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Ionic Liquids and Continuous Flow Processes

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Ionic Liquids and Continuous Flow Processes Volume 17 Number 5 May 2015 Pages 2589–3178 Green Chemistry Cutting-edge research for a greener sustainable future www.rsc.org/greenchem ISSN 1463-9262 TUTORIAL REVIEW Eduardo García-Verdugo et al. Ionic liquids and continuous fl ow processes: a good marriage to design sustainable processes Green Chemistry View Article Online TUTORIAL REVIEW View Journal | View Issue Ionic liquids and continuous flow processes: a good marriage to design sustainable processes Cite this: Green Chem., 2015, 17, 2693 Eduardo García-Verdugo,*a Belen Altava,a M. Isabel Burguete,a Pedro Lozanob and S. V. Luisa In the last few years the use of Ionic Liquids (ILs) as alternative solvents for (bio)catalytic processes has Received 4th December 2014, increased substantially, and the benefits and different approaches reported to combine continuous flow Accepted 2nd March 2015 systems and ILs are at the core of this overview. The synergy between both elements allowed us to high- DOI: 10.1039/c4gc02388a light their great potential in manufacturing both bulk and fine chemicals by new and greener (bio)catalytic www.rsc.org/greenchem processes. 1. Introduction backs and hazards associated with traditional solvents, replac- ing them with safer and more efficient alternatives. This can Creative Commons Attribution 3.0 Unported Licence. Over the last decade academia and industry have been working be achieved, ideally, through the design of new substances together in order to develop new greener alternative solvents.1 with specific and tailored properties. This is the case of ionic The main aim is to reduce significantly the important draw- liquids (ILs), for which the performance can be tuned to be as good as or even better than that of conventional solvents for many applications.2 The application of other alternative reac- a ı Departamento de Quí mica Inorgánica y Orgánica, Universidad Jaume I, tion media including, amongst others, water, supercritical Campus del Riu Sec, Avenida Sos Baynant s/n, E-12071 Castellón, Spain. fluids, switchable solvents and fluorous solvents is also envi- E-mail: [email protected], [email protected] 3 bDepartamento de Bioquímica y Biología Molecular “B” e Inmunología, Facultad de saged. In this regard, a variety of new chemical processes This article is licensed under a Química, Universidad de Murcia, E-30.100 Murcia, Spain. E-mail: [email protected] have been designed based on those alternative solvents in Open Access Article. Published on 18 March 2015. Downloaded 10/2/2021 6:00:51 PM. E. García-Verdugo was born in Belén Altava completed her 1972 in Talavera de Reina, degree in chemistry at the Uni- Spain. He obtained his chemistry versities of Valencia and Zara- degree at the University of Valen- goza and obtained her PhD cia (1995) and his PhD in chem- in chemistry at the University istry at the University Jaume I Jaume I of Castellón in 1996. (Spain) in 2001. Then, he After postdoctoral stays at the worked as a researcher at University of Düsseldorf with Nottingham University (UK) Professor G. Wulff and at Novar- under the supervision of tis (Basel) with Dr H. U. Blaser M. Poliakoff (until 2004). He she returned to Spain and returned to Spain and worked as obtained a permanent academic Eduardo García-Verdugo a Ramon y Cajal fellow at Uni- Belen Altava position at the University Jaume versity Jaume I until 2009, and I in 2001. Her main areas of then he obtained a permanent position as Cientifico Titular of research are directly related to green and sustainable chemistry CSIC at ICP (Madrid) (2009–2010). In 2010, he moved to a per- and involve the development of supported catalysts, asymmetric manent academic position at the University Jaume I. Currently, he catalysis, the preparation and application of new task specific is working on the integration of different so-called enabling tech- ionic liquids, in particular chiral ionic liquids, and the application niques (catalysis, polymeric materials, continuous flow processes, of these compounds and other amino acid derived systems for microreactors, bio-catalysis, neoteric solvents (ILs, SCFs)) to selective recognition. develop more efficient and greener organic transformations. This journal is © The Royal Society of Chemistry 2015 Green Chem.,2015,17, 2693–2713 | 2693 View Article Online Tutorial Review Green Chemistry order to exploit their advantages and to implement their use lenges of the chemical industry, achieving significant scientific in well-known chemical processes. and technological breakthroughs. Indeed, the examples here An additional factor that can contribute to implement the presented describe a series of techniques, methodologies and sustainability of a chemical transformation is the substitution approaches that could allow the development of new and more – of batch processes by flow processes.4 8 Advantages associated efficient chemical processes, not only