Secondary organic aerosol formation from primary aliphatic amines with NO3 radical
10.5194/acp-9-2051-2009
Crossref journal-article
Copernicus GmbH
Atmospheric Chemistry and Physics (3145)
Abstract

Abstract. Primary aliphatic amines are an important class of nitrogen containing compounds emitted from automobiles, waste treatment facilities and agricultural animal operations. A series of experiments conducted at the UC-Riverside/CE-CERT Environmental Chamber is presented in which oxidation of methylamine, ethylamine, propylamine, and butylamine with O3 and NO3 have been investigated. Very little aerosol formation is observed in the presence of O3 only. However, after addition of NO, and by extension NO3, large aerosol mass yields (~44% for butylamine) are seen. Aerosol generated was determined to be organic in nature due to the small fraction of NO and NO2 in the total signal (<1% for all amines tested) as detected by an aerosol mass spectrometer (AMS). We propose a reaction mechanism between carbonyl containing species and the parent amine leading to formation of particulate imine products. These findings can have significant impacts on rural communities with elevated nighttime PM loadings, when significant levels of NO3 exist.

Bibliography

Malloy, Q. G. J., Warren, B., Cocker III, D. R., Erupe, M. E., & Silva, P. J. (2009). Secondary organic aerosol formation from primary aliphatic amines with NO3 radical. Atmospheric Chemistry and Physics, 9(6), 2051–2060.

