History and Development of Ionic Liquids

Chapter 1 History and Development of Ionic Liquids Sumana Brahma, Sumana Brahma Indian Institute of Technology Madras, Department of Chemistry, IIT P.O., Chennai, 600036 IndiaSearch for more papers by this authorRamesh L. Gardas, Ramesh L. Gardas Indian Institute of Technology Madras, Department of Chemistry, IIT P.O., Chennai, 600036 IndiaSearch for more papers by this author Sumana Brahma, Sumana Brahma Indian Institute of Technology Madras, Department of Chemistry, IIT P.O., Chennai, 600036 IndiaSearch for more papers by this authorRamesh L. Gardas, Ramesh L. Gardas Indian Institute of Technology Madras, Department of Chemistry, IIT P.O., Chennai, 600036 IndiaSearch for more papers by this author Book Editor(s):Pardeep Singh, Pardeep Singh University of Delhi, PGDAV College, New Delhi, IndiaSearch for more papers by this authorSanchayita Rajkhowa, Sanchayita Rajkhowa The Assam Royal Global University, Assam, IndiaSearch for more papers by this authorAnik Sen, Anik Sen GITAM, Andhra Pradesh, IndiaSearch for more papers by this authorJyotirmoy Sarma, Jyotirmoy Sarma The Assam Kaziranga University, Assam, IndiaSearch for more papers by this author First published: 29 December 2023 https://doi.org/10.1002/9783527839520.ch1 AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary The widespread use of volatile organic compounds in many industrial chemical processes is an issue of great environmental concern. A novel class of molten salts called ionic liquids (ILs) can be potential benign alternatives for organic compounds. ILs possess a unique combination of particular properties, giving them increasing attention in academic and industrial research to exploit them as “sustainable solvents.” The potential applications of ILs are numerous as simple changes in the cation and anion combinations or the nature of the moieties attached to each ion allow their physical, chemical, and biological properties to be tailored for specific applications. This chapter provides an overview of the history and important developments in the field of ILs. References Abai , M. , Atkins , M.P. , Hassan , A. et al. ( 2015 ). An ionic liquid process for mercury removal from natural gas . Dalton Transactions 44 ( 18 ): 8617 – 8624 . https://doi.org/10.1039/c4dt03273j . 10.1039/C4DT03273J CASPubMedWeb of Science®Google Scholar Abbott , A.P. , Capper , G. , Davies , D.L. et al. ( 2003 ). Novel solvent properties of choline chloride/urea mixtures . Chemical Communication 1 : 70 – 71 . https://doi.org/10.1039/B210714G . 10.1039/b210714g CASWeb of Science®Google Scholar Abdul-Sada , A.K. , Greenway , A.M. , Seddon , K.R. , and Welton , T. ( 1989 ). Upon the existence of [A1 3 Cl l0 ] − in room temperature chloroaluminate ionic liquids . Organic Mass Spectrometry 24 ( 10 ): 917 – 918 . https://doi.org/10.1002/oms.1210241012 . 10.1002/oms.1210241012 CASGoogle Scholar Amarasekara , A.S. ( 2016 ). Acidic ionic liquids . Chemical Reviews 116 ( 10 ): 6133 – 6183 . https://doi.org/10.1021/acs.chemrev.5b00763 . 10.1021/acs.chemrev.5b00763 CASPubMedWeb of Science®Google Scholar Austen Angell , C. , Ansari , Y. , and Zhao , Z. ( 2012 ). Ionic liquids: past, present and future . Faraday Discussions 154 ( 1 ): 9 – 27 . https://doi.org/10.1039/c1fd00112d . 10.1039/C1FD00112D CASPubMedGoogle Scholar Bao , X. and Le , Z. ( 2010 ). Synthesis of chiral ionic liquids . Chinese Journal of Organic Chemistry 30 ( 6 ): 816 – 832 . https://doi.org/10.1021/jo020503i . 10.1021/jo020503i Web of Science®Google Scholar Baudequin , C. , Brégeon , D. , Levillain , J. et al. ( 2005 ). Chiral ionic liquids, a renewal for the chemistry of chiral solvents? Design, synthesis and applications for chiral recognition and asymmetric synthesis . Tetrahedron Asymmetry 16 ( 24 ): 3921 – 3945 . https://doi.org/10.1016/j.tetasy.2005.10.026 . 