New tracer compounds for secondary organic aerosol formation from β-caryophyllene oxidation

Atmospheric Environment

Volumn 80, Issue , 2013, Pages 122-130

  van Eijck, Anna ^a   Opatz, Till ^a   Taraborrelli, Domenico ^b   Sander, Rolf ^b   Hoffmann, Thorsten ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUTE FOR CHEMISTRY   (Germany)

Author keywords

Caryophyllene; Box model; Ozonolysis; Reaction chamber experiment; Sesquiterpene; SOA; Synthesis

Indexed keywords

BOX MODELS; CARYOPHYLLENE; OZONOLYSIS; REACTION CHAMBERS; SESQUITERPENES; SOA;

AEROSOLS; ATMOSPHERIC CHEMISTRY; CARBOXYLIC ACIDS; EXPERIMENTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OZONE; SYNTHESIS (CHEMICAL);

OXIDATION;

2 (2 CARBOXYETHYL) 3,3 DIMETHYLCYCLOBUTANECARBOXYLIC ACID; 3,3 DIMETHYL 2 (3 OXOBUTYL)CYCLOBUTANECARBOXYLIC ACID; BETA CARYOPHYLLINIC ACID; BETA CARYOPHYLLONIC ACID; BETA NOCARYOPHYLLONIC ACID; CARBOXYLIC ACID DERIVATIVE; CARYOPHYLLENE; CARYOPHYLLENE DERIVATIVE; OZONE; UNCLASSIFIED DRUG;

AEROSOL COMPOSITION; AEROSOL FORMATION; AIR SAMPLING; ATMOSPHERIC CHEMISTRY; ATMOSPHERIC MODELING; MIXING RATIO; ORGANIC COMPOUND; OXIDATION; OZONE; TERPENE; TRACER;

AMBIENT AIR; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PRIORITY JOURNAL; SECONDARY ORGANIC AEROSOL; SPECTROSCOPY; SYNTHESIS;

FINLAND; HYYTIALA; PIRKANMAA;

EID: 84883023970     PISSN: 13522310     EISSN: 18732844     Source Type: Journal    
DOI: 10.1016/j.atmosenv.2013.07.060     Document Type: Article

References (53)

