Formation of nitrogen-containing oligomers by methylglyoxal and amines in simulated evaporating cloud droplets

Environmental Science and Technology

Volumn 45, Issue 3, 2011, Pages 984-991

  De Haan, David O ^a,b   Hawkins, Lelia N ^a   Kononenko, Julia A ^a   Turley, Jacob J ^a   Corrigan, Ashley L ^a,c   Tolbert, Margaret A ^b   Jimenez, Jose L ^b  

^a UNIVERSITY OF SAN DIEGO   (United States)

^b UNIVERSITY OF COLORADO   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AEROSOL MASS SPECTROMETRY; AEROSOL PARTICLES; AMMONIUM SULFATE; AQUEOUS AEROSOLS; BIOMASS-BURNING; BULK SOLUTIONS; CLOUD DROPLETS; DIIMINES; DRYING DROPLETS; METHYLGLYOXAL; METHYLIMIDAZOLE; SCANNING MOBILITY PARTICLE SIZINGS; TIME-SCALES;

AMINATION; AMINO ACIDS; AMMONIUM COMPOUNDS; DROP FORMATION; ELECTROSPRAY IONIZATION; MAGNETIC RESONANCE; MASS SPECTROMETRY; NITROGEN; OLIGOMERS;

ATMOSPHERIC AEROSOLS;

AMINE; DIMETHYLIMIDAZOLE DERIVATIVE; IMIDAZOLE; IMINE; METHYLGLYOXAL; NITROGEN; OLIGOMER; UNCLASSIFIED DRUG;

ABSORPTION; AEROSOL; ALDEHYDE; AMINO ACID; AQUEOUS SOLUTION; CLOUD; CONCENTRATION (COMPOSITION); DROPLET; EVAPORATION; IONIZATION; MASS SPECTROMETRY; MOBILITY; NITROGEN; NUCLEAR MAGNETIC RESONANCE; NUMERICAL MODEL; PARTICLE SIZE; POLYMER;

AEROSOL; ARTICLE; BIOMASS; CHEMICAL REACTION; CLOUD; ELECTROSPRAY; EVAPORATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PARTICLE SIZE; ROOM TEMPERATURE;

AEROSOLS; AIR POLLUTANTS; AMINES; AMINO ACIDS; AMMONIUM SULFATE; ATMOSPHERE; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; METHYLAMINES; PARTICLE SIZE; PYRUVALDEHYDE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEAM; VOLATILIZATION;

EID: 79851473035     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es102933x     Document Type: Article

References (51)

