References

ACP

Atmospheric Chemistry and Physics

ACP

1680-7324

Copernicus GmbH

Göttingen, Germany

10.5194/acp-12-6323-2012

Identification and characterization of aging products in the glyoxal/ammonium sulfate system – implications for light-absorbing material in atmospheric aerosols

Kampf

C. J.

¹ Jakob

¹ Hoffmann

Institute for Inorganic and Analytical Chemistry, Johannes Gutenberg-University Mainz, 55128 Mainz, Germany

23 07 2012

12 14 6323 6333

This is an open-access article ditributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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The full text article is available as a PDF file from http://www.atmos-chem-phys.net/12/6323/2012/acp-12-6323-2012.pdf

In this study we report the identification of bicyclic imidazoles in aqueous aerosol mimics using HPLC-ESI-MS/MS. 2,2'-Biimidazole was identified to be a major contributor to the 280 nm absorbance band observed in mixtures of glyoxal and ammonium sulfate, despite the fact that its production rate is two orders of magnitude lower than the previously reported production rates of imidazole or imidazole-2-carboxaldehyde. The molar absorptivity of 2,2'-biimidazole was determined to be (36 690 ± 998) M<sup>−1</sup> cm<sup>−1</sup>. This demonstrates the necessity of molecular product identification at trace levels to enable a better understanding of relevant absorbing species. Additionally, the formation of lower polarity products including formamides of imidazoles is proposed. The role of imidazoles and other light-absorbing species in the formation of SOA and optical properties of SOA is discussed and potentially interesting fields for future investigations are outlined.

References 1

Altieri, K. E., Seitzinger, S. P., Carlton, A. G., Turpin, B. J., Klein, G. C., and Marshall, A. G.: Oligomers formed through in-cloud methylglyoxal reactions: Chemical composition, properties, and mechanisms investigated by ultra-high resolution FT-ICR mass spectrometry, Atmos. Environ., 42, 1476–1490, 2008.

Bones, D. L., Henricksen, D. K., Mang, S. A., Gonsior, M., Bateman, A. P., Nguyen, T. B., Cooper, W. J., and Nizkorodov, S. A.: Appearance of strong absorbers and fluorophores in limonene-O3 secondary organic aerosol due to NH4+-mediated chemical aging over long time scales, J. Geophys. Res., 115, D05023, http://dx.doi.org/10.1029/2009JD012864doi:10.1029/2009JD012864, 2010.

Carlton, A. G., Turpin, B. J., Altieri, K. E., Seitzinger, S., Reff, A., Lim, H. J., and Ervens, B.: Atmospheric oxalic acid and SOA production from glyoxal: Results of aqueous photooxidation experiments, Atmos. Environ., 41, 7588–7602, 2007.

Chiswell, B., Lions, F., and Morris, B. S.: Bidentate chelate compounds. III. Metal complexes of some pyridyl-imidazole derivatives, Inorg. Chem., 3, 110–114, 1964.

Cho, J. R., Cho, S. G., Goh, E. M., and Kim, J. K: Preparation method of 2,2'-bi-1H-imidazole using glyoxal and an ammonium salt, United States Patent, 6713631, 2003.

Clarisse, L., Clerbaux, C., Dentener, F., Hurtmans, D., and Coheur, F.: Global ammonia distribution derived from infrared satellite observations, Nat. Geosci., 2, 479–483, doi:10.1038/ngeo551, 2009.

Debus, H.: Über die Einwirkung des Ammoniaks auf Glyoxal, Liebigs Ann. Chem., 107, 199–208, 1858.

De Haan, D. O., Corrigan, A. L., Smith, K. W., Stroik, D. R., Turley, J. J., Lee, F. E., Tolbert, M. A., Jimenez, J. L., Cordova, K. E., and Ferrell, G. R.: Secondary organic aerosol-forming reactions of glyoxal with amino acids, Environ. Sci. Technol., 43, 2818–2824, 2009a.

De Haan, D. O., Tolbert, M. A., and Jimenez, J. L.: Atmospheric condensed-phase reactions of glyoxal with methylamine, Geophys. Res. Lett., 36, L11819, http://dx.doi.org/10.1029/2009GL037441doi:10.1029/2009GL037441, 2009b.

