Przemysl Chemiczny, Vol.85, No.8-9, 605-607, 2006
Epoxidation of (Z,E,E)-1,5,9-cyclododecatriene with hydrogen peroxide over phase transfer catalysts
Methyltrioctylammonium chloride (or bromide) was best and [(76:24) dimethyidioctadecyl + dihexadecyl]ammonium chloride or Bu4NCl was next best as a phase-transfer catalyst. Reaction was run 45 min at 50 degrees C with 0.7 wt.% catalyst, reactant ratio 1:1, and WO42-/PO43-/catalyst = 5:2.51 (by moles). The 1, 5 or 6-substituted sym. bromides and chlorides were inactive. Regardless of the salt type, epoxidation did not stop at the epoxide stage but followed to destroy the epoxy ring.