10.1016/j.tetasy.2005.10.026 CASWeb of Science®Google Scholar Binnemans , K. ( 2005 ). Ionic liquid crystals . Chemical Reviews 105 ( 11 ): 4148 – 4204 . https://doi.org/10.1021/cr0400919 . 10.1021/cr0400919 CASPubMedWeb of Science®Google Scholar Bonĥte , P. , Dias , A.-P. , Papageorgiou , N. et al. ( 1996 ). Hydrophobic, highly conductive ambient-temperature molten salts . Inorganic Chemistry 35 ( 5 ): 1168 – 1178 . https://doi.org/10.1021/ic951325x . 10.1021/ic951325x PubMedWeb of Science®Google Scholar Boon , J.A. , Levisky , J.A. , Pflug , J.L. , and Wilkes , J.S. ( 1986 ). Friedel-crafts reactions in ambient-temperature molten salts . Journal of Organic Chemistry 51 ( 4 ): 480 – 483 . https://doi.org/10.1021/jo00354a013 . 10.1021/jo00354a013 CASWeb of Science®Google Scholar Boucher , G. ( 2011 ). Book reviews: book reviews . Critical Sociology 37 ( 4 ): 493 – 497 . https://doi.org/10.1177/0261018311403863 . 10.1177/0261018311403863 Google Scholar Brahma , S. and Gardas , R.L. ( 2022 ). Effect of alkyl chain length and temperature on volumetric, acoustic and apparent molar properties of pyrrolidinium based ionic liquids in acetonitrile . Journal of Molecular Liquids 348 : 118067 . https://doi.org/10.1016/j.molliq.2021.118067 . 10.1016/j.molliq.2021.118067 Web of Science®Google Scholar Bulut , S. , Klose , P. , Huang , M.-M. et al. ( 2010 ). Synthesis of room-temperature ionic liquids with the weakly coordinating [Al(ORF)4]- anion (RF=C(H)(CF 3)2) and the determination of their principal physical properties . Chemistry - A European Journal 16 ( 44 ): 13139 – 13154 . https://doi.org/10.1002/chem.201000982 . 10.1002/chem.201000982 CASPubMedWeb of Science®Google Scholar Cao , X. , Roser , S. , Rezaeirad , B. et al. ( 2015 ). Ester modified pyrrolidinium based ionic liquids as electrolyte component candidates in rechargeable lithium batteries . Zeitschrift fur Anorganische und Allgemeine Chemie 641 ( 14 ): 2536 – 2542 . https://doi.org/10.1002/zaac.201500554 . 10.1002/zaac.201500554 CASWeb of Science®Google Scholar Chaturvedi , D. ( 2012 ). Recent developments on task specific ionic liquids . Current Organic Chemistry 15 ( 8 ): 1236 – 1248 . https://doi.org/10.2174/138527211795202997 . 10.2174/138527211795202997 Web of Science®Google Scholar Chen , F. , Yang , Z. , Chen , Z. et al. ( 2015 ). Density, viscosity, speed of sound, excess property and bulk modulus of binary mixtures of γ-butyrolactone with acetonitrile, dimethyl carbonate, and tetrahydrofuran at temperatures (293.15 to 333.15) K . Journal of Molecular Liquids 209 : 683 – 692 . https://doi.org/10.1016/j.molliq.2015.06.041 . 10.1016/j.molliq.2015.06.041 CASWeb of Science®Google Scholar Cui , X. , Zhang , S. , Shi , F. et al. ( 2010 ). The influence of the acidity of ionic liquids on catalysis . ChemSusChem 3 ( 9 ): 1043 – 1047 . https://doi.org/10.1002/cssc.201000075 . 10.1002/cssc.201000075 CASPubMedWeb of Science®Google Scholar Davis , J.H. ( 2004 ). Task-specific ionic liquids . Chemistry Letters 33 ( 9 ): 1072 – 1077 . https://doi.org/10.1246/cl.2004.1072 . 10.1246/cl.2004.1072 CASWeb of Science®Google Scholar Davis , J.H. and Forrester , K.J. ( 1999 ). Thiazolium-ion based organic ionic liquids (OILs). Novel oils which promote the benzoin condensation . Tetrahedron Letters 40 ( 9 ): 1621 – 1622 . https://doi.org/10.1016/S0040-4039(99)00025-8 . 10.1016/S0040-4039(99)00025-8 CASWeb of Science®Google Scholar Del Sesto , R.E. , Corley , C. , Robertson , A. , and Wilkes , J.S. ( 2015 ). Tetraalkylphosphonium-based ionic liquids . Journal of Organometallic Chemistry 690 ( 10 ): 2536 – 2542 . https://doi.org/10.1016/j.jorganchem.2004.09.060 . 