistical design of experiments (DoE) approach via response surface methodology. The effect of molar ratios of phenylboronic acid (1) and 4-bromophenol (2), temperature, the catalyst tetrakis(triphenylphosphine)palladium, and equivalence of aqueous tripotassium phosphate was studied in detail. The flow reactor profile was in good agreement with batch conditions and significant improvements to the overall reaction time and selectivity towards desired [1-1-biphenyl]-4-ol (3) was achieved. The Suzuki coupling reaction in batch condition would take on an average of 4 to 6 hours to complete, which was effectively accomplished in 60 to 70 minutes in this tubular reactor setup and could be operated continuously. The reaction model is in good agreement with the reaction conditions. Copyright © 2020 BCREC Group. All rights reserved

 

Keywords: Continuous flow chemistry; Suzuki coupling reaction; Customized flow reactor; Tubular reactor; Design of experiments (DoE)

Article Metrics:

  1. Yin, L., Liebscher, J. (2007). Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts. Chemical Reviews, 107, 133−173.
  2. Agrofoglio, L.A., Gillaizeau, I., Saito, Y. (2003). Palladium-assisted routes to nucleosides. Chemical Reviews, 103, 1875−1916.
  3. Crawford, K.A. (2014). Direct comparison of homogeneous and heterogeneous palladium (II) catalysts for Suzuki-Miyaura cross-coupling reactions. PhD Thesis, The University of Texas at Austin, USA.
  4. Barnard, B.C. (2008). Palladium-catalyzed C‐C Coupling: Then and Now. Platinum Metals Review, 52, 38−45.
  5. Johansson Seechurn, C.C., Kitching, M.O., Colacot, T.J., Snieckus, V. (20120. Palladium‐catalyzed cross‐coupling: a historical contextual perspective to the 2010 Nobel Prize. Angewandte Chemie International Edition, 51, 5062−5085.
  6. Len, C., Bruniaux, S., Delbecq, F., Parmar, V.S. (2017). Palladium-catalyzed Suzuki–Miyaura cross-coupling in continuous flow. Catalysts, 7, 146.
  7. Paterson, I., Davies, R.D., Marquez, R. (2001). Total synthesis of the callipeltoside aglycon. Angewandte Chemie, 113, 623−627.
  8. Hiyama, T., Hatanaka, Y. (1994). Palladium-catalyzed cross-coupling reaction of organometalloids through activation with fluoride ion. Pure and applied chemistry, 66, 1471−1478.
  9. Haswell, S.J., Watts, P. (2003). Green chemistry: synthesis in micro reactors. Green Chemistry, 5, 240−249.
  10. Wiles, C., Watts, P. (2012). Continuous flow reactors: a perspective. Green Chemistry, 14, 138−154.
  11. Newman, S.G., Jensen, K.F. (2013). The role of flow in green chemistry and engineering. Green chemistry, 15, 1456−1472.
  12. Wiles, C., Watts, P. (2014). Continuous process technology: a tool for sustainable production. Green Chemistry, 16, 55−62.
  13. Vaccaro, L., Lanari, D., Marrocchi, A., Strappaveccia, G. (2014). Flow approaches towards sustainability. Green Chemistry, 16, 3680−3704.
  14. Falß, S., Tomaiuolo, G., Perazzo, A., Hodgson, P., Yaseneva, P., Zakrzewski, J., Guido, S., Lapkin, A., Woodward, R., Meadows, R.E. (2016). A continuous process for Buchwald–Hartwig amination at micro-, lab-, and mesoscale using a novel reactor concept. Organic Process Research & Development, 20, 558−567.
  15. Suzuki, A. (2011). Cross‐coupling reactions of organoboranes: an easy way to construct C−C bonds (Nobel Lecture). Angewandte Chemie International Edition, 50, 6722−6737.
  16. Shu, W., Pellegatti, L., Oberli, M.A., Buchwald, S.L. (2011). Continuous‐Flow Synthesis of Biaryls Enabled by Multistep Solid‐Handling in a Lithiation/Borylation/Suzuki–Miyaura Cross‐Coupling Sequence. Angewandte Chemie, 123, 10853−10857.
  17. Kobayashi, S. (2016). Flow “fine” synthesis: high yielding and selective organic synthesis by flow methods. Chemistry–An Asian Journal, 11, 425−436.
  18. Geyer, K., Codee, J.D., Seeberger, P.H. (2006). Microreactors as tools for synthetic chemists—the chemists' round‐bottomed flask of the 21st century?. Chemistry–A European Journal, 12, 8434−8442.
  19. Delville, M.M., Nieuwland, P.J., Janssen, P., Koch, K., van Hest, J.C., Rutjes, F.P. (2011). Continuous flow azide formation: Optimization and scale-up. Chemical engineering journal, 167, 556−559.