taking into account clas- with flow systems include the improvement in mass and heat sical parameters such as yield, purity or selectivity, but also transfer, with significant intensification of the process, considering, for the overall equation, the environmental and making available systems working 24 h a day, 7 days a week hazard costs. Our goal in this review is to present some signifi- (24/7), or their easier optimization through the adjustments of cant cases highlighting the main advantages and some of the simple parameters such as flow, pressure or temperature. shortcomings found for the combined use of ILs and continu- In addition, the scale-up of flow processes is generally more ous flow technologies. easily attainable than for batch processes via different approaches such as the scale-out or the number-up.4 Although the advantages of flow chemistry were soon realized by the bulk chemistry industry, the situation is quite different in the 2. Continuous flow processes for the fine chemicals or pharmaceutical industries. Most industrial synthesis and scale-up of ILs petrochemical processes, and many of those for the prepa- ration of bulk chemicals, are carried out in flow, but batch pro- A wide variety of ILs can be designed, taking into account their cesses still dominate in other industrial areas, and a high modular character, considering structural elements such as pressure is currently being exerted to introduce flow processes the nature of the cation, the nature of the anion, the ion sub- there. In the last few years, there has been a blossoming of stitution patterns, the introduction of either bio-renewable or new developments in the field of the application of flow pro- chiral moieties, etc. Indeed, a wide range of structurally 10 Creative Commons Attribution 3.0 Unported Licence. cesses in complex organic syntheses, especially those based on different ILs has been reported. Besides, ILs can be regarded the application of microstructured devices.9 as “design solvents” not only because their structure can be Here, we shall focus on recent advances in the use of ILs, tailored on demand, but also because their physical and working alone or together with other neoteric solvents chemical properties can be tuned at the molecular level by (i.e. supercritical fluids), exploring their great potential to selecting the right combination of structural elements. These manufacture both bulk and fine chemicals by continuous flow unique opportunities offered by ILs have resulted in increasing systems. The combination of (bio)catalytic reactions in ILs their use as alternatives to classic organic solvents and their with continuous flow processes can fulfil the needs and chal- application in completely unexpected new fields.11 This article is licensed under a M. Isabel Burguete graduated in Pedro Lozano is a chemist born Open Access Article. Published on 18 March 2015. Downloaded 10/2/2021 6:00:51 PM. chemistry at the University of in 1961 in Ceutí, Spain. He Zaragoza in Spain and after a graduated in Sciences (chem- stay at the University of Pitts- istry) at the University of Murcia burgh (USA) under the supervi- in 1984. He received his PhD in sion of Dr J. Rebek, she Sciences (chemistry) from the completed her PhD at the Univer- University of Murcia in 1988. sity of Valencia in 1989 under Between 1990 and 1991 he spent the direction of Dr F. Gaviña two years at the Centre de Bioin- working on regulated crown génierie Gilbert Durand, Tou- ethers and convergent diacids. In louse (France) as a post-doctoral 1989 she took an academic fellow. In 1993, he returned to M. Isabel Burguete appointment at the University Pedro Lozano the Faculty of Chemistry at the Jaume I in Castellón (Spain) University of Murcia as Lecturer where she is currently Professor of organic chemistry. Her main in Biochemistry and Molecular Biology, being finally promoted to field of research is the development of new tools, in particular Full Professor in 2004. During the period 1996–2014, he was homogeneous and supported catalysis approaches, in green and Assistant-Dean of the Faculty of Chemistry and the coordinator of sustainable chemistry. the Biochemistry Degree at the University of Murcia. Since 2014, Prof. Lozano has been the Dean of the Faculty of Chemistry at the University of Murcia. His research activity has always been related to enzyme technology for green chemistry, and his particular research interest is in the use of enzymes in ionic liquids and supercritical fluids. 2694 | Green Chem.,2015,17, 2693–2713 This journal is © The Royal Society of Chemistry 2015 View Article Online Green Chemistry Tutorial Review In general, the synthesis of ILs is a simple process involving pound can be considered both a bulk IL and a source of the quarternisation of an amine, imidazole, pyridine or phos- various other ILs, through a two-step synthesis approach. phine, through an alkylation reaction, to form the corres- Thus, the first step involves the synthesis of a methylsulfate or ponding cation.
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