Cycloaddition of CO2 and epoxides catalyzed by imidazolium bromides under mild conditions: Influence of the cation on catalyst activity

Michael H. Anthofer, Michael E. Wilhelm, Mirza Cokoja, Iulius I E Markovits, Alexander Pöthig, J. Mink, Wolfgang A. Herrmann, Fritz E. Kühn

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

The synthesis and characterization of a library of imidazolium-based compounds of the type [R1R2R3im]Br (R 1 = H, CH3, benzyl (Bz), 1-(2,3,4,5,6-pentafluoro)benzyl (BzF5); R2 = H, CH3, C2H 5; R3 = n-butyl, n-octyl) are reported. All compounds were characterized by means of 1H and 13C NMR spectroscopy, elemental analysis and single crystal X-ray diffraction in the case of 1-Bz F5-3-n-octylimidazolium bromide and examined as catalysts for the cycloaddition of carbon dioxide and propylene oxide (PO) to yield propylene carbonate (PC). The catalyst screening shows the influence of different substituents (steric and ion pairing effects) on the catalytic activity. It is shown that the most active catalyst, 1-BzF5-3-n-octylimidazolium bromide (10), gives very good conversions and carbonate yields at 70°C and below 5 bar CO2 pressure, which is the lowest temperature for the synthesis of PC from PO and CO2 using metal-free catalysts. Catalyst 10 can be recycled and reused at least 10 times without loss of yield and activity. This journal is

Original languageEnglish
Pages (from-to)1749-1758
Number of pages10
JournalCatalysis Science and Technology
Volume4
Issue number6
DOIs
Publication statusPublished - 2014

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Cycloaddition
Epoxy Compounds
Bromides
Cations
Catalyst activity
Positive ions
Propylene
Catalysts
Carbonates
Oxides
Carbon Dioxide
Nuclear magnetic resonance spectroscopy
Carbon dioxide
Screening
Metals
Single crystals
Ions
X ray diffraction
Chemical analysis
Temperature

ASJC Scopus subject areas

  • Catalysis

Cite this

Cycloaddition of CO2 and epoxides catalyzed by imidazolium bromides under mild conditions : Influence of the cation on catalyst activity. / Anthofer, Michael H.; Wilhelm, Michael E.; Cokoja, Mirza; Markovits, Iulius I E; Pöthig, Alexander; Mink, J.; Herrmann, Wolfgang A.; Kühn, Fritz E.

In: Catalysis Science and Technology, Vol. 4, No. 6, 2014, p. 1749-1758.

Research output: Contribution to journalArticle

Anthofer, Michael H. ; Wilhelm, Michael E. ; Cokoja, Mirza ; Markovits, Iulius I E ; Pöthig, Alexander ; Mink, J. ; Herrmann, Wolfgang A. ; Kühn, Fritz E. / Cycloaddition of CO2 and epoxides catalyzed by imidazolium bromides under mild conditions : Influence of the cation on catalyst activity. In: Catalysis Science and Technology. 2014 ; Vol. 4, No. 6. pp. 1749-1758.
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