The epoxidation of 1-octene and propene with hydrogen peroxide is performed
using micellar catalysis. Linear terminal alkenes have successfully been e
poxidized with a homogeneous catalyst solubilized in an aqueous micellar so
lution. The best micellar system, in terms of reactivity and activity, cons
ists of a homogeneous porphyrin catalyst, Mn(TDCPP)Cl, solubilized in Trito
n X-100 micelles. The aggregation behavior of Triton X-100 micelles with an
d without different epoxidation catalysts has been studied. For the epoxida
tion of 1-octene with the Mn(TDCPP)Cl-Triton X-100 system, a conversion of
about 25% with a selectivity toward octene oxide in excess of 97% was obtai
ned after 30 min. The cocatalyst used was imidazole. The initial turnover f
requency was 250 h(-1). The Mn(TDCPP)Cl-Triton X-100 system showed excellen
t stability, and virtually no deactivation of the porphyrin catalyst was ob
served. The same epoxidation reaction carried out in a mixture of dichlorom
ethane and CH3CN had an initial turnover frequency of 392 h(-1), and the se
lectivity toward octene oxide was 94%.