1. Bahadur, R. ; Russell, L. M. ; Prather, K. Composition and morphology of individual combustion, biomass burning, and secondary organic particle types obtained using urban and coastal ATOFMS and STXM-NEXAFS measurements. Aerosol Sci. Technol. 2010, 44 (7), 551-562.
2. Murphy, D. M. ; Cziczo, D. J. ; Froyd, K. D. ; Hudson, P. K. ; Matthew, B. M. ; Middlebrook, A. M. ; Peltier, R. E. ; Sullivan, A. ; Thomson, D. S. ; Weber, R. J. Single-particle mass spectrometry of tropospheric aerosol particles. J. Geophys. Res. 2006, 111, D23S32.
3. Ramanathan, V. ; Li, F. ; Ramana, M. V. ; Praveen, P. S. ; Kim, D. ; Corrigan, C. E. ; Nguyen, H. ; Stone, E. A. ; Schauer, J. J. ; Carmichael, G. R. ; et al. Atmospheric brown clouds: hemispherical and regional variations in long-range transport, absorption, and radiative forcing. J. Geophys. Res. 2007, 112 (D12), D22S21.
4. Freedman, M. A. ; Hasenkopf, C. A. ; Beaver, M. R. ; Tolbert, M. A. Optical properties of internally mixed aerosol particles composed of dicarboxylic acids and ammonium sulfate. J. Phys. Chem. 2009, 113 (48), 13584-13592.
5. Santarpin, J. L. ; Li, R. ; Collins, D. R. Direct measurement of the hydration state of ambient aerosol populations. J. Geophys. Res. 2004, 109, D18209.
6. Moore, R. H. ; Raymond, T. M. HTDMA analysis of multicom- ponent dicarboxylic acid aerosols with comparison to UNIFAC and ZSR. J. Geophys. Res. 2008, 113, D04206.
7. 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. et al., Evolution of organic aerosols in the atmosphere. Science 2009, 326, 1525-1529.
8. Wang, X. ; Gao, S. ; Yang, X. ; Chen, H. ; Chen, J. ; Zhuang, G. ; Surratt, J. D. ; Chan, M. N. ; Seinfeld, J. H. Evidence for high molecular weight nitrogen-containing organic salts in urban aerosols. Environ. Sci. Technol. 2010, 44 (12), 4441-4446.
9. Laskin, A. ; Smith, J. S. ; Laskin, J. Molecular characterization of nitrogen-containing organic compounds in biomass burning aerosols using high-resolution mass spectrometry. Environ. Sci. Technol. 2009, 43 (10), 3764-3771.
10. Fu, T.-M. ; Jacob, D. J. ; Wittrock, F. ; Burrows, J. P. ; Vrekoussis, M. ; Henze, D. K. Global budgets of atmospheric glyoxal and methylglyoxal, and implications for formation of secondary organic aerosols. J. Geophys. Res. 2008, 113, D15303.
11. Stavrakou, T. ; Muller, J.-F. ; De Smedt, I. ; Van Roozendael, M. ; Kanakidou, M. ; Vrekoussis, M. ; Wittrock, F. ; Richter, A. ; Burrows, J. P. The continental source of glyoxal estimated by the synergistic use of spaceborne measurements and inverse modelling. Atmos. Chem. Phys. 2009, 9, 8431-8446.
12. Volkamer, R. ; San Martini, F. ; Molina, L. T. ; Salcedo, D. ; Jimenez, J. L. ; Molina, M. J. A missing sink for gas-phase glyoxal in Mexico City: formation of secondary organic aerosol. Geophys. Res. Lett. 2007, 34, L19807.
13. Liggio, J. ; Li, S.-M. ; McLaren, R. Reactive uptake of glyoxal by particulate matter. J. Geophys. Res. 2005, 110, D10304.
14. 2): seed effect on SOA yields due to organic photochemistry in the aerosol aqueous phase. Atmos. Chem. Phys. 2009, 9, 1907-1928.
15. Carlton, A. G. ; Turpin, B. J. ; Altieri, K. E. ; Seitzinger, S. ; Reff, A. ; Lim, H.-J. ; Ervens, B. Atmospheric oxalic acid and SOA production from glyoxal: results of aqueous photooxidation experiments. Atmos. Environ. 2007, 41 (35), 7588-7602. (Pubitemid 350064570)
16. 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. Atmos. Chem. Phys. 2009, 9, 3331-3345.
17. Shapiro, E. L. ; Szprengiel, J. ; Sareen, N. ; Jen, C. N. ; Giordano, M. R. ; McNeill, V. F. Light-absorbing secondary organic material formed by glyoxal in aqueous aerosol mimics. Atmos. Chem. Phys. 2009, 9, 2289-2300.
