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Ionic Liquids Vol. 5 No. 6 Enabling Technologies Ionic Liquids BASIL™ BASIONICS™ Ionic Liquids for Catalysis Ionic Liquids for Electrochemical Applications Enzymatic Reactions in Ionic Liquids Task-Specific Ionic Liquids CYPHOS® Phosphonium Ionic Liquids Imidazolium-Based Ionic Liquids Pyridinium-Based Ionic Liquids Pyrrolidinium-Based Ionic Liquids Ammonium-Based Ionic Liquids Phosphonium-Based Ionic Liquids sigma-aldrich.com/chemicalsynthesis 2 Introduction Sigma-Aldrich is proud to offer a new series of ChemFiles—called The strong ionic (Coulomb-) interaction within these substances results Enabling Technologies—to our Chemistry customers. Each piece will in a negligible vapor pressure (unless decomposition occurs), a non- highlight enabling products or technologies for chemical synthesis, drug flammable substance, and in a high thermally, mechanically as well discovery, and other areas of chemistry. as electrochemically stable product. In addition to this very interesting Ionic Liquids have experienced a comet-like boost in the last few years. combination of properties, they offer other favorable properties: for In this edition of ChemFiles, we highlight some current applications example, very appealing solvent properties and immiscibility with water of this fascinating class of new materials. We present over 50 new or organic solvents that result in biphasic systems. additions to our portfolio of 130+ Ionic Liquids, ranging from well- The choice of the cation has a strong impact on the properties of known imidazolium and pyridinium derivatives to ammonium, the Ionic Liquid and will often define the stability. The chemistry and pyrrolidinium, phosphonium, and sulfonium derivatives. At Sigma- functionality of the Ionic Liquid is, in general, controlled by the choice Aldrich, we are committed to being your preferred supplier for Ionic of the anion. The combination of a broad variety of cations and Liquids. Please visit sigma-aldrich.com/ionicliquids for a regular anions leads to a theoretically possible number of 1018 Ionic Liquids. update of the latest Ionic Liquids. If you cannot find a product for your However, a realistic number will be magnitudes lower. Today about specific research, “please bother us” at [email protected] 1000 Ionic Liquids are described in the literature, and approximately with new suggestions! 300 are commercially available. Typical structures combine organic cations with inorganic or organic anions: R3 R2 R4 N R N 1 R3 Introduction N N R2 R1 R2 R1 imidazolium pyridinium pyrrolidinium cation R4 R4 (organic) R1 R1 P R4 R N R 1 4 S R R R2 R2 2 3 phosphonium ammonium sulfonium O O O Ionic Liquids are a new class of purely ionic, salt-like materials that are R O S O H3C S O R3CS O liquid at unusually low temperatures. Currently, the “official” definition O O O of Ionic Liquids uses the boiling point of water as a point of reference: alkylsulfate tosylate methanesulfonate anion “Ionic Liquids are ionic compounds which are liquid below 100 °C.” (organic) More commonly, Ionic Liquids have melting points below room temperature; some of them even have melting points below 0 °C. O O N anion These new materials are liquid over a wide temperature range (300– S S PF6 BF4 Hal (inorganic) F C CF 400 °C) from the melting point to the decomposition temperature of 3 O O 3 the Ionic Liquid. If we compare a typical Ionic Liquid, e.g., 1-ethyl-3-methylimidazolium bis(trifluoromethyl- hexafluoro- tetrafluoro- halide sulfonyl)imide phosphate borate ethylsulfate (m.p. <-20 °C), with a typical inorganic salt, e.g., table salt (NaCl, m.p. 801 °C), it becomes obvious why there is a difference. The Ionic Liquid has a significantly lower symmetry! Furthermore, the The growing academic and industrial interest in Ionic Liquid charge of the cation as well as the charge of the anion is distributed technology is represented by the yearly increase in the number of over a larger volume of the molecule by resonance. As a consequence, publications (source Sci-Finder™): starting from far below 100 in 1990 the solidification of the Ionic Liquid will take place at lower to more than 1500 papers published last year. temperatures. In some cases, especially if long aliphatic side chains are involved, a glass transition is observed instead of a melting point. Publications per year anion, 1600 anion, large symmetric, 1400 large 1200 1000 cation, cation, symmetric, large, 800 small unsymmetric 600 No. of papers 400 200 0 1990 1992 1994 1996 1998 2000 2002 2004 Year TO ORDER: Contact your local Sigma-Aldrich office (see back cover), sigma-aldrich.com call 1-800-325-3010 (USA), or visit sigma-aldrich.com. US $ 3 Use and Applications References The reason for the increase in number of publications can be 1. Lubricants: Wang, H.; Lu, Q.; Ye, C.; Liu, W.; Cui, Z. Wear 2004, attributed to the unique properties of these new materials. Ultimately, 256, 44–48. the possible combinations of organic cations and anions places Artificial Muscles: Potential application, personal note. chemists in the position to design and fine-tune physical and chemical properties by introducing or combining structural motifs and, thereby, MALDI-TOF-Matrices: Armstrong, D. W.; Zhang, L. K.; He, L.; making tailor-made materials and solutions possible. The following Gross, M. L. Anal. Chem. 2001, 73, 3679–3686. chart summarizes important properties of Ionic Liquids and their GC-Head-Space-Solvents: Andre, M.; Loidl, J.; Schottenberger, 1 potential and current applications: H.; Bentivoglio, G.; Wurst, K.; Ongania, K.