Manganese Catalyzed Partial Oxidation of Light Alkanes
Abstract
The catalytic partial oxidation of methane is achieved at low temperatures (<200 °C) using manganese oxides and manganese salts in mixtures of trifluoroacetic acid and trifluoroacetic anhydride. Dioxygen is used as the in situ terminal oxidant. For Mn oxides (e.g., MnO2, Mn2O3, and Mn3O4), we studied stoichiometric methane partial oxidation in HTFA (TFA = trifluoroacetate). Using a Mn trifluoroacetate salt, at 180 °C and under 25 psig of methane, product selectivity for the mono-oxidized product methyl trifluoroacetate (MeTFA) is observed to be >90% at ~35% methane conversion at approximately 6 turnovers. Under our catalytic methane oxidation reaction conditions, MeTFA is stable against overoxidation, which explains the likely high selectivity at conversions >15%. Using combined experimental studies and DFT calculations, a mechanism involving soluble and molecular Mn species in the catalytic cycle is proposed. The proposed reaction pathway involves initial activation of MnII by dioxygen, cleavage of a methane C–H bond by a MnIII hydroxo intermediate, rebound of the methyl radical to generate MeTFA, and finally regeneration of the starting MnII complex. Also, this process is shown to be applicable to the oxidation of ethane, favoring the mono-oxidized product ethyl trifluoroacetate (EtTFA) and reaching ~46% conversion.
- Authors:
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[2];
[4];
[3];
[1];
[5];
[1];
[3];
[4];
[2];
[1]
- Univ. of Virginia, Charlottesville, VA (United States)
- California Institute of Technology (CalTech), Pasadena, CA (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Princeton Univ., NJ (United States)
- Argonne National Lab. (ANL), Lemont, IL (United States)
- San Rafael, CA (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Advanced Manufacturing Office; National Science Foundation (NSF)
- OSTI Identifier:
- 1883785
- Grant/Contract Number:
- AC05-00OR22725; AC02-06CH11357; CHE-1464578
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Catalysis
- Additional Journal Information:
- Journal Volume: 12; Journal Issue: 9; Journal ID: ISSN 2155-5435
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; methane functionalization; manganese; partial oxidation; natural gas; methanol; oxy-esterification; alkyls; hydrocarbons; oxidation; oxides; transition metals
Citation Formats
Coutard, Nathan, Musgrave, Charles B., Moon, Jisue, Liebov, Nichole S., Nielsen, Robert M., Goldberg, Jonathan M., Li, Meijun, Jia, Xiaofan, Lee, Sungsik, Dickie, Diane A., Schinski, William L., Wu, Zili, Groves, John T., Goddard, William A., and Gunnoe, T. Brent. Manganese Catalyzed Partial Oxidation of Light Alkanes. United States: N. p., 2022.
Web. doi:10.1021/acscatal.2c00982.
Coutard, Nathan, Musgrave, Charles B., Moon, Jisue, Liebov, Nichole S., Nielsen, Robert M., Goldberg, Jonathan M., Li, Meijun, Jia, Xiaofan, Lee, Sungsik, Dickie, Diane A., Schinski, William L., Wu, Zili, Groves, John T., Goddard, William A., & Gunnoe, T. Brent. Manganese Catalyzed Partial Oxidation of Light Alkanes. United States. https://doi.org/10.1021/acscatal.2c00982
Coutard, Nathan, Musgrave, Charles B., Moon, Jisue, Liebov, Nichole S., Nielsen, Robert M., Goldberg, Jonathan M., Li, Meijun, Jia, Xiaofan, Lee, Sungsik, Dickie, Diane A., Schinski, William L., Wu, Zili, Groves, John T., Goddard, William A., and Gunnoe, T. Brent. Tue .
"Manganese Catalyzed Partial Oxidation of Light Alkanes". United States. https://doi.org/10.1021/acscatal.2c00982. https://www.osti.gov/servlets/purl/1883785.
@article{osti_1883785,
title = {Manganese Catalyzed Partial Oxidation of Light Alkanes},
author = {Coutard, Nathan and Musgrave, Charles B. and Moon, Jisue and Liebov, Nichole S. and Nielsen, Robert M. and Goldberg, Jonathan M. and Li, Meijun and Jia, Xiaofan and Lee, Sungsik and Dickie, Diane A. and Schinski, William L. and Wu, Zili and Groves, John T. and Goddard, William A. and Gunnoe, T. Brent},
abstractNote = {The catalytic partial oxidation of methane is achieved at low temperatures (<200 °C) using manganese oxides and manganese salts in mixtures of trifluoroacetic acid and trifluoroacetic anhydride. Dioxygen is used as the in situ terminal oxidant. For Mn oxides (e.g., MnO2, Mn2O3, and Mn3O4), we studied stoichiometric methane partial oxidation in HTFA (TFA = trifluoroacetate). Using a Mn trifluoroacetate salt, at 180 °C and under 25 psig of methane, product selectivity for the mono-oxidized product methyl trifluoroacetate (MeTFA) is observed to be >90% at ~35% methane conversion at approximately 6 turnovers. Under our catalytic methane oxidation reaction conditions, MeTFA is stable against overoxidation, which explains the likely high selectivity at conversions >15%. Using combined experimental studies and DFT calculations, a mechanism involving soluble and molecular Mn species in the catalytic cycle is proposed. The proposed reaction pathway involves initial activation of MnII by dioxygen, cleavage of a methane C–H bond by a MnIII hydroxo intermediate, rebound of the methyl radical to generate MeTFA, and finally regeneration of the starting MnII complex. Also, this process is shown to be applicable to the oxidation of ethane, favoring the mono-oxidized product ethyl trifluoroacetate (EtTFA) and reaching ~46% conversion.},
doi = {10.1021/acscatal.2c00982},
journal = {ACS Catalysis},
number = 9,
volume = 12,
place = {United States},
year = {Tue Apr 19 00:00:00 EDT 2022},
month = {Tue Apr 19 00:00:00 EDT 2022}
}
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