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Title: 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 + NO 3 (~75%) and hydroxyacetone + CO + NO 3 (~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, HMMLmore » reacts primarily with H 2O 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.« less

Authors:
 [1];  [2];  [1];  [1];  [1];  [3];  [4];  [5];  [1];  [6];  [7]
  1. California Inst. of Technology (CalTech), Pasadena, CA (United States). Division of Geological and Planetary Sciences
  2. California Inst. of Technology (CalTech), Pasadena, CA (United States). Division of Chemistry and Chemical Engineering
  3. Univ. of Copenhagen (Denmark). The Niels Bohr Inst., Dept. of Chemistry
  4. Univ. of North Carolina, Chapel Hill, NC (United States). Dept. of Environmental Sciences and Engineering
  5. Pacific Northwest National Lab. (PNNL), Richland, WA (United States). W.R. Wiley Environmental Molecular Science Lab.
  6. California Inst. of Technology (CalTech), Pasadena, CA (United States). Division of Chemistry and Chemical Engineering, and Division of Engineering and Applied Science
  7. 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 Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1418487
Grant/Contract Number:  
SC0006626; AGS-1240604
Resource Type:
Accepted Manuscript
Journal Name:
Physical Chemistry Chemical Physics. PCCP (Print)
Additional Journal Information:
Journal Name: Physical Chemistry Chemical Physics. PCCP (Print); 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. 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., 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. doi: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 (Print)},
number = 27,
volume = 17,
place = {United States},
year = {2015},
month = {6}
}

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