Acs.chemrev.7b00246

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ionic liquids- reviews
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  Introduction: Ionic Liquids I onic liquids (ILs) are normally de 󿬁 ned as compoundscompletely composed of ions with melting point below 100 ° C. The  󿬁 rst IL (ethylammonium nitrate) was reported by Paul Walden in 1914, who at that time never realized that ILs would become a major scienti 󿬁 c area after almost one century. Actually, ILs as innovative  󿬂 uids have received wide attentiononly during the past two decades. The number of SCI paperspublished on ILs has exponentially increased from a few in1996 to >5000 in 2016, exceeding the annual growth rates of other popular scienti 󿬁 c areas. This indicates that more andmore researchers are engaged in studying this exciting area, with the outcomes being plentiful. A multidisciplinary study onILs is emerging, including chemistry, materials science,chemical engineering, and environmental science. Morespeci 󿬁 cally, some important fundamental viewpoints are now di ff  erent from the srcinal concepts, as insights into the natureof ILs become deeper. For example, the physicochemicalproperties of ILs are now recognized as ranging broadly fromthe oft quoted  “ nonvolatile, non- 󿬂 ammable, and air and waterstable ”  to those that are distinctly volatile,  󿬂 ammable, andunstable. This is attributed to numerous combinations of cations and anions that meet the de 󿬁 nition of ILs, leading to adiverse suite of behaviors. Regardless, ILs remain moredesirable than conventional volatile solvents and/or catalystsin many physical and chemical processes, often exhibiting “ green ”  and  “ designer ”  properties to a useful degree. As their chemical variety has grown, ILs have been furtherdivided into many types, e.g., room-temperature ILs (RTILs), 1 − 6 task-speci 󿬁 c ILs (TSILs), 7 ,8 polyionic liquids(PILs), 9 ,10 and supported IL membranes (SILMs) 11 ,12 thatinclude composites of  ILs supported on metal − organicframeworks (MOFs). 13 ,14 The hybrid organic − ionic nature of ILs and the resulting intermolecular interactions give rise to acomplex set of phenomena, creating an area of study that is both fascinating and challenging. Scientists and engineers areoften required to screen for suitable ILs quickly for a speci 󿬁 cprocess. For this purpose, the identi 󿬁 cation of structure − performance relationships disclosing the interplay among ILs,solutes, supports, and the components in mixtures becomes vital, requiring a close integration of experimental, theoretical,and computational methods. Thus, it is necessary to collect ourrecent  󿬁 ndings in this area and summarize the governing rules behind these complex phenomena. This compelled us to invitea number of prestigious scientists to contribute to this thematicissue on ILs for  Chemical Reviews . We should mention thatdeep eutectic solvents (DESs) are not highlighted in thisthematic issue because DESs and ILs form two quite di ff  erentsolvent families. For more detail on DESs, please see theexcellent review written by Smith, Abbott, and Ryder. 15 This issue covers a range of di ff  erent aspects of ILs, beginning with the multiscale science of ILs. It is evident that a better understanding of IL behavior at the microscopic scale will help to elucidate macroscopic  󿬂 uid phenomena, and thuspromote the industrial application of ILs. Dong, Liu, Dong,Zhang, and Zhang 16 discuss the multiscale aspects of ILs,ranging from the molecular level to the industrial level. Thepopular multiscale method srcinating from other disciplines was extended to IL s ystems. Furthermore, Izgorodina, Seeger,Scarborough, and Tan 17 give an overview on how to predict theenergetic, physical, and spectroscopic properties of ILs by means of quantum chemical methods and empirical ap-proaches. Among others, the COSMO-RS (conductor-likescreening model for real solvents) model, which is an  a priori predictive model, is the most widely used in the IL community,enabling theoretical calculations to decrease the amount of required experimental work. Zhang, Zhang, Zhang, and Deng 18 focus on the nanocon 󿬁 ned scale in ILs and the interactions between ILs and the pore walls inside porous materials; this brings to the ILs