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Ionic liquid

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960:. For example, ILs allow for the preparation of biopolymer materials in different forms (e.g. sponges, films, microparticles, nanoparticles, and aerogels) and better biopolymer chemical reactions, leading to biopolymer-based drug/gene-delivery carriers. Moreover, ILs enable the synthesis of chemically modified starches with high efficiency and degrees of substitution (DS) and the development of various starch-based materials such as thermoplastic starch, composite films, solid polymer electrolytes, nanoparticles and drug carriers. 794: 578: 616: 31: 997:
fluid. Although nitrate salts have been the medium of choice since the early 1980s, they freeze at 220 Â°C (428 Â°F) and thus require heating to prevent solidification. Ionic liquids such as have more favorable liquid-phase temperature ranges (-75 to 459 Â°C) and could therefore be excellent liquid thermal storage media and heat transfer fluids.
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Polymerized ionic liquids, poly(ionic liquid)s or polymeric ionic liquids, all abbreviated as PIL is the polymeric form of ionic liquids. They have half of the ionicity of ionic liquids since one ion is fixed as the polymer moiety to form a polymeric chain. PILs have a similar range of applications,
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Recognizing that approximately 50% of commercial pharmaceuticals are salts, ionic liquid forms of a number of pharmaceuticals have been investigated. Combining a pharmaceutically active cation with a pharmaceutically active anion leads to a Dual Active ionic liquid in which the actions of two drugs
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Room-temperature ionic liquids (RTILs) are dominated by salts derived from 1-methylimidazole, i.e., 1-alkyl-3-methylimidazolium. Examples include 1-ethyl-3-methyl- (EMIM), 1-butyl-3-methyl- (BMIM), 1-octyl-3 methyl (OMIM), 1-decyl-3-methyl-(DMIM), 1-dodecyl-3-methyl- (dodecylMIM). Other imidazolium
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applications. While the comparatively high cost of ionic liquids currently prevents their use as neat lubricants, adding ionic liquids in concentrations as low as 0.5 wt% may significantly alter the lubricating performance of conventional base oils. Thus, the current focus of research is on using
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focus the sun's energy onto a receiver, which can generate temperatures of around 600 Â°C (1,112 Â°F). This heat can then generate electricity in a steam or other cycle. For buffering during cloudy periods or to enable generation overnight, energy can be stored by heating an intermediate
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Barghi S.H.; Adibi M.; Rashtchian D. (2010). "An experimental study on permeability, diffusivity, and selectivity of CO2 and CH4 through [bmim][PF6] ionic liquid supported on an alumina membrane: Investigation of temperature fluctuations effects".
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ILs improve the catalytic performance of palladium nanoparticles. Furthermore, ionic liquids can be used as pre-catalysts for chemical transformations. In this regard dialkylimidazoliums such as Ac have been used in the combination with a base to generate
3817:; Barletta, Robert E.; O'Brien, Richard A.; Sykora, Richard E.; Stenson, Alexandra C.; West, Kevin N.; Horne, Howard E.; Hendrich, Jeffrey M.; Xiang, Kang Rui; Davis, James H. (2014). "On the Formation of a Protic Ionic Liquid in Nature". 778:
comparable with those of ionic liquids but the polymer architecture provides a better chance for controlling the ionic conductivity. They have extended the applications of ionic liquids for designing smart materials or solid electrolytes.
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is less soluble in ionic liquids than in many popular organic solvents, and hydrogen is only slightly soluble (similar to the solubility in water) and may vary relatively little between the more common ionic liquids. Many classes of
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Marcin Smiglak; W. Mathew Reichert; John D. Holbrey; John S. Wilkes; Luyi Sun; Joseph S. Thrasher; Kostyantyn Kirichenko; et al. (2006). "Combustible ionic liquids by design: is laboratory safety another ionic liquid myth?".
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and the imidazolium/pyridinium and halide/halogenoaluminate ratios. Two major drawbacks for some applications were moisture sensitivity and acidity or basicity. In 1992, Wilkes and Zawarotko obtained ionic liquids with 'neutral'
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and Rakshit, during preparation of the nitrite salts of ethylamine, dimethylamine, and trimethylamine observed that the reaction between ethylamine hydrochloride and silver nitrate yielded an unstable ethylammonium nitrite
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Yauheni U. Paulechka; Gennady J. Kabo; Andrey V. Blokhin; Oleg A. Vydrov; Joseph W. Magee & Michael Frenkel (2002). "Thermodynamic Properties of 1-Butyl-3-methylimidazolium Hexafluorophosphate in the Ideal Gas State".
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Mota-Martinez M. T.; Althuluth M.; Berrouk A.; Kroon M.C.; Peters Cor J. (2014). "High pressure phase equilibria of binary mixtures of light hydrocarbons in the ionic liquid 1-hexyl-3-methylimidazolium tetracyanoborate".
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Martyn J. Earle; José M.S.S. Esperança; Manuela A. Gilea; José N. Canongia Lopes; Luís P.N. Rebelo; Joseph W. Magee; Kenneth R. Seddon & Jason A. Widegren (2006). "The distillation and volatility of ionic liquids".
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Zhao, D.; Fei, Z.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. (2004). "Nitrile-Functionalized Pyridinium Ionic Liquids: Synthesis, Characterization, and Their Application in Carbon-Carbon Coupling Reactions".
