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Upgrading Light Hydrocarbons: A Tandem Catalytic System for Alkane/Alkene Coupling

Labinger, Jay A. and Leitch, David C. and Bercaw, John E. and Deimund, Mark A. and Davis, Mark E. (2015) Upgrading Light Hydrocarbons: A Tandem Catalytic System for Alkane/Alkene Coupling. Topics in Catalysis, 58 (7-9). pp. 494-501. ISSN 1022-5528. doi:10.1007/s11244-015-0380-2.

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Light hydrocarbons, with relatively low fuel value, are abundant from several sources, including mixed alkane/alkene refinery byproduct streams. A tandem system consisting of a compatible combination of a homogeneous alkane dehydrogenation catalyst (known to be kinetically efficient but thermodynamically disfavored at low temperatures) with an olefin dimerization catalyst could effect the coupling of an alkane and alkene to produce a heavier, more valuable fuel molecule (C_nH_(2n+2) + CnH_(2n) = C_(2n)H_(4n+2)), a reaction that is thermodynamically favorable below 250 °C. We have demonstrated that coupling with a tandem homogeneous catalyst, consisting of a pincer-ligated iridium alkane dehydrogenation catalyst and an organometallic tantalum alkene dimerization catalyst; the combination couples 1-hexene/n-heptane to C_(13)/C_(14) products at temperatures ranging from 100 to 150 °C, operating with up to 90 % cooperativity. This particular combination generates alkene products rather than the desired alkanes, however, because the regioselectivity of the dimerization catalyst preferentially yields highly substituted alkenes that are not reactive towards hydrogen transfer. A complete cycle should be attainable by combining the dehydrogenation catalyst with an alternate dimerization catalyst that gives mostly linear and monosubstituted alkenes; we have synthesized a novel class of nickel-exchanged zincosilicates that exhibit the desired dimerization catalytic behavior.

Item Type:Article
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URLURL TypeDescription ReadCube access
Labinger, Jay A.0000-0002-1942-9232
Davis, Mark E.0000-0001-8294-1477
Additional Information:© 2015 Springer Science+Business Media New York. Published online: 02 April 2015. We thank BP for supporting this work through the XC2 program. DCL thanks the National Science and Engineering Research Council of Canada for a postdoctoral fellowship.
Funding AgencyGrant Number
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Subject Keywords:Alkane/alkene coupling; Tandem catalysis; Alkane dehydrogenation; Alkene oligomerization; Light hydrocarbon upgrading
Issue or Number:7-9
Record Number:CaltechAUTHORS:20150407-092610476
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:56417
Deposited By: Tony Diaz
Deposited On:07 Apr 2015 19:20
Last Modified:10 Nov 2021 20:59

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