distinctly modi 󿬁 ed physicochemical properties when compared to the corresponding bulk liquid. The potentialapplications of nanocon 󿬁 ned ILs in catalysis, separation,ionogels, supercapacitors, carbonization, and lubrication arethoroughly reviewed.In many chemical reaction processes, ILs are suggested assolvents, catalysts, reagents, or combinations of these. Zhang,Song, and Han 19 provide a comprehensive review on thecatalytic conversion of cellulose, hemicellulose, lignin, andlignocellulosic biomass into value-added chemicals and fuelproducts, in which ILs act as the solvents or as IL-basedcatalysts. Various useful products can be obtained throughlignocellulose valorization using ILs. Qiao, Ma, Theyssen,Chen, and Hou 20 discuss an interesting family of ILs, i.e.temperature-responsive ILs, which are used for the thermo-regulated catalytic systems, such as hydroformylation, reduction with H 2  or CO, and coupling reactions. The working principleis that this type of IL can form a homogeneous mixture with thereactants and products, but be separated from them readily  when the reaction conditions are changed. From the viewpointof chemical engineering, the most important advantage is thatthe gas/liquid − solid mass transfer limitations, which may bethe rate-determining step in many catalytic transformations, can be overcome. Dai, Zhang, Huang, and Lei 21 provide a detailedreview of ILs in several important and typical selectiveoxidation reactions. ILs are preferable in this context as highly e ffi cient catalysts and innovative green solvents due to theirunique physical properties, including their nonvolatility,reaction rate acceleration e ff  ects, and high thermal stability.In particular, their use as  “  biphasic catalysts ”  , or  “ immobilizedcatalysts ”  obtained by immobilizing metal- or nonmetal-containing ILs onto mineral or polymer supports, is highlightedin detail.In separation processes, the selection of suitable solvents (orseparating agents) is a key for targeted process intensi 󿬁 cation. Ventura, e Silva, Quental, Mondal, Freire, and Coutinho 22 o ff  era detailed review on the use of ILs as solvents in the extractionand/or puri 󿬁 cation of bioactive compounds, ranging from smallorganic compounds to more complex molecules. Di ff  erent IL- Special Issue:  Ionic Liquids Published:  May 24, 2017 Editorialpubs.acs.org/CR © 2017 American Chemical Society  6633  DOI:10.1021/acs.chemrev.7b00246 Chem. Rev.  2017, 117, 6633 − 6635   based extraction processes are addressed, including liquid − liquid extraction, solid − liquid extraction, solid-phase extraction,and induced-precipitation techniques. The use of ILs can bringabout higher extraction yields and puri 󿬁 cation factors whencompared to conventional solvents and materials.The progress in IL science is closely related to thedevelopment of characterization techniques. Infrared (IR) andRaman spectroscopies have proven to provide exceptionalfundamental insight into ionic interactions and the resultingliquid structure in ILs. Paschoal, Faria, and Ribeiro 23 discuss theapplication of IR and Raman spectroscopies in the mid- andlow-frequency range in the bulk liquid, as well as inunderstanding the structural modi 󿬁 cations of ILs accompanyingphase transitions induced by variable temperature or pressure.To the best of our knowledge, it is the  󿬁 rst review on this topic,and we expect that many scientists and engineers will  󿬁 nd it to be a useful resource. Are ILs chemically stable? This topic is very important toensure that potential industrial application of ILs becomes areality. The review by Wang, Qin, Mu, Xue, and Gao 24 coversthe chemical stability and reactivity of popular imidazolium- based ILs, including thermal decomposition, hydrolysis, andnucleophilic reactions of anions under actual operatingconditions (e.g., high temperature, and the presence of water,air, or other gases). Thus, this review will provide a guide forfurther industrial application of ILs.Two reviews in this issue deal with innovative applications of ILs in emerging areas. Egorova, Gordeev, and Ananikov  25 discuss the biological activity of ILs and their applications indrug synthesis and drug delivery systems, with a particularemphasis on a novel active pharmaceutical ingredient − ionicliquid (APIL-IL) concept. In these cases, ILs are utilized ascomponents of drug or drug delivery systems, and in the dualroles of reaction media and catalysts in drug synthesis. In anentirely di ff  erent area, Watanabe, Thomas, Zhang, Ueno, Yasuda, and Dokko 26 discuss the application of ILs in energy storage and conversion materials and devices. They review theuse of ILs as electrolyte materials for Li/Na ion, Li/S, and Li/O 2  batteries, fuel cell electrolytes, and electrode materials,especially those including ionic-liquid-derived N-doped car- bons. Some ILs can meet the stringent criteria imposed by  various energy applications due to their unique properties,including non 󿬂 ammability, high electrochemical stability, andhigh ionic conductivity.Finally, we would like to thank all the authors for theirexcellent contributions to this thematic issue. We also thank theeditorial sta ff   of   Chemical Reviews  for their valuable suggestionsin initiating the thematic issue, as well as their hard work inhandling the manuscripts. We hope that young scientists andstudents who are engaged in studying this exciting area can bene 󿬁 t signi 󿬁 cantly from the publication of this collection of reviews and thereby make further important progress in the 󿬁 eld. Zhigang Lei * State Key Laboratory of Chemical Resource Engineering,Beijing University of Chemical Technology, China Biaohua Chen State Key Laboratory of Chemical Resource Engineering,Beijing University of Chemical Technology, China  Yoon-Mo Koo Department of Biological Engineering, Inha University,Korea Douglas R. MacFarlane School of Chemistry, Monash University, Australia AUTHOR INFORMATION Corresponding Author * E-mail: leizhg@mail.buct.edu.cn. ORCID Zhigang Lei:  0000-0001-7838-7207 Notes  Views expressed in this editorial are those of the authors andnot necessarily the views of the ACS. Biographies Zhigang Lei is a professor at the State Key Laboratory of ChemicalResource Engineering at Beijing University of Chemical Technology,China. He received his B.S. degree in 1995 from Wuhan Institute of Technology, and his Ph.D. degree in 2000 from Tsinghua University.Then, he became a postdoctoral researcher at Beijing University of Chemical Technology, working with Professor Chengyue Li. In 2003 − 2005, he worked as a researcher at the Research Center of SupercriticalFluid Technology (Tohoku University, Sendai, Japan). In 2005 − 2006,he received the world-famous Humboldt Fellowship and carried outhis research as Chair of Separation Science and Technology (Universita             ̈ t Erlange-Nu             ̈ rnberg, Erlangen, Germany). In 2006, hecame back to Beijing University of Chemical Technology. His currentresearch interests include chemical process intensi 󿬁 cation andpredictive molecular thermodynamics. He has contributed to about120 papers in international journals and one book entitled  Special Distillation Processes  , published by Elsevier B.V. (2005).Biaohua Chen is a professor at the State Key Laboratory of ChemicalResource Engineering at Beijing University of Chemical Technology,China. He received his Ph.D. degree in 1996 from China University of Petroleum (Beijing). In 2000, he was a visiting scholar at WashingtonUniversity in St. Louis and the University of Washington. He hasreceived two National Science and Technology Progress Prizes(second class), two provincial or ministerial level Science andTechnology Progress Prizes ( 󿬁 rst class), and one Natural ScienceProgress Prize. Now he is a member of the Standing Committee of theBeijing Chemical Industry Association and a member of the EditorialBoard of the  Journal of Petrochemical Universities  (China). His mainresearch interests are green chemistry and environmental catalysis. Hehas contributed to more than 150 papers in international journals. Yoon-Mo Koo is a Professor at the Department of BiologicalEngineering at Inha University, Korea. He received a B.S. degree(Seoul National University, Korea), an M.S. degree (KAIST, Korea)and a Ph.D. degree (Purdue University, USA), all in ChemicalEngineering. He served as the Dean of College of Engineering, InhaUniversity, and as the President of Korean Society of Biotechnology and Bioengineering, and he is currently a Member of the National Academy of Engineering, Korea. His