Sooting tendencies of aromatic hydrocarbons with oxygencontaining side-chains

Brian P. Beekley, Charles S. McEnally, Peter C. St John, Seonah Kim, Abhishek Jain, Hyunguk Kwon, Yuan Xuan, Lisa D. Pfefferle

    Research output: Contribution to conferencePaper

    Abstract

    Yield Sooting Index (YSI) was determined for 13 oxygen-containing aromatic compounds by measuring line-of-sight spectral radiance (LSSR) in a laminar non-premixed methane/air flame doped with 1000 ppm of each compound. The compounds included anisole (methoxybenzene), other aromatic ethers, and phenols. The presence of oxygen greatly reduced soot formation in some cases, but increased it in others. Thus oxygenated aromatics are potentially valuable as fuel components with intrinsically low particulate emissions, but the specific structure is important. Compounds containing an aromatic ring with an adjacent oxygen atom tended to have a lower sooting tendency than did compounds with oxygen atoms elsewhere in the side chain. This observation was quantitatively explored using Density Functional Theory (DFT) calculations. The bond dissociation energies for nine aromatic hydrocarbons and oxygenates were calculated using GGA B3LYP density functions with 6-31G(d) basis sets. When possible, unimolecular dissociation to phenoxy radical was favored and resulted in much lower YSIs than similar compounds where the oxygen atom was not adjacent to the aromatic ring. Structures that dissociated to benzyl radical had much higher sooting tendencies, sometimes by over a factor of two in comparison to phenoxyforming compounds.

    Original languageEnglish (US)
    StatePublished - Jan 1 2018
    Event2018 Spring Technical Meeting of the Eastern States Section of the Combustion Institute, ESSCI 2018 - State College, United States
    Duration: Mar 4 2018Mar 7 2018

    Other

    Other2018 Spring Technical Meeting of the Eastern States Section of the Combustion Institute, ESSCI 2018
    CountryUnited States
    CityState College
    Period3/4/183/7/18

    Fingerprint

    Aromatic Hydrocarbons
    Aromatic hydrocarbons
    oxygen atoms
    tendencies
    hydrocarbons
    Oxygen
    Atoms
    dissociation
    anisole
    Oxygen Compounds
    aromatic compounds
    rings
    soot
    oxygen
    Soot
    radiance
    phenols
    Particulate emissions
    line of sight
    particulates

    All Science Journal Classification (ASJC) codes

    • Mechanical Engineering
    • Physical and Theoretical Chemistry
    • Chemical Engineering(all)

    Cite this

    Beekley, B. P., McEnally, C. S., St John, P. C., Kim, S., Jain, A., Kwon, H., ... Pfefferle, L. D. (2018). Sooting tendencies of aromatic hydrocarbons with oxygencontaining side-chains. Paper presented at 2018 Spring Technical Meeting of the Eastern States Section of the Combustion Institute, ESSCI 2018, State College, United States.
    Beekley, Brian P. ; McEnally, Charles S. ; St John, Peter C. ; Kim, Seonah ; Jain, Abhishek ; Kwon, Hyunguk ; Xuan, Yuan ; Pfefferle, Lisa D. / Sooting tendencies of aromatic hydrocarbons with oxygencontaining side-chains. Paper presented at 2018 Spring Technical Meeting of the Eastern States Section of the Combustion Institute, ESSCI 2018, State College, United States.
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    abstract = "Yield Sooting Index (YSI) was determined for 13 oxygen-containing aromatic compounds by measuring line-of-sight spectral radiance (LSSR) in a laminar non-premixed methane/air flame doped with 1000 ppm of each compound. The compounds included anisole (methoxybenzene), other aromatic ethers, and phenols. The presence of oxygen greatly reduced soot formation in some cases, but increased it in others. Thus oxygenated aromatics are potentially valuable as fuel components with intrinsically low particulate emissions, but the specific structure is important. Compounds containing an aromatic ring with an adjacent oxygen atom tended to have a lower sooting tendency than did compounds with oxygen atoms elsewhere in the side chain. This observation was quantitatively explored using Density Functional Theory (DFT) calculations. The bond dissociation energies for nine aromatic hydrocarbons and oxygenates were calculated using GGA B3LYP density functions with 6-31G(d) basis sets. When possible, unimolecular dissociation to phenoxy radical was favored and resulted in much lower YSIs than similar compounds where the oxygen atom was not adjacent to the aromatic ring. Structures that dissociated to benzyl radical had much higher sooting tendencies, sometimes by over a factor of two in comparison to phenoxyforming compounds.",
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    Beekley, BP, McEnally, CS, St John, PC, Kim, S, Jain, A, Kwon, H, Xuan, Y & Pfefferle, LD 2018, 'Sooting tendencies of aromatic hydrocarbons with oxygencontaining side-chains', Paper presented at 2018 Spring Technical Meeting of the Eastern States Section of the Combustion Institute, ESSCI 2018, State College, United States, 3/4/18 - 3/7/18.

