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Epoxidation of olefins using a dichlorodioxomolybdenum(VI)-pyridylimine complex as catalyst

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JournalINORGANICA CHIMICA ACTA
DatePublished - 30 May 2012
Volume387
Number of pages6
Pages (from-to)234-239
Original languageEnglish

Abstract

The ligand N-(n-propyl)-2-pyridylmethanimine (pyim) and an immobilized analogue of this ligand (pyim-MTS) were prepared by the condensation reaction of 2-pyridinecarboxaldehyde with either n-propylamine or 3-aminopropyl groups covalently attached to a micelle-templated silica (MTS). Free and immobilized dioxomolybdenum(VI) complexes of the type MoO 2Cl 2(L 1) (L 1 = pyim (1), pyim-MTS) were then prepared by treatment of the organic ligand or ligand-silica with the solvent adduct MoO 2Cl 2(THF) 2. MoO 2Cl 2(pyim) (1) is a highly active catalyst for the epoxidation of olefins (cyclooctene (Cy), cyclododecene, 1-octene, trans-2-octene, R-(+)-limonene) at 55 °C using tert-butylhydroperoxide (TBHP) as the oxidant under solvent-free conditions, giving the corresponding epoxides as the only reaction products. A turnover frequency of 1855 mol mol Mo -1 h -1 was measured for the epoxidation of Cy, and the epoxide (CyO) was formed quantitatively within 4.5 h. The MTS-supported complex was less active, and exhibited temperature-dependent leaching of active species. As an alternative approach to facilitating catalyst recycling, complex 1 was investigated with the ionic liquid (IL) 1-butyl-3-methylimidazolium tetrafluoroborate as solvent. The 1/IL phase could be reused, giving ca. 95% CyO yield in each run.

    Research areas

  • Catalysis, Dioxomolybdenum(VI) complex, Ionic liquids, Olefin epoxidation, Pyridylimine ligand, Silica supports

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