Cyclohexene And Cyclooctene Epoxidation With Aqueous Hydrogen Peroxide Using Transition Metal-free Sol-gel Alumina As Catalyst

It is shown that sol-gel alumina calcined at 400°C is a very efficient catalyst for the epoxidation of cyclohexene and cyclooctene with aqueous 70 wt % hydrogen peroxide. The overall yield per g of catalyst was 0.28 mol of cyclohexene oxide in 5 cycles of 450 min each and 0.43 mol of cyclooctene oxide in 4 cycles of 750 min each. The selectivity for the epoxides was always better than 99%. However, the catalyst deactives slowly, which we believe is caused by a non-radical decomposition of hydrogen peroxide.3462-3281285Arends, I.W.C.E., Sheldon, R.A., (2002) Topics in Catalysis, 19, p. 133Lane, B.S., Burgess, K., (2003) Chem. Rev., 103, p. 2457Grigoropoulou, G., Clark, J.H., Elings, J.A., (2003) Green Chem., 5, p. 1Van Vliet, M.C.A., Mandelli, D., Arends, I.W.C.E., Schuchardt, U., Sheldon, R.A., (2001) Green Chem., 3, p. 243Mandelli, D., Van Vliet, M.C.A., Sheldon, R.A., Schuchardt, U., (2001) Appl. Catal. A, 219, p. 209Cesquini, R.G., Silva, J.M.S.E., Woitiski, C.B., Mandelli, D., Rinaldi, R., Schuchardt, U., (2002) Adv. Synth. Catal., 344, p. 911Misra, C., Industrial Alumina Chemicals (1986) ACS Monograph 184, , American Chemical Society, Washington, DCKabalka, G.W., Pagni, R.M., (1997) Tetrahedron, 53, p. 7999Woitiski, C.B., Ambiel, G., Schuchardt, U., Carvalho, W.A., Mandelli, D., (2002) Proceedings of the XVIII Iberoamerican Symposium on Catalysis, p. 35. , Isla Magarita, VenezuelaTsukada, T., Segawa, H., Yasumori, A., Okada, K., (1999) J. Mater. Chem., 9, p. 549Lefler, J.E., Miller, D.W., (1977) J. Am. Chem. Soc., 99, p. 480Rebek, J., McCready, R., (1979) Tetrahedron Lett., p. 4337Schuchardt, U., Carvalho, W.A., Spinace, E.V., (1993) Synlett, 10, p. 71