De Haan, D. O., Hawkins, L. N., Kononenko, J. A., Turley, J. J., Corrigan, A. L., Tolbert, M. A., and Jimenez, J. L.: Formation of Nitrogen-Containing Oligomers by Methylglyoxal and Amines in Simulated Evaporating Cloud Droplets, Environ. Sci. Technol., 45, 984–991, 2011.

Ervens, B., Turpin, B. J., and Weber, R. J.: Secondary organic aerosol formation in cloud droplets and aqueous particles (aqSOA): a review of laboratory, field and model studies, Atmos. Chem. Phys., 11, 11069–11102, http://dx.doi.org/10.5194/acp-11-11069-2011doi:10.5194/acp-11-11069-2011, 2011.

Fieselmann, B. F., Hendrickson, D. N., and Stucky, G. D: Synthesis, electron paramagnetic resonance, and magnetic studies of binuclear bis($\eta ^5$-cyclopentadienyl)titanium(III) compounds with bridging pyrazolate, biimidazolate, and bibenzimidazolate anions, Inorg. Chem., 17, 2078–2084, 1978.

Galloway, M. M., Chhabra, P. S., Chan, A. W. H., Surratt, J. D., Flagan, R. C., Seinfeld, J. H., and Keutsch, F. N.: Glyoxal uptake on ammonium sulphate seed aerosol: reaction products and reversibility of uptake under dark and irradiated conditions, Atmos. Chem. Phys., 9, 3331–3345, http://dx.doi.org/10.5194/acp-9-3331-2009doi:10.5194/acp-9-3331-2009, 2009.

Hastings, W. P., Koehler, C. A., Bailey, E. L., and De Haan, D. O.: Secondary organic aerosol formation by glyoxal hydration and oligomer formation: Humidity effects and equilibrium shifts during analysis, Environ. Sci. Technol., 39, 22, 8728–8735, 2005.

Holmes, F., Jones, K. M., and Torrible, E. G.: Complex-forming agents similar to 2,2'-bipyridyl. Part I. Some Ligands containing imidazole, J. Chem. Soc., 4790–4794, 1961.

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., Prevot, A. S. H., Seinfeld, J. H., Surratt, J. D., Szmigielski, R., and Wildt, J.: The formation, properties and impact of secondary organic aerosol: current and emerging issues, Atmos. Chem. Phys., 9, 5155–5236, http://dx.doi.org/10.5194/acp-9-5155-2009doi:10.5194/acp-9-5155-2009, 2009.

Jimenez, J. L., Canagaratna, M. R., Donahue, N. M., Prevot, A. S. H., Zhang, Q., Kroll, J. H., DeCarlo, P. F., Allan, J. D., Coe, H., Ng, N. L., Aiken, A. C., Docherty, K. S., Ulbrich, I. M., Grieshop, A. P., Robinson, A. L., Duplissy, J., Smith, J. D., Wilson, K. R., Lanz, V. A., Hueglin, C., Sun, Y. L., Tian, J., Laaksonen, A., Raatikainen, T., Rautiainen, J., Vaattovaara, P., Ehn, M., Kulmala, M., Tomlinson, J. M., Collins, D. R., Cubison, M. J., Dunlea, E. J., Huffman, J. A., Onasch, T. B., Alfarra, M. R., Williams, P. I., 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, J. Y., Zhang, Y. M., Dzepina, K., Kimmel, J. R., Sueper, D., Jayne, J. T., Herndon, S. C., Trimborn, A. M., Williams, L. R., Wood, E. C., Middlebrook, A. M., Kolb, C. E., Baltensperger, U., and Worsnop, D. R.: Evolution of Organic Aerosols in the Atmosphere, Science, 326, 1525–1529, 2009.

Kalberer, M., Paulsen, D., Sax, M., Steinbacher, M., Dommen, J., Prevot, A. S. H., Fisseha, R., Weingartner, E., Frankevich, V., Zenobi, R., and Baltensperger, U.: Identification of polymers as major components of atmospheric organic aerosols, Science, 303, 1659–1662, 2004.

Kua, J., Krizner H. E., and De Haan, D. O.: Thermodynamics and Kinetics of Imidazole Formation from Glyoxal, Methylamine, and Formaldehyde: A Computational Study, J. Phys. Chem. A, 115, 1667–1675, 2011.