10.1016/j.jorganchem.2004.09.060 Google Scholar Derouane , E.G. ( 2003 ). Catalysis in Chile . Cattech 7 ( 3 ): 104 – 105 . https://doi.org/10.1023/A:1024235221365. 10.1023/A:1024235221365 Google Scholar Ding , J. and Armstrong , D.W. ( 2005 ). Chiral ionic liquids: synthesis and applications . Chirality 17 ( 5 ): 281 – 292 . https://doi.org/10.1002/chir.20153 . 10.1002/chir.20153 CASPubMedWeb of Science®Google Scholar Döbbelin , M. , Azcune , I. , Bedu , M. et al. ( 2012 ). Synthesis of pyrrolidinium-based poly(ionic liquid) electrolytes with poly(ethylene glycol) side chains . Chemistry of Materials 24 ( 9 ): 1583 – 1590 . https://doi.org/10.1021/cm203790z . 10.1021/cm203790z CASWeb of Science®Google Scholar Drake , G. , Hawkins , T. , Brand , A. et al. ( 2003 ). Energetic, low-melting salts of simple heterocycles . Propellants, Explosives, Pyrotechnics 28 ( 4 ): 174 – 180 . https://doi.org/10.1002/prep.200300002 . 10.1002/prep.200300002 CASWeb of Science®Google Scholar Earle , M.J. , McCormac , P.B. , and Seddon , K.R. ( 1999 ). Diels-Alder reactions in ionic liquids: a safe recyclable alternative to lithium perchlorate-diethyl ether mixtures . Green Chemistry 1 ( 1 ): 23 – 25 . https://doi.org/10.1039/a808052f . 10.1039/a808052f CASWeb of Science®Google Scholar Evans , D.F. , Chen , S.H. , Schriver , G.W. , and Arnett , E.M. ( 1981 ). Thermodynamics of solution of nonpolar gases in a fused salt. “Hydrophobic bonding” behavior in a nonaqueous system . Journal of Americal Chemical Society 103 ( 2 ): 481 – 482 . 10.1021/ja00392a049 CASWeb of Science®Google Scholar Fraser , K.J. and MacFarlane , D.R. ( 2009 ). Phosphonium-based ionic liquids: an overview . Australian Journal of Chemistry 62 ( 4 ): 309 – 321 . https://doi.org/10.1071/CH08558 . 10.1071/CH08558 CASWeb of Science®Google Scholar Gabriel , S. ( 1891 ). Ueber einige Abkömmlinge des Aethylamins . Berichte der deutschen chemischen Gesellschaft 24 ( 1 ): 1110 – 1121 . https://doi.org/10.1002/cber.189102401200 . 10.1002/cber.189102401200 Google Scholar Gao , Y. , Twamley , B. , and Shreeve , J.M. ( 2004 ). The first (ferrocenylmethyl)imidazolium and (ferrocenylmethyl)triazolium room temperature ionic liquids . Inorganic Chemistry 43 ( 11 ): 3406 – 3412 . https://doi.org/10.1021/ic049961v . 10.1021/ic049961v CASPubMedWeb of Science®Google Scholar Giernoth , R. ( 2010 ). Task-specific ionic liquids . Angewandte Chemie 49 ( 16 ): 2834 – 2839 . https://doi.org/10.1002/anie.200905981 . 10.1002/anie.200905981 CASGoogle Scholar Gomes , J.M. , Silva , S.S. , and Reis , R.L. ( 2019 ). Biocompatible ionic liquids: fundamental behaviours and applications . Chemical Society Reviews 48 ( 15 ): 4317 – 4335 . https://doi.org/10.1039/c9cs00016j . 10.1039/C9CS00016J CASPubMedWeb of Science®Google Scholar Gorke , J. , Srienc , F. , and Kazlauskas , R. ( 2010 ). Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis . Biotechnology and Bioprocess Engineering 15 ( 1 ): 40 – 53 . https://doi.org/10.1007/s12257-009-3079-z . 10.1007/s12257-009-3079-z CASPubMedWeb of Science®Google Scholar Greer , A.J. , Jacquemin , J. , and Hardacre , C. ( 2020 ). Industrial applications of ionic liquids . Molecules 25 ( 21 ): 5207 . https://doi.org/10.3390/molecules25215207 . 10.3390/molecules25215207 CASPubMedWeb of Science®Google Scholar Hajipour , A.R. and Rafiee , F. ( 2009 ). Basic ionic liquids. A short review . Journal of the Iranian Chemical Society 6 ( 4 ): 647 – 678 . https://doi.org/10.1007/BF03246155 . 10.1007/BF03246155 CASWeb of Science®Google Scholar Harjani , J.R. , Nara , S.J. , and Salunkhe , M.M. ( 2002 ). Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation . Tetrahedron Letters 43 ( 6 ): 1127 – 1130 . https://doi.org/10.1016/S0040-4039(01)02341-3 . 