Probing autoxidation of oleic acid at air-water interface: A neglected and significant pathway for secondary organic aerosols formation

Albuquerque, 2014, The first step of biodiesel autoxidation by differential scanning calorimetry and DFT calculations, J. Therm. Anal. Calorim., 117, 799, 10.1007/s10973-014-3835-y Banerjee, 2019, Influence of inlet capillary temperature on the microdroplet chemistry studied by mass spectrometry, J. Phys. Chem., 123, 7704, 10.1021/acs.jpca.9b05703 Berndt, 2017, Direct probing of criegee intermediates from gas-phase ozonolysis using chemical ionization mass spectrometry, J. Am. Chem. Soc., 139, 13387, 10.1021/jacs.7b05849 Bianchi, 2019, Highly oxygenated organic molecules (HOM) from gas-phase Autoxidation involving peroxy radicals: a key contributor to atmospheric aerosol, Chem. Rev., 119, 3472, 10.1021/acs.chemrev.8b00395 Brimberg, 1993, ON the kinetics OF the autoxidation OF fats .2. Monounsaturated substrates, J. Am. Oil Chem. Soc., 70, 1063, 10.1007/BF02632143 Dobson, 2000, Atmospheric aerosols as prebiotic chemical reactors, Proc. Natl. Acad. Sci. U. S. A, 97, 11864, 10.1073/pnas.200366897 Enami, 2017, Criegee chemistry on aqueous organic surfaces, J. Phys. Chem. Lett., 8, 1615, 10.1021/acs.jpclett.7b00434 Enami, 2017, Efficient scavenging of Criegee intermediates on water by surface-active cis-pinonic acid, Phys. Chem. Chem. Phys., 19, 17044, 10.1039/C7CP03869K Enami, 2017, Criegee intermediates react with levoglucosan on water, J. Phys. Chem. Lett., 8, 3888, 10.1021/acs.jpclett.7b01665 Fan, 2020, Large contributions of biogenic and anthropogenic sources to fine organic aerosols in Tianjin, North China, Atmos. Chem. Phys., 20, 117, 10.5194/acp-20-117-2020 Gallimore, 2017, Online molecular characterisation of organic aerosols in an atmospheric chamber using extractive electrospray ionisation mass spectrometry, Atmos. Chem. Phys., 17, 14485, 10.5194/acp-17-14485-2017 Gallimore, 2017, Comprehensive modeling study of ozonolysis of oleic acid aerosol based on real-time, online measurements of aerosol composition, J. Geophys. Res. Atmos., 122, 4364, 10.1002/2016JD026221 Gao, 2019, Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer-Villiger reactions, Chem. Sci., 10, 10974, 10.1039/C9SC05112K Gao, 2019, Selective synthesis in microdroplets of 2-Phenyl-2,3-dihydrophthalazine-1,4-dione from phenyl hydrazine with phthalic anhydride or phthalic acid, Chem.-Eur. J., 25, 1466, 10.1002/chem.201805585 Giorio, 2017, Online quantification of criegee intermediates of alpha-pinene ozonolysis by stabilization with spin traps and proton-transfer reaction mass spectrometry detection, J. Am. Chem. Soc., 139, 3999, 10.1021/jacs.6b10981 Hearn, 2005, Ozonolysis of oleic acid particles: evidence for a surface reaction and secondary reactions involving Criegee intermediates, Phys. Chem. Chem. Phys., 7, 501, 10.1039/b414472d Ho, 2011, Summer and winter variations of dicarboxylic acids, fatty acids and benzoic acid in PM2.5 in Pearl Delta River Region, China, Atmos. Chem. Phys., 11, 2197, 10.5194/acp-11-2197-2011 Hodzic, 2020, Characterization of organic aerosol across the global remote troposphere: a comparison of ATom measurements and global chemistry models, Atmos. Chem. Phys., 20, 4607, 10.5194/acp-20-4607-2020 Huang, 2021, Accelerated reactions of amines with carbon dioxide driven by superacid at the microdroplet