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Isoprene epoxydiols as precursors to secondary organic aerosol formation: acid-catalyzed reactive uptake studies with authentic compounds.
Environ Sci Technol. 2012 Jan 03; 46(1):250-8.ES

Abstract

Isoprene epoxydiols (IEPOX), formed from the photooxidation of isoprene under low-NO(x) conditions, have recently been proposed as precursors of secondary organic aerosol (SOA) on the basis of mass spectrometric evidence. In the present study, IEPOX isomers were synthesized in high purity (>99%) to investigate their potential to form SOA via reactive uptake in a series of controlled dark chamber studies followed by reaction product analyses. IEPOX-derived SOA was substantially observed only in the presence of acidic aerosols, with conservative lower-bound yields of 4.7-6.4% for β-IEPOX and 3.4-5.5% for δ-IEPOX, providing direct evidence for IEPOX isomers as precursors to isoprene SOA. These chamber studies demonstrate that IEPOX uptake explains the formation of known isoprene SOA tracers found in ambient aerosols, including 2-methyltetrols, C(5)-alkene triols, dimers, and IEPOX-derived organosulfates. Additionally, we show reactive uptake on the acidified sulfate aerosols supports a previously unreported acid-catalyzed intramolecular rearrangement of IEPOX to cis- and trans-3-methyltetrahydrofuran-3,4-diols (3-MeTHF-3,4-diols) in the particle phase. Analysis of these novel tracer compounds by aerosol mass spectrometry (AMS) suggests that they contribute to a unique factor resolved from positive matrix factorization (PMF) of AMS organic aerosol spectra collected from low-NO(x), isoprene-dominated regions influenced by the presence of acidic aerosols.

Authors+Show Affiliations

Department of Environmental Sciences and Engineering, Gillings School of Global Public Health, The University of North Carolina at Chapel Hill , North Carolina, United States of America.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

22103348

Citation

Lin, Ying-Hsuan, et al. "Isoprene Epoxydiols as Precursors to Secondary Organic Aerosol Formation: Acid-catalyzed Reactive Uptake Studies With Authentic Compounds." Environmental Science & Technology, vol. 46, no. 1, 2012, pp. 250-8.
Lin YH, Zhang Z, Docherty KS, et al. Isoprene epoxydiols as precursors to secondary organic aerosol formation: acid-catalyzed reactive uptake studies with authentic compounds. Environ Sci Technol. 2012;46(1):250-8.
Lin, Y. H., Zhang, Z., Docherty, K. S., Zhang, H., Budisulistiorini, S. H., Rubitschun, C. L., Shaw, S. L., Knipping, E. M., Edgerton, E. S., Kleindienst, T. E., Gold, A., & Surratt, J. D. (2012). Isoprene epoxydiols as precursors to secondary organic aerosol formation: acid-catalyzed reactive uptake studies with authentic compounds. Environmental Science & Technology, 46(1), 250-8. https://doi.org/10.1021/es202554c
Lin YH, et al. Isoprene Epoxydiols as Precursors to Secondary Organic Aerosol Formation: Acid-catalyzed Reactive Uptake Studies With Authentic Compounds. Environ Sci Technol. 2012 Jan 3;46(1):250-8. PubMed PMID: 22103348.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isoprene epoxydiols as precursors to secondary organic aerosol formation: acid-catalyzed reactive uptake studies with authentic compounds. AU - Lin,Ying-Hsuan, AU - Zhang,Zhenfa, AU - Docherty,Kenneth S, AU - Zhang,Haofei, AU - Budisulistiorini,Sri Hapsari, AU - Rubitschun,Caitlin L, AU - Shaw,Stephanie L, AU - Knipping,Eladio M, AU - Edgerton,Eric S, AU - Kleindienst,Tadeusz E, AU - Gold,Avram, AU - Surratt,Jason D, Y1 - 2011/12/13/ PY - 2011/11/23/entrez PY - 2011/11/23/pubmed PY - 2012/5/9/medline SP - 250 EP - 8 JF - Environmental science & technology JO - Environ Sci Technol VL - 46 IS - 1 N2 - Isoprene epoxydiols (IEPOX), formed from the photooxidation of isoprene under low-NO(x) conditions, have recently been proposed as precursors of secondary organic aerosol (SOA) on the basis of mass spectrometric evidence. In the present study, IEPOX isomers were synthesized in high purity (>99%) to investigate their potential to form SOA via reactive uptake in a series of controlled dark chamber studies followed by reaction product analyses. IEPOX-derived SOA was substantially observed only in the presence of acidic aerosols, with conservative lower-bound yields of 4.7-6.4% for β-IEPOX and 3.4-5.5% for δ-IEPOX, providing direct evidence for IEPOX isomers as precursors to isoprene SOA. These chamber studies demonstrate that IEPOX uptake explains the formation of known isoprene SOA tracers found in ambient aerosols, including 2-methyltetrols, C(5)-alkene triols, dimers, and IEPOX-derived organosulfates. Additionally, we show reactive uptake on the acidified sulfate aerosols supports a previously unreported acid-catalyzed intramolecular rearrangement of IEPOX to cis- and trans-3-methyltetrahydrofuran-3,4-diols (3-MeTHF-3,4-diols) in the particle phase. Analysis of these novel tracer compounds by aerosol mass spectrometry (AMS) suggests that they contribute to a unique factor resolved from positive matrix factorization (PMF) of AMS organic aerosol spectra collected from low-NO(x), isoprene-dominated regions influenced by the presence of acidic aerosols. SN - 1520-5851 UR - https://www.unboundmedicine.com/medline/citation/22103348/Isoprene_epoxydiols_as_precursors_to_secondary_organic_aerosol_formation:_acid_catalyzed_reactive_uptake_studies_with_authentic_compounds_ L2 - https://doi.org/10.1021/es202554c DB - PRIME DP - Unbound Medicine ER -