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Mechanisms of Glycerol Dehydration

  • Mark R. Nimlos*
    Mark R. Nimlos
    National Bioenergy Center, National Renewable Energy Laboratory, Golden, Colorado 80401, U.S.A., Department of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia, and Rx-Innovation, Inc., Fort Collins, Colorado 80525, U.S.A.
     To whom correspondence should be addressed. E-mail: [email protected].
    More by Mark R. Nimlos
  • , 
  • Stephen J. Blanksby
    Stephen J. Blanksby
    National Bioenergy Center, National Renewable Energy Laboratory, Golden, Colorado 80401, U.S.A., Department of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia, and Rx-Innovation, Inc., Fort Collins, Colorado 80525, U.S.A.
    More by Stephen J. Blanksby
  • , 
  • Xianghong Qian
    Xianghong Qian
    National Bioenergy Center, National Renewable Energy Laboratory, Golden, Colorado 80401, U.S.A., Department of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia, and Rx-Innovation, Inc., Fort Collins, Colorado 80525, U.S.A.
    More by Xianghong Qian
  • , 
  • Michael E. Himmel
    Michael E. Himmel
    National Bioenergy Center, National Renewable Energy Laboratory, Golden, Colorado 80401, U.S.A., Department of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia, and Rx-Innovation, Inc., Fort Collins, Colorado 80525, U.S.A.
    More by Michael E. Himmel
  • , and 
  • David K. Johnson
    David K. Johnson
    National Bioenergy Center, National Renewable Energy Laboratory, Golden, Colorado 80401, U.S.A., Department of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia, and Rx-Innovation, Inc., Fort Collins, Colorado 80525, U.S.A.
    More by David K. Johnson
Cite this: J. Phys. Chem. A 2006, 110, 18, 6145–6156
Publication Date (Web):April 18, 2006
https://doi.org/10.1021/jp060597q
Copyright © 2006 American Chemical Society
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    Abstract

    Dehydration of neutral and protonated glycerol was investigated using quantum mechanical calculations (CBS-QB3). Calculations on neutral glycerol show that there is a high barrier for simple 1,2-dehydration, Ea = 70.9 kcal mol-1, which is lowered to 65.2 kcal mol-1 for pericyclic 1,3-dehydration. In contrast, the barriers for dehydration of protonated glycerol are much lower. Dehydration mechanisms involving hydride transfer, pinacol rearrangement, or substitution reactions have barriers between 20 and 25 kcal mol-1. Loss of water from glycerol via substitution results in either oxirane or oxetane intermediates, which can interconvert over a low barrier. Subsequent decomposition of these intermediates proceeds via either a second dehydration step or loss of formaldehyde. The computed mechanisms for decomposition of protonated glycerol are supported by the gas-phase fragmentation of protonated glycerol observed using a triple−quadrupole mass spectrometer.

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    Calculated structures of the reactants, transition states, and products. This material is available free of charge via the Internet at http://acs.pubs.org.

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