Continuous Gas-Phase Hydroformylation of a Highly Diluted Technical C4 Feed using Supported Ionic Liquid Phase Catalysts

被引:54
作者
Haumann, Marco [1 ]
Jakuttis, Michael [2 ]
Franke, Robert [3 ]
Schoenweiz, Andreas [2 ]
Wasserscheid, Peter [2 ]
机构
[1] FAU Busan Campus, Chem React Engn, Pusan 618230, South Korea
[2] FAU Erlangen Nurnberg, Lehrstuhl Chem Reakt Tech, D-91058 Erlangen, Germany
[3] EvonikOxeno GmbH, D-45772 Marl, Germany
关键词
hydroformylation; ionic liquids; isomerization; NMR spectroscopy; phosphorus; SILP CATALYSIS; SELECTIVE HYDROFORMYLATION; RHODIUM CATALYSTS; PROPENE; HYDROGENATION; COMPLEX; OLEFINS;
D O I
10.1002/cctc.201100117
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
The concept of supported ionic liquid phase (SILP) catalysis has been established in recent years by our group and others. Its application in continuous catalytic gas-phase processes provides a very attractive way to bridge the gap between homogeneous and heterogeneous catalysis. In this contribution, we extend SILP hydroformylation catalysis to reactions with a highly diluted, technical C4 feed containing 1.5?% 1-butene, 28.5?% 2-butenes, and 70?% of inert n-butane. To obtain the desired product, n-pentanal, the Rh-biphephos catalyst system was immobilized in the SILP system to allow for consecutive isomerization/hydroformylation activity. The resulting SILP catalyst material converted up to 81?% of the reactive butenes, with a residence time of 155 s in the reactor. An n-pentanal selectivity greater than 92?% was realized for more than 500 h time-on-stream in the continuous gas-phase reaction. Post-reaction NMR studies revealed no significant loss of the phosphite ligand through ligand oxidation during the reaction.
引用
收藏
页码:1822 / 1827
页数:6
相关论文
共 25 条
[1]  
Anderson J.L., 2008, IONIC LIQUIDS SYNTHE, V1, P103
[2]   Kinetic of isomerizing hydroformylation of truns-4-octene [J].
Behr, A ;
Obst, D ;
Schulte, C .
CHEMIE INGENIEUR TECHNIK, 2004, 76 (07) :904-910
[3]   Highly selective tandem isomerization-hydroformylation reaction of trans-4-octene to n-nonanal with rhodium-BIPHEPHOS catalysis [J].
Behr, A ;
Obst, D ;
Schulte, C ;
Schosser, T .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 206 (1-2) :179-184
[4]   HYDROFORMYLATION OF ALKENES BY USE OF RHODIUM COMPLEX CATALYSTS [J].
EVANS, D ;
OSBORN, JA ;
WILKINSON, G .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (12) :3133-+
[5]   REACTION OF HYDRIDOCARB NYLTRIS(TRIPHENYLPHOSPHINE)RHODIUM WITH CARBON MONOXIDE AND OF REACTION PRODUCTS HYDRIDODICARBONYLBIS(TRIPHENYLPHOSPHINE)RHODIUM AND DIMERIC SPECIES WITH HYDROGEN [J].
EVANS, D ;
YAGUPSKY, G ;
WILKINSO.G .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (11) :2660-&
[6]  
Frohning C.D., 2002, Hydroformylation in Applied Homogeneous Catalysis with Organometallic Compounds, P31
[7]   Continuous gas-phase hydroformylation of 1-butene using supported ionic liquid phase (SILP) catalysts [J].
Haumann, Marco ;
Dentler, Katrin ;
Joni, Joni ;
Riisager, Anders ;
Wasserscheid, Peter .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :425-431
[8]  
Jakuttis M., 2011, ANGEW CHEM, V123, P4584
[9]   Rhodium-Phosphite SILP Catalysis for the Highly Selective Hydroformylation of Mixed C4 Feedstocks [J].
Jakuttis, Michael ;
Schoenweiz, Andreas ;
Werner, Sebastian ;
Franke, Robert ;
Wiese, Klaus-Diether ;
Haumann, Marco ;
Wasserscheid, Peter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (19) :4492-4495
[10]   Markownikoff and anti-Markownikoff hydroamination with palladium catalysts immobilized in thin films of silica supported ionic liquids [J].
Jimenez, Oriol ;
Mueller, Thomas E. ;
Sievers, Carsten ;
Spirkl, Andreas ;
Lercher, Johannes A. .
CHEMICAL COMMUNICATIONS, 2006, (28) :2974-2976