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Catalytic oxidation of cyclohexane with hydrogen peroxide and a tetracopper(II) complex in an ionic liquid

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TL;DRAbstract

The catalytic peroxidative oxidation (with H 2 O 2 ) of cyclohexane in an ionic liquid (IL) using the tetracopper(II) complex [(CuL) 2 (μ 4 - O,O′,O′′,O′′′ -CDC)] 2 ·2H 2 O [HL = 2-(2-pyridylmethyleneamino)benzenesulfonic acid, CDC = cyclohexane-1,4-dicarboxylate] as a catalyst is reported. Significant improvements on the catalytic performance, in terms of product yield (up to 36%), TON (up to 529), reaction time, selectivity towards cyclohexanone and easy recycling (negligible loss in activity after three consecutive runs), are observed using 1-butyl-3-methylimidazolium hexafluorophosphate as the chosen IL instead of a molecular organic solvent including the commonly used acetonitrile. The catalytic behaviors in the IL and in different molecular solvents are discussed.

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The catalytic peroxidative oxidation (with H 2 O 2 ) of cyclohexane in an ionic liquid (IL) using the tetracopper(II) complex [(CuL) 2 (μ 4 - O,O′,O′′,O′′′ -CDC)] 2 ·2H 2 O [HL = 2-(2-pyridylmethyleneamino)benzenesulfonic acid, CDC = cyclohexane-1,4-dicarboxylate] as a catalyst is reported. Significant improvements on the catalytic performance, in terms of product yield (up to 36%), TON (up to 529), reaction time, selectivity towards cyclohexanone and easy recycling (negligible loss in activity after three consecutive runs), are observed using 1-butyl-3-methylimidazolium hexafluorophosphate as the chosen IL instead of a molecular organic solvent including the commonly used acetonitrile. The catalytic behaviors in the IL and in different molecular solvents are discussed.

Keywords

Ionic liquidCyclohexaneCyclohexanoneChemistryCatalysisHexafluorophosphateAcetonitrileHydrogen peroxide

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