Mechanism of the hydroxyl radical oxidation of methacryloyl peroxynitrate (MPAN) and its pathway toward secondary organic aerosol formation in the atmosphere

Nguyen, Tran B.; Bates, Kelvin H.; Crounse, John D.; Schwantes, Rebecca H.; Zhang, Xuan; Kjaergaard, Henrik G.; Surratt, Jason D.; Lin, Peng; Laskin, Alexander; Seinfeld, John H.; Wennberg, Paul O.

doi:10.1039/C5CP02001H

Title: Mechanism of the hydroxyl radical oxidation of methacryloyl peroxynitrate (MPAN) and its pathway toward secondary organic aerosol formation in the atmosphere

Journal Article · Fri Jun 12 00:00:00 EDT 2015 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/C5CP02001H· OSTI ID:1418487

Nguyen, Tran B. ^[1]; Bates, Kelvin H. ^[2]; Crounse, John D. ^[1]; Schwantes, Rebecca H. ^[1]; Zhang, Xuan ^[1]; Kjaergaard, Henrik G. ^[3]; Surratt, Jason D. ^[4]; Lin, Peng ^[5]; Laskin, Alexander ^[1]; Seinfeld, John H. ^[6]; Wennberg, Paul O. ^[7]

California Inst. of Technology (CalTech), Pasadena, CA (United States). Division of Geological and Planetary Sciences
California Inst. of Technology (CalTech), Pasadena, CA (United States). Division of Chemistry and Chemical Engineering
Univ. of Copenhagen (Denmark). The Niels Bohr Inst., Dept. of Chemistry
Univ. of North Carolina, Chapel Hill, NC (United States). Dept. of Environmental Sciences and Engineering
Pacific Northwest National Lab. (PNNL), Richland, WA (United States). W.R. Wiley Environmental Molecular Science Lab.
California Inst. of Technology (CalTech), Pasadena, CA (United States). Division of Chemistry and Chemical Engineering, and Division of Engineering and Applied Science
California Inst. of Technology (CalTech), Pasadena, CA (United States). Division of Geological and Planetary Sciences, and Division of Engineering and Applied Science

Methacryloyl peroxynitrate (MPAN), the acyl peroxynitrate of methacrolein, has been suggested to be an important secondary organic aerosol (SOA) precursor from isoprene oxidation. Yet, the mechanism by which MPAN produces SOA through reaction with the hydroxyl radical (OH) is unclear. We systematically evaluate three proposed mechanisms in controlled chamber experiments and provide the first experimental support for the theoretically-predicted lactone formation pathway from the MPAN + OH reaction, producing hydroxymethyl-methyl-α-lactone (HMML). The decomposition of the MPAN–OH adduct yields HMML + NO₃ (~75%) and hydroxyacetone + CO + NO₃ (~25%), out-competing its reaction with atmospheric oxygen. The production of other proposed SOA precursors, e.g., methacrylic acid epoxide (MAE), from MPAN and methacrolein are negligible (<2%). Furthermore, we show that the beta-alkenyl moiety of MPAN is critical for lactone formation. Alkyl radicals formed cold via H-abstraction by OH do not decompose to HMML, even if they are structurally identical to the MPAN–OH adduct. The SOA formation from HMML, from polyaddition of the lactone to organic compounds at the particle interface or in the condensed phase, is close to unity under dry conditions. However, the SOA yield is sensitive to particle liquid water and solvated ions. In hydrated inorganic particles, HMML reacts primarily with H₂O to produce the monomeric 2-methylglyceric acid (2MGA) or with aqueous sulfate and nitrate to produce the associated organosulfate and organonitrate, respectively. 2MGA, a tracer for isoprene SOA, is semivolatile and its accommodation in aerosol water decreases with decreasing pH. Conditions that enhance the production of neutral 2MGA suppress SOA mass from the HMML channel. In conclusion, considering the liquid water content and pH ranges of ambient particles, 2MGA will exist largely as a gaseous compound in some parts of the atmosphere.

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Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: SC0006626; AGS-1240604

OSTI ID:: 1418487

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Vol. 17, Issue 27; ISSN 1463-9076

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 93 works

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Biogenic emissions and land–atmosphere interactions as drivers of the daytime evolution of secondary organic aerosol in the southeastern US Nagori, Juhi; Janssen, Ruud H. H.; Fry, Juliane L. Atmospheric Chemistry and Physics, Vol. 19, Issue 2 https://doi.org/10.5194/acp-19-701-2019	journal	January 2019
Low-volatility compounds contribute significantly to isoprene secondary organic aerosol (SOA) under high-NO_x conditions Schwantes, Rebecca H.; Charan, Sophia M.; Bates, Kelvin H. Atmospheric Chemistry and Physics, Vol. 19, Issue 11 https://doi.org/10.5194/acp-19-7255-2019	journal	January 2019
A new model mechanism for atmospheric oxidation of isoprene: global effects on oxidants, nitrogen oxides, organic products, and secondary organic aerosol Bates, Kelvin H.; Jacob, Daniel J. Atmospheric Chemistry and Physics, Vol. 19, Issue 14 https://doi.org/10.5194/acp-19-9613-2019	journal	January 2019
The Caltech Photooxidation Flow Tube reactor: design, fluid dynamics and characterization Huang, Yuanlong; Coggon, Matthew M.; Zhao, Ran Atmospheric Measurement Techniques, Vol. 10, Issue 3 https://doi.org/10.5194/amt-10-839-2017	journal	January 2017
A steady-state continuous flow chamber for the study of daytime and nighttime chemistry under atmospherically relevant NO levels Zhang, Xuan; Ortega, John; Huang, Yuanlong Atmospheric Measurement Techniques, Vol. 11, Issue 5 https://doi.org/10.5194/amt-11-2537-2018	journal	January 2018
Molecular characterization of alkyl nitrates in atmospheric aerosols by ion mobility mass spectrometry Zhang, Xuan; Zhang, Haofei; Xu, Wen Atmospheric Measurement Techniques, Vol. 12, Issue 10 https://doi.org/10.5194/amt-12-5535-2019	journal	January 2019
Chemistry and deposition in the Model of Atmospheric composition at Global and Regional scales using Inversion Techniques for Trace gas Emissions (MAGRITTE v1.1) – Part 1: Chemical mechanism Müller, Jean-François; Stavrakou, Trissevgeni; Peeters, Jozef Geoscientific Model Development, Vol. 12, Issue 6 https://doi.org/10.5194/gmd-12-2307-2019	journal	January 2019
Examining the effects of anthropogenic emissions on isoprene-derived secondary organic aerosol formation during the 2013 Southern Oxidant and Aerosol Study (SOAS) at the Look Rock, Tennessee, ground site Budisulistiorini, S. H.; Li, X.; Bairai, S. T. Atmospheric Chemistry and Physics Discussions, Vol. 15, Issue 5 https://doi.org/10.5194/acpd-15-7365-2015	journal	January 2015
Source apportionment of fine particulate matter in Houston, Texas: Insights to secondary organic aerosols Al-Naiema, Ibrahim M.; Hettiyadura, Anusha P. S.; Wallace, Henry W. Atmospheric Chemistry and Physics Discussions https://doi.org/10.5194/acp-2018-343	journal	April 2018
Assessing the role of anthropogenic and biogenic sources on PM₁ over southern West Africa using aircraft measurements Brito, Joel; Freney, Evelyn; Dominutti, Pamela Karlsruhe https://doi.org/10.5445/ir/1000079354	text	January 2018

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