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Ferenc Darvas, György Dormán, Volker Hessel, Steven V. Ley (Eds.)
Flow Chemistry
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Flow Chemistry

Volume 2: Applications

Edited by
Ferenc Darvas, György Dormán, Volker Hessel,
Steven V. Ley
Editors
Dr. Ferenc Darvas Prof. Volker Hessel
InnoStudio Inc. EC&MS Research
Graphisoft Park University of Adelaide
Záhony u.7 Engineering North Building
Budapest 1031 Adelaide, SA 5005
Hungary Australia
[email protected] [email protected]

Prof. György Dormán

ThalesNano Nanotechnology Inc. Prof. Steven V. Ley
Graphisoft Park Department of Chemistry
Zahony u. 7 University of Cambridge
Budapest 1031 Lensfield Road
Hungary Cambridge CB2 1EW
[email protected] United Kingdom
[email protected]

ISBN 978-3-11-069361-4
e-ISBN (PDF) 978-3-11-069369-0
e-ISBN (EPUB) 978-3-11-069376-8

Library of Congress Control Number: 2021940758

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie;
detailed bibliographic data are available on the Internet at http://dnb.dnb.de.

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Cover image: Royalty Free Stock Illustration, ID: 1701258115; designer: jijomathaidesigners,
Idukki, India
Typesetting: Integra Software Services Pvt. Ltd.
Printing and binding: CPI books GmbH, Leck

www.degruyter.com
Preface
In the last decade, the field of flow chemistry has advanced tremendously and a
plethora of applications have been reported in different fields at an unparalleled
speed. The characteristics of flow reactors are their exceptionally fast heat and mass
transfer. Using so-called microreactors, virtually instantaneous mixing can be achieved
for all but the fastest reactions. Similarly, the accumulation of heat, formation of hot
spots, and dangers of thermal runaways can be prevented. As a result of the small reac-
tor volumes, the overall safety of the process is significantly improved, even when
harsh reaction conditions are used. Thus, this technology offers a unique way to per-
form ultrafast, exothermic reactions, and allows the execution of reactions which
proceed via highly unstable or even explosive intermediates. In addition, efficient
telescoping of reaction sequences can be beneficial in terms of minimizing the
number of unit operations and avoiding intermediate isolations, which are of par-
ticular interest to the pharmaceutical industry where complex multistep sequen-
ces often need to be performed. In contrast to what existed only a few years ago,
the flow chemistry literature is now full of publications from not only academic
groups but also from scientists working in the industry reporting the results of
their many different research activities in this field.
Despite the fact that there appears to be ample literature in the flow chemistry
space ‒ including several extensive monographs, books, and highly cited review ar-
ticles ‒ there is a lack of suitable textbooks that can be used for teaching purposes
and that can explain the fundamentals to newcomers to the field. A complaint often
heard from companies is that there are not enough scientists with the unique training
and skillsets of a flow chemist, that is, a person having been educated at the interface
of synthetic chemistry and chemical engineering, with additional expertise – for ex-
ample – in analytical chemistry and data-rich experimentation/machine learning.
The first edition of the present Graduate Textbook on Flow Chemistry published in
2014 was, therefore, a highly welcome and urgently needed addition to the steadily
growing flow chemistry literature! Now, several years on, the second edition of this
textbook is released. The original format has been kept the same, namely, a separa-
tion into two independent volumes, one dealing with fundamentals, and a second
volume, more relating to the many diverse applications that can be realized with this
enabling technique. Both volumes not only discuss basic theory but also leave ample
room for discussing practical considerations. The individual 22 chapters have been
authored by experts in their respective fields, wisely chosen by the editors of this text-
book, now ‒ in addition to the original editorial team (Ferenc Darvas, Volker Hessel
and György Dormán) ‒ also including Steven Ley.

https://doi.org/10.1515/9783110693690-202
VI Preface

It is my hope and genuine expectation that the second edition of this Graduate
Textbook on Flow Chemistry will become the standard reference work in the field,
both at the university level and at other research institutions, where scientists have
to get familiar with this rapidly developing field.