18. +). J. Phys. Chem. 2009, 113 (1), 231-237.
19. De Haan, D. O. ; Corrigan, A. L. ; Smith, K. W. ; Stroik, D. R. ; Turley, J. T. ; Lee, F. E. ; Tolbert, M. A. ; Jimenez, J. L. ; Cordova, K. E. ; Ferrell, G. R. Secondary organic aerosol-forming reactions of glyoxal with amino acids. Environ. Sci. Technol. 2009, 43 (8), 2818-2824.
20. De Haan, D. O. ; Tolbert, M. A. ; Jimenez, J. L. Atmospheric condensed-phase reactions of glyoxal with methylamine. Geophys. Res. Lett. 2009, 36, L11819.
21. Ervens, B. ; Volkamer, R. Glyoxal processing by aerosol multiphase chemistry: towards a kinetic modeling framework of secondary organic aerosol formation in aqueous particles. Atmos. Chem. Phys. 2010, 10, 8219-8244.
22. Matsunaga, S. ; Mochida, M. ; 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. 2004, 109, D04302.
23. Zhao, J. ; Levitt, N. P. ; Zhang, R. ; Chen, J. Heterogeneous reactions of methylglyoxal in acidic media: implications for secondary organic aerosol formation. Environ. Sci. Technol. 2006, 40 (24), 7682-7687. (Pubitemid 46012562)
24. Kroll, J. H. ; Ng, N. L. ; Murphy, S. M. ; Varutbangkul, V. ; Flagan, R. C. ; Seinfeld, J. H. Chamber studies of secondary organic aerosol growth by reactive uptake of simple carbonyl compounds. J. Geophys. Res. 2005, 110, D23207.
25. Ervens, B. ; Feingold, G. ; Frost, G. J. ; Kreidenweis, S. M. A modeling study of aqueous production of dicarboxylic acids: 1. Chemical pathways and speciated organic mass production. J Geophys. Res. 2004, 109, D15205.
26. Altieri, K. E. ; Seitzinger, S. P. ; Carlton, A. G. ; Turpin, B. J. ; Klein, G. C. ; 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. 2008, 42, 1476-1490.
27. De Haan, D. O. ; Corrigan, A. L. ; Tolbert, M. A. ; Jimenez, J. L. ; Wood, S. E. ; Turley, J. J. Secondary organic aerosol formation by self-reactions of methylglyoxal and glyoxal in evaporating droplets. Environ. Sci. Technol. 2009, 43 (21), 8184-8190.
28. Sareen, N. ; Schwier, A. N. ; Shapiro, E. L. ; Mitroo, D. ; McNeill, V. F. Secondary organic material formed by methylglyoxal in aqueous aerosol mimics. Atmos. Chem. Phys. 2010, 10, 997-1016.
29. Shumaev, K. B. ; Gubkina, S. A. ; Kumskova, E. M. ; Shepelkova, G. S. ; Ruuge, E. K. ; Lankin, V. Z. Superoxide formation as a result of interaction of L-lysine with dicarbonyl compounds and its possible mechanism. Biochem. (Moscow) 2009, 74 (4), 461-466.
30. DeCarlo, P. F. ; Kimmel, J. R. ; Trimborn, A. ; Northway, M. J. ; Jayne, J. T. ; Aiken, A. C. ; Gonin, M. ; Fuhrer, K. ; Horvath, T. ; Docherty, K. S. et al. , Field-deployable, high-resolution, time- of-flight aerosol mass spectrometer. Anal. Chem. 2006, 78 (24), 8281-8289. (Pubitemid 44927604)
31. 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. et al. , Chemical and microphysical characterization of ambient aerosols with the Aerodyne aerosol mass spectrometer. Mass Spectrom. Rev. 2007, 26 (2), 185-222. (Pubitemid 46491711)
32. DeCarlo, P. ; Slowik, J. G. ; Worsnop, D. R. ; Davidovits, P. ; Jimenez, J. L. Particle morphology and density characterization by combined mobility and aerodynamic diameter measurements. Part 1: Theory. Aerosol Sci. Tecnol. 2004, 38, 1185-1205. (Pubitemid 40075872)
33. Aiken, A. C. ; DeCarlo, P. F. ; Jimenez, J. L. Elemental analysis of organic species with electron ionization of high-resolution mass spectrometry. Anal. Chem. 2007, 79, 8350-8358. (Pubitemid 350060037)