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as a solvent for pulp and paper. The "valorization" of cellulose, i.e. its conversion to more valuable chemicals, has been achieved by the use of ionic liquids. Representative products are glucose esters,
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J. S. Wilkes; J. A. Levisky; R. A. Wilson; C. L. Hussey (1982). "Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis".
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J. M. Crosthwaite; M. J. Muldoon; J. K. Dixon; J. L. Anderson & J. F. Brennecke (2005). "Phase transition and decomposition temperatures, heat capacities and viscosities of pyridinium ionic liquids".
1175:, and self-grooms with it, an action which de-toxifies the fire ant venom. The mixed venoms chemically react with one another to form an ionic liquid, the first naturally occurring IL to be described. 2900:
Fort D.A, Swatloski R.P., Moyna P., Rogers R.D., Moyna G. (2006). "Use of ionic liquids in the study of fruit ripening by high-resolution 13C NMR spectroscopy: 'green' solvents meet green bananas".
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Xuehui Li; Jinggan Zhao; Qianhe Li; Lefu Wang & Shik Chi Tsang (2007). "Ultrasonic chemical oxidative degradations of 1,3-dialkylimidazolium ionic liquids and their mechanistic elucidations".
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Ch. Jagadeeswara Rao, K.A. Venkatesan, K. Nagarajan, T.G. Srinivasan and P. R. Vasudeva Rao, Electrodeposition of metallic uranium at near ambient conditions from room-temperature ionic liquid,
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James P. Armstrong; Christopher Hurst; Robert G. Jones; Peter Licence; Kevin R. J. Lovelock; Christopher J. Satterley & Ignacio J. Villar-Garcia (2007). "Vapourisation of ionic liquids".
302:, mixtures of ionic and non-ionic solid substances which have much lower melting points than the pure compounds. Certain mixtures of nitrate salts can have melting points below 100 Â°C. 2271: 596:
was detected below −100 Â°C in the case of N-methyl-N-alkylpyrrolidinium cations fluorosulfonyl-trifluoromethanesulfonylimide (FTFSI). Low-temperature ionic liquids (below 130 
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E. F. Borra; O. Seddiki; R. Angel; D. Eisenstein; P. Hickson; K. R. Seddon & S. P. Worden (2007). "Deposition of metal films on an ionic liquid as a basis for a lunar telescope".
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Rñy, Prafulla Chandra; Rakshit, Jitendra Nath (1911). "CLXVII.—Nitrites of the alkylammonium bases: ethylammonium nitrite, dimethylammonium nitrite, and trimethylammonium nitrite".
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H. L. Chum; V. R. Koch; L. L. Miller; R. A. Osteryoung (1975). "Electrochemical scrutiny of organometallic iron complexes and hexamethylbenzene in a room-temperature molten salt".
367:, a heavy yellow liquid which on immersion in a mixture of salt and ice could not be solidified and was probably the first report of room-temperature ionic liquid. Later in 1914, 607:
Water is a common impurity in ionic liquids, as it can be absorbed from the atmosphere and influences the transport properties of RTILs, even at relatively low concentrations.
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streams. This has been achieved using lower temperature extraction processes than current approaches and could help avoid incinerating plastics or dumping them in landfill.
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Michel Armand; Frank Endres; Douglas R. MacFarlane; Hiroyuki Ohno & Bruno Scrosati (2009). "Ionic-liquid materials for the electrochemical challenges of the future".
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ILs can aid the recycling of synthetic goods, plastics, and metals. They offer the specificity required to separate similar compounds from each other, such as separating
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cations are 1-butyl-2,3-dimethylimidazolium (BMMIM or DBMIM) and 1,3-di(N,N-dimethylaminoethyl)-2-methylimidazolium (DAMI). Other N-heterocyclic cations are derived from
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R. J. Gale; R. A. Osteryoung (1979). "Potentiometric investigation of dialuminium heptachloride formation in aluminum chloride-1-butylpyridinium chloride mixtures".
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ILs are typically colorless viscous liquids. They are often moderate to poor conductors of electricity, and rarely self-ionize. They do, however, have a very large
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J. Stoimenovski; D. R. MacFarlane; K. Bica; R. D. Rogers (2010). "Crystalline vs. Ionic Liquid Salt Forms of Active Pharmaceutical Ingredients: A Position Paper".
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Kore, Rajkumar; Scurto, Aaron M.; Shiflett, Mark B. (2020). "Review of Isobutane Alkylation Technology Using Ionic Liquid-Based Catalysts—Where Do We Stand?".
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D. R. MacFarlane; J. Golding; S. Forsyth; M. Forsyth & G. B. Deacon (2001). "Low viscosity ionic liquids based on organic salts of the dicyanamide anion".
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Petkovic, Marija; Seddon, Kenneth R.; Rebelo, LuĂ­s Paulo N.; Pereira, Cristina Silva (2011-02-22). "Ionic liquids: a pathway to environmental acceptability".
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by ILs has attracted interest. A patent application from 1930 showed that 1-alkylpyridinium chlorides dissolve cellulose. Following in the footsteps of the
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of up to six volts (versus 1.23 for water) supporting more energy-dense metals. Energy densities from 900 to 1600 watt-hours per kilogram appear possible.