October, 2021 C. Oliver Kappe

Professor
University of Graz, Austria
Acknowledgments
Since the publication of the first edition of the Graduate Textbook on Flow Chemistry
in 2014, the field has advanced tremendously. Thus, the original editors, Ferenc
Darvas, György Dormán, and Volker Hessel, joined by Steven V. Ley, have decided
to write a new edition, which, besides providing a broad introduction to the subject,
also covers the current state of continuous-flow chemistry and also discusses practi-
cal considerations and emerging fields.
The editors would like to express their sincere gratitude to the many people
who have helped to bring this book to fruition. First and foremost, the editors ex-
press their heartfelt appreciation to all authors and coauthors for their outstanding
contribution, cooperation, enthusiasm, spirit, and constructive comments through-
out the planning and writing of the new chapters.
A very special thanks are due to all the instrument suppliers for their contribu-
tion to the “Technology overview/Overview of the devices” chapter (AM Technology,
Corning, Little Things Factory, Microinnova, Syrris, ThalesNano, Uniqsis, Vapourtec,
and Zaiput).
The editors’ thanks are extended to Szilvia Gilmore (Flow Chemistry Society) for
her tireless efforts for coordinating and monitoring the whole project and to Réka
Darvas for the great cover design, for the second time.
The editors are immensely grateful to the editorial team at De Gruyter Publish-
ing House, especially to Nadja Schedensack, our ever-patient Project Manager, Kris-
tin Berber-Nerlinger, for all the preliminary organization and preparation work, and
Karin Sora, Vice President STEM, for the wonderful support and guidance.
Finally, the editors want to thank C. Oliver Kappe for the visionary introduction
to the textbook.

https://doi.org/10.1515/9783110693690-203
Contents
Preface V

Acknowledgments VII

About the editors XI

Contributing authors XIII

Gabriele Laudadio and Timothy Noël

1 Photochemical transformations in continuous-flow reactors 1

Martin Linden, Maximilian M. Hielscher, Balázs Endrődi, Csaba Janáky and

Siegfried R. Waldvogel
2 Electrochemical processes in flow 31

D. V. Ravi Kumar, Suneha Patil and Amol A. Kulkarni

3 Continuous flow methods for synthesis of functional materials 69

Tanja Junkers
4 Polymer synthesis in continuous flow 99

Genovéva Filipcsei, Zsolt Ötvös, Réka Angi, Balázs Buchholcz, Ádám Bódis
and Ferenc Darvas
5 Flow chemistry for nanotechnology 135

Francesco Ferlin, Nam Nghiep Tran, Aikaterini Anastasopoulou, Marc Escribà

Gelonch, Daniela Lanari, Federica Valentini, Volker Hessel and Luigi Vaccaro
6 From green chemistry principles to sustainable flow chemistry 159

Antonio M. Rodríguez, Iván Torres-Moya, Angel Díaz-Ortiz, Antonio de la Hoz

and Jesús Alcázar
7 Flow chemistry in fine chemical production 193

Kai Wang, Jian Deng, Chencan Du and Guangsheng Luo

8 Scale-up of flow chemistry system 229
X Contents

Sara Miralles-Comins, Elena Alvarez, Pedro Lozano and Victor Sans

9 Exothermic advanced manufacturing techniques in reactor engineering:
3D printing applications in flow chemistry 259

Francesca Paradisi and László Poppe

10 Continuous-flow biocatalysis with enzymes and cells 277

Steven V. Ley, Oliver S. May, Oliver M. Griffiths and Karin Sowa

11 Outlook, future directions, and emerging applications 313

Answers to the study questions 347

Index 359
About the editors
Dr. Ferenc Darvas acquired his degrees in Budapest, Hungary (medical
chemistry MS, computer sciences BS, PhD in experimental biology). He has
been teaching in Hungary, Spain, Austria, and the USA. Dr. Darvas has been
involved in introducing microfluidics/flow chemistry methodologies for
synthetizing drug candidates since the late 1990s, which led him to found
ThalesNano, the inventor of H-Cube®, and the recipient of the R&D100 Award
(Technical Oscar), twice.
Dr. Darvas was awarded Senator Honoris Causa by the University of
Szeged, Hungary (2019), and as Fellow of the American Chemical Society
(2016). Dr. Darvas is also the founder and active president of the Flow Chemistry Society,
Switzerland, founder and editorial board member of the Journal of Flow Chemistry, founder of the
Space Chemistry Consortium, organizer of the Space Chemistry Symposium series at ACS, and
initiator of the world’s first anti-Covid drug discovery experiments on ISS.

