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Multiphase Ozonolysis of Oleic Acid-Based Lipids: Quantitation of Major Products and Kinetic Multilayer Modeling

Cite this: Environ. Sci. Technol. 2022, 56, 12, 7716–7728
Publication Date (Web):June 7, 2022
https://doi.org/10.1021/acs.est.2c01163
Copyright © 2022 American Chemical Society

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    Abstract

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    Commonly found in atmospheric aerosols, cooking oils, and human sebum, unsaturated lipids rapidly decay upon exposure to ozone, following the Criegee mechanism. Here, the gas-surface ozonolysis of three oleic acid-based compounds was studied in a reactor and indoors. Under dry conditions, quantitative product analyses by 1H NMR indicate up to 79% molar yield of stable secondary ozonides (SOZs) in oxidized triolein and methyl oleate coatings. Elevated relative humidity (RH) significantly suppresses the SOZ yields, enhancing the formation of condensed-phase aldehydes and volatile C9 products. Along with kinetic parameters informed by molecular dynamics simulations, these results were used as constraints in a kinetic multilayer model (KM-GAP) simulating triolein ozonolysis. Covering a wide range of coating thicknesses and ozone levels, the model predicts a much faster decay near the gas–lipid interface compared to the bulk. Although the dependence of RH on SOZ yields is well predicted, the model overestimates the production of H2O2 and aldehydes. With negligible dependence on RH, the product composition for oxidized oleic acid is substantially affected by a competitive reaction between Criegee intermediates (CIs) and carboxylic acids. The resulting α-acyloxyalkyl hydroperoxides (α-AAHPs) have much higher molar yields (29–38%) than SOZs (12–16%). Overall, the ozone–lipid chemistry could affect the indoor environment through “crust” accumulation on surfaces and volatile organic compound (VOC) emission. In the atmosphere, the peroxide formation and changes in particle hygroscopicity may have effects on climate. The related health impacts are also discussed.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.est.2c01163.

    • (1) Indoor ozonolysis of triolein coatings, (2) 1H-qNMR measurements, (3) kinetic multilayer modeling of triolein ozonolysis, (4) molecular dynamics simulations, (5) time-dependent evolution of secondary ozonides, and (6) sensitivity tests of kinetic parameters (PDF)

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    Cited By

    This article is cited by 12 publications.

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