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C Pretti; C Chiappe; D Pieraccini; M Gregori; F Abramo; G Monni & L Intorre (2006). "Acute toxicity of ionic liquids to the zebrafish (Danio rerio)".
3507: 2549: 1885: 2935: 1421: 204:, manifested in high melting points. Some salts, especially those with organic cations, have low lattice energies and thus are liquid at or below 1185: 35: 3302: 3142: 3084: 721: 3023: 291:, that melts at −21 Â°C (−6 Â°F); and 1-butyl-3,5-dimethylpyridinium bromide which becomes a glass below −24 Â°C (−11 Â°F). 3674:
J Ranke; S Stolte; R Störmann; J Arning & B Jastorff (2007). "Design of sustainable chemical products – the example of ionic liquids".
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processes, allowing for relatively easy separation of products and/or unreacted substrate(s). Gas solubility follows the same trend, with
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Charles Graenacher, Manufacture and Application of New Cellulose Solutions and Cellulose Derivatives Produced therefrom, US 1934/1943176.
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Banqui Wu; Ramana G. Reddy & Robin D. Rogers (2001). "Novel ionic liquid thermal storage for solar thermal electric power systems".
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P) are less common but offer some advantageous properties. Some examples of phosphonium cations are trihexyl(tetradecyl)phosphonium (P
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Beyond cellulose, ILs have also shown potential in the dissolution, extraction, purification, processing and modification of other
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Many applications have been considered, but few have been commercialized. ILs are used in the production of gasoline by catalyzing
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Zhou, Feng; Liang, Yongmin; Liu, Weimin (2009-08-19). "Ionic liquid lubricants: designed chemistry for engineering applications".
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Richard P. Swatloski; Scott K. Spear; John D. Holbrey & Robin D. Rogers (2002). "Dissolution of Cellose with Ionic Liquids".
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Tripathi, Alok Kumar (2021). "Ionic liquid–based solid electrolytes (ionogels) for application in rechargeable lithium battery".
1111:. However, the claimed ecological advantage of ionic liquids has been questioned repeatedly and is yet to be demonstrated from a 589:
under vacuum conditions at temperatures near 300 Â°C. The vapor is not made up of separated ions, but consists of ion pairs.
3782: 2879: 640:: 4-methyl-N-butyl-pyridinium (MBPy) and N-octylpyridinium (C8Py). Conventional quaternary ammonium cations also form ILs, e.g. 3194: 2429: 1454: 1375: 17: 3263: 2515: 209: 2621:"Ionic Liquids as Precatalysts in the Highly Stereoselective Conjugate Addition of α,ÎČ‐Unsaturated Aldehydes to Chalcones" 2053: 2726: 2566: 1902: 1107:
ionic liquids as additives to lubricating oils, often with the motivation to replace widely used, ecologically harmful
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A. Lapkin; P. K. Plucinski; M. Cutler (2006). "Comparative assessment of technologies for extraction of artemisinin".
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ILs can extract specific compounds from plants for pharmaceutical, nutritional and cosmetic applications, such as the
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Reiter, Jakub (2 Sep 2012). "Fluorosulfonyl-(trifluoromethanesulfonyl)imide ionic liquids with enhanced asymmetry".
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Ionic liquids' low volatility effectively eliminates a major pathway for environmental release and contamination.
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J. S. Wilkes; M. J. Zaworotko (1992). "Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids".
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Plechkova, Natalia V.; Seddon, Kenneth R. (2008). "Applications of ionic liquids in the chemical industry".
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Table salt NaCl and ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide at 27 Â°ĐĄ
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ILs have a wide liquid range. Some ILs do not freeze down to very low temperatures (even −150 Â°C), The
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between the molecules of ordinary liquids. Because of these strong interactions, salts tend to have high
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The discovery date of the "first" ionic liquid is disputed, along with the identity of its discoverer.
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Ignatyev, Igor; Charlie Van Doorslaer; Pascal G.N. Mertens; Koen Binnemans; Dirk. E. de Vos (2011).
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Wilkes, John S. (2002). "A Short History of Ionic Liquids—from Molten Salts to Neoteric Solvents".
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is below a specific temperature, such as 100 Â°C (212 Â°F). While ordinary liquids such as
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often completely miscible. Solubility differences can be exploited in biphasic catalysis, such as
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R. E. Teixeira (2012). "Energy-efficient extraction of fuel and chemical feedstocks from algae".
601: 208:. Examples include compounds based on the 1-ethyl-3-methylimidazolium (EMIM) cation and include: 151:(NaCl), for example, melts at 801 Â°C (1,474 Â°F) into a liquid that consists largely of 2789: 839:(NHCs). These imidazolium based NHCs are known to catalyse a number transformations such as the 3887: 2797: 2050: 1026: 500: 3481:
Somers, Anthony E.; Howlett, Patrick C.; MacFarlane, Douglas R.; Forsyth, Maria (2013-01-21).
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BermĂșdez, MarĂ­a-Dolores; JimĂ©nez, Ana-Eva; Sanes, JosĂ©; CarriĂłn, Francisco-JosĂ© (2009-08-04).