Prof. György Dormán obtained his PhD in organic chemistry from the
Technical University of Budapest, Hungary, in 1986. Between 1982–1988
and 1996–1999, he worked at Sanofi – Chinoin in Budapest in various
research positions. In 1988–1989, he spent a postdoctoral year in the UK
(University of Salford). Between 1992 and 1996, he was a visiting scientist
at the State University of New York, Stony Brook. Between 1999 and
2008, he served ComGenex/AMRI as chief scientific officer. In 2008, he
joined ThalesNano and worked as a director of Scientific Innovation
until 2015. Since 2016, he is a consultant of InnoStudio Inc. In 2011, he
became honorary professor at the University of Szeged. He is an author
of 116 scientific papers and book chapters. He is a member of the editorial board of Molecular Diversity
and Mini-Reviews in Medicinal Chemistry and member of the advisory board of Journal of Flow
Chemistry.

Prof. Volker Hessel studied chemistry at Mainz University and received his PhD
in 1993. Further career steps were as follows: 1994, Institut für Mikrotechnik
Mainz/D as vice director R&D and director R&D; 2005, Eindhoven University of
Technology/NL as professor; 2019, at the University of Warwick/UK as part-
time professor. In 2018, he was appointed as deputy dean (research) and
professor at the University of Adelaide, Australia. He is research director of
Adelaide’s Andy Thomas Centre of Space Resources.
Prof. Hessel’s research is on microfluidic and plasma processes and their
application to health, chemistry, agrifood, and space. He has published 502
peer-reviewed papers (h-index: 61, Scopus) and was authority in the Parliament Enquete Commission
“Future of Chemical Industry.” He received the AIChE Award “Excellence in Process Development
Research” and the IUPAC-ThalesNano Prize in Flow Chemistry, as well as the ERC Advanced/Proof of
Concept/Synergy and FET OPEN Grants.

https://doi.org/10.1515/9783110693690-205
XII About the editors

Prof. Steven V. Ley obtained his PhD from Loughborough University, UK, and
completed postdoctoral studies at the Ohio State University, USA, and
Imperial College London, UK. He was appointed to the staff of Imperial
College, London, becoming professor in 1983 and head of department in
1989. He was elected to the Royal Society, London, in 1990, moved to
Cambridge University to the 1702 Chair of Chemistry in 1992, and was
president of the Royal Society of Chemistry 2000–02. Steve’s research
interests include many aspects of organic chemistry, including synthesis,
products, methodology, biotransformations, enabling technologies, and, in
particular, natural extensive work on flow chemistry. He has been the recipient of numerous
international awards, including the IUPAC-ThalesNano Prize in Flow Chemistry and, recently, the
prestigious ACS Arthur C. Cope Award.
Contributing authors
Jesús Alcázar Ferenc Darvas
Discovery Chemistry InnoStudio Inc.
Janssen Pharmaceutical Companies of J&J Graphisoft Park
Janssen-Cilag, S.A. Záhony u.7
45007 Toledo, Spain 1031 Budapest, Hungary
[email protected] [email protected]
Chapter 7 Chapter 5

Elena Alvarez Jian Deng

Dept Bioquimica, Biologia Molecular e Department of Chemical Engineering
Inmunologia State Key Laboratory of Chemical Engineering
Facultad de Quimica Tsinghua University
Universidad de Murcia Beijing 100084, China
Campus Reg Excelencia Int Mare Nostrum [email protected]
E-30100 Murcia, Spain Chapter 8
Chapter 9
Angel Díaz-Ortiz
Aikaterini Anastasopoulou Facultad de Ciencias y Tecnologías Químicas
Department of Chemical and Biomolecular Universidad de Castilla-La Mancha
Engineering 13071 Ciudad Real, Spain
University of Delaware [email protected]
Newark, DE 19716, USA Chapter 7
[email protected]
Chapter 6 Chencan Du
Department of Chemical Engineering
Ádám Bódis State Key Laboratory of Chemical Engineering
InnoStudio Inc. Tsinghua University
Graphisoft Park Beijing 100084, China
Záhony u.7 [email protected]
1031 Budapest, Hungary Chapter 8
[email protected]
Chapter 5 Balázs Endrődi
Department of Physical Chemistry and
Balázs Buchholcz Materials Science
InnoStudio Inc. University of Szeged
Graphisoft Park Szeged
Záhony u.7 Hungary
1031 Budapest, Hungary [email protected]
[email protected] Chapter 2
Chapter 5

