Sustainable epoxidation of electron-poor Olefins with hydrogen peroxide in ionic liquids and recovery of the products with Supercritical CO2

被引：31
作者：
Bortolini, O
Campestrini, S
Conte, V
Fantin, G
Fogagnolo, M
Maietti, S
机构：
[1] Univ Ferrara, Dipartimento Chim, I-44100 Ferrara, Italy
[2] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy
[3] Univ Padua, Dipartimento Chim Organ, I-35131 Padua, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 24期
关键词：
epoxidation; green chemistry; ionic liquids; peroxides; supercritical fluids;
D O I：
10.1002/ejoc.200300442
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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-] = [BF4-], [CF3SO3-], [PF6-] [N(CF3SO2)(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 CO2. The ionic liquid was then recovered and reused in subsequent cycles. (C) Wiley-VCH Verlag GmbH & Co.KGaA, 69451 Weinheim, Germany, 2003.
引用
收藏
页码：4804 / 4809
页数：6
相关论文
共 40 条
[1]  
ABRAHM MA, 1997, ACS S SERIES, V670
[2]  
[Anonymous], ANGEW CHEM
[3]   Catalytic asymmetric epoxidation of enones under phase-transfer catalyzed conditions [J].
Arai, S ;
Tsuge, H ;
Oku, M ;
Miura, M ;
Shioiri, T .
TETRAHEDRON, 2002, 58 (08) :1623-1630
[4]   Hydrophobic, highly conductive ambient-temperature molten salts [J].
Bonhote, P ;
Dias, AP ;
Papageorgiou, N ;
Kalyanasundaram, K ;
Gratzel, M .
INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178
[5]   FRIEDEL CRAFTS REACTIONS IN AMBIENT-TEMPERATURE MOLTEN-SALTS [J].
BOON, JA ;
LEVISKY, JA ;
PFLUG, JL ;
WILKES, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :480-483
[6]   Epoxidation of electrophilic alkenes in ionic liquids [J].
Bortolini, O ;
Conte, V ;
Chiappe, C ;
Fantin, G ;
Fogagnolo, M ;
Maietti, S .
GREEN CHEMISTRY, 2002, 4 (02) :94-96
[7]   Trihalide-based ionic liquids. Reagent-solvents for stereoselective iodination of alkenes and alkynes [J].
Bortolini, O ;
Bottai, M ;
Chiappe, C ;
Conte, V ;
Pieraccini, D .
GREEN CHEMISTRY, 2002, 4 (06) :621-627
[8]  
Campestrini S, 2001, ADV SYNTH CATAL, V343, P819, DOI 10.1002/1615-4169(20011231)343:8<819::AID-ADSC819>3.0.CO
[9]  
2-Y
[10]   New procedures for the Julia-Colonna asymmetric epoxidation: synthesis of (+)-clausenamide [J].
Cappi, MW ;
Chen, WP ;
Flood, RW ;
Liao, YW ;
Roberts, SM ;
Skidmore, J ;
Smith, JA ;
Williamson, NM .
CHEMICAL COMMUNICATIONS, 1998, (10) :1159-1160
1234