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Polymerized Ionic Liquids, Editor: Ali Eftekhari, Royal Society of Chemistry, Cambridge 2018,
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Classically, ILs consist of salts of unsymmetrical, flexible organic cations with symmetrical
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Uwe Schaller; Thomas Keicher; Volker Weiser; Horst Krause; Stefan Schlechtriem (2010-07-10).
3742: 2929: 1112: 372: 299: 3049:"Ionic liquids for the preparation of biopolymer materials for drug/gene delivery: a review" 510:, which can be as low as 10 Pa. Many have low combustibility and are thermally stable. 317:
nitrate (m.p. 52–55 Â°C) was reported in 1888 by S. Gabriel and J. Weiner. In 1911
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steps, protic ionic liquids can be created more easily by simply mixing the acid and base.
318: 298:, liquids that contain both ions and neutral molecules, and in particular to the so-called 70:
state at ambient conditions. In some contexts, the term has been restricted to salts whose
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A. Eftekhari; O. Seddiki (2017). "Synthesis and Properties of Polymerized Ionic Liquids".
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Ionic Liquid Devices, Editor: Ali Eftekhari, Royal Society of Chemistry, Cambridge 2018,
2272:"Physicochemical properties of phosphonium-based and ammonium-based protic ionic liquids" 1596: 1557: 798: 732: 665: 460: 432:
or tetrahalogenoaluminate anions, were developed as potential electrolytes in batteries.
420:(m.p. 12 Â°C). In the 1970s and 1980s, ionic liquids based on alkyl-substituted 197: 3225: 2154: 2109: 2066: 2019: 1964: 1718: 3458: 3431: 3407: 3380: 3134: 3076: 3015: 2871: 2823: 2719: 2702: 2497: 2337: 2242:
K. J. Fraser; D. R. MacFarlane (2009). "Phosphonium-Based Ionic Liquids: An Overview".
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Ionic liquids' aquatic toxicity is as severe as or more so than many current solvents.
902: 836: 748: 747:. In contrast to other ionic liquids, which generally are formed through a sequence of 645: 641: 534: 3105:
Ren, Fei; Wang, Jinwei; Xie, Fengwei; Zan, Ke; Wang, Shuo; Wang, Shujun (2020-04-06).
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The IL 1-butyl-3-methylimidazolium chloride has been investigated for the recovery of
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Chen, Li; Mullen, Genevieve E.; Le Roch, Myriam; Cassity, Cody G.; Gouault, Nicolas;
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For the imidazolium halogenoaluminate salts, their physical properties—such as
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R. M. Barrer (1943). "The Viscosity of Pure Liquids. II. Polymerised Ionic Melts".
1565: 1536: 1501: 1491: 1442: 1336: 1298: 1254: 1157: 1038: 1025:. ILs are attractive because of their low vapor pressure. Furthermore, ILs have an 989: 818: 744: 563: 205: 129: 63: 2674: 2547:
Meindersma, G. Wytze; Maase, Matthias; De Haan, André B. (2007). "Ionic Liquids".
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to enhance finish, appearance, and drying properties. ILs are used for dispersing
3861: 3337: 3198: 2980:"Recent Advances of Using Ionic Liquids for Biopolymer Extraction and Processing" 2408: 2389: 2333: 1800: 865: 693: 542: 148: 83: 3365: 3255: 1772: 3814: 2244: 1726: 1144: 1083: 1068: 538: 507: 295: 201: 137: 3502: 3448: 3397: 2690: 1582: 1569: 1528: 1496: 1446: 3882: 3876: 3712: 3595: 3552: 3130: 3072: 3003: 2722:"BIOnic Liquids: Imidazolium-based Ionic Liquids with Antimicrobial Activity" 2558: 2493: 2220: 1894: 1734: 1687: 1641: 1531: 906: 709: 673: 530: 440: 71: 2581: 2269: 3838: 3830: 3767: 3729: 3696: 3660: 3603: 3560: 3467: 3416: 3241: 3011: 2995: 2921: 2819: 2776: 2720:
Frank Postleb; Danuta Stefanik; Harald Seifert & Ralf Giernoth (2013).
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Some ionic liquids have been shown to reduce friction and wear in basic
894:, and alkylgycosides. IL 1-butyl-3-methylimidazolium chloride dissolves 577: 310:
The term "ionic liquid" in the general sense was used as early as 1943.
3854: 3709: 3676: 3175: 3122: 3064: 2964: 2292: 2117: 1328: 1171:, alkaloid-based venom. The Tawny crazy ant then exudes its own venom, 1168: 1148: 1129: 929: 787: 600:) have been proposed as the fluid base for an extremely large diameter 425: 193: 3783:"Synthesis, Characterization and Combustion of Triazolium Based Salts" 3688: 3616: 2811: 2768: 2597: 2212: 1934: 1340: 1259: 1242: 813:
iodide, which functions as a catalyst to rearrange the monoepoxide of
793: 128:. Salts that are liquid at near-ambient temperature are important for 3759: 3721: 3645:
D. Zhao; Y. Liao & Z. Zhang (2007). "Toxicity of Ionic Liquids".
3631: 3587: 3544: 3233: 2913: 2458: 2074: 1540: 1302: 1205: 1099: 1095: 878: 814: 514: 503:, enabling electrochemical refinement of otherwise intractable ores. 436: 144: 2256: 2196: 2028: 2003: 1623: 1763:
Paul Walden (1914), Bull. Acad. Sci. St. Petersburg, pages 405-422.