10.1016/S0040-4039(01)02341-3 CASWeb of Science®Google Scholar Hasaninejad , A. , Zare , A. , Shekouhy , M. , and Rad , A.J. ( 2010 ). Catalyst-free one-pot four component synthesis of polysubstituted imidazoles in neutral ionic liquid 1-butyl-3-methylimidazolium bromide . Journal of Combinatorial Chemistry 12 ( 6 ): 844 – 849 . https://doi.org/10.1021/cc100097m . 10.1021/cc100097m CASPubMedGoogle Scholar Haverhals , L.M. , Reichert , W.M. , Long , H.C. , and Trulove , P.C. ( 2010 ). Natural fiber welding . Macromolecular Materials and Engineering 295 ( 5 ): 425 – 430 . https://doi.org/10.1002/mame.201000005 . 10.1002/mame.201000005 CASWeb of Science®Google Scholar Hayes , R. , Warr , G.G. , and Atkin , R. ( 2015 ). Structure and nanostructure in ionic liquids . Chemical Reviews 115 ( 13 ): 6357 – 6426 . https://doi.org/10.1021/cr500411q . 10.1021/cr500411q CASPubMedWeb of Science®Google Scholar Hough , W.L. , Smiglak , M. , Rodríguez , H. et al. ( 2007 ). The third evolution of ionic liquids: active pharmaceutical ingredients . New Journal of Chemistry. 3 : 1429 – 1436 . https://doi.org/10.1039/b706677p . 10.1039/b706677p Google Scholar Hurley , F.H. and WIer , T.P. ( 1951 ). Electrodeposition of metals from fused quaternary ammonium salts . Journal of The Electrochemical Society 98 ( 5 ): 203 . https://doi.org/10.1149/1.2778132 . 10.1149/1.2778132 CASWeb of Science®Google Scholar Hurley , F.H. and WIer , T.P. ( 1951 ). The electrodeposition of aluminum from nonaqueous solutions at room temperature . Journal of The Electrochemical Society 98 ( 5 ): 207 . https://doi.org/10.1149/1.2778133 . 10.1149/1.2778133 CASWeb of Science®Google Scholar Inman , G. , Nlebedim , I.C. , and Prodius , D. ( 2022 ). Application of ionic liquids for the recycling and recovery of technologically critical and valuable metals . Energies 15 ( 2 ): 628 . https://doi.org/10.3390/en15020628 . 10.3390/en15020628 CASWeb of Science®Google Scholar Ishida , Y. , Miyauchi , H. , and Saigo , K. ( 2002 ). Design and synthesis of a novel imidazolium-based ionic liquid with planar chirality . Chemical Communications 2 ( 19 ): 2240 – 2241 . https://doi.org/10.1039/b206495b . 10.1039/b206495b Google Scholar Jónsson , E. ( 2020 ). Ionic liquids as electrolytes for energy storage applications—a modelling perspective . Energy Storage Materials 25 : 827 – 835 . https://doi.org/10.1016/j.ensm.2019.08.030 . 10.1016/j.ensm.2019.08.030 Web of Science®Google Scholar Jtket , T.M.K. , White , P.S. , and Tornieporth-oetting , I.C. ( 1996 ). Reaction of hydrazinium azide with sulfuric acid: the X-ray structure of [N 2 H 6 ][SO 4 ] . Polyhedron 5387 ( 15 ): 2579 – 2582 . Google Scholar Lee , S.G. ( 2006 ). Functionalized imidazolium salts for task-specific ionic liquids and their applications . Chemical Communications 10 : 1049 – 1063 . https://doi.org/10.1039/b514140k . 10.1039/b514140k CASPubMedWeb of Science®Google Scholar Lei , Z. , Chen , B. , Koo , Y.-M. , and MacFarlane , D.R. ( 2017 ). Introduction: ionic liquids . Chemical Reviews 117 ( 10 ): 6633 – 6635 . https://doi.org/10.1021/acs.chemrev.7b00246 . 10.1021/acs.chemrev.7b00246 PubMedWeb of Science®Google Scholar Lin , I.J.B. and Vasam , C.S. ( 2005 ). Metal-containing ionic liquids and ionic liquid crystals based on imidazolium moiety . Journal of Organometallic Chemistry 690 ( 15 ): 3498 – 3512 . https://doi.org/10.1016/j.jorganchem.2005.03.007 . 10.1016/j.jorganchem.2005.03.007 CASWeb of Science®Google Scholar Liu , Y. , Hua , R. , Xu , C. , and Sua , H. ( 2008 ). Alkylation of isobutene with 2-butene using composite ionic liquid catalysts . Applied Catalysis A: General 346 ( 1–2 ): 189 – 193 . https://doi.org/10.1016/j.apcata.2008.05.024 . 