Center
for Enabling New Technologies Through Catalysis
A NSF Center for Chemical Innovation
A NSF Center for Chemical Innovation
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Center
for Enabling New Technologies Through Catalysis
A NSF Center for Chemical Innovation |
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Alkane
Metathesis
Senior Investigators: Prof. Alan Goldman (Rutgers), Prof. Maurice Brookhart (UNC-CH), Prof. Susannah Scott (UCSB), Prof. Richard Schrock (MIT). As the global supply of petroleum decreases, interest in finding new ways to use existing feedstocks increases. In particular, the ability to convert low-molecular-weight alkanes to high-molecular-weight alkanes yields additional sources of transportation fuel such as diesel. When Fischer-Tropsch catalysis and subsequent hydrocracking are used to convert alternative fuel sources (methane, coal, shale, and biomass) to liquids a mixture of low- and high-molecular-weight alkanes is produced. It would be beneficial to convert the low-molecular-weight alkanes to alkanes in the C9-C19 range. These types of transformations can likely be achieved through "alkane metathesis". A method for achieving alkane metathesis has been conceived and developed by this CENTC team. As illustrated below for hexane, a homogeneous catalyst system is employed to redistribute the carbon and hydrogen chains. Hexane is redistributed to give a distribution of linear alkanes from C2 up to C20. With one of the catalyst systems employing decane as the initial substrate, an equilibrium distribution of alkanes was obtained under the reaction conditions used. Patents and Published Papers: Goldman,
A. S.; Brookhart, M.; MacArthur, A. R.; Ahuja,
R.; Huang, Z. “A dual catalyst system for
alkane metathesis”, U.S. Patent 7,902,417,
issued March 8, 2011.
Brookhart, M.; Goldman, A.; Carson, E.; Huang, Z.; Kundu, S. K. “Supported Iridium Catalysts”, PCT Int. Appl. (2008), WO 2008153869 A2 20081218. Yuan, J.; Townsend, E. M.; Schrock, R. R.; Goldman, A. S.; Muller, P.; Takase, M. T. “Preparation of Tungsten-Based Olefin Metathesis Catalysts Supported on Alumina” Adv. Chem. Synth., 2011, 353, 1985-1992. (DOI: 10.1002/adsc.201100200) Findlater, M.; Goldman, A. S.; Brookhart, M. S. “Alkane Dehydrogenation” Ch. 4 in Alkane C-H Activation by Single-Site Metal Catalysis, P. J. Perez, Ed.; Catalysis by Metal Complexes, Vol. 38, Springer, New York, 2011. Vicente, B. C.; Huang, Z.; Brookhart, M.; Goldman, A. S.; Scott, S. L. " Reactions of phosphinites with oxide surfaces: a new method for anchoring organic and organometallic complexes”, Dalton Trans., 2011, 40, 4268-4274. (DOI: 10.1039/C0DT01369B) Choi, J.; MacArthur, A.; Brookhart, M.; Goldman, A. S. “Dehydrogenation and Related Reactions Catalyzed by Iridium Pincer Complexes”, Chem. Rev., 2011, 111, 1761-1770. (DOI: 10.1021/cr1003503) Punji, B.; Emge, T. J.; Goldman, A. S., "A Highly Stable Adamantyl-Substituted Pincer-Ligated Iridium Catalyst for Alkane Dehydrogenation", Organometallics, 2010, 29, 2702-2709. (DOI: 10.1021/om100145q) Huang, Z.; White, P. S.; Brookhart, M., "Ligand Exchanges and Selective Catalytic Hydrogenation in Molecular Single Crystals", Nature, 2010, 465, 598-601. (DOI: 10.1038/nature09085) Findlater, M.; Bernskoetter, W. H.; Brookhart, M., "Proton-Catalyzed Hydrogenation of a d8 Ir(I) Complex Yields a trans Ir(III) Dihydride", J. Am. Chem. Soc., 2010, 132, 4534-4535. (DOI: 10.1021/ja100168w) Huang, Z.; Rolfe, E.; Carson, E. C.; Brookhart, M.; Goldman, A. S.; El-Khalafy, S. H.; MacArthur, A. H. R. , "Efficient Heterogeneous Dual Catalyst Systems for Alkane Metathesis", Adv. Synth. Catal., 2010, 352, 125-135 (DOI 10.1002/adsc.200900539) Kundu, S.; Choliy, Y.; Zhuo, G.; Ahuja, R.; Emge, T. J.; Warmuth, R.; Brookhart, M.; Krogh-Jespersen, K.; Goldman, A. S. "Rational Design and Synthesis of Highly Active Pincer-Iridium Catalysts for Alkane Dehydrogenation", Organometallics, 2009, 28, 5432-5444. (DOI: 10.1021/om900568f) Goldman, A. S.; Brookhart, M.; Huang, Z.; Krogh-Jespersen, K.; Kundu, S.; Scott, S. L. "Transition-metal-based catalytic systems for the dehydrogenation and metathesis of alkanes. Solution-phase and solid-supported iridium-based pincer catalysts." Prepr. Symp. - Am. Chem. Soc., Div. Fuel Chem., 2009, 54, 213-215. Huang, Z.; Brookhart, M.; Goldman, A. S.; Kundu, S.; Ray, A.; Scott, S. L.; Vicente, B. C. “Highly active and recyclable heterogeneous iridium pincer catalysts for transfer dehydrogenation of alkanes” Adv. Synth. Catal., 2009, 351, 188-206. (DOI: 10.1002/adsc.200800615) Bailey, B. C.; Schrock, R. R.; Kundu, S.; Goldman, A. S.; Huang, Z.; Brookhart, M. "Evaluation of Molybdenum and Tungsten Metathesis Catalysts for Homogeneous Tandem Alkane Metathesis", Organometallics, 2009, 28(1), 355–360. (DOI: 10.1021/om800877q) Ahuja, R.; Kundu, S.; Goldman, A. S.; Brookhart, M.; Vicente, B. C.; Scott, S. L. “Catalytic Ring Expansion, Contraction, and Metathesis-Polymerization of Cycloalkanes” ChemComm., 2008, 253-255. (DOI: 10.1039/b712197k) |
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The Center for Enabling New Technologies
Through Catalysis is a National Science Foundation
Center for Chemical Innovation
© 2009 Center for Enabling New Technologies Through Catalysis Contact: centcweb@u.washington.edu |