1. Arey J., Crowley D.E., Crowley M., Resketo M., Lester J. Hydrocarbon emissions from natural vegetation in California's south coast air basin. Atmospheric Environment 1995, 29:2977-2988.
2. 3 with a series of terpenes. Atmospheric Environment 2002, 36:4347-4355.
3. Bonn B., Moortgat G.K. Sesquiterpene ozonolysis: origin of atmospheric new particle formation from biogenic hydrocarbons. Geophysical Research Letters 2003, 30. 10.1029/2003GL017000.
4. Calogirou A., Kotzias D., Kettrup A. Product analysis of the gas-phase reaction of β-caryophyllene with ozone. Atmospheric Environment 1997, 31:283-285.
5. Chan M.N., Surratt J.D., Chan A.W.H., Schilling K., Offenberg J.H., Lewandowski M., Edney E.O., Kleindienst T.E., Jaoui M., Edgerton E.S., Tanner R.L., Shaw S.L., Zheng M., Knipping E.M., Seinfeld J.H. Influence of aerosol acidity on the chemical composition of secondary organic aerosol from β-caryophyllene. Atmospheric Chemistry and Physics 2011, 11:1735-1751.
6. Dekermenjian M., Allen D.T., Atkinson R., Arey J. FTIR analysis of aerosol formed in the ozone oxidation of sesquiterpenes. Aerosol Science and Technology 1999, 30:349-363.
7. Ding X., Wang X.-M., Zheng M. The influence of temperature and aerosol acidity on biogenic secondary organic aerosol tracers: observations at a rural site in the central Pearl River Delta region, South China. Atmospheric Environment 2011, 45:1303-1311.
8. Dobson H., Bergström G. The ecology and evolution of pollen odors. Plant Systematics and Evolution 2000, 222:63-87.
9. Duhl T.R., Helmig D., Guenther A. Sesquiterpene emission from vegetation: a review. Biogeosciences 2008, 5:761-777.
10. Fu P., Kawamura K., Chen J., Barrie L.A. Isoprene, monoterpene, and sesquiterpene oxidation products in the high Arctic aerosols during Late Winter to Early summer. Environmental Science and Technology 2009, 43:4022-4028.
11. Fuzzi S., Andreae M.O., Huebert B.J., Kulmala M., Bond T.C., Boy M., Doherty S.J., Guenther A., Kanakidou M., Kawamura K., Kerminen V.-M., Lohmann U., Russell L.M., Pöschl U. Critical assessment of the current state of scientific knowledge, terminology, and research needs concerning the role of organic aerosols in the atmosphere, climate, and global change. Atmospheric Chemistry and Physics 2006, 6:2017-2038.
12. Goldstein A.H., McKay M., Kurpius M.R., Schade G.W., Lee A., Holzinger R., Rasmussen R.A. Forest thinning experiment confirms ozone deposition to forest canopy is dominated by reaction with biogenic VOCs. Geophysical Research Letters 2004, 31. 10.1029/2004GL021259.
13. Gottlieb H.E., Kotlyar V., Nudelman A. NMR chemical shifts of common laboratory solvents as trace impurities. Journal of Organic Chemistry 1997, 62:7512-7515.
14. Griffin R.J., Cocker D.R., Flagan R.C., Seinfeld J.H. Organic aerosol formation from the oxidation of biogenic hydrocarbons. Journal of Geophysical Research 1999, 104:3555-3567.
15. Grosjean D., Williams E.L., Grosjean E., Andino J.M., Seinfeld J.H. Atmospheric oxidation of biogenic hydrocarbons: reaction of ozone with β-pinene, D-limonene and trans-caryophyllene. Environmental Science and Technology 1993, 27:2754-2758.
16. Hakola H., Tarvainen V., Bäck J., Ranta H., Bonn B., Rinne J., Kulmala M. Seasonal variation of mono- and sesquiterpene emission rates of Scots pine. Biogeosciences 2006, 3:93-101.
17. 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 T.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. Atmospheric Chemistry and Physics 2009, 9:5155-5236.
18. Heil M., Kost C. Priming of indirect defences. Ecology Letters 2006, 9:813-817.
19. Helmig D., Ortega J., Duhl T., Tanner D., Guenther A., Harley P., Wiedinmyer C., Milford J., Sakulyanontvittaya T. Sesquiterpene emissions from pine trees - identifications, emission rates and flux estimates for the contiguous United States. Environmental Science and Technology 2007, 41:1545-1553.
20. 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. Atmospheric Chemistry and Physics 2008, 8:2405-2421.
21. Hoffmann T. Adsorptive preconcentration technique including oxidant scavenging for the measurement of reactive natural hydrocarbons in ambient air. Fresenius' Journal of Analytical Chemistry 1995, 351:41-47.
