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Ionic Liquids as Micellar Agents in Perrhenate-catalysed Olefin Epoxidation

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Schäffer, Johannes ; Alber, Monika ; Korth, Wolfgang ; Cokoja, Mirza ; Jess, Andreas:
Ionic Liquids as Micellar Agents in Perrhenate-catalysed Olefin Epoxidation.
Chair of Inorganic and Metal-Organic Chemistry Technical University of Munich
In: ChemistrySelect. Bd. 2 (11 Dezember 2017) Heft 35 . - S. 11891-11898.
ISSN 2365-6549
DOI: 10.1002/slct.201702709

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Abstract

The perrhenate-catalysed epoxidation of cyclooctene with aqueous H2O2 was performed in micellar media using imidazolium-based ionic liquids (ILs) as surfactants. The catalytic performance of perrhenate was greatly increased in micellar media compared to IL used as neat solvent which allows for efficient use both of catalyst and IL. The choice of the surfactant alkyl chain length (C6 to C12) as well as the counterion (BF4−, TfO−, Cl−) is crucial for achieving high reaction rates. The positive effect of the addition of surfactants relies on formation of micelles. Best results are obtained for BF4− anion with long alkyl chain imidazolium cations, outperforming results for previously reported perrhenate ILs, while the use of Cl− anion leads only to similar reactivity. Cross-over experiments revealed that the catalytically active micellar species forms in situ and that the BF4− anion promotes the reaction beyond a mere change in ionic strength. The use of Cl− anion as surfactant counterion bears potential as a novel approach for rapid screening of potentially catalytically active anions, which is exemplarily shown for tungstate anion.

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Publikationsform: Artikel in einer Zeitschrift
Begutachteter Beitrag: Ja
Keywords: Epoxidation; ionic liquids; micellar catalysis; perrhenate; surfactant
Institutionen der Universität: Fakultäten > Fakultät für Ingenieurwissenschaften
Fakultäten > Fakultät für Ingenieurwissenschaften > Lehrstuhl Chemische Verfahrenstechnik
Fakultäten > Fakultät für Ingenieurwissenschaften > Lehrstuhl Chemische Verfahrenstechnik > Lehrstuhl Chemische Verfahrenstechnik - Univ.-Prof. Dr.-Ing. Andreas Jess
Fakultäten
Titel an der UBT entstanden: Ja
Themengebiete aus DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
600 Technik, Medizin, angewandte Wissenschaften > 600 Technik
600 Technik, Medizin, angewandte Wissenschaften > 620 Ingenieurwissenschaften
600 Technik, Medizin, angewandte Wissenschaften > 660 Chemische Verfahrenstechnik
Eingestellt am: 28 Feb 2018 07:38
Letzte Änderung: 28 Feb 2018 07:38
URI: https://eref.uni-bayreuth.de/id/eprint/42404