Skip to main content
SpringerLink
Log in

Tracers for Biogenic Secondary Organic Aerosol from α-Pinene and Related Monoterpenes: An Overview

  • Conference paper
  • First Online:
Book cover Disposal of Dangerous Chemicals in Urban Areas and Mega Cities

Abstract

In this review, we first address the terpenoid composition of ambient fine rural aerosol to give a report on the current state of knowledge in regard to the molecular characterisation of biogenic secondary organic aerosol tracers. The major known, recently elucidated, and still unknown tracers, which can be detected at a significant relative abundance, are listed and briefly discussed. In a second part, we provide a historic account on the discovery of 3-methyl-1,2,3-butanetricarboxylic acid, which involved a long search with several failures and a final success, and propose a revised formation pathway. Finally, we present some brief conclusions and perspectives.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Christoffersen TS, Hjorth J, Horie O, Jensen NR, Kotzias D, Molander L, Neeb P, Ruppert L, Winterhalter R, Virkkula A, Wirtz K, Larsen BR (1998) cis-Pinic acid, a possible precursor for organic aerosol formation from ozonolysis of α-pinene. Atmos Environ 32:1657–1661

    Article  CAS  Google Scholar 

  2. Claeys M, Szmigielski R, Kourtchev I, Van der Veken P, Vermeylen R, Maenhaut W, Jaoui M, Kleindienst TE, Lewandowski M, Offenberg JH, Edney EO (2007) Hydroxydicarboxylic acids: novel markers for secondary organic aerosol from the photooxidation of α-pinene. Environ Sci Technol 41:1628–1634

    Article  CAS  Google Scholar 

  3. Claeys M, Iinuma Y, Szmigielski R, Surratt JD, Blockhuys F, Van Alsenoy C, Böge O, Sierau B, Gómez-González Y, Vermeylen R, Van der Veken P, Shahgholi M, Chan AWH, Herrmann H, Seinfeld JH, Maenhaut W (2009) Terpenylic acid and related compounds from the oxidation of α-pinene: implications for new particle formation and growth above forest. Environ Sci Technol 43:6976–6982

    Article  CAS  Google Scholar 

  4. Gao Y, Hall WA IV, Johnston MV (2010) Molecular composition of monoterpene secondary organic aerosol at low mass loading. Environ Sci Technol 44:7897–7902

    Article  CAS  Google Scholar 

  5. George IJ, Abbatt JPD (2010) Chemical evolution of secondary organic aerosol from OH-initiated heterogeneous oxidation. Atmos Chem Phys 10:5551–5563

    Article  CAS  Google Scholar 

  6. Glasius M, Duane M, Larsen BR (1999) Determination of polar terpene oxidation products in aerosols by liquid chromatography-ion trap mass spectrometry. J Chromatogr A 833:121–135

    Article  CAS  Google Scholar 

  7. Glasius M, Lahaniati M, Calogirou A, Di Bella D, Jensen NR, Hjorth J, Duane M, Kotzias D, Larsen BR (2000) Carboxylic acids in secondary aerosols from oxidation of cyclic monoterpenes by ozone. Environ Sci Technol 34:1001–1010

    Article  CAS  Google Scholar 

  8. Gómez-González Y, Surratt JD, Cuyckens F, Szmigielski R, Vermeylen R, Jaoui M, Lewandowski M, Offenberg JH, Kleindienst TE, Edney EO, Blockhuys F, Van Alsenoy C, Maenhaut W, Claeys M (2008) Characterization of organosulfates from the photooxidation of isoprene and unsaturated fatty acids in ambient aerosol using liquid chromatography/(-)electrospray ionization mass spectrometry. J Mass Spectrom 43:371–382

    Article  Google Scholar 

  9. Gómez-González Y, Wang W, Vermeylen R, Chi X, Neirynck J, Janssens IA, Maenhaut W, Claeys M (2012) Chemical characterization of atmospheric aerosols during a 2007 summer field campaign at Brasschaat, Belgium: sources and source processes of biogenic secondary organic aerosol. Atmos Chem Phys 12:125–138

    Article  Google Scholar 

  10. Hallquist M, Wenger JC, Baltensperger U, Rudich Y, Simpson D, Claeys M, Dommen J, Donahue NM, George C, Goldstein AH, Hamilton JF, Herrmann H, Hoffmann T, Iinuma Y, Jang M, Jenkin ME, Jimenez JL, Kiendler-Scharr A, Maenhaut W, McFiggans G, Mentel TF, Monod A, Prévôt ASH, Seinfeld JH, Surratt JD, Szmigielski R, Wildt J (2009) The formation, properties and impact of secondary organic aerosol: current and emerging issues. Atmos Chem Phys 9:5155–5236