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Fundamentals of ionic liquids : from chemistry to applications
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Ionic liquids have many potential applications. They are powerful
3673: 2754: 1200: 1006: 969: 957: 953: 949: 918: 914: 882: 586: 571: 551: 518: 444: 182: 177:). Conversely, when an ionic liquid is cooled, it often forms an 133: 121: 3864:, free database on toxicology and ecotoxicology of ionic liquids 3322: 627:. Both cationic and anionic components have been widely varied. 554:
varies with side chain lengths on the cation and with choice of
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reported one of the first stable room-temperature ionic liquids
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Chen, Jin; Xie, Fengwei; Li, Xiaoxi; Chen, Ling (2018-09-17).
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Jiangshui Luo; Olaf Conrad & Ivo F. J. Vankelecom (2012).
1441:. Green Chemistry and Sustainable Technology. Cham: Springer. 1132:
can degrade solutions of imidazolium-based ionic liquids with
716:). Magnetic ionic liquids can be synthesized by incorporating 615: 3107:"Applications of ionic liquids in starch chemistry: a review" 2852:"Synthesis of glucose esters from cellulose in ionic liquids" 1478:
Greer, Adam; Jacquemin, Johan; Hardacre, Christopher (2020).
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MacFarlane, Douglas; Kar, Mega; Pringle, Jennifer M. (2017).
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L.Ta; A. Axelsson; J. Bilj; M. Haukka; H. Sundén (2014).
550:, The miscibility of ionic liquids with water or organic 90: 3812: 1229:
Trioctylmethylammonium bis(trifluoromethylsulfonyl)imide
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systems. Concentrating solar thermal facilities such as
570:, and are precursors salts in the preparation of stable 513:
The solubility properties of ILs are diverse. Saturated
50:
Proposed structure of an imidazolium-based ionic liquid.
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https://pubs.rsc.org/en/content/ebook/978-1-78801-053-5
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https://pubs.rsc.org/en/content/ebook/978-1-78801-183-9
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Typical anions in ionic liquids include the following:
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testing, and their polar nature makes them candidate
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ILs are potential heat transfer and storage media in
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Greaves, Tamar L.; Drummond, Calum J. (2008-01-01).
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Hayes, Robert; Warr, Gregory G.; Atkin, Rob (2015).
2977: 2516:"Ionic liquid alkylation technology receives award" 2197:"Protic Ionic Liquids: Properties and Applications" 1621: 925:can be monitored as a function of banana ripening. 541:gas showing good solubility in many ionic liquids. 2978:Mahmood, Hamayoun; Moniruzzaman, Muhammad (2019). 2479: 2001: 1583:Mixture of nitrate salts with m.p. below 100 deg C 3042: 3040: 2419: 294:Low-temperature ionic liquids can be compared to 3874: 1471: 817:. This process was commercialized as a route to 491:), allowing a much wider range of applications. 2482:Industrial & Engineering Chemistry Research 2444: 2194: 1186:1-Butyl-3-methylimidazolium hexafluorophosphate 36:1-butyl-3-methylimidazolium hexafluorophosphate 3037: 2948: 2550:Ullmann's Encyclopedia of Industrial Chemistry 1886:Ullmann's Encyclopedia of Industrial Chemistry 1243:"Structure and Nanostructure in Ionic Liquids" 1240: 722:1-butyl-3-methylimidazolium tetrachloroferrate 147:or vaporizing usually yields an ionic liquid. 3256:"Betting on a Metal-Air Battery Breakthrough" 3104: 3046: 1318: 801:(gasoline component) as practiced by Chevron. 