  20. Zhang, C., Zhang, J., Luo, G. (2016). Kinetic study and intensification of acetyl guaiacol nitration with nitric acid—acetic acid system in a microreactor. Journal of Flow Chemistry, 6, 309−314.
  21. Anxionnaz, Z., Cabassud, M., Gourdon, C., Tochon, P. (2008). Heat exchanger/reactors (HEX reactors): concepts, technologies: state-of-the-art. Chemical Engineering and Processing: Process Intensification, 47, 2029−2050.
  22. Koch, K., van Weerdenburg, B.J., Verkade, J.M., Nieuwland, P.J., Rutjes, F.P., van Hest, J.C. (2009). Optimizing the deprotection of the amine protecting p-methoxyphenyl group in an automated microreactor platform. Organic Process Research & Development, 13, 1003−1006.
  23. Becker, R., van den Broek, S.B.A., Nieuwland, P.J., Koch, K., Rutjes, F.P. (2012). Optimisation and Scale-up of α-Bromination of Acetophenone in a Continuous Flow Microreactor. Journal of Flow Chemistry, 2, 87−91.
  24. Fabry, D.C., Sugiono, E., Rueping, M., Meunier, F.C. (2016). Reaction Chemistry & Engineering. Chem. Eng., 1, 165.
  25. Nieuwland, P.J., Koch, K., van Harskamp, N., Wehrens, R., van Hest, J.C., Rutjes, F.P. (2010). Flash Chemistry Extensively Optimized: High‐Temperature Swern–Moffatt Oxidation in an Automated Microreactor Platform. Chemistry–An Asian Journal, 5, 799−805.
  26. Nagaki, A., Kim, H., Usutani, H., Matsuo, C., Yoshida, J.I. (2010). Generation and reaction of cyano-substituted aryllithium compounds using microreactors. Organic & biomolecular chemistry, 8, 1212−1217.
  27. Hafner, A., Filipponi, P., Piccioni, L., Meisenbach, M., Schenkel, B., Venturoni, F., Sedelmeier, J. (2016). A simple scale-up strategy for organolithium chemistry in flow mode: From feasibility to kilogram quantities. Organic process research & development, 20, 1833−1837.
  28. Gioiello, A., Mancino, V., Filipponi, P., Mostarda, S., Cerra, B. (2016). Concepts and optimization strategies of experimental design in continuous-flow processing. Journal of Flow Chemistry, 6, 167−180.
  29. Nunn, C., DiPietro, A., Hodnett, N., Sun, P., Wells, K.M. (2018). High-Throughput Automated Design of Experiment (DoE) and Kinetic Modeling to Aid in Process Development of an API. Organic Process Research & Development, 22, 54−61.
  30. Afzal, a., Muhammad, I.A., Muhammad, Y., Hayat, K., Mansoor, u.H.S. (2013). A comparative study of alkaline hydrolysis of ethyl acetate using design of experiments. Iranian journal of chemistry and chemical engineering, 32, 33−47.
  31. Asprey, S.P., Macchietto, S. (2000). Statistical tools for optimal dynamic model building. Computers & Chemical Engineering, 24, 1261−1267.
  32. Montgomery, D.C. (2017). Design and Analysis of Experiments. New York: John Wiley & sons.
  33. Lazic, Z.R. (2006). Design of Experiments in Chemical Engineering: A Practical Guide. New Jersey: John Wiley & Sons.
  34. Franceschini, G., Macchietto, S. (2008). Model-based design of experiments for parameter precision: State of the art. Chemical Engineering Science, 63, 4846−4872.
  35. Atkinson, A.C., Bogacka, B., Bogacki, M.B. (1998). D-and T-optimum designs for the kinetics of a reversible chemical reaction. Chemometrics and Intelligent Laboratory Systems, 43, 185−198.
  36. Gupta, A., Balomajumder, C. (2015). Residence time distribution study for continuous column packed with tea waste biomass. Integrated Research Advances, 2, 5−10.
  37. Anderson, N.G. (2001). Practical use of continuous processing in developing and scaling up laboratory processes. Organic Process Research & Development, 5, 613−621.
  38. Garcia-Serna, J., García-Verdugo, E., Hyde, J.R., Fraga-Dubreuil, J., Yan, C., Poliakoff, M., Cocero, M.J. (2007). Modelling residence time distribution in chemical reactors: A novel generalised n-laminar model: Application to supercritical CO2 and subcritical water tubular reactors. The Journal of Supercritical Fluids, 41, 82−91.
  39. Klose, F., Wolff, T., Thomas, S., Seidel-Morgenstern, A. (2003). Concentration and residence time effects in packed bed membrane reactors. Catalysis today, 82, 25−40.
  40. Istadi, I., Suherman, S., Buchori, L. (2010). Optimization of reactor temperature and catalyst weight for plastic cracking to fuels using response surface methodology. Bulletin of Chemical Reaction Engineering & Catalysis, 5 (2), 103-111, DOI: 10.9767/bcrec.5.2.797.103-111