22. Hoffmann T., Odum J.R., Bowman F., Collins D., Klockow D., Flagan R.C., Seinfeld J.H. Formation of organic aerosols from the oxidation of biogenic hydrocarbons. Journal of Atmospheric Chemistry 1997, 26:189-222.
23. Hoffmann T., Bandur R., Hoffmann S., Warscheid B. On-line characterisation of gaseous and particulate organic analytes using atmospheric pressure chemical ionisation mass spectrometry. Spectrochimica Acta B 2002, 57:1635-1648.
24. Jaoui M., Leungsakul S., Kamens R.M. Gas and particle products distribution from the reaction of β-caryophyllene with ozone. Journal of Atmospheric Chemistry 2003, 45:261-287.
25. Jaoui M., Lewandowski M., Kleindienst T.E., Offenberg J.H., Edney E.O. β-caryophyllinic acid: an atmospheric tracer for β-caryophyllene secondary organic aerosol. Geophysical Research Letters 2007, 34. 10.1029/2006GL028827.
26. Jenkin M.E., Saunders S.M., Derwent R.G., Pilling M.J. Construction and application of a master chemical mechanism (MCM) for modelling tropospheric chemistry. Abstracts of Papers of the American Chemical Society 1997, 214. 116-COLL.
27. Kanakidou M., Seinfeld J.H., Pandis S.N., Barnes I., Dentener F.J., Facchini M.C., Van Dingenen R., Ervens B., Nenes A., Nielsen C.J., Swietlicki E., Putaud J.P., Balkanski Y., Fuzzi S., Horth J., Moortgat G.K., Winterhalter R., Myhre C.E.L., Tsigaridis K., Vignati E., Stephanou E.G., Wilson J. Organic serosol and global climate modeling: a review. Atmospheric Chemistry and Physics 2005, 5:1053-1123.
28. Kanawati B., Herrmann F., Joniec S., Winterhalter R., Moortgat G.K. Mass spectrometric characterization of β-caryophyllene ozonolysis products in the aerosol studied using an electrospray triple quadrupole and time-of-flight analyzer hybrid system and density functional theory. Rapid Communications in Mass Spectrometry 2008, 22:165-186.
29. Kesselmeier J., Staudt M. Biogenic volatile organic compounds (VOC): an overview on emission. Physiology and Ecology, Journal of Atmospheric Chemistry 1999, 33:23-88.
30. Kim S., Guenther A., Karl T., Greenberg J. Contributions of primary and secondary biogenic VOC to total OH reactivity during the CABINEX (Community Atmosphere-Biosphere Interactions Experiments)-09 field campaign. Atmospheric Chemistry and Physics 2011, 11. 10.5194/acp-11-8613-2011.
31. Kleindienst T.E., Jaoui M., Lewandowski M., Offenberg J.H., Lewis C.W., Bhave P.V., Edney E.O. Estimates of the contributions of biogenic and anthropogenic hydrocarbons to secondary organic aerosol at a southeastern US location. Atmospheric Environment 2007, 41:8288-8300.
32. Knudsen J.T., Tollsten L., Bergström L.G. Floral scents - a checklist of volatile compounds isolated by head-space techniques. Phytochemistry 1993, 33:253-280.
33. Kückelmann U., Warscheid B., Hoffmann T. On-line characterization of organic aerosols formed from biogenic precursors using atmospheric pressure chemical ionization mass spectrometry. Analytical Chemistry 2000, 72:1905-1912.
34. Lee A., Goldstein A.H., Kroll J.H., Ng N.L., Varutbangkul V., Flagan R.C., Seinfeld J.H. Gas-phase products and secondary aerosol yields from the photooxidation of 16 different terpenes. Journal of Geophysical Research 2006, 111:D17305.
35. Lee A., Goldstein A.H., Keywood M.D., Gao S., Varutbangkul V., Bahreini R., Ng N.L., Flagan R.C., Seinfeld J.H. Gas-phase products and secondary aerosol yields from the ozonolysis of ten different terpenes. Journal of Geophysical Research 2006, 111:D17302.
36. Lewandowski M., Jaoui M., Offenberg J.H., Kleindienst T.E., Edney E.O., Sheesley R.J., Schauer J.J. Primary and secondary contributions to ambient PM in the midwestern United States. Environmental Science and Technology 2008, 42:3303-3309.
37. Li Y.J., Chen Q., Guzman M.I., Chan C.K., Martin S.T. Second-generation products contribute substantially to the particle-phase organic material produced by β-caryophyllene ozonolysis. Atmospheric Chemistry and Physics 2011, 11:121-132.