Authors 6
  1. Q. G. J. Malloy (first)
  2. (additional)
  3. B. Warren (additional)
  4. D. R. Cocker III (additional)
  5. M. E. Erupe (additional)
  6. P. J. Silva (additional)
References 29 Referenced 87
  1. 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, 2001. (10.1021/es0015444)
  2. Bailey, D., Cativiela, J. P., Descary, B., Grantz, D., Hamilton, K. D., Martin, P. E., Meyer, D., Mullinax, D., Simunovic, C. A., Sweet, J., Warner, D., and Watson, J.: Dairy Emissions Factors for Volatile Organic Compounds, San Joaquin Valley Air Pollution Control District, Fresno, CA, 2005.
  3. Barsanti, K. C., McMurry, P. H., and Smith, J. N.: The potential contribution of organic salts to new particle growth, Atmos. Chem. Phys. Discuss., 8, 20723–20748, 2008. (10.5194/acpd-8-20723-2008)
  4. Beddows, D. C. S., Donovan, R. J., Harrison, R. M., Heal, M. R., Kinnersley, R. P., King, M. D., Nicholson, D. H., and Thompson, K. C.: Correlations in the chemical composition of rural background atmospheric aerosol in the UK determined in real time using time-of-flight mass spectrometry, J. Environ. Monitor., 6, 124–133, 2004. (10.1039/b311209h)
  5. Bowman, F. M., Odum, J. R., Seinfeld, J. H., and Pandis, S. N.: Mathematical model for gas-particle partitioning of secondary organic aerosols, Atmos. Environ., 31, 3921–3931, 1997. (10.1016/S1352-2310(97)00245-8)
  6. Carter, W. P. L., Cocker, D. R., Fitz, D. R., Malkina, I. L., Bumiller, K., Sauer, C. G., Pisano, J. T., Bufalino, C., and Song, C.: A new environmental chamber for evaluation of gas-phase chemical mechanisms and secondary aerosol formation, Atmos. Environ., 39, 7768–7788, 2005. (10.1016/j.atmosenv.2005.08.040)
  7. Cheung, A., Struble, E., He, J. Y., Yang, C., Wang, E., Thurston, D. E., and Liu, P.: Direct liquid chromatography determination of the reactive imine SJG-136 (NSC 694501), J. Chromatogr. B, 822, 10–20, 2005. (10.1016/j.jchromb.2005.04.027)
  8. Cocivera, M., Fyfe, C. A., Effio, A., Vaish, S. P., and Chen, H. E.: Flow Nuclear Magnetic-Resonance Study of Dehydration of Tetrahedral Intermediate Resulting from Addition of Hydroxylamine to Acetaldehyde, J. Am. Chem. Soc., 98, 1573–1578, 1976. (10.1021/ja00422a049)
  9. 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., Worsnop, D. R., and Jimenez, J. L.: Field-deployable, high-resolution, time-of-flight aerosol mass spectrometer, Anal. Chem., 78, 8281–8289, 2006. (10.1021/ac061249n)
  10. Finlayson-Pitts, B. and Pitts, J. N.: Chemistry of the Upper and Lower Atmosphere, Academic Press, 2000.
  11. Glagolenko, S. and Phares, D. J.: Single-particle analysis of ultrafine aerosol in College Station, Texas, J. Geophys. Res.-Atmos., 109, D18205, https://doi.org/10.1029/2004JD004621, 2004. (10.1029/2004JD004621)
  12. Haddrell, A. E. and Agnes, G. R.: A class of heterogeneous/multiphase organic reactions studied on droplets/particles levitated in a laboratory environment: aldehyde plus 1,8-diaminonaphthalene equals imine, Atmos. Environ., 38, 545–556, 2004. (10.1016/j.atmosenv.2003.10.011)
  13. Jencks, W. P.: Studies on the Mechanism of Oxime and Semicarbazone Formation, J. Am. Chem. Soc., 81, 475–481, 1959. (10.1021/ja01511a053)
  14. Lalevee, J., Allonas, X., and Fouassier, J. P.: N-H and alpha(C-H) bond dissociation enthalpies of aliphatic amines, J. Am. Chem. Soc., 124, 9613–9621, 2002. (10.1021/ja0204168)
  15. Manahan, S. E.: Environmental Chemistry, 4th Ed., Lewis, 1990.
  16. Murphy, D. M. and Thomson, D. S.: Chemical composition of single aerosol particles at Idaho Hill: Positive ion measurements, J. Geophys. Res.-Atmos., 102, 6341–6352, 1997 (10.1029/96JD00858)
  17. Murphy, S. M., Sorooshian, A., Kroll, J. H., Ng, N. L., Chhabra, P., Tong, C., Surratt, J. D., Knipping, E., Flagan, R. C., and Seinfeld, J. H.: Secondary aerosol formation from atmospheric reactions of aliphatic amines, Atmos. Chem. Phys., 7, 2313–2337, 2007. (10.5194/acp-7-2313-2007)
  18. Myrdal, P. B. and Yalkowsky, S. H.: Estimating pure component vapor pressures of complex organic molecules, Ind. Eng. Chem. Res., 36, 2494–2499, 1997. (10.1021/ie950242l)
  19. 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. (10.1021/es950943+)
  20. Pedersen, E. J., Urbansky, E. T., Marinas, B. J., and Margerum, D. W.: Formation of cyanogen chloride from the reaction of monochloramine with formaldehyde, Environ. Sci. Technol., 33, 4239–4249, 1999. (10.1021/es990153q)
  21. Pitts, J. N., Grosjean, D., Vancauwenberghe, K., Schmid, J. P., and Fitz, D. R.: Photo-Oxidation of Aliphatic-Amines under Simulated Atmospheric Conditions – Formation of Nitrosamines, Nitramines, Amides, and Photo-Chemical Oxidant, Environ. Sci. Technol., 12, 946–953, 1978. (10.1021/es60144a009)
  22. Schade, G. W. and Crutzen, P. J.: Emission of Aliphatic-Amines from Animal Husbandry and Their Reactions – Potential Source of N2O and HCN, J. Atmos. Chem., 22, 319–346, 1995. (10.1007/BF00696641)
  23. Seinfeld, J. H. and Pandis, S. N.: Atmospheric Chemistry and Physics: From Air pollution to Climate Change, John Wiley and Sons, Inc., 1998. (10.1063/1.882420)
  24. Silva, P., Erupe, M., Malloy, Q. G. J., Li, Q., Warren, B., Price, D., Elias, J., 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, 2008. (10.1021/es703016v)
  25. Smith, J. N., Dunn, M. J., VanReken, T. M., Iida, K., Stolzenberg, M. R., McMurry, P. H., and Huey, L. G.: Chemical Composition of Atmospheric Nanoparticles Formed from Nucleation in Tecamac, Mexico: Evidence for an Important Role of Organic Species in Nanoparticle Growth, Geophys. Res. Lett., 35, L04808, https://doi.org/10.1029/2007GL032523, 2008. (10.1029/2007GL032523)
  26. Tan, P. V., Evans, G. J., Tsai, J., Owega, S., Fila, M. S., and Malpica, O.: On-line analysis of urban particulate matter focusing on elevated wintertime aerosol concentrations, Environ. Sci. Technol., 36, 3512–3518, 2002. (10.1021/es011448i)
  27. Wang, S. C. and Flagan, R. C.: Scanning Electrical Mobility Spectrometer, Aerosol Sci. Tech., 13, 230–240, 1990. (10.1080/02786829008959441)
  28. Westerholm, R., Li, H., and Almen, J.: Estimation of Aliphatic Amine Emissions in Automobile Exhausts, Chemosphere, 27, 1381–1384, 1993. (10.1016/0045-6535(93)90231-S)
  29. Zahardis, J., Geddes, S., and Petrucci, G. A.: The ozonolysis of primary aliphatic amines in fine particles, Atmos. Chem. Phys., 8, 1181–1194, 2008. (10.5194/acp-8-1181-2008)
Dates
Type When
Created 15 years, 4 months ago (April 29, 2010, 10:10 a.m.)
Deposited 6 months, 3 weeks ago (Feb. 15, 2025, 11:48 p.m.)
Indexed 3 months ago (June 6, 2025, 1:29 p.m.)
Issued 16 years, 5 months ago (March 23, 2009)
Published 16 years, 5 months ago (March 23, 2009)
Published Online 16 years, 5 months ago (March 23, 2009)
Funders 0

None

@article{Malloy_2009, title={Secondary organic aerosol formation from primary aliphatic amines with NO3 radical}, volume={9}, ISSN={1680-7324}, url={http://dx.doi.org/10.5194/acp-9-2051-2009}, DOI={10.5194/acp-9-2051-2009}, number={6}, journal={Atmospheric Chemistry and Physics}, publisher={Copernicus GmbH}, author={Malloy, Q. G. J. and Warren, B. and Cocker III, D. R. and Erupe, M. E. and Silva, P. J.}, year={2009}, month=mar, pages={2051–2060} }