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Mass spectrometric characterization of organosulfates related to secondary organic aerosol from isoprene

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Safi Shalamzari, Mohammad Ryabtsova, Oxana Kahnt, Ariane Vermeylen, Reinhilde Herent, Marie-France [UCL] Quetin-Leclercq, Joëlle [UCL] Claeys, Magda

RATIONALE: A considerable fraction of atmospheric particulate fine matter consists of organosulfates, with some of the most polar ones originating from the oxidation of isoprene. Their structural characterization provides insights into the nature of gas-phase precursors as well as into formation pathways. METHODS: The structures of unknown polar organosulfates present in ambient particulate fine matter were characterized using liquid chromatography/(-)electrospray ionization mass spectrometry (LC/(-)ESI-MS), including ion trap MS(n) and accurate mass measurements, derivatization of the carbonyl group into 2,4-dinitrophenylhydrazones, detailed interpretation of the MS data, and in a selected case comparison of their LC and MS behavior with that of synthesized reference compounds. RESULTS: Polar organosulfates with molecular weights (MWs) of 156, 170, 184 and 200 were attributed to/or confirmed as derivatives of glycolic acid (156), lactic acid (170), 1,2-dihydroxy-3-butanone (184), glycolic acid glycolate (200), 2-methylglyceric acid (200), and 2,3-dihydroxybutanoic acid (200). In the case of the MW 184 compound an unambiguous assignment was obtained through synthesis of reference compounds. CONCLUSIONS: A more complete structural characterization of polar organosulfates that originate from isoprene secondary organic aerosol was achieved. An important atmospheric finding is the presence of an organosulfate that is related to methyl vinyl ketone, a major gas-phase oxidation product of isoprene. In addition, minor polar organosulfates related to crotonaldehyde were identified.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2013
Language Anglais
Journal information "Rapid Communications in Mass Spectrometry" - Vol. 27, no.7, p. 784-794 (2013)
Peer reviewed yes
Publisher JohnWiley & Sons Ltd. ((United Kingdom) Chichester)
issn 0951-4198
e-issn 1097-0231
Publication status Publié
Affiliation UCL - SSS/LDRI - Louvain Drug Research Institute
MESH Subject Aerosols ; Sulfates ; Butadienes ; Chromatography, Liquid ; Hemiterpenes ; Mass Spectrometry ; Models, Molecular ; Molecular Weight ; Organic Chemicals ; Pentanes
Links
  1. Müller J.-F., Stavrakou T., Wallens S., De Smedt I., Van Roozendael M., Potosnak M. J., Rinne J., Munger B., Goldstein A., Guenther A. B., Global isoprene emissions estimated using MEGAN, ECMWF analyses and a detailed canopy environment model, 10.5194/acp-8-1329-2008
  2. Claeys M., Formation of Secondary Organic Aerosols Through Photooxidation of Isoprene, 10.1126/science.1092805
  3. Henze D. K., Seinfeld J. H., Ng N. L., Kroll J. H., Fu T.-M., Jacob D. J., Heald C. L., Global modeling of secondary organic aerosol formation from aromatic hydrocarbons: high- vs. low-yield pathways, 10.5194/acp-8-2405-2008
  4. Carlton A. G., Wiedinmyer C., Kroll J. H., A review of Secondary Organic Aerosol (SOA) formation from isoprene, 10.5194/acp-9-4987-2009
  5. Hallquist M., Wenger J. C., Baltensperger U., Rudich Y., Simpson D., Claeys M., Dommen J., Donahue N. M., George C., Goldstein A. H., Hamilton J. F., Herrmann H., Hoffmann T., Iinuma Y., Jang M., Jenkin M. E., Jimenez J. L., Kiendler-Scharr A., Maenhaut W., McFiggans G., Mentel Th. F., Monod A., Prévôt A. S. H., Seinfeld J. H., Surratt J. D., Szmigielski R., Wildt J., The formation, properties and impact of secondary organic aerosol: current and emerging issues, 10.5194/acp-9-5155-2009
  6. Surratt Jason D., Kroll Jesse H., Kleindienst Tadeusz E., Edney Edward O., Claeys Magda, Sorooshian Armin, Ng Nga L., Offenberg John H., Lewandowski Michael, Jaoui Mohammed, Flagan Richard C., Seinfeld John H., Evidence for Organosulfates in Secondary Organic Aerosol, 10.1021/es062081q
