Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/74942
Type: Artigo de periódico
Title: The chemical reactivity of some terpenes investigated by alumina catalyzed epoxidation with hydrogen peroxide and by DFT calculations
Author: Silva, JMDE
Vinhado, FS
Mandelli, D
Schuchardt, U
Rinaldi, R
Abstract: The selectivity of the alumina catalyzed epoxidation of (S)-limonene, citronelal, citral, citronelol and (1S)-(alpha)-pinene with aqueous 70 wt% and anhydrous 24 wt% hydrogen peroxide is described. DFT molecular orbital calculations were used aiming at a better understanding of the reactivity of these terpenes. The more nucleophilic carbon-carbon double bond, which has a higher molecular orbital energy, is preferentially epoxidized (site-selectivity). Furthermore, a preference for epoxidation in competition with other possible reactions is observed for citronelal, citral, citronelol and (IS)-(alpha)-pinene (chemo-selectivity). Nonetheless, we were not able to achieve a stereo-selective epoxidation of the terpenes using alumina and hydrogen peroxide. (c) 2006 Elsevier B.V. All rights reserved.
Subject: epoxidation
terpenes
DFT calculation
alumina
hydrogen peroxide
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.molcata.2006.02.042
Date Issue: 2006
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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