https://doi.org/10.1515/9783110693690-206
XIV Contributing authors

Francesco Ferlin Maximilian Hielscher

Laboratory of Green S.O.C. Department of Chemistry
Dipartimento di Chimica, Biologia e Johannes Gutenberg University Mainz
Biotecnologie Germany
Università degli Studi di Perugia [email protected]
Perugia, Italy Chapter 2
[email protected]
Antonio de la Hoz
Chapter 6
Facultad de Ciencias y Tecnologías Químicas
Universidad de Castilla-La Mancha
Genovéve Filipcsei
13071 Ciudad Real, Spain
Tavanta Therapeutics Hungary Inc.
[email protected]
Madarász Viktor u. 47
Chapter 7
1138 Budapest, Hungary
[email protected]
Csaba Janáky
Chapter 5
Department of Physical Chemistry and
Materials Science
Marc Escribà Gelonch
University of Szeged
Laboratoire de Génie des Procédées
Szeged
Catalytiques
Hungary
Centre National de la Recherche Scientifique
[email protected]
(CNRS)
Chapter 2
CPE-Lyon, France
[email protected]
Tanja Junkers
Chapter 6
Polymer Reaction Design Group
School of Chemistry
Oliver M. Griffiths
Monash University
Yusuf Hamied Department of Chemistry
Clayton, VIC 3800, Australia
University of Cambridge
[email protected]
Cambridge, CB2 1EW, UK
Chapter 4
[email protected]
Chapter 11
Amol A. Kulkarni
Chem. Eng. Proc. Dev. Division
Volker Hessel
CSIR-National Chemical Laboratory
School of Chemical Engineering and
Pashan, Pune, India
Advanced Materials
[email protected]
University of Adelaide
Chapter 3
Adelaide, Australia

and Daniela Lanari

School of Engineering Laboratory of Green S.O.C.
University of Warwick Dipartimento di Chimica, Biologia e
Coventry CV4 7AL, UK Biotecnologie
[email protected] Università degli Studi di Perugia
Chapter 6 Perugia, Italy
[email protected]
Chapter 6
 Contributing authors XV

Gabriele Laudadio Sara Miralles-Comins

Flow Chemistry Van’t Hoff Institute for Institute of Advanced Materials (INAM)
Molecular Sciences Universitat Jaume I
University of Amsterdam Avda. Sos Baynat s/n
Amsterdam, The Netherlands 12071 Castellon, Spain
[email protected] [email protected]
Chapter 1 Chapter 9

Timothy Noël
Steven V. Ley
Flow Chemistry Van’t Hoff Institute for
Yusuf Hamied Department of Chemistry
Molecular Sciences
University of Cambridge
University of Amsterdam
Cambridge CB2 1EW, UK
Amsterdam, The Netherlands
[email protected]
[email protected]
Chapter 11
Chapter 1

Martin Linden
Zsolt Ötvös
Department of Chemistry
Tavanta Therapeutics Hungary Inc.
Johannes Gutenberg University Mainz
Madarász Viktor u. 47
Mainz,
1138 Budapest, Hungary
Germany
[email protected]
[email protected]
Chapter 5
Chapter 2

Francesca Paradisi
Guangsheng Luo
Department of Chemistry and Biochemistry
Department of Chemical Engineering
University of Bern
State Key Laboratory of Chemical Engineering
Bern, Switzerland
Tsinghua University
[email protected]
Beijing 100084, China
Chapter 10
[email protected]
Chapter 8
Suneha Patil
Chem. Eng. Proc. Dev. Division
Pedro Lozano
CSIR-National Chemical Laboratory
Dept Bioquimica, Biologia Molecular e
Pashan, Pune, India
Inmunologia
[email protected]
Facultad de Quimica
Chapter 3
Universidad de Murcia
Campus Reg Excelencia Int Mare Nostrum
László Poppe
E-30100 Murcia, Spain
Department for Organic Chemistry and
Chapter 9
Technology
Budapest University of Technology and
Oliver S. May
Economics
Yusuf Hamied Department of Chemistry
Budapest, Hungary
University of Cambridge
[email protected]
Cambridge CB2 1EW, UK
Chapter 10
[email protected]
Chapter 11
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