  7. Iinuma Yoshiteru, Müller Conny, Böge Olaf, Gnauk Thomas, Herrmann Hartmut, The formation of organic sulfate esters in the limonene ozonolysis secondary organic aerosol (SOA) under acidic conditions, 10.1016/j.atmosenv.2007.03.007
  8. Iinuma Yoshiteru, Müller Conny, Berndt Torsten, Böge Olaf, Claeys Magda, Herrmann Hartmut, Evidence for the Existence of Organosulfates from β-Pinene Ozonolysis in Ambient Secondary Organic Aerosol, 10.1021/es070938t
  9. Surratt Jason D., Gómez-González Yadian, Chan Arthur W. H., Vermeylen Reinhilde, Shahgholi Mona, Kleindienst Tadeusz E., Edney Edward O., Offenberg John H., Lewandowski Michael, Jaoui Mohammed, Maenhaut Willy, Claeys Magda, Flagan Richard C., Seinfeld John H., Organosulfate Formation in Biogenic Secondary Organic Aerosol, 10.1021/jp802310p
  10. Gómez-González Yadian, Surratt Jason D., Cuyckens Filip, Szmigielski Rafal, Vermeylen Reinhilde, Jaoui Mohammed, Lewandowski Michael, Offenberg John H., Kleindienst Tadeusz E., Edney Edward O., Blockhuys Frank, Van Alsenoy Christian, Maenhaut Willy, Claeys Magda, Characterization of organosulfates from the photooxidation of isoprene and unsaturated fatty acids in ambient aerosol using liquid chromatography/(−) electrospray ionization mass spectrometry, 10.1002/jms.1329
  11. Surratt J. D., Chan A. W. H., Eddingsaas N. C., Chan M., Loza C. L., Kwan A. J., Hersey S. P., Flagan R. C., Wennberg P. O., Seinfeld J. H., Reactive intermediates revealed in secondary organic aerosol formation from isoprene, 10.1073/pnas.0911114107
  12. Smith S. J., van Aardenne J., Klimont Z., Andres R. J., Volke A., Delgado Arias S., Anthropogenic sulfur dioxide emissions: 1850–2005, 10.5194/acp-11-1101-2011
  13. Paulot F., Crounse J. D., Kjaergaard H. G., Kurten A., St. Clair J. M., Seinfeld J. H., Wennberg P. O., Unexpected Epoxide Formation in the Gas-Phase Photooxidation of Isoprene, 10.1126/science.1172910
  14. Pierotti David, Wofsy S. C., Jacob D., Rasmussen R. A., Isoprene and its oxidation products: Methacrolein and methyl vinyl ketone, 10.1029/jd095id02p01871
  15. Atkinson Roger, Arey Janet, Gas-phase tropospheric chemistry of biogenic volatile organic compounds: a review, 10.1016/s1352-2310(03)00391-1
  16. Ion A. C., Vermeylen R., Kourtchev I., Cafmeyer J., Chi X., Gelencsér A., Maenhaut W., Claeys M., Polar organic compounds in rural PM2.5 aerosols from K-puszta, Hungary, during a 2003 summer field campaign: Sources and diel variations, 10.5194/acp-5-1805-2005
  17. Kourtchev Ivan, Copolovici Lucian, Claeys Magda, Maenhaut Willy, Characterization of Atmospheric Aerosols at a Forested Site in Central Europe, 10.1021/es803055w
  18. Douglas Donald J., Frank Aaron J., Mao Dunmin, Linear ion traps in mass spectrometry, 10.1002/mas.20004
  19. CHI Y, FENG Y, WEN S, LU H, YU Z, ZHANG W, SHENG G, FU J, Determination of carbonyl compounds in the atmosphere by DNPH derivatization and LC–ESI-MS/MS detection, 10.1016/j.talanta.2006.11.018
  20. Miller J. H., Gardner W. P., Gonzalez R. R., UHPLC Separation with MS Analysis for Eight Carbonyl Compounds in Mainstream Tobacco Smoke, 10.1093/chromsci/48.1.12
  21. Kahnt Ariane, Iinuma Yoshiteru, Böge Olaf, Mutzel Anke, Herrmann Hartmut, Denuder sampling techniques for the determination of gas-phase carbonyl compounds: A comparison and characterisation of in situ and ex situ derivatisation methods, 10.1016/j.jchromb.2011.02.028
  22. Claeys Magda, Wang Wan, Vermeylen Reinhilde, Kourtchev Ivan, Chi Xuguang, Farhat Yasmeen, Surratt Jason D., Gómez-González Yadian, Sciare Jean, Maenhaut Willy, Chemical characterisation of marine aerosol at Amsterdam Island during the austral summer of 2006–2007, 10.1016/j.jaerosci.2009.08.003
  23. Lu Ta-Jung, Yang Jyh-Ferng, Sheu Lij-Jyi, An Efficient Method for the Acetalization of .alpha.,.beta.-Unsaturated Aldehydes, 10.1021/jo00114a055
