Oxidation of Polycyclic Aromatic Hydrocarbons with Hydrogen Peroxide in the Presence of Transition Metal Mono-Substituted Keggin-Type Polyoxometalates
authors Estrada, AC; Simoes, MMQ; Santos, ICMS; Neves, MGPMS; Cavaleiro, JAS; Cavaleiro, AMV
nationality International
journal CHEMCATCHEM
author keywords aromatic compounds; hydrogen peroxide; oxidation; PAHs; polyoxometalates
keywords IRON-SUBSTITUTED POLYOXOTUNGSTATES; RADICAL-INITIATED REACTIONS; SELECTIVE OXIDATION; CATALYTIC-OXIDATION; MOLECULAR-SIEVES; PHASE OXIDATION; GAS-PHASE; ANTHRACENE; NAPHTHALENE; OXYGEN
abstract The oxidation of anthracene, naphthalene, 1-ethylnaphthalene, and 2-ethylnaphthalene with environmentally benign hydrogen peroxide has been studied in the presence of the tetrabutylammonium salts of iron and manganese mono-substituted Keggin-type polyoxometalates [XW(11)M(H(2)O)O(39)](n-) (X=P, Si, or B, M=Mn(III) or Fe(III)). The reactions were performed under homogeneous conditions at 80 degrees C, using acetonitrile as the solvent. For all the catalysts studied, anthracene was selectively oxidized to 9,10-anthraquinone at 100% conversion in the presence of [BW(11)Mn(H(2)O)O(39)](6-). The oxidation of 1-ethylnaphthalene and 2-ethylnaphthalene occurs mainly at the alkyl substituent, along with the formation of phthalic anhydrides, which resulted from aromatic ring oxidation, with iron substituted anions. Naphthalene could not be oxidized with the conditions used. To understand the reaction pathways, the oxidation of several products was performed in the presence of [PW(11)Fe(H(2)O)O(39)](4-). Under the conditions used, the oxidation of vinylnaphthalene derivatives gave rise to mainly carbon-carbon double-bond cleavage, affording the corresponding naphthaldehydes in high yields (> 67%). Possible reaction pathways are presented and the role of different catalysts is discussed.
publisher WILEY-BLACKWELL
issn 1867-3880
year published 2011
volume 3
issue 4
beginning page 771
ending page 779
digital object identifier (doi) 10.1002/cctc.201000264
web of science category Chemistry, Physical
subject category Chemistry
unique article identifier WOS:000289259200024
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journal impact factor (jcr 2016): 4.803
5 year journal impact factor (jcr 2016): 4.765
category normalized journal impact factor percentile (jcr 2016): 80.345
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