Manganese Catalyzed Partial Oxidation of Light Alkanes

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

doi:10.1021/acscatal.2c00982

Manganese Catalyzed Partial Oxidation of Light Alkanes

Journal Article · Tue Apr 19 00:00:00 EDT 2022 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.2c00982· OSTI ID:1883785

Coutard, Nathan ^[1]; ^[2]; Moon, Jisue ^[3]; Liebov, Nichole S. ^[1]; Nielsen, Robert M. ^[2]; ^[4]; ^[3]; ^[1]; ^[5]; ^[1]; Schinski, William L. ^[6]; ^[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)

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 Mn^II by dioxygen, cleavage of a methane C–H bond by a Mn^III hydroxo intermediate, rebound of the methyl radical to generate MeTFA, and finally regeneration of the starting Mn^II 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.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Advanced Manufacturing Office

Grant/Contract Number:: AC02-06CH11357; AC05-00OR22725

OSTI ID:: 1883785

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 9 Vol. 12; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
alkyls
hydrocarbons
manganese
methane functionalization
methanol
natural gas
oxidation
oxides
oxy-esterification
partial oxidation
transition metals

Manganese Catalyzed Partial Oxidation of Light Alkanes

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