Search for: All records

Abstract The industrial importance of the CC double bond difunctionalization in vegetable oils/fatty acid chains motivates computational studies aimed at helping to improve experimental protocols. The CC double bond epoxidation is studied with hydrogen peroxide, peracetic acid (CH₃CO₃H), and performic acid (HCO₃H) oxidizing agents. The epoxide ring‐opening mechanism is calculated in the presence of ZnCl₂, NiCl₂, and FeCl₂Lewis acidic catalysts. Computations show that H₂O₂(∆G^‡= 39 kcal/mol,TS1_HP) is not an effective oxidizing agent compared to CH₃CO₃H (∆G^‡= 29.8 kcal/mol,TS1_PA) and HCO₃H (∆G^‡= 26.7 kcal/mol,TS1_PF). The FeCl₂(∆G^‡= 14.7 kcal/mol,TS1_FC) coordination to the epoxide oxygen facilitates the ring‐opening via lower energy barriers compared to the ZnCl₂(∆G^‡= 19.5 kcal/mol,TS1_ZC) and NiCl₂(∆G^‡= 29.4 kcal/mol,TS1_NC) coordination. ZnCl₂was frequently utilized as a catalyst in laboratory‐scale procedures. The energetic span model identifies the FeCl₂(FC) catalytic cycle as the best option for the epoxide ring‐opening.