    Sooting tendencies of aromatic hydrocarbons with oxygencontaining side-chains. / Beekley, Brian P.; McEnally, Charles S.; St John, Peter C.; Kim, Seonah; Jain, Abhishek; Kwon, Hyunguk; Xuan, Yuan; Pfefferle, Lisa D.

    2018. Paper presented at 2018 Spring Technical Meeting of the Eastern States Section of the Combustion Institute, ESSCI 2018, State College, United States.

    Research output: Contribution to conferencePaper

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    T1 - Sooting tendencies of aromatic hydrocarbons with oxygencontaining side-chains

    AU - Beekley, Brian P.

    AU - McEnally, Charles S.

    AU - St John, Peter C.

    AU - Kim, Seonah

    AU - Jain, Abhishek

    AU - Kwon, Hyunguk

    AU - Xuan, Yuan

    AU - Pfefferle, Lisa D.

    PY - 2018/1/1

    Y1 - 2018/1/1

    N2 - Yield Sooting Index (YSI) was determined for 13 oxygen-containing aromatic compounds by measuring line-of-sight spectral radiance (LSSR) in a laminar non-premixed methane/air flame doped with 1000 ppm of each compound. The compounds included anisole (methoxybenzene), other aromatic ethers, and phenols. The presence of oxygen greatly reduced soot formation in some cases, but increased it in others. Thus oxygenated aromatics are potentially valuable as fuel components with intrinsically low particulate emissions, but the specific structure is important. Compounds containing an aromatic ring with an adjacent oxygen atom tended to have a lower sooting tendency than did compounds with oxygen atoms elsewhere in the side chain. This observation was quantitatively explored using Density Functional Theory (DFT) calculations. The bond dissociation energies for nine aromatic hydrocarbons and oxygenates were calculated using GGA B3LYP density functions with 6-31G(d) basis sets. When possible, unimolecular dissociation to phenoxy radical was favored and resulted in much lower YSIs than similar compounds where the oxygen atom was not adjacent to the aromatic ring. Structures that dissociated to benzyl radical had much higher sooting tendencies, sometimes by over a factor of two in comparison to phenoxyforming compounds.

    AB - Yield Sooting Index (YSI) was determined for 13 oxygen-containing aromatic compounds by measuring line-of-sight spectral radiance (LSSR) in a laminar non-premixed methane/air flame doped with 1000 ppm of each compound. The compounds included anisole (methoxybenzene), other aromatic ethers, and phenols. The presence of oxygen greatly reduced soot formation in some cases, but increased it in others. Thus oxygenated aromatics are potentially valuable as fuel components with intrinsically low particulate emissions, but the specific structure is important. Compounds containing an aromatic ring with an adjacent oxygen atom tended to have a lower sooting tendency than did compounds with oxygen atoms elsewhere in the side chain. This observation was quantitatively explored using Density Functional Theory (DFT) calculations. The bond dissociation energies for nine aromatic hydrocarbons and oxygenates were calculated using GGA B3LYP density functions with 6-31G(d) basis sets. When possible, unimolecular dissociation to phenoxy radical was favored and resulted in much lower YSIs than similar compounds where the oxygen atom was not adjacent to the aromatic ring. Structures that dissociated to benzyl radical had much higher sooting tendencies, sometimes by over a factor of two in comparison to phenoxyforming compounds.

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    Beekley BP, McEnally CS, St John PC, Kim S, Jain A, Kwon H et al. Sooting tendencies of aromatic hydrocarbons with oxygencontaining side-chains. 2018. Paper presented at 2018 Spring Technical Meeting of the Eastern States Section of the Combustion Institute, ESSCI 2018, State College, United States.