    Article  CAS  Google Scholar 

  11. Hatakeyama S, Izumi K, Fukuyama T, Akimoto H (1989) Reactions of ozone with alpha-pinene and beta-pinene in air – yields of gaseous and particulate products. J Geophys Res Atmos 94:13013–13024

    Article  CAS  Google Scholar 

  12. Hoffmann T, Odum JR, Bowman F, Collins D, Klockow D, Flagan RC, Seinfeld JH (1997) Formation of organic aerosols from the oxidation of biogenic hydrocarbons. J Atmos Chem 26:189–222

    Article  CAS  Google Scholar 

  13. Hoffmann T, Bandur R, Marggraf U, Linscheid M (1998) Molecular composition of organic aerosols formed in the α-pinene/O3 reaction: implications for new particle formation processes. J Geophys Res Atmos 103:25569–25578

    Article  CAS  Google Scholar 

  14. Iinuma Y, Müller C, Böge O, Gnauk T, Herrmann H (2007) The formation of organic sulfate esters in the limonene ozonolysis secondary organic aerosol (SOA) under acidic conditions. Atmos Environ 41:5571–5583

    Article  CAS  Google Scholar 

  15. Iinuma Y, Müller C, Berndt T, Böge O, Claeys M, Herrmann H (2007) Evidence for the existence of organosulfates from beta-pinene ozonolysis in ambient secondary organic aerosol. Environ Sci Technol 41:6678–6683

    Article  CAS  Google Scholar 

  16. Iinuma Y, Böge O, Keywood M, Gnauk T, Herrmann H (2009) Diaterebic acid acetate and diaterpenylic acid acetate: atmospheric tracers for secondary organic aerosol formation from 1,8-cineole oxidation. Environ Sci Technol 43:280–285

    Article  CAS  Google Scholar 

  17. Jang M, Kamens RM (1999) Newly characterized products and composition of secondary aerosols from the reaction of α-pinene and ozone. Atmos Environ 33:459–474

    Article  CAS  Google Scholar 

  18. Jaoui M, Kleindienst TE, Lewandowski M, Offenberg JH, Edney EO (2005) Identification and quantification of aerosol polar oxygenated compounds bearing carboxylic or hydroxyl groups: 2 organic tracer compounds from monoterpenes. Environ Sci Technol 39:5661–5673

    Article  CAS  Google Scholar 

  19. Jimenez JL, Canagaratna MR, Donahue NM, Prévôt ASH, Zhang Q, Kroll JH, DeCarlo PF, Allan JD, Coe H, Ng NL, Aiken AC, Docherty KS, Ulbrich IM, Grieshop AP, Robinson AL, Duplissy J, Smith JD, Wilson KR, Lanz VA, Hueglin C, Sun YL, Tian J, Laaksonen A, Raatikainen T, Rautiainen J, Vaattovaara P, Ehn M, Kulmala M, Tomlinson JM, Collins DR, Cubison MJ, Dunlea EJ, Huffman JA, Onasch TB, Alfarra MR, Williams PI, Bower K, Kondo Y, Schneider J, Drewnick F, Borrmann S, Weimer S, Demerjian K, Salcedo D, Cottrell L, Griffin R, Takami A, Miyoshi T, Hatakeyama S, Shimono A, Sun JY, Zhang YM, Dzepina K, Kimmel JR, Sueper D, Jayne JT, Herndon SC, Trimborn AM, Williams LR, Wood EC, Middlebrook AM, Kolb CE, Baltensperger U, Worsnop DR (2009) Evolution of organic aerosols in the atmosphere. Science 326:1525–1529

    Article  CAS  Google Scholar 

  20. Kourtchev I, Copolovici L, Claeys M, Maenhaut W (2009) Characterization of atmospheric aerosols at a forested site in Central Europe. Environ Sci Technol 43:4665–4671

    Article  CAS  Google Scholar 

  21. Kristensen K, Glasius M (2011) Organosulfates and oxidation products from biogenic hydrocarbons in fine aerosols from a forest in North West Europe during spring. Atmos Environ 45:4546–4556

    Article  CAS  Google Scholar 

  22. Kroll JH, Seinfeld JH (2008) Chemistry of secondary organic aerosol: formation and evolution of low-volatility organics in the atmosphere. Atmos Environ 42:3593–3624

