Abstract
AbstractThe industrial importance of the CC double bond difunctionalization in vegetable oils/fatty acid chains motivates computational studies aimed at helping to improve experimental protocols. The CC 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 FeCl2 Lewis acidic catalysts. Computations show that H2O2 (∆G‡ = 39 kcal/mol, TS1HP) is not an effective oxidizing agent compared to CH3CO3H (∆G‡ = 29.8 kcal/mol, TS1PA) and HCO3H (∆G‡ = 26.7 kcal/mol, TS1PF). The FeCl2 (∆G‡ = 14.7 kcal/mol, TS1FC) coordination to the epoxide oxygen facilitates the ring‐opening via lower energy barriers compared to the ZnCl2 (∆G‡ = 19.5 kcal/mol, TS1ZC) and NiCl2 (∆G‡ = 29.4 kcal/mol, TS1NC) coordination. ZnCl2 was 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.
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