NanoSelect Precious Metal Catalysts and their Use in Asymmetric Heterogeneous Catalysis

被引:15
作者
Kirby, Fiona [1 ]
Moreno-Marrodan, Carmen [2 ]
Baan, Zoltan [3 ]
Bleeker, Bas F. [1 ]
Barbaro, Pierluigi [2 ]
Berben, Peter H. [1 ]
Witte, Peter T. [1 ]
机构
[1] BASF Nederland BV, NL-3454 ZG De Meern, Netherlands
[2] CNR, ICCOM, I-50019 Florence, Italy
[3] BASF SE, D-67056 Ludwigshafen, Germany
关键词
asymmetric hydrogenation; heterogeneous catalysis; nanoparticles; palladium; platinum; PALLADIUM NANOPARTICLES; HYDROGENATION; PD; PLATINUM; COLLOIDS; ENANTIOSELECTIVITY; SELECTIVITY;
D O I
10.1002/cctc.201402310
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
We studied the surface modification of supported colloidal precious metal catalysts. Chiral compounds derived from cinchona alkaloids and prolinol were synthesized and used as stabilizers/reductants to yield Pd and Pt colloidal nanoparticles. The new Pd catalysts were found to be highly active and selective catalysts for the semihydrogenation of 3-hexyn-1-ol to cis-3-hexen-1-ol. The stabilizers affected the activity of the catalyst but not the selectivity. The catalysts were also evaluated in the asymmetric hydrogenation of methyl pyruvate and isophorone. No enantioselectivity was observed, which indicated that surface modification by the stabilizer did not induce chirality in the substrate. Achiral supported Pd and Pt colloidal catalysts were modified with cinchonidine. The modified Pt catalysts demonstrated a high activity for the hydrogenation of methyl pyruvate and a modest enantioselectivity of 47%, which indicated that the chiral induction of supported colloidal catalysts is possible by modifying the catalyst surface with a chiral reagent.
引用
收藏
页码:2904 / 2909
页数:6
相关论文
共 26 条
[1]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[2]  
Astruc D., 2005, Angew. Chem, V117, P8062, DOI DOI 10.1002/ange.200500766
[3]   Emerging strategies in sustainable fine-chemical synthesis: asymmetric catalysis by metal nanoparticles [J].
Barbaro, Pierluigi ;
Dal Santo, Vladimiro ;
Liguori, Francesca .
DALTON TRANSACTIONS, 2010, 39 (36) :8391-8402
[4]  
Blaser H.U., 2004, ASYMMETRIC CATALYSIS, P91
[5]   Synthesis of monodisperse Au, Pt, Pd, Ru and Ir nanoparticles in ethylene glycol [J].
Bonet, F ;
Delmas, V ;
Grugeon, S ;
Urbina, RH ;
Silvert, PY ;
Tekaia-Elhsissen, K .
NANOSTRUCTURED MATERIALS, 1999, 11 (08) :1277-1284
[6]   Enantioselective hydrogenations on platinum colloids [J].
Bonnemann, H ;
Braun, GA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (17) :1992-1995
[7]   Enantioselectivity control with metal colloids as catalysts [J].
Bonnemann, H ;
Braun, GA .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1200-1202
[8]  
BONNEMANN H, 1996, ANGEW CHEM, V108, P2120
[9]   Chemoselective Hydrogenation of Functionalized Nitroarenes using Supported Mo Promoted Pt Nanoparticles [J].
Boymans, Evert ;
Boland, Susan ;
Witte, Peter T. ;
Mueller, Christian ;
Vogt, Dieter .
CHEMCATCHEM, 2013, 5 (02) :431-434
[10]   Factors affecting the size of polymer stabilized Pd nanoparticles [J].
Choo, HP ;
Liew, KY ;
Liu, HF .
JOURNAL OF MATERIALS CHEMISTRY, 2002, 12 (04) :934-937