화학공학소재연구정보센터
Applied Catalysis A: General, Vol.258, No.1, 93-98, 2004
Palladium catalyzed oxidation of monoterpenes: multistep electron transfer catalytic systems Pd(OAc)(2)/benzoquinone/M(OAc)(2) (M = Cu, Co or Mn) for the allylic oxidation of limonene with dioxygen
Oxidation of limonene (1) with dioxygen in acetic acid solutions containing catalytic amounts of Pd(OAc)(2), benzoquinone and M(OAc)(2) (M = Cu, Co or Mn) has been developed. Main reaction products are three isomeric allylic acetates, i.e., trans-2-acetoxy-p-mentha-1(7),8-diene (2), perilla acetate (3) and trans-carveyl acetate (4). A good control of chemo- and regioselectivities has been achieved through the addition of p-toluenesulfonic acid. The systems with Cu(OAc)(2) have shown the most promising results. Acetate 2, which has a mild scent of flower or fruit and can be useful as a component of synthetic fragrances, has been obtained in higher than 90% chemoselectivity at 90-95% limonene conversions. (C) 2003 Elsevier B.V. All rights reserved.