10.1016/j.apcata.2008.05.024 CASWeb of Science®Google Scholar Liu , F. , Jing , G. , Lv , B. , and Zhou , Z. ( 2017 ). High regeneration efficiency and low viscosity of CO 2 capture in a switchable ionic liquid activated by 2-amino-2-methyl-1-propanol . International Journal of Greenhouse Gas Control 60 : 162 – 171 . https://doi.org/10.1016/j.ijggc.2017.03.017 . 10.1016/j.ijggc.2017.03.017 CASWeb of Science®Google Scholar Liu , F. , Yu , J. , Qazi , A.B. et al. ( 2021 ). Metal-based ionic liquids in oxidative desulfurization: a critical review . Environmental Science and Technology 55 ( 3 ): 1419 – 1435 . https://doi.org/10.1021/acs.est.0c05855 . 10.1021/acs.est.0c05855 CASPubMedWeb of Science®Google Scholar MacFarlane , D.R. , Kar , M. , and Pringle , J.M. ( 2017 ). An introduction to ionic liquids . Fundamentals of Ionic Liquids 1 – 25 . https://doi.org/10.1002/9783527340033.ch1 . 10.1002/9783527340033.ch1 Google Scholar Mainar , A.R. , Iruina , E. , Colmenaresa , L.C. et al. ( 2018 ). An overview of progress in electrolytes for secondary zinc-air batteries and other storage systems based on zinc . Journal of Energy Storage 15 : 304 – 328 . https://doi.org/10.1016/j.est.2017.12.004 . 10.1016/j.est.2017.12.004 Web of Science®Google Scholar Marsh , K.N. , Deev , A. , Wu , A.C.-T. et al. ( 2002 ). Room temperature ionic liquids as replacements for conventional solvents—a review . Korean Journal of Chemical Engineering 19 : 357 – 362 . https://doi.org/10.1007/BF02697140 . 10.1007/BF02697140 CASWeb of Science®Google Scholar Newington , I. , Perez-Arlandis , J.M. , and Welton , T. ( 2007 ). Ionic liquids as designer solvents for nucleophilic aromatic substitutions . Organic Letters 9 ( 25 ): 5247 – 5250 . https://doi.org/10.1021/ol702435f . 10.1021/ol702435f CASPubMedWeb of Science®Google Scholar Ohno , H. ( 2007 ). Design of ion conductive polymers based on ionic liquids . Macromolecular Symposia 249–250 ( 1 ): 551 – 556 . https://doi.org/10.1002/masy.200750435 . 10.1002/masy.200750435 CASWeb of Science®Google Scholar Onwukamike , K.N. , Tassaing , T. , Grelier , S. et al. ( 2018 ). Detailed understanding of the DBU/CO 2 switchable solvent system for cellulose solubilization and derivatization . ACS Sustainable Chemistry and Engineering 6 ( 1 ): 1496 – 1503 . https://doi.org/10.1021/acssuschemeng.7b04053 . 10.1021/acssuschemeng.7b04053 CASWeb of Science®Google Scholar Paquin , F. , Rivnay , J. , Salleo , A. et al. ( 2015 ). Multi-phase semicrystalline microstructures drive exciton dissociation in neat plastic semiconductors . Journal of Materials Chemistry C 3 : 10715 – 10722 . https://doi.org/10.1039/b000000x . 10.1039/C5TC02043C CASWeb of Science®Google Scholar Phillips , B.S. and Zabinski , J.S. ( 2004 ). Ionic liquid lubrication effects on ceramics in a water environment . Tribology Letters 17 ( 3 ): 533 – 541 . https://doi.org/10.1023/B:TRIL.0000044501.64351.68. 10.1023/B:TRIL.0000044501.64351.68 CASWeb of Science®Google Scholar Plechkova , N.V. and Seddon , K.R. ( 2008 ). Applications of ionic liquids in the chemical industry . Chemical Society Reviews 37 ( 1 ): 123 – 150 . https://doi.org/10.1039/b006677j . 10.1039/B006677J CASPubMedWeb of Science®Google Scholar Poole , C.F. ( 2004 ). Chromatographic and spectroscopic methods for the determination of solvent properties of room temperature ionic liquids . Journal of Chromatography A 1037 ( 1–2 ): 49 – 82 . https://doi.org/10.1016/j.chroma.2003.10.127 . 10.1016/j.chroma.2003.10.127 CASPubMedWeb of Science®Google Scholar Privalova , E. , Nurmi , M. , Marañóna , M.S. et al. ( 2012 ). CO 2 removal with “switchable” versus “classical” ionic liquids . Separation and Purification Technology 97 : 42 – 50 . https://doi.org/10.1016/j.seppur.2012.01.047 . 