34. Tolocka, M. P. ; Jang, M. ; Ginter, J. M. ; Cox, F. J. ; Kamens, R. M. ; Johnston, M. V. Formation of oligomers in secondary organic aerosol. Environ. Sci. Technol. 2004, 38 (5), 1428-1434. (Pubitemid 38270687)
35. Altieri, K. E. ; Carlton, A. G. ; Lim, H.-J. ; Turpin, B. J. ; Seitzinger, S. P. Evidence for oligomer formation in clouds: reactions of isoprene oxidation products. Environ. Sci. Technol. 2006, 40 (16), 4956-4960.
36. Igawa, M. ; Munger, J. W. ; Hoffmann, M. R. Analysis of aldehydes in cloud- and fogwater samples by HPLC with a postcolumn reaction detector. Environ. Sci. Technol. 1989, 23 (5), 556-561. (Pubitemid 19120741)
37. Munger, J. W. ;Jacob, D. J. ;Daube, B. C. ;Horowitz, L. W. ;Keene, W. C. ; Heikes, B. G. Formaldehyde, glyoxal, and methylglyoxal in air and cloudwater at a rural mountain site in central Virginia. J. Geophys. Res. 1995, 100 (D5), 9325-9333. (Pubitemid 26436858)
38. van Pinxteren, D. ; Plewka, A. ; Hofmann, D. ; Muller, K. ; Kram- berger, H. ; Svrcina, B. ; Bachmann, K. ; Jaeschke, W. ; Mertes, S. ; Collett, J. L. , Jr. ; et al. Schmucke hill cap cloud and valley stations aerosol characterisation during FEBUKO (II): organic compounds. Atmos. Environ. 2005, 39, 4305-4320.
39. Matsumoto, K. ; Kawai, S. ; Igawa, M. Dominant factors controlling concentrations of aldehydes in rain, fog, dew water, and in the gas phase. Atmos. Environ. 2005, 39, 7321-7329.
40. Mopp er, K. ; Zika, R. G. Free amino acids in marine rains: evidence for oxidation and potential role in nitrogen cycling. Nature 1987, 325, 246-249. (Pubitemid 17279285)
41. 2.5) and fog waters from Northern California. Atmos. Environ. 2003, 37, 2247-2258. (Pubitemid 36428945)
42. Krizner, H. E. ; De Haan, D. O. ; Kua, J. Thermodynamics and kinetics of methylglyoxal dimer formation: A computational study. J. Phys. Chem. 2009, 113 (25), 6994-7001.
43. Allan, J. D. ; Jimenez, J. L. ; Williams, P. I. ; Alfarra, M. R. ; Bower, K. N. ; Jayne, J. T. ; Coe, H. ; Worsnop, D. R. Quantitative sampling using an Aerodyne aerosol mass spectrometer 1. Techniques of data interpretation and error analysis. J. Geophys. Res. 2003, 108 (D3), 4090.
44. 2). J. Geophys. Res. 2003, 108 (D10), 4318.
45. Chan, M. N. ; Choi, M. Y. ; Ng, N. L. ; Chan, C. K. Hygroscopicity of water-soluble organic compounds in atmospheric aerosols: amino acids and biomass derived organic species. Environ. Sci. Technol. 2005, 39 (6), 1555-1562. (Pubitemid 40387709)
46. Biskos, G. ; Paulsen, D. ; Russell, L. M. ; Buseck, P. R. ; Martin, S. T. Prompt deliquescence and efflorescence of aerosol nanoparticles. Atmos. Chem. Phys. 2006, 6, 4633-4642. (Pubitemid 44600398)
47. Zelenyuk, A. ; Imre, D. ; Cuadra-Rodriguez, L. A. Evaporation of water from particles in the aerodynamic lens inlet: An experimental study. Anal. Chem. 2006, 78 (19), 6942-6947. (Pubitemid 44522547)
48. Weast, R. C. CRC Handbook of Chemistry and Physics; The Chemical Rubber Publishing Co. : Cleveland, OH, 1972.
49. Denkenberger, K. A. ; Moffet, R. C. ; Holecek, J. C. ; Rebotier, T. P. ; Prather, K. A. Real-time, single-particle measurements of oligomers in aged ambient aerosol particles. Environ. Sci. Technol. 2007, 41 (15), 5439-5446. (Pubitemid 47221767)
50. Ma, Y. ; Hays, M. D. Thermal extraction-two-dimensional gas chromatography-mass spectrometry with heart-cutting for nitrogen heterocyclics in biomass burning aerosols. J. Chro- matogr. , Sect. A 2008, 1200, 228-234.
51. Namiki, M. Chemistry of Maillard reactions: recent studies on the browning reaction mechanism and the development of antioxidants and mutagens. Adv. Food Res. 1988, 32, 115-185.