3530: 3381:"Ionic Liquids as Advanced Lubricant Fluids" 2934:: CS1 maint: multiple names: authors list ( 1593: 1420:: CS1 maint: multiple names: authors list ( 1225:which uses ionic liquid in its car batteries 1021:ILs can replace water as the electrolyte in 963: 909:analysis. In this way the entire complex of 3284:Examples are the TEGO brand dispersers by 1922:Journal of Chemical & Engineering Data 1878: 1876: 1665: 1624:"Ueber einige Abkömmlinge des Propylamins" 1480:"Industrial Applications of Ionic Liquids" 1361: 781: 132:applications, and have been considered as 3855:Ionic Liquids Biological Effects Database 3501: 3457: 3447: 3406: 3396: 2801: 2739: 2027: 1889:. Weinheim: Wiley-VCH. pp. 550–551. 1505: 1495: 1355: 1258: 824: 447:—could be adjusted by changing the 2793:Journal of the American Chemical Society 2422:Commercial Applications of Ionic Liquids 2319: 1438:Commercial Applications of Ionic Liquids 1434: 1314: 1312: 872: 792: 765:) and tributyl(tetradecyl)phosphonium (P 614: 576: 93:. These substances are variously called 45: 29: 3819:Angewandte Chemie International Edition 1873: 1428: 1192:) for an often encountered ionic liquid 1167:), the latter spray them with a toxic, 979: 581:Cations commonly found in ionic liquids 558:. They can be functionalized to act as 517:compounds are generally only sparingly 14: 3875: 3429: 3288:, used in their Pliolite brand paints. 2095: 1700: 1391: 1389: 1387: 1288: 1214:software for ionic liquids simulations 772: 525:show somewhat greater solubility, and 3868:Corresponding states for ionic fluids 3483:"A Review of Ionic Liquid Lubricants" 3266:from the original on November 6, 2009 3179:International Solar Energy Conference 2528:from the original on January 25, 2022 2190: 2188: 1309: 1067:have been investigated for capturing 89:, ionic liquids are largely made of 2098:Physical Chemistry Chemical Physics 2054:Physical Chemistry Chemical Physics 1384: 1140:to relatively innocuous compounds. 1032: 604:telescope to be based on the Moon. 24: 2185: 2004:"Volatile times for ionic liquids" 1234: 1000: 846: 727: 494: 25: 3899: 3848: 1052: 2727:Zeitschrift fĂŒr Naturforschung B 1701:Tanner, Eden E. L. (July 2022). 1400:. Weinheim, Germany: Wiley-VCH. 1364:An Introduction to Ionic Liquids 1321:"Room-Temperature Ionic Liquids" 901:pulp and with an additional 15% 3806: 3795:from the original on 2016-03-07 3774: 3736: 3703: 3667: 3638: 3610: 3567: 3524: 3513:from the original on 2018-11-04 3474: 3423: 3372: 3344: 3316: 3305:from the original on 2016-01-09 3291: 3278: 3248: 3203: 3186: 3169: 3156: 3145:from the original on 2021-01-24 3098: 3087:from the original on 2021-01-22 3026:from the original on 2021-01-22 2971: 2942: 2893: 2882:from the original on 2017-08-30 2834: 2783: 2748: 2713: 2668: 2657:from the original on 2021-09-30 2612: 2575: 2540: 2508: 2473: 2438: 2420:Shiflett, Mark B., ed. (2020). 2413: 2394: 2375: 2369:10.1016/j.eurpolymj.2017.03.033 2348: 2313: 2302:from the original on 2017-09-22 2263: 2235: 2132: 2089: 2044: 1995: 1941: 1911: 1850: 1823: 1794: 1766: 1757: 1694: 1659: 1648:from the original on 2020-02-07 1615: 1587: 1208:, or studies of ions in liquids 1196:Ionic liquids in carbon capture 1059:Ionic liquids in carbon capture 674:bis-trifluoromethanesulfonimide 212:, EMIMAc (acetate anion), EMIM 2280:Journal of Materials Chemistry 1622:S. Gabriel; J. Weiner (1888). 1576: 1547: 1522: 1282: 13: 1: 3430:Minami, Ichiro (2009-06-24). 2628:Chemistry: A European Journal 1276: 885:process, which uses hydrated 196:is usually stronger than the 3432:"Ionic Liquids in Tribology" 3338:10.1016/j.memsci.2010.06.047 3164:Journal of Nuclear Materials 2334:10.1016/j.mtener.2021.100643 1703:"Ionic liquids charge ahead" 1362:Freemantle, Michael (2009). 1089: 1016: 972:and other metals from spent 829: 610: 594:glass transition temperature 143:Any salt that melts without 7: 3366:10.1016/j.fluid.2013.09.015 3326:Journal of Membrane Science 2757:Journal of Natural Products 2002:Peter Wasserscheid (2006). 1179: 181:—which may be either 10: 3904: 2796:. 124/18 (18): 4974–4975. 2424:. Springer International. 1727:10.1038/s41557-022-00975-4 1368:Royal Society of Chemistry 1056: 887:N-methylmorpholine N-oxide 821:, but later discontinued. 630: 625:weakly coordinating anions 585:Some ionic liquids can be 521:in ionic liquids, whereas 457:weakly coordinating anions 305: 82:are predominantly made of 34:The chemical structure of 3503:10.3390/lubricants1010003 3449:10.3390/molecules14062286 3398:10.3390/molecules14082888 2691:10.1007/s11095-009-0030-0 1570:10.1016/j.jct.2005.03.013 1497:10.3390/molecules25215207 1447:10.1007/978-3-030-35245-5 1118: 964:Nuclear fuel reprocessing 805:An IL based on tetraalkyl 682:trifluoromethanesulfonate 651: 42:), a common ionic liquid. 