Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates

Vansco, Michael F.; Caravan, Rebecca L.; Zuraski, Kristen; Winiberg, Frank A.  F.; Au, Kendrew; Trongsiriwat, Nisalak; Walsh, Patrick J.; Osborn, David L.; Percival, Carl J.; Khan, M. Anwar H.; Shallcross, Dudley E.; Taatjes, Craig A.; Lester, Marsha I.

doi:10.1021/acs.jpca.0c02138

Title: Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates

Journal Article · Tue Apr 07 00:00:00 EDT 2020 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.0c02138· OSTI ID:1633329

Vansco, Michael F. ^[1]; Caravan, Rebecca L. ^[2]; Zuraski, Kristen ^[3];

^[3]; Au, Kendrew ^[4]; Trongsiriwat, Nisalak ^[1];

^[1];

^[5]; Percival, Carl J. ^[3];

^[6]; Shallcross, Dudley E. ^[6];

^[4];

^[1]

Univ. of Pennsylvania, Philadelphia, PA (United States)
California Institute of Technology (CalTech), Pasadena, CA (United States). Jet Propulsion Lab. (JPL); Sandia National Lab. (SNL-CA), Livermore, CA (United States); Argonne National Lab. (ANL), Argonne, IL (United States)
California Institute of Technology (CalTech), Pasadena, CA (United States). Jet Propulsion Lab. (JPL)
Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States
Bristol Univ. (United Kingdom)

Ozonolysis of isoprene, one of the most abundant volatile organic compounds emitted into the Earth’s atmosphere, generates two four-carbon unsaturated Criegee intermediates, methyl vinyl ketone oxide (MVK-oxide) and methacrolein oxide (MACR-oxide). The extended conjugation between the vinyl substituent and carbonyl oxide groups of these Criegee intermediates facilitates rapid electrocyclic ring closures that form 5-membered cyclic peroxides, known as dioxoles. This research discusses the first experimental evidence of this novel decay pathway, which is predicted to be the dominant atmospheric sink for specific conformational forms of MVK-oxide (anti) and MACR-oxide (syn) with the vinyl substituent adjacent to the terminal O atom. The resulting dioxoles are predicted to undergo rapid unimolecular decay to oxygenated hydrocarbon radical products, including acetyl, vinoxy, formyl, and 2-methyl-vinoxy radicals. In the presence of O₂, these radicals rapidly react to form peroxy radicals (ROO), which quickly decay via carbon-centered radical intermediates (QOOH) to stable carbonyl products that are identified in this work. The carbonyl products are detected under thermal conditions (298 K, 10 torr He) using multiplexed photoionization mass spectrometry (MPIMS). The main products (and associated relative abundances) originating from unimolecular decay of anti-MVK-oxide and subsequent reaction with O₂ are formaldehyde (88 ± 5%), ketene (9 ± 1%) and glyoxal (3 ± 1%). Those identified from the unimolecular decay of syn-MACR-oxide and subsequent reaction of O₂ are acetaldehyde (37 ± 7%), vinyl alcohol (9 ± 1%), methylketene (2 ± 1%), and acrolein (52 ± 5%). In addition to the stable carbonyl products, the secondary peroxy chemistry also generates OH or HO₂ radical co-products.

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Research Organization:: Univ. of Pennsylvania, Philadelphia, PA (United States); Argonne National Laboratory (ANL), Argonne, IL (United States); Sandia National Lab. (SNL-NM), Albuquerque, NM (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Sandia National Lab. (SNL-CA), Livermore, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; USDOE National Nuclear Security Administration (NNSA); National Aeronautics and Space Administration (NASA); National Science Foundation (NSF)

Grant/Contract Number:: FG02-87ER13792; NA0003525; AC02-06CH11357; AC02-05CH11231; CHE-1902509; AC04-94AL85000

OSTI ID:: 1633329

Alternate ID(s):: OSTI ID: 1644072; OSTI ID: 1660372; OSTI ID: 1782236

Report Number(s):: SAND-2020-7131J

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 124, Issue 18; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 24 works

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Title: Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates

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