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Catalyst-Free Epoxidation of Limonene to Limonene Dioxide
Limonene
dioxide is a platform molecule for the production of new
biopolymers. First attempts at limonene epoxidation were made by using
low-coordination titanium supported on SBA-16 as the catalyst using <i>tert</i>-butyl hydroperoxide as the oxidizing agent, but no
limonene dioxide was obtained. When limonene was substituted by 1,2-limonene
oxide, the yield of limonene dioxide was only 13% in the same conditions.
Two other techniques, both using in situ generated dimethyl dioxirane
by the reaction of acetone with Oxone, have been studied and compared.
These reactions are carried out in semibatch conditions and at room
temperature. The first double epoxidation of limonene was performed
in a conventional biphasic organic–water system and the other
in excess acetone. The former epoxidation of limonene using ethyl
acetate as the organic phase allowed reaching 95% conversion and yielding
33% of limonene dioxide. In comparison, when the reaction was performed
in acetone, a limonene dioxide yield of 97% was observed under optimized
conditions. The double epoxidation of limonene should be carried out
at room temperature with a flowrate of 4 mL min<sup>–1</sup> of aqueous Oxone for a period of 45 min with a stoichiometric excess
of 30% of Oxone