3648:CLEAN - Soil, Air, Water 3533:Chemical Society Reviews 2559:10.1002/14356007.l14_l01 2494:10.1021/acs.iecr.0c03418 2357:European Polymer Journal 1895:10.1002/14356007.l14_l01 1642:10.1002/cber.18880210288 809:iodide is a solvent for 27:Salt in the liquid state 3747:Chemical Communications 3197:March 12, 2009, at the 2678:Pharmaceutical Research 2553:. Weinheim: Wiley-VCH. 2521:Oil and Gas Engineering 1859:Chemical Communications 1435:Shiflett, Mark (2020). 1155:When Tawny crazy ants ( 1147:many ionic liquids are 843:and the OTHO reaction. 837:N-heterocyclic carbenes 782:Commercial applications 720:anions, illustrated by 166:) and chloride anions ( 3831:10.1002/anie.201404402 3661:10.1002/clen.200600015 3354:Fluid Phase Equilibria 2996:10.1002/biot.201900072 2640:10.1002/chem.201404288 2322:Materials Today Energy 1319:Thomas Welton (1999). 1177: 1027:electrochemical window 825:Potential applications 802: 797:IL-catalyzed route to 620: 602:spinning liquid-mirror 582: 501:electrochemical window 300:deep eutectic solvents 136:due to their very low 51: 43: 2984:Biotechnology Journal 2741:10.5560/ZNB.2013-3150 1153: 1084:purifying natural gas 873:Biopolymer processing 796: 618: 580: 373:ethylammonium nitrate 49: 33: 18:Magnetic ionic liquid 3262:. November 5, 2009. 1867:10.1039/c39920000965 1680:10.1039/CT9119901470 1668:J. Chem. Soc., Trans 1609:10.1039/tf9433900059 1161:) combat fire ants ( 986:solar thermal energy 980:Solar thermal energy 841:benzoin condensation 733:Protic ionic liquids 198:Van der Waals forces 84:electrically neutral 3825:(44): 11762–11765. 3226:2009NatMa...8..621A 3166:, 408 (2011) 25–29. 2868:10.1515/hf.2011.161 2634:(43): 13889–13893. 2524:. January 2, 2018. 2488:(36): 15811–15838. 2287:(38): 20574–20579. 2163:10.1038/nature05909 2155:2007Natur.447..979B 2110:2013PCCP...15.2565R 2067:2007PCCP....9..982A 2020:2006Natur.439..797W 1973:10.1038/nature04451 1965:2006Natur.439..831E 1844:10.1021/ic50196a044 1832:Inorganic Chemistry 1817:10.1021/ic00133a078 1788:10.1021/ja00844a081 1719:2022NatCh..14..842T 1597:Trans. Faraday Soc. 1558:J. Chem. Thermodyn. 1109:lubricant additives 1023:metal-air batteries 976:and other sources. 877:The dissolution of 799:2,4-dimethylpentane 773:Poly(ionic liquid)s 666:hexafluorophosphate 461:hexafluorophosphate 124:and can be used as 95:liquid electrolytes 3860:2021-04-21 at the 3815:Fadamiro, Henry Y. 3123:10.1039/C9GC03738A 3065:10.1039/C8GC01120F 2965:10.1039/C2GC16225C 2407:2019-03-30 at the 2388:2019-03-30 at the 2293:10.1039/C2JM34359B 2118:10.1039/c2cp43066e 1629:Chemische Berichte 1164:Solenopsis invicta 994:solar power towers 905:, lends itself to 903:dimethyl sulfoxide 803: 646:tetrabutylammonium 642:tetraethylammonium 621: 583: 548:chemical reactions 535:hydrocarbonylation 52: 44: 3788:. pp. 1–23. 3754:(24): 2554–2556. 3716:(19): 1875–1880. 3689:10.1021/cr050942s 3260:Technology Review 3059:(18): 4169–4200. 2812:10.1021/ja025790m 2769:10.1021/np060375j 2763:(11): 1653–1664. 2734:(10): 1123–1128. 2598:10.1021/ja0463482 2586:J. Am. Chem. Soc. 2431:978-3-030-35245-5 2213:10.1021/cr068040u 2149:(7147): 979–981. 1935:10.1021/je025591i 1883:"Ionic liquids". 1782:(11): 3264–3265. 1776:J. Am. Chem. Soc. 1535:(16): 1430–1431. 1456:978-3-030-35244-8 1377:978-1-84755-161-0 1341:10.1021/cr980032t 1260:10.1021/cr500411q 1253:(13): 6357–6426. 1134:hydrogen peroxide 1039:dispersing agents 990:parabolic troughs 739:transfer from an 735:are formed via a 658:tetrafluoroborate 506:They exhibit low 477:tetrafluoroborate 16:(Redirected from 3895: 3843: 3842: 3810: 3804: 3803: 3801: 3800: 3794: 3787: 3778: 3772: 3771: 3760:10.1039/b602086k 3740: 3734: 3733: 3722:10.1039/b618384k 3707: 3701: 3700: 3683:(6): 2183–2206. 3671: 3665: 3664: 3642: 3636: 3635: 3632:10.1039/b511554j 3614: 3608: 3607: 3588:10.1039/c004968a 3582:(3): 1383–1403. 3571: 3565: 3564: 3545:10.1039/b817899m 3528: 3522: 3521: 3519: 3518: 3512: 3505: 3487: 3478: 3472: 3471: 3461: 3451: 3442:(6): 2286–2305. 3427: 3421: 3420: 3410: 3400: 3391:(8): 2888–2908. 