    Article  CAS  Google Scholar 

  23. Kroll JH, Donahue NM, Jimenez JL, Kessler SH, Canagaratna MR, Wilson KR, Altieri KE, Mazzoleni LR, Wozniak AS, Bluhm H, Mysak ER, Smith JD, Kolb CE, Worsnop DR (2011) Carbon oxidation state as a metric for describing the chemistry of atmospheric organic aerosol. Nat Chem 3:133–139

    Article  CAS  Google Scholar 

  24. Kubátová A, Vermeylen R, Claeys M, Cafmeyer J, Maenhaut W, Roberts G, Artaxo P (2000) Carbonaceous aerosol characterization in the Amazon basin, Brasil: novel dicarboxylic acids and related compounds. Atmos Environ 34:5037–5051

    Article  Google Scholar 

  25. Larsen BR, Lahaniati M, Calogirou A, Kotzias D (1998) Atmospheric oxidation products of terpenes: a new nomenclature. Chemosphere 37:1207–1220

    Article  CAS  Google Scholar 

  26. Larsen BR, Di Bella D, Glasius M, Winterhalter R, Jensen NR, Hjorth J (2001) Gas-phase OH oxidation of monoterpenes: gaseous and particulate products. J Atmos Chem 38:231–276

    Article  CAS  Google Scholar 

  27. Maenhaut W, Wang W, Chi X (2011) Semivolatile behaviour and filter sampling artifacts for dicarboxylic acids during summer campaigns at three forested sites in Europe. Boreal Environ Res 16:273–287

    CAS  Google Scholar 

  28. Müller L, Reinnig M-C, Warnke J, Hoffmann T (2008) Unambiguous identification of esters as oligomers in secondary organic aerosol formed from cyclohexene and cyclohexene/α-pinene ozonolysis. Atmos Chem Phys 8:1423–1433

    Article  Google Scholar 

  29. Müller L, Reinnig M-C, Naumann KH, Saathoff H, Mentel TF, Donahue N, Hoffmann T (2011) Formation of 3-methyl-1,2,3-butanetricarboxylic acid via gas phase oxidation of pinonic acid – a mass spectrometric study of SOA aging. Atmos Chem Phys Discuss 11:19443–19476

    Article  Google Scholar 

  30. Nizkorodov SA, Laskin J, Laskin A (2011) Molecular chemistry of organic aerosols through the application of high resolution mass spectrometry. Phys Chem Chem Phys 13:3612–3629

    Article  CAS  Google Scholar 

  31. Putman AL, Offenberg JH, Fisseha R, Kundu S, Rahn TA, Mazzoleni LR (2012) Ultrahigh-resolution FT-ICR mass spectrometry characterization of α-pinene ozonolysis SOA. Atmos Environ 46:164–172

    Article  CAS  Google Scholar 

  32. Reinhardt A, Emmenegger C, Gerrits B, Panse C, Dommen J, Baltensperger U, Zenobi R, Kalberer M (2007) Ultrahigh mass resolution and accurate mass measurements as a tool to characterize oligomers in secondary organic aerosols. Anal Chem 79:4074–4082

    Article  CAS  Google Scholar 

  33. Surratt JD, Kroll JH, Kleindienst TE, Edney EO, Claeys M, Sorooshian A, Ng NL, Offenberg JH, Lewandowski M, Jaoui M, Flagan RC, Seinfeld JH (2007) Evidence for organosulfates in secondary organic aerosol. Environ Sci Technol 41:517–527

    Article  CAS  Google Scholar 

  34. Surratt JD, Gómez-González Y, Chan AWH, Vermeylen R, Shahgholi M, Kleindienst TE, Edney EO, Offenberg JH, Lewandowski M, Jaoui M, Maenhaut W, Claeys M, Flagan RC, Seinfeld JH (2008) Organosulfate formation in biogenic secondary organic aerosol. J Phys Chem A 112:8345–8378

    Article  CAS  Google Scholar 

  35. Surratt JD, Chan AWH, Eddingsaas NC, Chan MN, Loza CL, Kwan AJ, Hersey SP, Flagan RC, Wennberg PO, Seinfeld JH (2010) Reactive intermediates revealed in secondary organic aerosol formation from isoprene. Proc Natl Acad Sci USA 107:6640–6645

    Article  CAS  Google Scholar 

  36. Szmigielski R, Surratt JD, Gómez-González Y, Van der Veken P, Kourtchev I, Vermeylen R, Blockhuys F, Jaoui M, Kleindienst TE, Lewandowski M, Offenberg JH, Edney EO, Seinfeld JH, Maenhaut W, Claeys M (2007) 3–methyl-1,2,3–butanetricarboxylic acid: an atmospheric tracer for terpene secondary organic aerosol. Geophys Res Lett 34:L24811. doi: 10.1029/2007GL031338

