Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published April 25, 2009 | public
Journal Article

A mechanistic explanation for selectivity in the conversion of methanol to 2,2,3-trimethylbutane (triptane): Moderate acidity allows kinetic control to operate

Abstract

Methanol is converted to hydrocarbons by reaction with ZnI2 or InI3 at 200 °C, with surprisingly high selectivity (yields on the order of 20%) to a single highly branched alkane, 2,2,3-trimethylbutane (triptane). Mechanistic studies demonstrate that the previously proposed mechanism, which proceeds via a carbocation-based route that involves methylation of olefins and hydride transfer to carbocations, can account quantitatively for the selectivity. Differences in product distribution between the Zn- and In-based systems represent quantitative, not qualitative, differences in behavior, and can be attributed to the slightly higher effective acidity of the latter.

Additional Information

© 2009 Elsevier Inc. Received 26 November 2008; revised 10 February 2009; accepted 15 February 2009. Available online 9 March 2009. We thank Drs. Glenn Sunley and Jay Winkler, and Professors John Bercaw, Enrique Iglesia and Vernon Gibson, for valuable discussions. This work was supported by BP through the MC2 program.

Additional details

Created:
August 21, 2023
Modified:
October 18, 2023