Silicone composites of Novozym®435 (silcoat-NZ435) demonstrate improved leaching and mechanical stability compared to native Novozym®435 (NZ435). Here, the application scope of this novel enzyme preparation has been broadened significantly by the transfer from single-phase esterification to a complex chemoenzymatic epoxidation reaction in a three-phase system. The reaction gave up to 80% yields with almost 100% selectivity in 50 h when operated in the absence of mass transfer limitations. Characterization of the system revealed that octanoic acid inhibited the reaction at concentrations around 6M. The silcoat-NZ435 catalyst could be reused over five days with less than 50% loss in activity when 5M H2O2 was present. H2O2 was also identified as the component which deactivates the enzyme at high concentration (17.5 M) demanding spatial separation of the silcoat-NZ435 for optimal operation.