    Article  Google Scholar 

  37. Vereecken L, Peeters J (2002) Enhanced H-atom abstraction from pinonaldehyde, pinonic acid, pinic acid, and related compounds: theoretical study of C–H bond strengths. Phys Chem Chem Phys 4:467–472

    Article  CAS  Google Scholar 

  38. Yasmeen F, Vermeylen R, Szmigielski R, Iinuma Y, Böge O, Herrmann H, Maenhaut W, Claeys M (2010) Terpenylic acid and related compounds: precursors for dimers in secondary organic aerosol from the ozonolysis of α- and β-pinene. Atmos Chem Phys 10:9383–9392

    Article  CAS  Google Scholar 

  39. Yasmeen F, Szmigielski R, Vermeylen R, Gómez-González Y, Surratt JD, Chan AWH, Seinfeld JH, Maenhaut W, Claeys M (2011) Mass spectrometric characterization of isomeric terpenoic acids from the oxidation of α-pinene, β-pinene, d-limonene, and Δ3-carene in fine forest aerosol. J Mass Spectrom 46:425–442

    Article  CAS  Google Scholar 

  40. Yu JZ, Flagan RC, Seinfeld JH (1998) Identification of products containing –COOH, –OH, and –C=O in atmospheric oxidation of hydrocarbons. Environ Sci Technol 32:2357–2370

    Article  CAS  Google Scholar 

  41. Yu JZ, Cocker DR III, Griffin RJ, Flagan RC, Seinfeld JH (1999) Gas-phase ozone oxidation of monoterpenes: gaseous and particulate products. J Atmos Chem 34:207–258

    Article  CAS  Google Scholar 

  42. Zhang YY, Müller L, Winterhalter R, Moortgat GK, Hoffmann T, Pöschl U (2010) Seasonal cycle and temperature dependence of pinene oxidation products, dicarboxylic acids and nitrophenols in fine and coarse air particulate matter. Atmos Chem Phys 10:7859–7873

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Research at the Universities of Antwerp and Ghent was supported by the Belgian Federal Science Policy Office, the Research Foundation – Flanders (FWO), and the Special Research Funds of the Universities of Antwerp and Ghent. Rafal Szmigielski was supported by a Marie Curie Intra-European fellowship. We also acknowledge the close collaboration during the past several years with Tad Kleindienst, Ed Edney, and coworkers, at the US Environmental Protection Agency (Research Triangle Park, NC, USA), Jason Surratt, John Seinfeld, and coworkers, at the California Institute of Technology (Pasadena, CA, USA), and Yoshi Iinuma, Hartmut Herrmann, and coworkers, at the Leibniz-Institute for Tropospheric Research (Leipzig, Germany).

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, BE-2610, Antwerp, Belgium

    Magda Claeys, Reinhilde Vermeylen, Wu Wang, Mohammad Safi Shalamzari & Willy Maenhaut

  2. Laboratory of Environmental Chemistry, Institute of Physical Chemistry, Polish Academy of Sciences (PAS), Kasprzaka 44/52 St., 01-224, Warsaw, Poland

    Rafal Szmigielski

Authors
  1. Magda Claeys
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rafal Szmigielski
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Reinhilde Vermeylen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wu Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mohammad Safi Shalamzari
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Willy Maenhaut
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Magda Claeys .

Editor information

Editors and Affiliations

  1. FB C Mathematik / Naturwissenschaften, FG Physikalische Chemie, Bergische Universität Wuppertal, Gaußstr. 20, Wuppertal, 42119, Germany

    Ian Barnes

  2. Institute of Physical Chemistry PAS, Kasprzaka str. 44/52, Warsaw, 01-224, Poland

    Krzysztof J. Rudziński

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer Science+Business Media Dordrecht

About this paper

Cite this paper

Claeys, M., Szmigielski, R., Vermeylen, R., Wang, W., Shalamzari, M.S., Maenhaut, W. (2013). Tracers for Biogenic Secondary Organic Aerosol from α-Pinene and Related Monoterpenes: An Overview. In: Barnes, I., Rudziński, K. (eds) Disposal of Dangerous Chemicals in Urban Areas and Mega Cities. NATO Science for Peace and Security Series C: Environmental Security. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-5034-0_18

Download citation

Publish with us

Policies and ethics

Search

Navigation