Atmospheric Chemistry and Physics Discussions www.atmos-chem-phys-discuss.net 1680-7367 1680-7375 8 6 2008 10.5194/acpd-8-20799-2008 http://www.atmos-chem-phys-discuss.net/8/20799/2008/ http://www.atmos-chem-phys-discuss.net/8/20799/2008/acpd-8-20799-2008.html http://www.atmos-chem-phys-discuss.net/8/20799/2008/acpd-8-20799-2008.pdf 20799 20838 2008-12-12 Glyoxal uptake on ammonium sulphate seed aerosol: reaction products and reversibility of uptake under dark and irradiated conditions M. M. Galloway P. S. Chhabra A. W. H. Chan J. D. Surratt R. C. Flagan J. H. Seinfeld F. N. Keutsch Dept. of Chemistry, University of Wisconsin-Madison, Madison, WI, USA Dept. of Chemical Engineering, California Institute of Technology, Pasadena, CA, USA Dept. of Chemistry, California Institute of Technology, Pasadena, CA, USA Dept. of Environmental Science and Engineering California Institute of Technology, Pasadena, CA, USA Chamber studies of glyoxal uptake onto neutral ammonium sulphate aerosol were performed under dark and irradiated conditions to gain further insight into processes controlling glyoxal uptake onto ambient aerosol. Organic fragments from glyoxal dimers and trimers were observed within the aerosol under dark and irradiated conditions; glyoxal oligomer formation and overall organic growth were found to be reversible under dark conditions. Analysis of high-resolution time-of-flight aerosol mass spectra provides evidence for irreversible formation of carbon-nitrogen (C-N) compounds in the aerosol. These compounds are likely to be imidazoles formed by reaction of glyoxal with the ammonium sulphate seed. To the authors' knowledge, this is the first time C-N compounds resulting from condensed phase reactions with ammonium sulphate seed have been detected in aerosol. Organosulphates were not detected under dark conditions. However, active oxidative photochemistry, similar to that found in cloud processing, was found to occur within aerosol during irradiated experiments. Organosulphates, carboxylic acids, and organic esters were identified within the aerosol. Our study suggests that both C-N compound formation and photochemical processes should be considered in models of secondary organic aerosol formation via glyoxal. Angelino, S., Suess, D. T., and Prather, K. A.: Formation of aerosol particles from reactions of secondary and tertiary alkylamines: Characterization by aerosol time-of-flight mass spectrometry, Environ. Sci.\ Technol., 35, 3130–3138, doi:10.1021/es0015444, 2001. Canagaratna, M. R., Jayne, J. T., Jimenez, J. L., Allan, J. D., Alfarra, M. R., Zhang, Q., Onasch, T. B., Drewnick, F., Coe, H., Middlebrook, A., Delia, A., Williams, L. R., Trimborn, A. M., Northway, M. J., DeCarlo, P. F., Kolb, C. E., Davidovits, P., and Worsnop, D. R.: Chemical and microphysical characterization of ambient aerosols with the Aerodyne Aerosol Mass Spectrometer, Mass. Spectrom. Rev., 26, 185–222, doi:10.1002/mas.20115, 2007. 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, doi:10.1016/j.atmosenv.2007.05.035, 2007. Cocker, D. R., Flagan, R. C., and Seinfeld, J. H.: State-of-the-art chamber facility for studying atmospheric aerosol chemistry, Environ. Sci.\ Technol., 35, 2594–2601, doi:10.1021/es0019169, 2001. Corrigan, A. L., Hanley, S. W., and De~Haan, D. O.: Uptake of glyoxal by organic and inorganic aerosol, Environ. Sci. Technol., 42, 4428–4433, doi:10.1021/es7032394, 2008. de Gouw, J. A., Middlebrook, A. M., Warneke, C., Goldan, P. D., Kuster, W. C., Roberts, J. M., Fehsenfeld, F. C., Worsnop, D. R., Canagaratna, M. R., Pszenny, A. A. P., Keene, W. C., Marchewka, M., Bertman, S. B., and Bates, T. S.: Budget of organic carbon in a polluted atmosphere: Results from the New England air quality study in 2002, J. Geophys. Res.