Journal
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
Volume 426, Issue -, Pages 593-599Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.molcata.2016.10.021
Keywords
Sandwich-type polyoxometalates; Monoterpenes; Cyclooctene; Oxidation
Categories
Funding
- FCT/MEC [FCT UID/QUI/00062/2013]
- CICECO [FCT UID/CTM/50011/2013]
- FEDER
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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.
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