-H. Anal. Chem. 2005, LUBRICANTS & ADDITIVES 77, 702–705. • lubricants • fuel additives Protein-Crystallization: Ionic Liquids Technologies, Patent pending. SEPARATION • gas seperations Bio-Catalysis: Moriguchi, T.; Yanagi, T.; Kunimori, M. J. Org. ELECTROELASTIC • extractive distillation MATERIALS Chem. 2000, 65, 8229–8238. • extraction • artificial muscles • membranes Hayakawa, Y.; Kawai, R. Hirata, A. J. Am. Chem Soc. 2001, 123, • robotics IONIC LIQUIDS 8165–8176. Eckstein, M.; Filho, M. V.; Liese, A.; Kragl, U. Chem. Comm. 2004, • thermal stability ELECTROLYTES • low vapor pressure 1084–1085. • fuel cells • electric conductivity ANALYTICS Liu, Y.; Wang, M.; Li, J.; Li, Z.; He, P; Liu, H.; Li, J. Chem. Comm. • sensors • interesting solvent properties • MALDI-TOF-matrices • biphasic systems possible • batteries • GC-head-space-solvents 2005, 1778–1780. • supercaps • liquid crystalline structures • protein-crystallization • metal finishing • high electroelasticity Organic Synthesis & Catalysis: For a general overview see: • coating • high heat capacity • non flammability Wasserscheid, P.; Welton, T. Ionic Liquids in Synthsis; Wiley-VCH: Weinheim, 2003. Introduction SOLVENTS Deep Desulfuration: Bösmann, A.; Datsevich, L.; Jess, A.; Lauter, HEAT STORAGE • thermal fluids • bio-catalysis A.; Schmitz, C.; Wasserscheid, P. Chem. Comm. 2001, 2494–2495 • organic reactions & catalysis Nakashima, K.; Kubota, F.; Maruyama, T.; Goto, M. Chem. Mater. LIQUID CRYSTALS • Nano-particle-synthesis • displays • polymerization 2003, 15, 1825–1829. © IOLITEC 2005. Nano-Particle-Synthesis: Zhou, Y.; Antonietti, M. J. Am. Chem. Soc. 2003, 125, 14960–14961; Chem. Mater. 2004, 16, 544–550. The corresponding applications of Ionic Liquids can be divided in Liquid Crystals: Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., their use as process chemicals and performance chemicals. In 1948, Dalton Trans. 1999, 2133–2139. this class of electrically conducting materials (1-butylpyridinium Haristoy, D.; Tsiourvas, D. Chem. Mater. 2003, 15, 2079–2083. chloride/AlCl3) first drew attention for their use as electrolytes for electrodeposition of aluminium.2 This field is still the subject of current Thermal Fluids: Wu, B.; Reddy, R. G.; Rogers, R. D. Proceedings research efforts. Other important applications in this context are their of Solar Forum, 2001. use as electrolytes for batteries and fuel cells. See also: Ionic Liquids Technologies GmbH & Co. KG, http://www.iolitec.de. The major breakthrough came with the advent of less corrosive, air-stable materials in 1992. Wilkes and Zaworotko introduced Fuel Cells: Yanes, E. G.; Gratz, S. R.; Baldwin, M. J.; Anal. Chem. 1-ethyl-3-methylimidazolium tetrafluoroborate and focused on 2001, 73, 3838–3844. 3 solvent applications. Although 1-butyl-3-methylimidazolium Sensors: See also: http://www.iolitec.de. hexafluorophosphate and -tetrafluoroborate still dominate the current literature, there are better choices with respect to Supercaps: Sato, T; Masuda, G; Takagi, K. Electrochim. Acta performance and handling. It was demonstrated in aqueous media 2004, 49, 3603–3611. the hexafluorophosphate anion and the tetrafluoroborate anion Metal Finishing: Zell, C. A.; Freyland, W. Langmuir 2003, 19, will degrade, resulting in the formation of HF, a noxious and 7445–7450. aggressive acid. Scheeren, C. W.; Machado, G.; Dupont, J.; Fichtner, P.F.P.; Texeira, Over the past five years, other interesting applications were S.R. Inorg. Chem. 2003, 42, 4738–4742. suggested, derived from the unique combination of physical Huang, J.-F.; Sun, I.-W. J. Chromat. A, 2003, 1007, 39–45. properties. For example, the use of Ionic Liquids as thermal fluids Gas Separations: Scovazzo, P; Kieft, J.; Finan, D. A.; Koval, C.; combines their heat capacity with thermal stability and a negligible DuBios, D.; Noble, R. J. Membr. Sci. 2004, 238, 57–63. vapor pressure. It is quite feasible to expect that many more applications will be brought forward by potential users and some of Extractive Distillation: Jork, C.; Seiler, M.; Beste, Y.-A.; Arlt, W. them will be realized in the next couple of years. In order to enable J. Chem. Eng. Data 2004, 49, 852–857. potential users to make use of Ionic Liquids, it will be necessary to Extraction: Uerdingen, M.; Chem. unserer Zeit 2004, 38, 212–213. give technological support and to make a range of Ionic Liquids Membranes: Branco, L. C.; Crespo, J. G.; Afonso, C. A. M. available for testing. This support also includes the development of Angew. Chem. 2002, 104, 2895–2897. toxicological data and government required notification as well as the Fortunato, R.; Afonso, C. A. M.; Reis, M. A. M.; Crespo, J.
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  • HR2-214 Ionic Liquid Screen Documents
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