10.1016/j.seppur.2012.01.047 CASWeb of Science®Google Scholar Qian , W. , Texter , J. , and Yan , F. ( 2017 ). Frontiers in poly(ionic liquid)s: syntheses and applications . Chemical Society Reviews 46 ( 4 ): 1124 – 1159 . https://doi.org/10.1039/c6cs00620e . 10.1039/C6CS00620E CASPubMedWeb of Science®Google Scholar Robinson , J. and Osteryoung , R.A. ( 1979 ). An electrochemical and spectroscopic study of some aromatic hydrocarbons in the room temperature molten salt system aluminum chloride-n-butylpyridinium chloride . Journal of the American Chemical Society 101 ( 2 ): 323 – 327 . https://doi.org/10.1021/ja00496a008 . 10.1021/ja00496a008 CASWeb of Science®Google Scholar Rogers , R.D. and Seddon , K.R. ( 2003 ). Ionic liquids—solvents of the future? Science 302 ( 5646 ): 792 – 793 . https://doi.org/10.1126/science.1090313 . 10.1126/science.1090313 PubMedWeb of Science®Google Scholar Salamone , J.C. , Israel , S.C. , Taylor , P. , and Snider , B. ( 1973 ). Polyvinylimidazolium salts of varying hydrophilic-hydrophobic character . Journal Polymer Science 73 ( 45 ): 65 – 73 . https://doi.org/10.1002/polc.5070450106 . 10.1002/polc.5070450106 Google Scholar Sawant , A.D. , Raut , D.G. , Darvatkar , N.B. , and Salunkhe , M.M. ( 2011 ). Recent developments of task-specific ionic liquids in organic synthesis . Green Chemistry Letters and Reviews 4 ( 1 ): 41 – 54 . https://doi.org/10.1080/17518253.2010.500622 . 10.1080/17518253.2010.500622 CASWeb of Science®Google Scholar Shaplov , A.S. , Marcilla , R. , and Mecerreyes , D. ( 2015 ). Recent advances in innovative polymer electrolytes based on poly(ionic liquid)s . Electrochimica Acta 175 : 18 – 34 . https://doi.org/10.1016/j.electacta.2015.03.038 . 10.1016/j.electacta.2015.03.038 CASWeb of Science®Google Scholar Sharma , M. , Mondal , D. , Sequeira , R.A. et al. ( 2021 ). Syntheses and characterization of few bio-ionic liquids comprising of cholinium cation and plant derived carboxylic acids as anions . Journal of the Indian Chemical Society 98 ( 11 ): 100205 . https://doi.org/10.1016/j.jics.2021.100205 . 10.1016/j.jics.2021.100205 Web of Science®Google Scholar Shiflett , M.B. ( 2020 ). Commercial Applications of Ionic Liquids . Cham : Springer https://doi.org/10.1007/978-3-030-35245-5 . 10.1007/978-3-030-35245-5 Google Scholar Singh , A. , Kaur , N. , and Kumar Chopra , H. ( 2019 ). Chiral recognition methods in analytical chemistry: role of the chiral ionic liquids . Critical Reviews in Analytical Chemistry ', Taylor & Francis 49 ( 6 ): 553 – 569 . https://doi.org/10.1080/10408347.2019.1565985 . 10.1080/10408347.2019.1565985 CASPubMedWeb of Science®Google Scholar Hayashi , S. and Hamaguchi , H.-o. ( 2004 ). Discovery of a magnetic ionic liquid [bmim]FeCl 4 . Chemistry Letters 33 ( 12 ): 1590 – 1591 . https://doi.org/10.1246/cl.2004.1590 . 10.1246/cl.2004.1590 CASWeb of Science®Google Scholar Smiglak , M. , Reichert , W.M. , Holbrey , J.D. et al. ( 2006 ). Combustible ionic liquids by design: is laboratory safety another ionic liquid myth? Chemical Communications 24 : 2554 – 2556 . https://doi.org/10.1039/b602086k . 10.1039/b602086k CASWeb of Science®Google Scholar Stettner , T. and Balducci , A. ( 2021 ). Protic ionic liquids in energy storage devices: past, present and future perspective . Energy Storage Materials 40 : 402 – 414 . https://doi.org/10.1016/j.ensm.2021.04.036 . 10.1016/j.ensm.2021.04.036 Web of Science®Google Scholar Tan , J. , Ji , Y. , Deng , W. , and Su , Y. ( 2021 ). Process intensification in gas/liquid/solid reaction in trickle bed reactors: a review . Petroleum Science 18 ( 4 ): 1203 – 1218 . https://doi.org/10.1016/j.petsci.2021.07.007 . 10.1016/j.petsci.2021.07.007 CASWeb of Science®Google Scholar Tang , J. , Radosz , M. , and Shen , Y. ( 2008 ). Poly(ionic liquid)s as optically transparent microwave-absorbing materials . Macromolecules 41 ( 2 ): 493 – 496 . https://doi.org/10.1021/ma071762i . 