  24. Page Patrick, Blonski Casimir, Périé Jacques, Synthesis of phosphono analogues of dihydroxyacetone phosphate and glyceraldehyde 3-phosphate, 10.1016/s0968-0896(99)00065-6
  25. Handbook of Reagents for Organic Synthesis, 84 (1999)
  26. Reinnig Marc-Christopher, Müller Lars, Warnke Jörg, Hoffmann Thorsten, Characterization of selected organic compound classes in secondary organic aerosol from biogenic VOCs by HPLC/MS n, 10.1007/s00216-008-1964-5
  27. Knowles Jonathan P., Whiting Andrew, The Effects of Ring Size and Substituents on the Rates of Acid-Catalysed Hydrolysis of Five- and Six-Membered Ring Cyclic Ketone Acetals, 10.1002/ejoc.200700244
  28. Maenhaut Willy, Raes Nico, Chi Xuguang, Cafmeyer Jan, Wang Wan, Chemical composition and mass closure for PM2.5 and PM10 aerosols at K-puszta, Hungary, in summer 2006, 10.1002/xrs.1062
  29. Birch M. E., Cary R. A., Elemental Carbon-Based Method for Monitoring Occupational Exposures to Particulate Diesel Exhaust, 10.1080/02786829608965393
  30. Olson Corey N., Galloway Melissa M., Yu Ge, Hedman Curtis J., Lockett Matthew R., Yoon Tehshik, Stone Elizabeth A., Smith Lloyd M., Keutsch Frank N., Hydroxycarboxylic Acid-Derived Organosulfates: Synthesis, Stability, and Quantification in Ambient Aerosol, 10.1021/es201039p
  31. Galloway M. M., Chhabra P. S., Chan A. W. H., Surratt J. D., Flagan R. C., Seinfeld J. H., Keutsch F. N., Glyoxal uptake on ammonium sulphate seed aerosol: reaction products and reversibility of uptake under dark and irradiated conditions, 10.5194/acp-9-3331-2009
  32. Fu Tzung-May, Jacob Daniel J., Wittrock Folkard, Burrows John P., Vrekoussis Mihalis, Henze Daven K., Global budgets of atmospheric glyoxal and methylglyoxal, and implications for formation of secondary organic aerosols, 10.1029/2007jd009505
  33. Tuazon Ernesto C., Atkinson Roger., Mac Leod Helene., Biermann Heinz W., Winer Arthur M., Carter William P. L., Pitts James N., Yields of glyoxal and methylglyoxal from the nitrogen oxide(NOx)-air photooxidations of toluene and m- and p-xylene, 10.1021/es00130a017
  34. Gross Michael L, Charge-remote fragmentation: an account of research on mechanisms and applications, 10.1016/s1387-3806(00)00372-9
  35. Liteplo, Ethylene oxide (2003)
  36. Yu G., Keutsch F. N., Atmospheric organic-phase photo-sensitized epoxidation of alkenes by α-dicarbonyls, 10.5194/acpd-12-15115-2012
  37. Kesselmeier J., Staudt M., 10.1023/a:1006127516791
  38. Yasmeen Farhat, Vermeylen Reinhilde, Maurin Nicolas, Perraudin Emilie, Doussin Jean-François, Claeys Magda, Characterisation of tracers for aging of α-pinene secondary organic aerosol using liquid chromatography/negative ion electrospray ionisation mass spectrometry, 10.1071/en11148
  39. Minerath Emily C., Casale Mia T., Elrod Matthew J., Kinetics Feasibility Study of Alcohol Sulfate Esterification Reactions in Tropospheric Aerosols, 10.1021/es8004333
  40. Rudziński K. J., Gmachowski L., Kuznietsova I., Reactions of isoprene and sulphoxy radical-anions – a possible source of atmospheric organosulphites and organosulphates, 10.5194/acp-9-2129-2009
  41. Nozière Barbara, Ekström Sanna, Alsberg Tomas, Holmström Sara, Radical-initiated formation of organosulfates and surfactants in atmospheric aerosols : ORGANOSULFATES AND SURFACTANTS IN AEROSOLS, 10.1029/2009gl041683
  42. Perri Mark J., Lim Yong B., Seitzinger Sybil P., Turpin Barbara J., Organosulfates from glycolaldehyde in aqueous aerosols and clouds: Laboratory studies, 10.1016/j.atmosenv.2010.03.031
Bibliographic reference Safi Shalamzari, Mohammad ; Ryabtsova, Oxana ; Kahnt, Ariane ; Vermeylen, Reinhilde ; Herent, Marie-France ; et. al. Mass spectrometric characterization of organosulfates related to secondary organic aerosol from isoprene. In: Rapid Communications in Mass Spectrometry, Vol. 27, no.7, p. 784-794 (2013)
Permanent URL http://hdl.handle.net/2078.1/134909