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Related Experiment Videos

Methane activation and oxidation in sulfuric acid.

Alain Goeppert1, Peter Dinér, Per Ahlberg

  • 1Laboratoire de Physico-Chimie des Hydrocarbures, Institut de Chimie, UMR 7513, Université Louis Pasteur 4, rue Blaise Pascal, 67070 Strasbourg Cedex, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 31, 2002
PubMed
Summary

Methane acts as a sigma base, undergoing rapid protonation with sulfuric acid at high temperatures. This hydrogen-deuterium exchange reaction, studied via DFT, reveals bifunctional transition states and activation energies close to experimental values.

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Chemical Kinetics

Background:

  • Alkanes typically exhibit low reactivity.
  • Sulfuric acid is a strong acid capable of complex chemical reactions.
  • High-temperature reactions involving alkanes and strong acids are industrially relevant.

Purpose of the Study:

  • To investigate the mechanism of hydrogen-deuterium (H/D) exchange between methane and sulfuric acid.
  • To elucidate the role of methane as a sigma base in this reaction.
  • To compare theoretical calculations with experimental data for activation energy.

Main Methods:

  • Experimental observation of H/D exchange at 270-330°C.
  • Density Functional Theory (DFT) studies to model transition states.

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  • Calculation of potential activation energies for the reaction mechanism.

    • Main Results:

    • Methane behaves as a sigma base, undergoing reversible protonation.
    • DFT studies identified bifunctional transition states involving proton transfer and hydrogen abstraction.
    • Calculated activation energy (174 kJ mol⁻¹) closely matched the experimental value (176 kJ mol⁻¹).
    • Solvation effects slightly reduced the activation energy.
    • An competing oxidative pathway producing CO₂, SO₂, and water was observed.

    Conclusions:

    • The study confirms methane's sigma basicity and protonation by sulfuric acid at high temperatures.
    • The theoretical model accurately predicts the experimental activation energy for H/D exchange.
    • The reaction pathway is influenced by competing acid-base and oxidative processes.