The recyclability of Co(III)-salen catalysts, where salen is defined by (R,R)-N,N -bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediamine, for the hydrolytic kinetic resolution (HKR) of racemic epichlorohydrin is a strong function of the counterion of the Co(III)-salen catalyst. The nature of the counterion determines whether the HKR reaction follows primarily a bimetallic or monometallic reaction path, which significantly affects catalyst recyclability. For example, Co(III)-salen initially containing the nucleophilic Cl -counterion catalyzes the HKR of epichlorohydrin according to a bimetallic reaction path but loses activity upon recycle, as Cl -is replaced with OH -during the reaction. In contrast, a Co(III)-salen catalyst containing non-nucleophilic SbF 6 -counterion catalyzes the reaction according to a monometallic reaction path and is quite stable during multiple recycles, albeit at a low rate with less selectivity. A mixed catalyst system with Co(III)-salen initially containing Cl -to which Co(III)-salen with SbF 6
-is later added demonstrates high activity and high stability to recycling. Additional experiments with Co(III)-salen initially containing the acetate counterion reveal a progressive decline in activity with multiple recycles even after regeneration with acetic acid between runs, suggesting a destructive role of the regeneration process.