10.1021/ma071762i CASWeb of Science®Google Scholar Tavares , A.P.M. , Rodríguez , O. , and Macedo , E.A. ( 2012 ). New generations of ionic liquids applied to enzymatic biocatalysis . In: Ionic Liquids—New Aspects for the Future , 537 – 556 . London : IntechOpen https://doi.org/10.5772/51897 . Google Scholar Thanh , G.V. , Pegot , B. , and Loupy , A. ( 2004 ). Solvent-free microwave-assisted preparation of chiral ionic liquids from (−)-N-methylephedrine . European Journal of Organic Chemistry 5 : 1112 – 1116 . https://doi.org/10.1002/ejoc.200300601 . 10.1002/ejoc.200300601 CASWeb of Science®Google Scholar Thuy Pham , T.P. , Cho , C.W. , and Yun , Y.S. ( 2010 ). Environmental fate and toxicity of ionic liquids: a review . Water Research 44 ( 2 ): 352 – 372 . https://doi.org/10.1016/j.watres.2009.09.030 . 10.1016/j.watres.2009.09.030 CASPubMedWeb of Science®Google Scholar Turguła , A. , Stęsik , K. , Materna , K. et al. ( 2020 ). Third-generation ionic liquids with: N-alkylated 1,4-diazabicyclo[2.2.2]octane cations and pelargonate anions . RSC Advances 10 ( 15 ): 8653 – 8663 . https://doi.org/10.1039/d0ra00766h . 10.1039/D0RA00766H CASPubMedWeb of Science®Google Scholar Vishwakarma , S. ( 2014 ). Ionic liquids-designer solvents for green chemistry . International Journal of Basic Sciences and Applied Computing (IJBSAC) 1 ( 1 ). Google Scholar Wang , X. , Chi , Y. , and Mu , T. ( 2014 ). A review on the transport properties of ionic liquids . Journal of Molecular Liquids. 193 : 262 – 266 . https://doi.org/10.1016/j.molliq.2014.03.011 . 10.1016/j.molliq.2014.03.011 CASWeb of Science®Google Scholar Wasserscheid , P. , Bösmann , A. , and Bolm , C. ( 2002 ). Synthesis and properties of ionic liquids derived from the “chiral pool” . Chemical Communications 2 ( 3 ): 200 – 201 . https://doi.org/10.1039/b109493a . 10.1039/b109493a Google Scholar Watanabe , M. , Thomas , M.L. , Zhang , S. et al. ( 2017 ). Application of ionic liquids to energy storage and conversion materials and devices . Chemical Reviews 117 ( 10 ): 7190 – 7239 . https://doi.org/10.1021/acs.chemrev.6b00504 . 10.1021/acs.chemrev.6b00504 CASPubMedWeb of Science®Google Scholar Weiß , N. , Gabi Thielemann , G. , Nagel , K. et al. ( 2021 ). The influence of the cation structure on the basicity-related polarity of ionic liquids . Physical Chemistry Chemical Physics 23 ( 47 ): 26750 – 26760 . https://doi.org/10.1039/d1cp03986e . 10.1039/D1CP03986E CASPubMedWeb of Science®Google Scholar Welton , T. ( 2018 ). Ionic liquids: a brief history . Biophysical Reviews. Biophysical Reviews 10 ( 3 ): 691 – 706 . https://doi.org/10.1007/s12551-018-0419-2 . 10.1007/s12551-018-0419-2 CASPubMedGoogle Scholar Werner , S. , Szesni , N. , Kaiser , M. et al. ( 2012 ). A scalable preparation method for silp and scill ionic liquid thin-film materials . Chemical Engineering and Technology 35 ( 11 ): 1962 – 1967 . https://doi.org/10.1002/ceat.201200210 . 10.1002/ceat.201200210 CASWeb of Science®Google Scholar Wilkes , J.S. ( 2002 ). A short history of ionic liquids—from molten salts to neoteric solvents . Green Chemistry 4 ( 2 ): 73 – 80 . https://doi.org/10.1039/b110838g . 10.1039/b110838g CASWeb of Science®Google Scholar Wilkes , J.S. and Zaworotko , M.J. ( 1992 ). Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids . Journal of the Chemical Society, Chemical Communications 13 : 965 – 967 . https://doi.org/10.1039/C39920000965 . 10.1039/c39920000965 CASWeb of Science®Google Scholar Xu , J. , Liu , B. , Wu , W. et al. ( 2006 ). Basic ionic liquid as catalysis and reaction medium: a novel and green protocol for the markovnikov addition of N-heterocycles to vinyl esters, using a task-specific ionic liquid, [bmIm]OH . Journal of Organic Chemistry 7 ( 10 ): 3991 – 3993 . 