Iron-substituted polyoxotungstates as catalysts in the oxidation of indane and tetralin with hydrogen peroxide
authors Estrada, AC; Simoes, MMQ; Santos, ICMS; Neves, MGPMS; Silva, AMS; Cavaleiro, JAS; Cavaleiro, AMV
nationality International
journal APPLIED CATALYSIS A-GENERAL
author keywords Polyoxometalates; Polyoxotungstates; Oxidation; Hydrogen peroxide; Indane; Tetralin
keywords KEGGIN-TYPE POLYOXOTUNGSTATES; AEROBIC OXIDATION; MOLECULAR-OXYGEN; BIPHASIC AUTOXIDATION; PHASE OXIDATION; ANION CHARGE; METAL; HYDROCARBONS; TUNGSTOPHOSPHATES; POLYOXOMETALATE
abstract The homogeneous liquid phase oxidation of indane and tetralin with hydrogen peroxide catalysed by tetrabutylammonium salts of iron(III)-substituted polyoxotungstates of general formula [XW(11)Fe(H(2)O)O(39)](n-), X=P, Si or B is described. The system presented here gives rise to benzylic monooxygenation and dioxygenation products. Indane oxidation reactions produce also dehydrogenation and hydroperoxidation products. As a result, 1H-indene and indane hydroperoxide are formed. Interestingly, tetralin gives rise to the cleavage of carbon-carbon bond, producing 4-(2-hydroxyphenyl)butanal. In the present conditions, this aldehyde is probably arising from tetralin hydroperoxide. Depending on the reaction conditions, moderate selectivities for the corresponding ketones are obtained, affording conversions as high as 59% and 34% for indane and tetralin, respectively. In order to understand the reactions pathway, the oxidation of 1-indanol, 1-indanone, 1H-indene, 1-tetralol and 1-tetralone is also carried out with an iron(Ill)-substituted polyoxotungstate as catalyst and H(2)O(2) as oxidant. The results show that 1-indanol and 1-tetralol give an important contribution for the formation of the corresponding ketones. As far as we know, the use of iron-substituted polyoxotungstates in the oxidation of these arenes is presented for the first time. (C) 2009 Elsevier B.V. All rights reserved.
publisher ELSEVIER SCIENCE BV
issn 0926-860X
year published 2009
volume 366
issue 2
beginning page 275
ending page 281
digital object identifier (doi) 10.1016/j.apcata.2009.07.022
web of science category Chemistry, Physical; Environmental Sciences
subject category Chemistry; Environmental Sciences & Ecology
unique article identifier WOS:000270644800007
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