interface, Chem. Sci., 12, 2242, 10.1039/D0SC05625A Huang, 2020, Abundant biogenic oxygenated organic aerosol in atmospheric coarse particles: plausible sources and atmospheric implications, Environ. Sci. Technol., 54, 1425, 10.1021/acs.est.9b06311 Islam, 2019, Environmental and toxicological assessment of nanodiamond-like materials derived from carbonaceous aerosols, Sci. Total Environ., 679, 209, 10.1016/j.scitotenv.2019.04.446 Jorga, 2020, Measurement of formation rates of secondary aerosol in the ambient urban atmosphere using a dual smog chamber system, Environ. Sci. Technol., 54, 1336, 10.1021/acs.est.9b03479 Kim, 2016, Charging and coagulation of radioactive and nonradioactive particles in the atmosphere, Atmos. Chem. Phys., 16, 3449, 10.5194/acp-16-3449-2016 King, 2009, Oxidation of oleic acid at the air-water interface and its potential effects on cloud critical supersaturations, Phys. Chem. Chem. Phys., 11, 7699, 10.1039/b906517b King, 2004, Laser tweezers Raman study of optically trapped aerosol droplets of Seawater and oleic acid reacting with ozone: implications for cloud-droplet properties, J. Am. Chem. Soc., 126, 16710, 10.1021/ja044717o Kramer, 2019, formation of polycyclic aromatic hydrocarbon oxidation products in alpha-pinene secondary organic aerosol particles formed through ozonolysis, Environ. Sci. Technol., 53, 6669, 10.1021/acs.est.9b01732 Kusaka, 2021, The photochemical reaction of phenol becomes ultrafast at the air–water interface, Nat. Chem., 1 Lamberson, 2014, Unusual kinetic isotope effects of deuterium reinforced polyunsaturated fatty acids in tocopherol-mediated free radical chain oxidations, J. Am. Chem. Soc., 136, 838, 10.1021/ja410569g Lee, 2019, Spontaneous generation of hydrogen peroxide from aqueous microdroplets, Proc. Natl. Acad. Sci. U. S. A, 116, 19294, 10.1073/pnas.1911883116 Li, 2018, Self-catalytic reaction of SO3 and NH3 to produce sulfamic acid and its implication to atmospheric particle formation, J. Am. Chem. Soc., 140, 11020, 10.1021/jacs.8b04928 Li, 2020, 703 Lyu, 2020, In situ measurements of molecular markers facilitate understanding of dynamic sources of atmospheric organic aerosols, Environ. Sci. Technol., 54, 11058, 10.1021/acs.est.0c02277 Møller, 2020, Atmospheric autoxidation of amines, Environ. Sci. Technol., 54, 11087, 10.1021/acs.est.0c03937 Møller, 2019, Stereoselectivity in atmospheric autoxidation, J. Phys. Chem. Lett., 10, 6260, 10.1021/acs.jpclett.9b01972 Ma, 2020, Autoxidation mechanism for atmospheric oxidation of tertiary amines: implications for secondary organic aerosol formation, Chemosphere, 129207 Michael, 2009, Highly charged cloud particles in the atmosphere of Venus, J. Geophys. Res.-Planets, 114, 10.1029/2008JE003258 Nam, 2017, Abiotic production of sugar phosphates and uridine ribonudeoside in aqueous microdroplets, Proc. Natl. Acad. Sci. U. S. A, 114, 12396, 10.1073/pnas.1714896114 Niu, 2017, Indoor secondary organic aerosols formation from ozonolysis of monoterpene: an example of D-limonene with ammonia and potential. impacts on pulmonary inflammations, Sci. Total Environ., 579, 212, 10.1016/j.scitotenv.2016.11.018 Ostrom, 2017, Modeling the role of highly oxidized multifunctional organic molecules for the growth of new particles over the boreal forest region, Atmos. Chem. Phys., 17, 8887, 10.5194/acp-17-8887-2017 Pfrang, 2010, Coupling aerosol surface and bulk