-Atmos., 110, D16305, doi:10.1029/2004JD005623, 2005. Debus, H.: Ueber die einwirkung des ammoniaks auf glyoxal, Annalen der Chemie und Pharmacie, 107, 199–208, doi:10.1002/jlac.18581070209, 1858. Denkenberger, K. A., Moffet, R. C., Holecek, J. C., Rebotier, T. P., and Prather, K. A.: Real-time, single-particle measurements of oligomers in aged ambient aerosol particles, Environ. Sci. Technol., 41, 5439–5446, doi:10.1021/es070329l, 2007. Ervens, B., Carlton, A. G., Turpin, B. J., Altieri, K. E., Kreidenweis, S. M., and Feingold, G.: Secondary organic aerosol yields from cloud-processing of isoprene oxidation products, Geophys. Res. Lett., 35, L02816, doi:10.1029/2007GL031828, 2008. Fratzke, A. R. and Reilly, P. J.: Thermodynamic and kinetic analysis of the dimerization of aqueous glyoxal, Int. J. Chem. Kinet., 18, 775–789, 1986. Fu, T. M., Jacob, D. J., Wittrock, F., Burrows, J. P., Vrekoussis, M., and Henze, D. K.: Global budgets of atmospheric glyoxal and methylglyoxal, and implications for formation of secondary organic aerosols, J. Geophys.\ Res.-Atmos., 113, D15303, doi:10.1029/2007JD009505, 2008. Gómez-González, Y., Surratt, J. D., Cuyckens, F., Szmigielski, R., Vermeylen, R., Jaoui, M., Lewandowski, M., Offenberg, J. H., Kleindienst, T. E., Edney, E. O., Blockhuys, F., Van~Alsenoy, C., Maenhaut, W., and Claeys, M.: 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, doi:10.1002/jms.1329, 2008. Gross, D. S., Galli, M. E., Kalberer, M., Prevot, A. S. H., Dommen, J., Alfarra, M. R., Duplissy, J., Gaeggeler, K., Gascho, A., Metzger, A., and Baltensperger, U.: Real-time measurement of oligomeric species in secondary organic aerosol with the aerosol time-of-flight mass spectrometer, Anal.\ Chem., 78, 2130–2137, doi:10.1021/ac060138l, 2006. Heald, C. L., Jacob, D. J., Park, R. J., Russell, L. M., Huebert, B. J., Seinfeld, J. H., Liao, H., and Weber, R. J.: A large organic aerosol source in the free troposphere missing from current models, Geophys. Res. Lett., 32, L18809, doi:10.1029/2005GL023831, 2005. Huisman, A. J., Hottle, J. R., Coens, K. L., DiGangi, J. P., Galloway, M. M., Kammrath, A., and Keutsch, F. N.: Laser-induced phosphorescence for the in situ detection of glyoxal at part per trillion mixing ratios, Anal. Chem., 80, 5884–5891, doi:10.1021/ac800407b, 2008. Jang, M. S., Czoschke, N. M., Lee, S., and Kamens, R. M.: Heterogeneous atmospheric aerosol production by acid-catalyzed particle-phase reactions, Science, 298, 814–817, doi:10.1126/science.1075798, 2002. Keywood, M. D., Varutbangkul, V., Bahreini, R., Flagan, R. C., and Seinfeld, J. H.: Secondary organic aerosol formation from the ozonolysis of cycloalkenes and related compounds, Environ. Sci. Technol., 38, 4157–4164, doi:10.1021/es035363o, 2004. Kroll, J. H., Ng, N. L., Murphy, S. M., Varutbangkul, V., Flagan, R. C., and Seinfeld, J. H.: Chamber studies of secondary organic aerosol growth by reactive uptake of simple carbonyl compounds, J. Geophys. Res., 110, D23207, doi:10.1029/2005JD006004, 2005. Liggio, J., Li, S., and McLaren, R.: Heterogeneous reactions of glyoxal on particulate matter: Identification of acetals and sulphate esters, Environ.\ Sci. Technol., 39, 1532–1541, doi:10.1021/es048375y, 2005a. Liggio, J., Li, S., and McLaren, R.: Reactive uptake of glyoxal by particulate matter, J. Geophys. Res., 110, D10304, doi:10.1029/2004JD005113, 2005b. Loeffler, K. W., Koehler, C. A., Paul, N. M., and DeHaan, D. O.: Oligomer formation in evaporating aqueous glyoxal and methyl glyoxal solutions, Environ. Sci. Technol., 40, 6318–6323, doi:10.1021/es060810w, 2006. Matsunaga, S., Mochida, M., and Kawamura, K.: Variation on the atmospheric concentrations of biogenic carbonyl compounds and their removal processes in the northern forest at moshiri, hokkaido island in japan, J. Geophys. Res., 109, D04302, doi:10.1029/2003JD004100, 2004. Myriokefalitakis, S., Vrekoussis, M., Tsigaridis, K., Wittrock, F., Richter, A., Brühl, C., Volkamer, R., Burrows, J. P., and Kanakidou, M.: The influence of natural and anthropogenic secondary sources on the glyoxal global distribution, Atmos. Chem. Phys., 8, 4965–4981, 2008. Na, K., Song, C., Switzer, C., and Cocker, D. R.: Effect of ammonia on secondary organic aerosol formation from alpha-pinene ozonolysis in dry and humid conditions, Environ. Sci. Technol., 41, 6096–6102, doi:10.1021/es061956y, 2007. Na, K., Song, C., and Cocker, D. R.: Formation of secondary organic aerosol from the reaction of styrene with ozone in the presence and absence of ammonia and water, Atmos. Environ., 40, 1889–1900, doi:10.1016/j.atmosenv.2005.10.063, 2006. NIST Webbook: available at: http://webbook.nist.gov/cgi/cbook.cgi?Name=glyoxal&Units=SI, last access: 5~September~2008. 