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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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Scorpionate complexes of vanadium(III or IV) as catalyst precursors for solvent-free cyclohexane oxidation with dioxygen

Gopal S. Mishra1 / Telma F. S. Silva2 / Luísa M. D. R. S. Martins1 / Armando J. L. Pombeiro1

1Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, TU Lisbon, Av. Rovisco Pais, 1049-001, Lisbon, Portugal

2Área Científica de Física, ISEL, R. Conselheiro Emídio Navarro, 1959-007, Lisbon, Portugal

3Departamento de Engenharia Química, ISEL, R. Conselheiro Emídio Navarro, 1959-007, Lisbon, Portugal

Conference

International Symposium on Chemistry and Biological Chemistry of Vanadium, International Vanadium Symposium, V, Vanadium , 6th, Lisbon, Portugal, 2008-07-17–2008-07-19

Citation Information: Pure and Applied Chemistry. Volume 81, Issue 7, Pages 1217–1227, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: 10.1351/PAC-CON-08-10-08, May 2009

Publication History

Published Online:
2009-05-29

The V-scorpionate vanadium complexes [VCl3{HC(pz)3}] (pz = pyrazolyl) and [VCl3{SO3C(pz)3}] catalyze cyclohexane oxidation with dioxygen, to cyclohexanol (the main product) and cyclohexanone, under solvent-free conditions. [VCl3{HC(pz)3}] provides the best activity (13 % conversion into the ketone and alcohol, with high selectivity, at the O2 pressure of 15 atm, at 140 ºC, 18 h reaction time). The reaction is further promoted (to 15 % conversion) by pyrazinecarboxylic acid (PCA). The use of C- or O-radical traps supports the involvement of a free-radical reaction mechanism. Several reaction parameters have been varied in a systematic study, directed toward optimization of the process.

Keywords: cyclohexane; dioxygen; homogeneous catalysis; scorpionates; vanadium; water-soluble complexes

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