3376: 3370: 3369: 3348: 3342: 3341: 3332:(1–2): 346–352. 3320: 3314: 3313: 3311: 3310: 3295: 3289: 3282: 3276: 3275: 3273: 3271: 3252: 3246: 3245: 3234:10.1038/nmat2448 3213:Nature Materials 3207: 3201: 3190: 3184: 3183: 3173: 3167: 3160: 3154: 3153: 3151: 3150: 3117:(7): 2162–2183. 3102: 3096: 3095: 3093: 3092: 3044: 3035: 3034: 3032: 3031: 2975: 2969: 2968: 2946: 2940: 2939: 2933: 2925: 2914:10.1039/B515177P 2897: 2891: 2890: 2888: 2887: 2847: 2841: 2838: 2832: 2831: 2805: 2787: 2781: 2780: 2752: 2746: 2745: 2743: 2717: 2711: 2710: 2672: 2666: 2665: 2663: 2662: 2656: 2625: 2616: 2610: 2609: 2592:(48): 15876–82. 2579: 2573: 2572: 2544: 2538: 2537: 2535: 2533: 2512: 2506: 2505: 2477: 2471: 2470: 2459:10.1039/b006677j 2442: 2436: 2435: 2417: 2411: 2398: 2392: 2379: 2373: 2372: 2352: 2346: 2345: 2317: 2311: 2310: 2308: 2307: 2301: 2276: 2267: 2261: 2260: 2239: 2233: 2232: 2201:Chemical Reviews 2192: 2183: 2182: 2136: 2130: 2129: 2104:(7): 2565–2571. 2093: 2087: 2086: 2075:10.1039/b615137j 2048: 2042: 2041: 2031: 1999: 1993: 1992: 1945: 1939: 1938: 1915: 1909: 1908: 1880: 1871: 1870: 1854: 1848: 1847: 1838:(6): 1603–1605. 1827: 1821: 1820: 1811:(3): 1263–1264. 1798: 1792: 1791: 1770: 1764: 1761: 1755: 1754: 1707:Nature Chemistry 1698: 1692: 1691: 1663: 1657: 1656: 1654: 1653: 1636:(2): 2669–2679. 1619: 1613: 1612: 1591: 1585: 1580: 1574: 1573: 1551: 1545: 1544: 1541:10.1039/b103064g 1526: 1520: 1519: 1509: 1499: 1475: 1469: 1468: 1432: 1426: 1425: 1419: 1411: 1393: 1382: 1381: 1359: 1353: 1352: 1335:(8): 2071–2084. 1325: 1316: 1307: 1306: 1303:10.1039/b110838g 1286: 1272: 1262: 1247:Chemical Reviews 1158:Nylanderia fulva 1081: 1080: 1079: 1033:Dispersing agent 819:2,5-dihydrofuran 707: 706: 705: 702: 490: 489: 488: 474: 473: 472: 419: 418: 417: 407: 406: 405: 395: 394: 393: 385: 384: 366: 365: 364: 354: 353: 352: 342: 341: 340: 332: 331: 290: 289: 288: 278: 277: 276: 268: 267: 259: 258: 248: 247: 246: 236: 235: 234: 226: 225: 206:room temperature 202:lattice energies 176: 175: 174: 165: 164: 163: 130:electric battery 21: 3903: 3902: 3898: 3897: 3896: 3894: 3893: 3892: 3873: 3872: 3862:Wayback Machine 3851: 3846: 3811: 3807: 3798: 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Soc. Rev 3566: 3523: 3473: 3422: 3371: 3343: 3315: 3299:"C&E News" 3290: 3277: 3247: 3220:(8): 621–629. 3202: 3185: 3168: 3155: 3097: 3036: 2970: 2959:(2): 419–427. 2941: 2908:(7): 714–716. 2892: 2862:(4): 417–425. 2842: 2833: 2782: 2747: 2712: 2685:(4): 521–526. 2667: 2611: 2574: 2568:978-3527306732 2567: 2539: 2507: 2472: 2453:(1): 123–150. 2447:Chem. Soc. Rev 2437: 2430: 2412: 2393: 2374: 2347: 2312: 2262: 2251:(4): 309–321. 2245:Aust. J. 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Rev. 1277:References 1169:lipophilic 1130:Ultrasound 1113:life-cycle 1100:lubricants 788:alkylation 757:cations (R 644:(TEA) and 426:pyridinium 194:ionic bond 3596:1460-4744 3553:1460-4744 3436:Molecules 3385:Molecules 3139:213702088 3131:1463-9270 3081:106290272 3073:1463-9270 3020:207833124 3004:1860-7314 2876:101737591 2798:CiteSeerX 2707:207224631 2502:225512999 2342:233581904 2221:0009-2665 1751:250181516 1735:1755-4349 1688:0368-1645 1603:: 59–67. 1484:Molecules 1465:211088946 1416:cite book 1206:Ioliomics 1090:Tribology 1017:Batteries 879:cellulose 830:Catalysis 815:butadiene 749:synthesis 611:Varieties 587:distilled 527:aldehydes 515:aliphatic 437:viscosity 155:cations ( 87:molecules 3858:Archived 3839:25045040 3790:Archived 3768:16779475 3730:17702165 3697:17564479 3604:21116514 3561:19690739 3508:Archived 3468:19553900 3417:19701132 3303:Archived 3264:Archived 3242:19629083 3195:Archived 3143:Archived 3085:Archived 3024:Archived 3012:31677240 2922:16465316 2880:Archived 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Index

Magnetic ionic liquid

1-butyl-3-methylimidazolium hexafluorophosphate

salt
liquid
melting point
water
gasoline
electrically neutral
molecules
ions
solvents
electrolytes
electric battery
sealants
vapor pressure
decomposing
Sodium chloride
sodium
ionic solid
crystalline
glassy
ionic bond
Van der Waals forces
lattice energies
room temperature
EMIM:Cl
dicyanamide
ionic solutions

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