CHEMADA

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CHEMADA
ROOM TEMPERATURE IONIC LIQUIDS (RTIL)
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CHEMADA
Topics

• What are Ionic Liquids?
• What makes Ionic Liquids interesting?
• How can they be made?
• Applications
• Recent developments
• What does CHEMADA offer?

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Room Temperature Ionic Liquids
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.
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Melting points of some salts and salts mixtures
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Room Temperature Ionic Liquids
Properties
High ionic conductivity Non volatile Non
flammable High thermal stability Highly solvating
- yet not coordinating Good solvents for many
inorganic and organic compounds
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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

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Typical Preparation Routes for Ionic Liquids
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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.
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Asymmetric Hydrogenation of Enamides in a
Biphasic System bmimPF6/iPrOH
S. Guernik, A. Wolfson, M. Herzkovitz, N.
Greenspoon, S. Geresh, Chem. Commun., 2001, 22,
2314
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CHEMADA
Chiral catalyst
M. J. Burk, J. E. Feaster, W. A. Nugent, R. L.
Harlow J. Am. Chem. Soc. 1993, 115, 10125
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Results
ee (R-S)100/(RS)
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Friedel Crafts Sulfonylations
Nara, S. J. Harjani, J. R. Salunkhe M. M. J.
Org. Chem 2001, 66, 8616,
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Palladium catalyzed allylic alkylations
Ross, J. Chen, W. Xu, L. Xiao, J.
Organometalics 2000
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Lipase Catalyzed kinetic resolution
Schofer, S. H. Kaftzik, N. Wasserschied, P.
Kragl, U. Chem Commun. 2001, 425.
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Ionic Liquids have been demonstrated to be
advantageous for many reaction types
Enzymatic reactions Alkoxycarbonylation Olefin
dimerization Diels-Alder Oxidations
Catalytic hydrogenetions Hydroformylations Heck
reactions Suzuki coupling Stille Coupling
Ionic liquids in Synthesis, Wasserscheid , P and
Welton, T (eds) Wiley VCH, p. 41 2002.
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Room Temperature Ionic Liquids
1-Butyl-3-methylimidazolium hexafluorophosphate b
mimPF6- CAS 174501-64-5
1-Butyl-3-methylimidazolium tetrafluoroborate bmi
mBF4- CAS 174501-65-6
1-Butyl-3-methylimidazolium bromotrichloroaluminat
e bmimAlCl3Br- CAS 405140-68-3
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