Epoxidation of partially norbornylized linseed oil

A new cycloaliphatic epoxide functionalized monomer was prepared from partially norbornylized linseed oil (Dilulin®). Epoxidation was accomplished using three different approaches: peracetic acid, dioxirane, and hydrogen peroxide. Dioxirane was generated from potassium peroxomonosulfate and acetone. Hydrogen peroxide was used with a quaternary ammonium tetrakis(diperoxotungsto) phosphate(3-) as an epoxidation catalyst. The epoxidation reactions were monitored by FT-IR, and the products were characterized using 1H, 13C NMR, FT-IR, FT-Raman, and electrospray ionization (ESI) mass spectroscopy. For all three approaches, the effect of reaction time, temperature, catalyst concentration, and pH was investigated. Out of the three approaches, the hydrogen peroxide epoxidation was preferred on the basis of yield and ease of purification. The kinetic data were obtained only for the hydrogen peroxide approach. The reaction was found to be first-order with respect to the alkene double bond and 1.4th-order with respect to the catalyst. ln kap2 versus 1/T for the epoxidation reaction using H2O2 as epoxidation reagent.