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Comptes Rendus Chimie
Volume 18, n° 7
pages 758-765 (juillet 2015)
Doi : 10.1016/j.crci.2015.03.018
Received : 21 January 2015 ;  accepted : 30 Mars 2015
Catalytic oxidation of cyclohexane with hydrogen peroxide and a tetracopper(II) complex in an ionic liquid
 

Ana P.C. Ribeiro a , Luísa M.D.R.S. Martins a, b , Susanta Hazra a , Armando J.L. Pombeiro a,
a Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, avenue Rovisco Pais, 1049-001 Lisbon, Portugal 
b Chemical Engineering Department, ISEL, R. Conselheiro Emídio Navarro, 1959-007 Lisboa, Portugal 

Corresponding author. Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, avenue Rovisco Pais, 1049–001 Lisbon, Portugal.
Abstract

The catalytic peroxidative oxidation (with H2 O2 ) of cyclohexane in an ionic liquid (IL) using the tetracopper(II) complex [(CuL)24 -O,O′,O′′,O′′′ -CDC)]2 ·2H2 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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Keywords : Tetranuclear copper complex, Catalysis, Alkane functionalization, Peroxidative oxidation of cyclohexane, Ionic liquid, Electrochemistry, Ionic conductivity




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