Catalytic homogeneous oxidation of monoterpenes and cyclooctene with hydrogen peroxide in the presence of sandwich-type tungstophosphates [M-4(H2O)(2)(PW9O34)(2)](n-) M = Co-II, Mn-II and Fe-III

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abstract

Catalytic efficiency of tetrabutylammonium salts of sandwich tungstophosphates B-alpha-[M-4(H2O)(2)(PW9O34)(2)](n-), M = Co-II, Mn-II, Fe-III was studied in the oxidation of (R)-(+)-limonene, geraniol, linalool, linalyl acetate, carveol, and cis-cyclooctene with hydrogen peroxide, in acetonitrile. Oxidation of (R)-(+)-limonene gave limonene-1,2-diol as main product. Epoxidation of linalool takes place preferentially at the more substituted 6,7-double bond, the corresponding 6,7-epoxide reacting further, yielding furano- and pyrano-oxides, via intramolecular cyclization. Oxidation of linalyl acetate occurred preferentially at the more substituted 6,7-double bond for Mn-4(PW9)(2), affording 6,7-epoxide at 82% selectivity. Linalyl acetate 1,2-epoxide was the major product with 51% and 77% selectivity for Co-4(PW9)(2) and Fe-4(PW9)(2), respectively. Oxidation of carveol occurred with very good conversions in the presence of Mn-4(PW9)(2), Co-4(PW9)(2) and Fe-4(PW9)(2), yielding carvone and carveol 1,2-epoxide in similar amounts. Oxidation of cis-cyclooctene gave only the epoxide, while oxidation of geraniol at room temperature afforded 2,3-epoxygeraniol as the major product. (C) 2016 Elsevier B.V. All rights reserved.

keywords

METAL-SUBSTITUTED POLYOXOTUNGSTATES; KEGGIN-TYPE POLYOXOTUNGSTATES; HIGH-VALENT MANGANESE; SELECTIVE OXIDATION; LIMONENE EPOXIDATION; COMPLEX HETEROPOLYTUNGSTATES; HETEROGENEOUS PERFORMANCE; CRYSTAL-STRUCTURE; ACTIVE CATALYSTS; ALKENE OXIDATION

subject category

Chemistry

authors

Santos, ICMS; Gamelas, JAF; Duarte, TAG; Simoes, MMQ; Neves, MGPMS; Cavaleiro, JAS; Cavaleiro, AMV

our authors

foto Ana Maria Vieira Silva Viana Cavaleiro

Ana Maria Vieira Silva Viana Cavaleiro

Full professor
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Isabel Cristina Maia da Silva Santos Vieira

Junior Researcher
foto José António Ferreira Gamelas

José António Ferreira Gamelas

Post-Doc Fellowship

Groups

G1 - Porous Materials and Nanosystems

Projects

CICECO - Aveiro Institute of Materials (UID/CTM/50011/2013)

acknowledgements

Thanks are due to FCT/MEC for the financial support to QOPNA (FCT UID/QUI/00062/2013) and CICECO (FCT UID/CTM/50011/2013), through national founds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement.

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Publication Details

type
Journal Article
year
2017
journal
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
volume
426
publisher
ELSEVIER SCIENCE BV
issn
1381-1169
isbn
1873-314X
digital object identifier
10.1016/j.molcata.2016.10.021
web of science article identifier
WOS:000391075700038

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