Mechanism of the hydroxyl radical oxidation of methacryloyl peroxynitrate (MPAN) and its pathway toward secondary organic aerosol formation in the atmosphere
Abstract
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 primarilymore »
- Authors:
-
- 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
- Publication Date:
- Research Org.:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER)
- OSTI Identifier:
- 1418487
- Grant/Contract Number:
- SC0006626; AGS-1240604
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Physical Chemistry Chemical Physics. PCCP
- Additional Journal Information:
- Journal Volume: 17; Journal Issue: 27; Journal ID: ISSN 1463-9076
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
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., and Wennberg, Paul O. Mechanism of the hydroxyl radical oxidation of methacryloyl peroxynitrate (MPAN) and its pathway toward secondary organic aerosol formation in the atmosphere. United States: N. p., 2015.
Web. doi:10.1039/C5CP02001H.
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. Mechanism of the hydroxyl radical oxidation of methacryloyl peroxynitrate (MPAN) and its pathway toward secondary organic aerosol formation in the atmosphere. United States. https://doi.org/10.1039/C5CP02001H
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., and Wennberg, Paul O. Fri .
"Mechanism of the hydroxyl radical oxidation of methacryloyl peroxynitrate (MPAN) and its pathway toward secondary organic aerosol formation in the atmosphere". United States. https://doi.org/10.1039/C5CP02001H. https://www.osti.gov/servlets/purl/1418487.
@article{osti_1418487,
title = {Mechanism of the hydroxyl radical oxidation of methacryloyl peroxynitrate (MPAN) and its pathway toward secondary organic aerosol formation in the atmosphere},
author = {Nguyen, Tran B. and Bates, Kelvin H. and Crounse, John D. and Schwantes, Rebecca H. and Zhang, Xuan and Kjaergaard, Henrik G. and Surratt, Jason D. and Lin, Peng and Laskin, Alexander and Seinfeld, John H. and Wennberg, Paul O.},
abstractNote = {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.},
doi = {10.1039/C5CP02001H},
journal = {Physical Chemistry Chemical Physics. PCCP},
number = 27,
volume = 17,
place = {United States},
year = {Fri Jun 12 00:00:00 EDT 2015},
month = {Fri Jun 12 00:00:00 EDT 2015}
}
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The Caltech Photooxidation Flow Tube reactor: design, fluid dynamics and characterization
journal, January 2017
- Huang, Yuanlong; Coggon, Matthew M.; Zhao, Ran
- Atmospheric Measurement Techniques, Vol. 10, Issue 3
A steady-state continuous flow chamber for the study of daytime and nighttime chemistry under atmospherically relevant NO levels
journal, January 2018
- Zhang, Xuan; Ortega, John; Huang, Yuanlong
- Atmospheric Measurement Techniques, Vol. 11, Issue 5
Molecular characterization of alkyl nitrates in atmospheric aerosols by ion mobility mass spectrometry
journal, January 2019
- Zhang, Xuan; Zhang, Haofei; Xu, Wen
- Atmospheric Measurement Techniques, Vol. 12, Issue 10
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
journal, January 2019
- Müller, Jean-François; Stavrakou, Trissevgeni; Peeters, Jozef
- Geoscientific Model Development, Vol. 12, Issue 6
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
journal, January 2015
- Budisulistiorini, S. H.; Li, X.; Bairai, S. T.
- Atmospheric Chemistry and Physics Discussions, Vol. 15, Issue 5
Source apportionment of fine particulate matter in Houston, Texas: Insights to secondary organic
aerosols
journal, April 2018
- Al-Naiema, Ibrahim M.; Hettiyadura, Anusha P. S.; Wallace, Henry W.
- Atmospheric Chemistry and Physics Discussions
Assessing the role of anthropogenic and biogenic sources on PM₁ over southern West Africa using aircraft measurements
text, January 2018
- Brito, Joel; Freney, Evelyn; Dominutti, Pamela
- Karlsruhe