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, doi:10.1021/es950943+, 1996. Pankow, J. F.: An absorption-model of gas-particle partitioning of organic-compounds in the atmosphere, Atmos. Environ., 28, 185–188, 1994a. Pankow, J. F.: An absorption-model of the gas aerosol partitioning involved in the formation of secondary organic aerosol, Atmos. Environ., 28, 189–193, 1994b. Reinhardt, A., Emmenegger, C., Gerrits, B., Panse, C., Dommen, J., Baltensperger, U., Zenobi, R., and Kalberer, M.: Ultrahigh mass resolution and accurate mass measurements as a tool to characterize oligomers in secondary organic aerosols, Anal. Chem., 79, 4074–4082, doi:10.1021/ac062425v, 2007. Schweitzer, F., Magi, L., Mirabel, P., and George, C.: Uptake rate measurements of methanesulfonic acid and glyoxal by aqueous droplets, J.\ Phys. Chem. A, 102, 593–600, doi:10.1021/jp972451k, 1998. SciFinder Scholar: Calculated using Advanced Chemistry Development (ACD/Labs) Software V8.14 for Solaris (1994–2008 ACD/Labs),last access: 26~September~2008. Silva, P. J., Erupe, M. E., Price, D., Elias, J., Malloy, Q. G. J., Li, Q., Warren, B., and Cocker, D. R.: Trimethylamine as precursor to secondary organic aerosol formation via nitrate radical reaction in the atmosphere, Environ. Sci. Technol., 42, 4689–4696, doi:10.1021/es703016v, 2008. Sorooshian, A., Varutbangkul, V., Brechtel, F. J., Ervens, B., Feingold, G., Bahreini, R., Murphy, S. M., Holloway, J. S., Atlas, E. L., Buzorius, G., Jonsson, H., Flagan, R. C., and Seinfeld, J. H.: Oxalic acid in clear and cloudy atmospheres: Analysis of data from International Consortium for Atmospheric Research on Transport and Transformation 2004, J. Geophys.\ Res.-Atmos., 111, D23S45, doi:10.1029/2005JD006880, 2006. Spaulding, R. S., Schade, G. W., Goldstein, A. H., and Charles, M. J.: Characterization of secondary atmospheric photooxidation products: Evidence for biogenic and anthropogenic sources, J. Geophys. Res., 108, 4247, doi:10.1029/2002JD002478, 2003. Surratt, J. D., Gómez-González, 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, doi:10.1021/jp802310p, 2008. Surratt, J. D., Kroll, J. H., Kleindienst, T. E., Edney, E. O., Claeys, M., Sorooshian, A., Offenberg, J. H., Lewandowski, M., Jaoui, M., Flagan, R. C., and Seinfeld, J. H.: Evidence for organosulfates in secondary organic aerosol, Environ. Sci. Technol., 41, 517–527, doi:10.1021/es062081q, 2007. Volkamer, R., Jimenez, J. L., San Martini, F., Dzepina, K., Zhang, Q., Salcedo, D., Molina, L. T., Worsnop, D. R., and Molina, M. J.: Secondary organic aerosol formation from anthropogenic air pollution: Rapid and higher than expected, Geophys. Res. Lett., 33, L17811, doi:10.1029/2006GL026899, 2006. Volkamer, R., San Martini, F., Molina, L. T., Salcedo, D., Jimenez, J. L., and Molina, M. J.: A missing sink for gas-phase glyoxal in Mexico City: Formation of secondary organic aerosol, Geophys. Res. Lett., 34, L19807, doi:10.1029/2007GL030752, 2007. Volkamer, R., Ziemann, P. J., and Molina, M. J.: Secondary organic aerosol formation from acetylene (\chemC_2H_2): seed effect on SOA yields due to organic photochemistry in the aerosol aqueous phase, Atmos. Chem. Phys.\ Discuss., 8, 14841–14892, 2008. Whipple, E. B.: The structure of glyoxal in water, J. Am. Chem. Soc., 92, 7183–7186, doi:10.1021/ja00727a027, 1970. 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. S., 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 species in organic aerosols in anthropogenically-influenced Northern Hemisphere midlatitudes, Geophys.\ Res. Lett., 34, L13801, doi:10.1029/2007GL029979, 2007. Zhou, X. and Mopper, K.: Apparent partition coefficients of 15~carbonyl compounds between air and seawater and between air and freshwater, implications for air-sea exchange, Environ. Sci. Technol., 24, 1864–1869, doi:10.1021/es00082a013, 1990.