Easy Epoxidation of Monoterpenes from Common Starting Materials

Epoxidation of monoterpenes, α-pinene, β-pinene, limonene, α-terpinene, and (R)-carvone was carried out by the in situ production of a peroxyacid rather than direct addition of such an expensive and difficult to handle chemical. Previous reports showed use of metal catalysts with high yields, while...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2020-05, Vol.31 (5), p.1086-1092
Main Authors: Bermudez, John, Rojas, Giovanni, Benitez, Ricardo, Franco, Jaime
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:Epoxidation of monoterpenes, α-pinene, β-pinene, limonene, α-terpinene, and (R)-carvone was carried out by the in situ production of a peroxyacid rather than direct addition of such an expensive and difficult to handle chemical. Previous reports showed use of metal catalysts with high yields, while methodologies without catalysts at high temperature showed yields lower than 30%. The authors report a methodology that produces peroxyacetic acid in situ yielding up to 75% pure epoxide at room temperature avoiding the use of catalysts. The products were analyzed by gas chromatography mass spectrometry (GC-MS), and structures were characterized by 1H and 13C nuclear magnetic resonance (NMR).
ISSN:0103-5053
1678-4790
DOI:10.21577/0103-5053.20190253