chemistry with a kinetic double layer model (K2-SUB): oxidation of oleic acid by ozone, Atmos. Chem. Phys., 10, 4537, 10.5194/acp-10-4537-2010 Praske, 2018, Atmospheric autoxidation is increasingly important in urban and suburban North America, Proc. Natl. Acad. Sci. U. S. A, 115, 64, 10.1073/pnas.1715540115 Qiu, 2020, Proton-catalyzed decomposition of a-hydroxyalkyl-hydroperoxides in water, Environ. Sci. Technol., 54, 10561, 10.1021/acs.est.0c03438 Rossignol, 2016, Atmospheric photochemistry at a fatty acid-coated air-water interface, Science, 353, 699, 10.1126/science.aaf3617 Ruiz-Lopez, 2019, A new mechanism of acid rain generation from HOSO at the air-water interface, J. Am. Chem. Soc., 141, 16564, 10.1021/jacs.9b07912 Scales, 2004, Electrodynamic structure of charged dust clouds in the earth's middle atmosphere, New J. Phys., 6, 10.1088/1367-2630/6/1/012 Shang, 2016, SO2 uptake on oleic acid: a new formation pathway of organosulfur compounds in the atmosphere, Environ. Sci. Technol. Lett., 3, 67, 10.1021/acs.estlett.6b00006 Shiraiwa, 2010, Kinetic multi-layer model of aerosol surface and bulk chemistry (KM-SUB): the influence of interfacial transport and bulk diffusion on the oxidation of oleic acid by ozone, Atmos. Chem. Phys., 10, 3673, 10.5194/acp-10-3673-2010 Vaida, 2017, Prebiotic phosphorylation enabled by microdroplets, Proc. Natl. Acad. Sci. Unit. States Am., 114, 12359, 10.1073/pnas.1717373114 Venter, 2006, Droplet dynamics and ionization mechanisms in desorption electrospray ionization mass spectrometry, Anal. Chem., 78, 8549, 10.1021/ac0615807 Virtanen, 2010, An amorphous solid state of biogenic secondary organic aerosol particles, Nature, 467, 824, 10.1038/nature09455 Wang, 2011, The role of nebulizer gas flow in electrosonic spray ionization (ESSI), J. Am. Soc. Mass Spectrom., 22, 1234, 10.1007/s13361-011-0124-x Wei, 2020, Accelerated reaction kinetics in microdroplets: overview and recent developments, Annu. Rev. Phys. Chem., 71, 31, 10.1146/annurev-physchem-121319-110654 Yan, 2017, Two-phase reactions in microdroplets without the use of phase-transfer catalysts, Angew. Chem. Int. Ed., 56, 3562, 10.1002/anie.201612308 Yan, 2018, Preparative microdroplet synthesis of carboxylic acids from aerobic oxidation of aldehydes, Chem. Sci., 9, 5207, 10.1039/C8SC01580E Yao, 2019, Multiphase reactions between secondary organic aerosol and sulfur dioxide: kinetics and contributions to sulfate formation and aerosol aging, Environ. Sci. Technol. Lett., 6, 768, 10.1021/acs.estlett.9b00657 Zhang, 2018, Cholesterol provides nonsacrificial protection of membrane lipids from chemical damage at air-water interface, Proc. Natl. Acad. Sci. U. S. A, 115, 3255, 10.1073/pnas.1722323115 Zhang, 2017, Time resolved study of hydroxyl radical oxidation of oleic acid at the air-water interface, Chem. Phys. Lett., 683, 76, 10.1016/j.cplett.2017.05.051 Zhong, 2020, Ultrafast enzymatic digestion of proteins by microdroplet mass spectrometry, Nat. Commun., 11, 10.1038/s41467-020-14877-x Zhu, 2020, Hydration, solvation, and isomerization of methylglyoxal at the air/water interface: new mechanistic pathways, J. Am. Chem. Soc., 142, 5574, 10.1021/jacs.9b09870 Zhu, 2019, Organosulfur compounds formed from heterogeneous reaction between SO2 and particulate-bound unsaturated fatty acids in ambient air, Environ. Sci. Technol. Lett., 6, 318, 10.1021/acs.estlett.9b00218