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CHEMADA ROOM TEMPERATURE IONIC LIQUIDS (RTIL) February 2003 1

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What are Ionic Liquids? What makes Ionic Liquids interesting? How can they be made? Applications Recent developments What does CHEMADA offer? Topics 2 February 2003 CHEMADA

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Room Temperature Ionic Liquids are salts that are liquid over a wide range of temperatures, including room temperature. They are environmentally friendly alternatives to organic solvents for extractions, catalysis, separations and electrochemistry. Room Temperature Ionic Liquids 3 February 2003 CHEMADA

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Melting points of some salts and salts mixtures 4 CHEMADA February 2003

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High ionic conductivity Non volatile Non flammable High thermal stability Highly solvating - yet not coordinating Good solvents for many inorganic and organic compounds Room Temperature Ionic Liquids 5 CHEMADA February 2003 Properties

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Typical IL Cations N-alkylpyridinium 1,3-dialkylimidazolium Typical IL Anions [PF6]- for moisture stable, water immiscible IL [BF4]- for moisture stable, but water miscible IL [AlCl4-] (or other Lewis acids) decomposes in water CHEMADA 6 February 2003

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Typical Preparation Routes for Ionic Liquids 7 February 2003 CHEMADA

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Effect of the Cation on Melting Points of [PF6]- IL 1. J. G. Huddleston, A. F. Visser, W. M. Reichert, H. D. Willdver, R. A. Broker, R. D. Rogers, Green Chem., 2001, (3), 156 2. Holbrey J. D.; Rogers, R. D.; Ionic liquids in Synthesis, Wasserscheid , P and Welton, T (eds) Wiley VCH, p. 41 2002. 8 February 2003 CHEMADA

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Asymmetric Hydrogenation of Enamides in a Biphasic System [bmim][PF6]/iPrOH S. Guernik, A. Wolfson, M. Herzkovitz, N. Greenspoon, S. Geresh, Chem. Commun., 2001, 22, 2314 9 February 2003 CHEMADA

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Chiral catalyst M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow; J. Am. Chem. Soc. 1993, 115, 10125 10 February 2003 CHEMADA

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Results %ee = (R-S)*100/(R+S) 11 February 2003 CHEMADA

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Nara, S. J.; Harjani, J. R.; Salunkhe M. M.; J. Org. Chem 2001, 66, 8616, Friedel Crafts Sulfonylations 12 February 2003 CHEMADA

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Ross, J.; Chen, W.; Xu, L.; Xiao, J.; Organometalics 2000 Palladium catalyzed allylic alkylations 13 February 2003 CHEMADA

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Schofer, S. H.; Kaftzik, N.; Wasserschied, P.; Kragl, U.; Chem Commun. 2001, 425. Lipase Catalyzed kinetic resolution 14 February 2003 CHEMADA

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Ionic Liquids have been demonstrated to be advantageous for many reaction types Catalytic hydrogenetions Hydroformylations Heck reactions Suzuki coupling Stille Coupling Enzymatic reactions Alkoxycarbonylation Olefin dimerization Diels-Alder Oxidations Ionic liquids in Synthesis, Wasserscheid , P and Welton, T (eds) Wiley VCH, p. 41 2002. 15 February 2003 CHEMADA

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Room Temperature Ionic Liquids 1-Butyl-3-methylimidazolium hexafluorophosphate [bmim]+PF6- CAS# [174501-64-5] 1-Butyl-3-methylimidazolium tetrafluoroborate [bmim]+BF4- CAS# [174501-65-6] 1-Butyl-3-methylimidazolium bromotrichloroaluminate [bmim]+AlCl3Br- CAS# [405140-68-3] 16 February 2003 CHEMADA

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