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. 

Published Papers:

"Evaluation of Molybdenum and Tungsten Metathesis Catalysts for Homogeneous Tandem Alkane Metathesis" B. C. Bailey, R. R. Schrock, S. Kundu, A. S. Goldman, Z. Huang and M. Brookhart, Organometallics 2009, 28(1), 355–360. http://pubs.acs.org/doi/abs/10.1021/om800877q

"Catalytic Ring Expansion, Contraction, and Metathesis-Polymerization of Cycloalkanes" R. Ahuja, S. Kundu, A. S. Goldman, M. Brookhart, B. C. Vicente, and S. L. Scott Chem. Commun. 2008, 253-255. http://www.rsc.org/publishing/journals/CC/article.asp?doi=B712197K

"Catalytic Alkane Metathesis by Tandem Alkane-Dehydrogenation–Olefin-Metathesis" A. S. Goldman, A. H. Roy, Z. Huang, R. Ahuja, W. Schinski, and M. Brookhart Science 2006, 312, 257-261. http://www.sciencemag.org/cgi/reprint/312/5771/257.pdf

"Highly active and recyclable heterogeneous iridium pincer catalysts for transfer dehydrogenation of alkanes" Huang, Z.; Brookhart, M.; Goldman, A. S.; Kundu, S.; Ray, A.; Scott, S. L.; Vicente, B. C. Adv. Synth. Catal. 2009, 351, 188-206.
(DOI: 10.1002/adsc.200800615)

"Transition-metal-based catalytic systems for the dehydrogenation and metathesis of alkanes. Solution-phase and solid-supported iridium-based pincer catalysts" Goldman, A. S.; Brookhart, M.; Huang, Z.; Krogh-Jespersen, K.; Kundu, S.; Scott, S. L. Prepr. Symp. - Am. Chem. Soc., Div. Fuel Chem.> 2009, 54, 213-215.

"Rational Design and Synthesis of Highly Active Pincer-Iridium Catalysts for Alkane Dehydrogenation" Kundu, S.; Choliy, Y.; Zhuo, G.; Ahuja, R.; Emge, T. J.; Warmuth, R.; Brookhart, M.; Krogh-Jespersen, K.; Goldman, A. S. Organometallics 2009, 28, 5432-5444.
(DOI: 10.1021/om900568f)