10.1021/jo0600914 Google Scholar Yang , Z. and Pan , W. ( 2005 ). Ionic liquids: green solvents for nonaqueous biocatalysis . Enzyme and Microbial Technology 37 ( 1 ): 19 – 28 . https://doi.org/10.1016/j.enzmictec.2005.02.014 . 10.1016/j.enzmictec.2005.02.014 CASWeb of Science®Google Scholar Ye , C. , Liu , W. , Chen , Y. , and Yu , L. ( 2001 ). Room-temperature ionic liquids: a novel versatile lubricant . Chemical Communications 21 : 2244 – 2245 . https://doi.org/10.1039/b106935g . 10.1039/b106935g CASPubMedWeb of Science®Google Scholar Yoshida , Y. and Gunzi Saito , G. ( 2006 ). Influence of structural variations in 1-alkyl-3-methylimidazolium cation and tetrahalogenoferrate(III) anion on the physical properties of the paramagnetic ionic liquids . Journal of Material Chemistry 16 : 1254 – 1262 . https://doi.org/10.1039/B515391C . 10.1039/b515391c CASWeb of Science®Google Scholar Yuan , J. and Antonietti , M. ( 2011 ). Poly(ionic liquid)s: polymers expanding classical property profiles . Polymer 52 ( 7 ): 1469 – 1482 . https://doi.org/10.1016/j.polymer.2011.01.043 . 10.1016/j.polymer.2011.01.043 CASWeb of Science®Google Scholar Yuan , J. , Mecerreyes , D. , and Antonietti , M. ( 2013 ). Poly(ionic liquid)s: an update . Progress in Polymer Science 38 ( 7 ): 1009 – 1036 . https://doi.org/10.1016/j.progpolymsci.2013.04.002 . 10.1016/j.progpolymsci.2013.04.002 CASWeb of Science®Google Scholar Zhang , Q. and Shreeve , J.M. ( 2014 ). Energetic ionic liquids as explosives and propellant fuels: a new journey of ionic liquid chemistry . Chemical Reviews 114 ( 20 ): 10527 – 10574 . https://doi.org/10.1021/cr500364t . 10.1021/cr500364t CASPubMedWeb of Science®Google Scholar Zhao , D. , Liao , Y. , and Zhang , Z.D. ( 2007 ). Toxicity of ionic liquids . Clean—Soil, Air, Water 35 ( 1 ): 42 – 48 . https://doi.org/10.1002/clen.200600015 . 10.1002/clen.200600015 Web of Science®Google Scholar Chum , H.L. , Koch , V.R. , Miller , L.L. , and Osteryoung , R.A. ( 1975 ). An electrochemical scrutiny of organometallic iron complexes and hexamethylbenzene in a room temperature molten salt . Journal of American Chemical Society 97 : 3264 – 3265 . https://doi.org/10.1021/ja00844a081 . 10.1021/ja00844a081 CASWeb of Science®Google Scholar Hough , L.W. , Smiglak , M. , Rodrıguez , H. et al. ( 2007 ). The third evolution of ionic liquids: active pharmaceutical ingredients . New Journal of Chemistry 31 : 1429 – 1436 . https://doi.org/10.1039/B706677P . 10.1039/b706677p CASWeb of Science®Google Scholar Wilkes , J.S. , Levisky , J.A. , Wilson , R.A. , and Hussey , C.L. ( 1982 ). Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis . Inorganic Chemistry 21 ( 3 ): 1263 – 1264 . https://doi.org/10.1021/ic00133a078 . 10.1021/ic00133a078 CASWeb of Science®Google Scholar Parshall , G.W. ( 1972 ). Catalysis in molten salt media . Journal of American Chemical Society 94 : 8716 – 8719 . https://doi.org/10.1021/ja00780a013 . 10.1021/ja00780a013 CASWeb of Science®Google Scholar Santos , E. , Albo , J. , and Irabien , A. ( 2014 ). Magnetic ionic liquids: synthesis, properties and applications . RSC Advance 4 : 40008 – 40018 . https://doi.org/10.1039/C4RA05156D . 10.1039/C4RA05156D CASWeb of Science®Google Scholar Hice , S.A. , Clark , K.D. , Anderson , J.L. , and Brehm-Stecher , B.F. ( 2019 ). Capture, concentration, and detection of salmonella in Foods using magnetic ionic liquids and recombinase polymerase amplification . Analytical Chemistry 91 : 1113 – 1120 . https://doi.org/10.1021/acs.analchem.8b04751 . 10.1021/acs.analchem.8b04751 CASPubMedWeb of Science®Google Scholar Handbook of Ionic Liquids: Fundamentals, Applications, and Sustainability ReferencesRelatedInformation