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Published November 10, 2006 | Supplemental Material
Journal Article Open

On the Mechanism of the Conversion of Methanol to 2,2,3-Trimethylbutane (Triptane) over Zinc Iodide


Methanol is converted to a mixture of hydrocarbons by reaction with zinc iodide at 200 °C with one highly branched alkane, 2,2,3-trimethylbutane (triptane), being obtained in surprisingly high selectivity. Mechanistic studies implicate a two-stage process, the first involving heterogeneously catalyzed formation of a carbon−carbon-bonded species, probably ethylene, that undergoes homogeneously catalyzed sequential cationic methylation to higher hydrocarbons. The first stage can be bypassed by addition of olefins, higher alcohols, or arenes, which act as initiators. Rationales for the particular activity of zinc iodide and for the selectivity to triptane are proposed.

Additional Information

© 2006 American Chemical Society. Received 29 August 2006. Published online 19 October 2006. Published in print 1 November 2006. Work at Caltech was supported by BP through the MC2 program. We thank Steve Cook, Gail Heath, and Matthew Deaves for assistance in performing some preliminary experiments on this system, Eugene Zaluzek for obtaining the PIANO analysis, and Philip Howard, Enrique Iglesia, Tom Knox, and Theo Fleisch for useful discussions.

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