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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".

Alkane metathesis
                      redistributes alkane mixture

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)

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