Kulshrestha, U. C., Saxena, A., Kumar, N., Kumari, K. M., and Srivastava, S. S.: Chemical composition and association of size-differentiated aerosols at a suburban site in a semi-arid tract of India, J. Atmos. Chem., 29, 109–118, 1998.

Liggio, J., Li, S. M., and McLaren, R.: Heterogeneous reactions of glyoxal on particulate matter: Identification of acetals and sulfate esters, Environ. Sci. Technol., 39, 1532–1541, 2005a.

Liggio, J., Li, S. M., and McLaren, R.: Reactive uptake of glyoxal by particulate matter, J. Geophys. Res. Atmos., 110, D10304, http://dx.doi.org/10.1029/2004JD005113doi:10.1029/2004JD005113, 2005b.

Lim, Y. B., Tan, Y., Perri, M. J., Seitzinger, S. P., and Turpin, B. J.: Aqueous chemistry and its role in secondary organic aerosol (SOA) formation, Atmos. Chem. Phys., 10 10521–10539, http://dx.doi.org/10.5194/acp-10-10521-2010doi:10.5194/acp-10-10521-2010, 2010.

Loeffler, K. W., Koehler, C. A., Paul, N. M., and De Haan, D. O.: Oligomer formation in evaporating aqueous glyoxal and methyl glyoxal solutions, Environ. Sci. Technol., 40, 6318–6323, 2006.

Mao, F., Mano, N., and Heller, A.: Long tethers binding redox centers to polymer backbones enhance electron transport in enzyme "wiring" hydrogels, J. Am. Chem. Soc., 125, 4951–4957, 2003.

Noziere, B., Dziedzic, P., and Cordova, A.: Products and kinetics of the liquid-phase reaction of glyoxal catalyzed by ammonium ions (NH4+), J. Phys. Chem. A, 113, 231-237, 2009.

Odum, J. R., Hoffmann, T., Bowman, F., Collins, D., Flagan, R. C., and Seinfeld, J. H.: Gas/particle partitioning and secondary organic aerosol yields, Environ. Sci. Technol., 30, 2580–2585, 1996.

Pankow, J. F.: An absorption model of the gas/aerosol partitioning involved in the formation of secondary organic aerosol, Atmos. Environ., 28, 189–193, 1994.

Parashar, D. C., Kulshrestha, U. C., and Jain, M.: Precipitation and aerosol studies in India, Environ. Monit. Assess., 66, 47–61, 2001.

Sareen, N., Schwier, A. N., Shapiro, E. L., Mitroo, D., and McNeill, V. F.: Secondary organic material formed by methylglyoxal in aqueous aerosol mimics, Atmos. Chem. Phys., 10, 997–1016, http://dx.doi.org/10.5194/acp-10-997-2010doi:10.5194/acp-10-997-2010, 2010.

Schwier, A. N., Sareen, N., Mitroo, D., Shapiro, E. L., and McNeill, V. F.: Glyoxal-Methylglyoxal Cross-Reactions in Secondary Organic Aerosol Formation, Environ. Sci. Technol., 44, 6174–6182, 2010.

See, S. W., Wang, Y. H., and Balasubramanian, R.: Contrasting reactive oxygen species and transition metal concentrations in combustion aerosols, Environ. Res., 103, 317–324, 2007.

Seinfeld, J. H. and Pandis, S. N.: Atmospheric chemistry and physics: From air pollution to climate change, 2nd Edn., Wiley, Hoboken, 2006.

Shapiro, E. L., Szprengiel, J., Sareen, N., Jen, C. N., Giordano, M. R., and McNeill, V. F.: Light-absorbing secondary organic material formed by glyoxal in aqueous aerosol mimics, Atmos. Chem. Phys., 9, 2289–2300, http://dx.doi.org/10.5194/acp-9-2289-2009doi:10.5194/acp-9-2289-2009, 2009.

Surratt, J. D., Kroll, J. H., Kleindienst, T., E., Edney, E. O., Claeys, M., Sorooshian, A., Ng, N. L., Offenberg, J. H., Lewandowski, M., Jaoui, M., Flagan, R., and Seinfeld, J. H.: Evidence for organosulfates in secondary organic aerosol, Environ. Sci. Technol., 41, 517–527, http://dx.doi.org/10.1021/es062081qdoi:10.1021/es062081q, 2007.

