A Multifunction Pd/Sc(OTf)3/Ionic Liquid Catalyst System for the Tandem One-Pot Conversion of Phenol to ε-Caprolactam

被引:46
作者
Shin, Ju Yeon [1 ]
Jung, Da Jung [1 ]
Lee, Sang-gi [1 ]
机构
[1] Ewha Womans Univ, Dept Chem & Nano Sci BK21, Seoul 120750, South Korea
关键词
multifunction catalyst; tandem catalysis; hydrogenation; phenol; caprolactam; VAPOR-PHASE HYDROGENATION; BECKMANN REARRANGEMENT; SUPPORTED PD; CYCLOHEXANONE OXIME; CASCADE REACTIONS; IONIC LIQUIDS; AQUEOUS-PHASE; PALLADIUM; KETOXIMES; MILD;
D O I
10.1021/cs400009w
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A multifunction Pd/Sc(OTf)(3)/ionic liquid catalyst for the tandem one-pot conversion of phenol to e-caprolactam is reported. Pd and Sc(OTf)(3) cooperate to catalyze the hydrogenation of phenol to cyclohexanone with excellent conversion (>99.9%) and selectivity (>99.9%), whereas Sc(OTf)(3) and an ionic liquid, [bmim] [PF6], cooperate to catalyze the tandem transformation of the resulting cyclohexanone to cyclohexanone oxime and the Beckmann rearrangement affording epsilon-caprolactam.
引用
收藏
页码:525 / 528
页数:4
相关论文
共 66 条
[1]   Hydrogen bond driven chemical reactions:: Beckmann rearrangement of cyclohexanone oxime into ε-caprolactam in supercritical water [J].
Boero, M ;
Ikeshoji, T ;
Liew, CC ;
Terakura, K ;
Parrinello, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (20) :6280-6286
[2]   Vapour phase hydrogenation of phenol over Pd/C catalysts: A relationship between dispersion, metal area and hydrogenation activity [J].
Chary, Komandur V. R. ;
Naresh, Dhachapally ;
Vishwanathan, V. ;
Sadakane, Masahiro ;
Ueda, Wataru .
CATALYSIS COMMUNICATIONS, 2007, 8 (03) :471-477
[3]   Hydrogenation of Phenol in Supercritical Carbon Dioxide Catalyzed by Palladium Supported on Al-MCM-41: A Facile Route for One-Pot Cyclohexanone Formation [J].
Chatterjee, M. ;
Kawanami, H. ;
Sato, M. ;
Chatterjee, A. ;
Yokoyama, T. ;
Suzuki, T. .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) :1912-1924
[4]   Selective reduction of phenol derivatives to cyclohexanones in water under microwave irradiation [J].
Cheng, Haiyang ;
Liu, Ruixia ;
Wang, Qiang ;
Wu, Chaoyong ;
Yu, Yancun ;
Zhao, Fengyu .
NEW JOURNAL OF CHEMISTRY, 2012, 36 (04) :1085-1090
[5]   Pd/MgO: Catalyst characterization and phenol hydrogenation activity [J].
Claus, P ;
Berndt, H ;
Mohr, C ;
Radnik, J ;
Shin, EJ ;
Keane, MA .
JOURNAL OF CATALYSIS, 2000, 192 (01) :88-97
[6]   Facile Beckmann rearrangement of ketoximes mediated by yttrium triflate [J].
De, SK .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2004, 36 (04) :383-386
[7]   Hydrogenation of Arenes by Dual Activation: Reduction of Substrates Ranging from Benzene to C60 Fullerene under Ambient Conditions [J].
Deshmukh, Ravindra R. ;
Lee, Ji Woong ;
Shin, Ueon Sang ;
Lee, Jin Yong ;
Song, Choong Eui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8615-8617
[8]   Hydrogenation of phenol in aqueous phase with palladium on activated carbon catalysts [J].
Diaz, E. ;
Mohedano, A. F. ;
Calvo, L. ;
Gilarranz, M. A. ;
Casas, J. A. ;
Rodriguez, J. J. .
CHEMICAL ENGINEERING JOURNAL, 2007, 131 (1-3) :65-71
[9]  
DODGSON I, 1989, CHEM IND-LONDON, P830
[10]   Cyanuric chloride as a mild and active Beckmann rearrangement catalyst [J].
Furuya, Y ;
Ishihara, K ;
Yamamoto, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11240-11241