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Sustainable Epoxidation of Electron‐Poor Olefins with Hydrogen Peroxide in Ionic Liquids and Recovery of the Products with Supercritical CO 2
Author(s) -
Bortolini Olga,
Campestrini Sandro,
Conte Valeria,
Fantin Giancarlo,
Fogagnolo Marco,
Maietti Silvia
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300442
Subject(s) - ionic liquid , chemistry , supercritical fluid , hydrogen peroxide , epoxide , yield (engineering) , aqueous solution , inorganic chemistry , organic chemistry , green chemistry , catalysis , materials science , metallurgy
An efficient procedure is described for the epoxidation of electron‐deficient olefins, in particular Vitamin K 3 and analogues, with aqueous basic solutions of hydrogen peroxide in different ambient temperature ionic liquids (ILs) [bmim + ][X − ] {[bmim + ] = 1‐butyl‐3‐methylimidazolium; [X − ] = [BF 4 − ], [CF 3 SO 3 − ], [PF 6 − ], [N(CF 3 SO 2 ) 2 − ]}. Various factors affecting epoxide yield (in the range 80−99%), reaction rate and reproducibility have been examined. The almost quantitative extraction of the epoxides from the reaction media has been obtained with supercritical CO 2 . The ionic liquid was then recovered and reused in subsequent cycles. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)