No citation recorded.

Copyright (c) 2020 Bulletin of Chemical Reaction Engineering & Catalysis License URL: http://creativecommons.org/licenses/by-sa/4.0

Author(s) Rights

As a journal Author, you have rights for a large range of uses of your article, including use by your employing institute or company. These Author rights can be exercised without the need to obtain specific permission. Authors publishing in BCREC journals have wide rights to use their works for teaching and scholarly purposes without needing to seek permission, including: use for classroom teaching by Author or Author's institutionand presentation at a meeting or conference and distributing copies to attendees; use for internal training by author's company; distribution to colleagues for their reseearch use; use in a subsequent compilation of the author's works; inclusion in a thesis or dissertation; reuse of portions or extracts from the article in other works (with full acknowledgement of final article); preparation of derivative works (other than commercial purposes) (with full acknowledgement of final article); voluntary posting on open web sites operated by author or author’s institution for scholarly purposes (should follow CC by SA License).

Authors can copy and redistribute the material in any medium or format, as well as remix, transform, and build upon the material for any purpose, even commercially, but they must give appropriate credit (cite to the article or content), provide a link to the license, and indicate if changes were made. If you remix, transform, or build upon the material, you must redistribute your contributions under the same license as the original.

Copyright Transfer Agreement (for Publishing)

The Authors submitting a manuscript do so on the understanding that if accepted for publication, copyright publishing of the article shall be assigned/transferred to Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University/Masyarakat Katalis Indonesia - Indonesian Catalyst Society (MKICS) as Publisher of the journal. Upon acceptance of an article, authors will be asked to complete a 'Copyright Transfer Agreement' (see more information on this). An e-mail will be sent to the corresponding author confirming receipt of the manuscript together with a 'Copyright Transfer Agreement' form by online version of this agreement.

Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University/Masyarakat Katalis Indonesia-Indonesian Catalyst Society (MKICS), the Editors and the Advisory International Editorial Board make every effort to ensure that no wrong or misleading data, opinions or statements be published in the journal. In any way, the contents of the articles and advertisements published in the Bulletin of Chemical Reaction Engineering & Catalysis are sole and exclusive responsibility of their respective authors and advertisers.

Remember, even though we ask for a transfer of copyright, our journal authors retain (or are granted back) significant scholarly rights as mention before.

The Copyright Transfer Agreement (CTA) Form can be downloaded here: [Copyright Transfer Agreement (CTA) Form BCREC 2020] 


The copyright form should be signed electronically and send to the Editorial Office in the form of original e-mail below:  

Prof. Dr. I. Istadi (Editor-in-Chief)
Editorial Office of Bulletin of Chemical Reaction Engineering & Catalysis
Department of Chemical Engineering, Diponegoro University
Jl. Prof. Soedarto, Kampus Undip Tembalang, Semarang, Central Java, Indonesia 50275
Telp.: +62-24-7460058, Fax.: +62-24-76480675
E-mail: bcrec[at]live.undip.ac.id