research interests include biological separation and puri 󿬁 cation, microbial mixed culture, andionic liquids. He has contributed to more than 140 papers ininternational journals. He was the organizing committee chairman of the 6th International Congress on Ionic Liquids (COIL-6), held on June 16 − 20, 2015, in Jeju, Korea.Douglas R. MacFarlane is an Australian Laureate Fellow at MonashUniversity. He is also the program leader of the Energy Program at the Australian Centre for Electromaterials Science. His research interestsfocus on a broad range of ionic liquid properties and applications. He was a Ph.D. graduate from Austen Angell ’ s group at Purdue and after Chemical Reviews  Editorial DOI:10.1021/acs.chemrev.7b00246 Chem. Rev.  2017, 117, 6633 − 6635 6634  postdoctoral fellowships in France and New Zealand took up anacademic position at Monash in 1983. He has published more than600 papers and 30 patents. He was elected to the Australian Academy of Sciences in 2007 and to the Australian Academy of TechnologicalSciences and Engineering in 2009. REFERENCES (1) Hallett, J. P.; Welton, T. Room-Temperature Ionic Liquids:Solvents for Synthesis and Catalysis. 2.  Chem. Rev.  2011  ,  111  , 3508 − 3576.(2) Bara, J. E.; Carlisle, T. K.; Gabriel, C. J.; Camper, D.; Finotello, A.; Gin, D. L.; Nobel, R. D. Guide to CO 2  Separations in Imidazolium-Based Room-Temperature Ionic Liquids.  Ind. Eng. Chem. Res.  2009  , 48  , 2739 − 2751.(3) Lei, Z.; Dai, C.; Chen, B. Gas Solubility in Ionic Liquid.  Chem.Rev.  2014  ,  114  , 1289 − 1326.(4) Lei, Z.; Dai, C.; Zhu, J.; Chen, B. 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Rev.  2017  ,  46   , 1124 − 1159.(10) Rojas, M. F.; Bernard, F. L.; Aquino, A.; Borges, J.; Dalla Vecchia, F.; Menezes, S.; Ligabue, R.; Einloft, S. Poly(ionic liquid)s asEfficient Catalyst in Transformation of CO 2  to Cyclic Carbonate.  J. Mol. Catal. A: Chem.  2014  ,  392  , 83 − 88.(11) Wickramanayake, S.; Hopkinson, D.; Myers, C.; Hong, L.; Feng, J.; Seol, Y.; Plasynski, D.; Zeh, M.; Luebke, D. Mechanically RobustHollow Fiber Supported Ionic Liquid Membranes for CO 2  Separation Applications.  J. Membr. Sci.  2014  ,  470  , 52 − 59.(12) Scovazzo, P.; Havard, D.; McShea, M.; Mixon, S.; Morgan, D.Long-term, Continuous Mixed-gas Dry Fed CO 2 /CH 4  and CO 2 /N 2 Separation Performance and Selectivities for Room Temperature IonicLiquid Membranes.  J. Membr. Sci.  2009  ,  327   , 41 − 48.(13) Khan, N. A.; Hasan, Z.; Jhung, S. H. Ionic Liquids Supported onMetal-Organic Frameworks: Remarkable Adsorbents for AdsorptiveDesulfurization.  Chem. - Eur. 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Catalytic Transformation of Lignocellulose into Chemicals and Fuel Products in Ionic Liquids. Chem. Rev.  2017  , DOI: 10.1021/acs.chemrev.6b00457.(20) Qiao, Y.; Ma, W.; Theyssen, N.; Chen, C.; Hou, Z.Temperature-Responsive Ionic Liquids: Fundamental Behaviors andCatalytic Applications.  Chem. Rev.  2017  , DOI: 10.1021/acs.chem-rev.6b00652.(21) Dai, C.; Zhang, J.; Huang, C.; Lei, Z. Ionic Liquids in SelectiveOxidation: Catalysts and Solvents.  Chem. Rev.  2017  , DOI: 10.1021/acs.chemrev.7b00030.(22) Ventura, S. P. M.; e Silva, F. A.; Quental, M. V.; Mondal, D.;Freire, M. G.; Coutinho, J. A. P. Ionic-Liquid-Mediated Extraction andSeparation Processes for Bioactive Compounds: Past, Present, andFuture Trends.  Chem. Rev.  2017  , DOI: 10.1021/acs.chemrev.6b00550.(23) Paschoal, V. H.; Faria, L. F. O.; Ribeiro, M. C. C. VibrationalSpectroscopy of Ionic Liquids.  Chem. Rev.  2017  , DOI: 10.1021/acs.chemrev.6b00461.(24) Wang, B.; Qin, L.; Mu, T.; Xue, Z.; Gao, G. Are Ionic LiquidsChemically Stable?  Chem. Rev.  2017  , DOI: 10.1021/acs.chem-rev.6b00594.(25) Egorova, K. S.; Gordeev, E. G.; Ananikov, V. P. Biological Activity of Ionic Liquids and Their Application in Pharmaceutics andMedicine.  Chem. Rev.  2017  , DOI: 10.1021/acs.chemrev.6b00562.(26) Watanabe, M.; Thomas, M. L.; Zhang, S.; Ueno, K.; Yasuda, T.;Dokko, K. Application of Ionic Liquids to Energy Storage andConversion Materials and Devices.  Chem. Rev.  2017  , DOI: 10.1021/acs.chemrev.6b00504. Chemical Reviews  Editorial DOI:10.1021/acs.chemrev.7b00246 Chem. Rev.  2017, 117, 6633 − 6635 6635
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