Surratt, J. D., Gomez-Gonzalez, Y., Chan, A. W. H., Vermeylen, R., Shahgholi, M., Kleindienst, T. E., Edney, E. O., Offenberg, J. H., Lewandowski, M., Jaoui, M., Maenhaut, W., Claeys, M., Flagan, R. C., and Seinfeld, J. H.: Organosulfate formation in biogenic secondary organic aerosol, J. Phys. Chem. A, 112, 8345–8378, http://dx.doi.org/10.1021/jp802310pdoi:10.1021/jp802310p, 2008.

Tan, Y., Perri, M. J., Seitzinger S. P., and Turpin, B. J.: Effects of precursor concentration and acidic sulfate in aqueous glyoxal-OH radical oxidation and implications for secondary organic aerosol, Environ. Sci. Technol., 43, 8105–8112, http://dx.doi.org/10.1021/es901742fdoi:10.1021/es901742f, 2009.

Tan, Y., Carlton, A. G., Seitzinger, S. P., and Turpin, B. J.: SOA from methylglyoxal in clouds and wet aerosols: Measurement and prediction of key products, Atmos. Environ., 44, 5218–5226, 2010.

Trainic, M., Riziq, A. A., Lavi, A., Flores, J. M., and Rudich, Y.: The optical, physical and chemical properties of the products of glyoxal uptake on ammonium sulfate seed aerosols, Atmos. Chem. Phys., 11, 9697–9707, http://dx.doi.org/10.5194/acp-11-9697-2011doi:10.5194/acp-11-9697-2011, 2011.

Trainic, M., Riziq, A. A., Lavi, A., and Rudich, Y.: The role of interfacial water in the heterogeneous uptake of glyoxal by mixed glycine and ammonium sulfate aerosols, J. Phys. Chem. A., 116, 5948–5957, doi:10.1021/jp2104837, 2012.

Yasmeen, F., Sauret, N., Gal, J. -F, Maria, P.-C, Massi, L., Maenhaut, W., and Claeys, M.: Characterization of oligomers from methylglyoxal under dark conditions: a pathway to produce secondary organic aerosol through cloud processing during nighttime, Atmos. Chem. Phys., 10, 3803–3812, http://dx.doi.org/10.5194/acp-10-3803-2010doi:10.5194/acp-10-3803-2010, 2010.

Yu, G., Bayer A. R., Galloway, M. M., Korshavn, K. J., Fry, C. G., and Keutsch, F. N.: Glyoxal in Aqueous Ammonium Sulfate Solutions: Products, Kinetics and Hydration Effects, Environ. Sci. Technol., 45, 6336–6342, 2011.

Zhao, J., Levitt, N. P., Zhang, R. Y., and Chen, J. M.: Heterogeneous reactions of methylglyoxal in acidic media: Implications for secondary organic aerosol formation, Environ. Sci. Technol., 40, 7682–7687, 2006.

Zhang, Q., Jimenez, J. L., Canagaratna, M. R., Allan, J. D., Coe, H., Ulbrich, I., Alfarra, M. R., Takami, A., Middlebrook, A. M., Sun, Y. L., Dzepina, K., Dunlea, E., Docherty, K., DeCarlo, P. F., Salcedo, D., Onasch, T., Jayne, J. T., Miyoshi, T., Shimono, A., Hatakeyama, S., Takegawa, N., Kondo, Y., Schneider, J., Drewnick, F., Borrmann, S., Weimer, S., Demerjian, K., Williams, P., Bower, K., Bahreini, R., Cottrell, L., Griffin, R. J., Rautiainen, J., Sun, J. Y., Zhang, Y. M., and Worsnop, D. R.: Ubiquity~~~and~~~dominance~~ of~~ oxygenated ~~speciesin~~organic\noindent aerosols in anthropogenically-influenced Northern Hemisphere midlatitudes, Geophys. Res. Lett., 34, L13801, http://dx.doi.org/10.1029/2007GL029979doi:10.1029/2007GL029979, 2007.