38. Ng N.L., Kroll J.H., Keywood M.D., Bahreini R., Varutbangkul V., Flagan R.C., Seinfeld J.H. Contribution of first- versus second-generation products to secondary organic aerosols formed in the oxidation of biogenic hydrocarbons. Environmental Science and Technology 2006, 40:2283-2297.
39. 24). Part II: a theoretical study. Physical Chemistry Chemical Physics 2009, 11:4173-4183.
40. Parshintsev J., Nurmi J., Kilpeläinen I., Hartonen K., Kulmala M., Riekkola M.J. Preparation of β-caryophyllene oxidation products and their determination in ambient aerosol samples. Analytical and Bioanalytical Chemistry 2008, 390:913-919.
41. Parshintsev J., Hyötyläinen T., Hartonen K., Kulmala M., Riekkola M.J. Solid-phase extraction of organic compounds in atmospheric aerosol particles collected with the particle-into-liquid sampler and analysis by liquid chromatography-mass spectrometry. Talanta 2010, 80:1170-1176.
42. Porter N.A., Scott D.M., Rosenstein I.J., Giese B., Veit A., Zeitz H.G. Stereoselective intermolecular radical additions to amide-substituted alkenes. Journal of the American Chemical Society 1991, 113:1791-1799.
43. Sander R., Baumgaertner A., Gromov S., Harder H., Jöckel P., Kerkweg A., Kubistin D., Regelin E., Riede H., Sandu A., Taraborrelli D., Tost H., Xie Z.-Q. The atmospheric chemistry box model CAABA/MECCA_3.0. Geoscientific Model Development Discussions 2011, 4:373-380.
44. Saunders S.M., Jenkin M.E., Derwent R.G., Pilling M.J. Protocol for the development of the Master Chemical Mechanism, MCM v3 (Part A): tropospheric degradation of non-aromatic volatile organic compounds. Atmospheric Chemistry and Physics 2003, 3:161-180.
45. Seinfeld J.H., Pandis S.N. Atmospheric Chemistry and Physics, From Air Pollution to Climate Change 1998, John Wiley & Sons, Inc., Hoboken, New Jersey. second ed.
46. Shu Y., Atkinson R. Atmospheric lifetimes and fates of a series of sesquiterpenes. Journal of Geophysical Research 1995, 100:7275-7281.
47. Tarvainen V., Hakola H., Hellén H., Bäck J., Hari P., Kulmala M. Temperature and light dependence of the VOC emissions of Scots pine. Atmospheric Chemistry and Physics 2005, 5:989-998.
48. Thorenz U., Kundel M., Müller L., Hoffmann T. Generation of standard gas mixtures of halogenated, aliphatic, and aromatic compounds and prediction of the individual output rates based on molecular formular and boiling point. Analytical and Bioanalytical Chemistry 2012, 10.1007/s00216-012-6202-5.
49. Turlings T.C.J., Loughrin J.H., McCall P.J., Röse U.S.R., Lewis W.J., Tumlinson J.H. How caterpillar-damaged plants protect themselves by attracting parasitic wasps. Proceedings of the National Academy of Sciences of the United States of America 1995, 92:4169-4174.
50. Walborsky H.M., Davis R.H., Howton D.R. Atotal synthesis of linoleic acid. Journal of the American Chemical Society 1951, 73:2590-2594.
51. Warnke J., Bandur R., Hoffmann T. Capillary-HPLC-ESI-MS/MS method for the determination of acidic products from the oxidation of monoterpenes in atmospheric aerosol samples. Analytical and Bioanalytical Chemistry 2006, 385:34-45.
52. Williams J., Crowley J., Fischer H., Harder H., Martinez M., Petäjä T., Rinne J., Bäck J., Boy M., Dal Maso M., Hakala J., Kajos M., Keronen P., Rantala P., Aalto J., Aaltonen H., Paatero J., Vesala T., Hakola H., Levula J., Pohja T., Herrmann F., Auld J., Mesarchaki E., Song W., Yassaa N., Nölscher A., Johnson A.M., Custer T., Sinha V., Thieser J., Pouvesle N., Taraborrelli D., Tang M.J., Bozem H., Hosaynali-Beygi Z., Axinte R., Oswald R., Novelli A., Kubistin D., Hens K., Javed U., Trawny K., Breitenberger C., Hidalgo P.J., Ebben C.J., Geiger F.M., Corrigan A.L., Russell L.M., Ouwersloot H.G., Vilà-Guerau de Arellano J., Ganzeveld L., Vogel A., Beck M., Bayerle A., Kampf C.J., Bertelmann M., Köllner F., Hoffmann T., Valverde J., González D., Riekkola M.-L., Kulmala M., Lelieveld J. The summertime boreal forest field measurement intensive (HUMPPA-COPEC-2010): an overview of meteorological and chemical influences. Atmospheric Chemistry and Physics 2011, 11:10599-10618.
53. 24). Part I: an experimental study. Physical Chemistry Chemical Physics 2009, 11:4152-4172.