Silicone composites of Novozym (R) 435 (silcoat-NZ435) demonstrate improved leaching and mechanical stability compared to native Novozym (R) 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 chemo-enzymatic 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 6?M. The silcoat-NZ435 catalyst could be reused over five days with less than 50?% loss in activity when 5?M 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.