DOI QR코드

DOI QR Code

Review on the Analytical Methods and Ambient Concentrations of Organic Nitrogenous Compounds in the Atmosphere

대기 유기질소화합물의 분석방법 및 농도

  • Choi, Na Rae (Department of Environmental Science & Engineering, Ewha Womans University) ;
  • Kim, Yong Pyo (Department of Chemical Engineering & Materials Science, Ewha Womans University)
  • 최나래 (이화여자대학교 공과대학 환경공학과) ;
  • 김용표 (이화여자대학교 공과대학 화학신소재공학과)
  • Received : 2017.11.08
  • Accepted : 2018.01.09
  • Published : 2018.02.28

Abstract

The analytical methods and their ambient levels of organic nitrogenous compounds such as nitrosamines, nitramines (nitroamines), imines, amides and nitro-polycyclic aromatic hydrocarbons (nitro-PAHs) in the atmosphere are summarized and discussed. Sampling for the analysis of organic nitrogenous compounds was mostly conducted using high volume air sampler. The direct liquid extraction (DLE) using sonification and the pressurized liquid extraction (PLE) using the accelerated solvent extraction (ASE) have been frequently employed for the extraction of organic nitrogenous compounds in the atmospheric samples. After extraction, clean-up via filtration and the solid phase extraction (SPE) and concentrations using nitrogen and rotary evaporator have been generally conducted but in some studies the clean-up and concentration steps have been omitted to prevent the loss of analyte and improve the recovery rate of the analytical procedure. Instrumental analysis was mainly carried out using gas chromatography (GC) or the high performance liquid chromatography (HPLC) coupled with the single quadrupole mass spectrometer or tandem mass spectrometer in the electron ionization (EI), positive chemical ionization (PCI) and negative chemical ionization (NCI) mode and analysis sensitivity of nitrosamines and nitramines were higher in NCI mode. Desirable sampling and analysis methods for analyzing particulate organic nitrogenous compounds are suggested.

Keywords

References

  1. Akyuz, M., Ata, S. (2013) Seasonal variations of particle-associated nitrosamines by gas chromatography-mass spectrometry in the atmospheric environment of Zonguldak, Turkey, Environmental Science and Pollution Research, 20, 7398-7412. https://doi.org/10.1007/s11356-013-1758-y
  2. Alam, M.S., Keyte, I.J., Yin, J., Stark, C., Jones, A.M., Harrison, R.M. (2015) Diurnal variabililty of polycyclic aromatic compound (PAC) concentrations: Relationship with meteorological conditions and inferred sources, Atmospheric Environment, 122, 427-438. https://doi.org/10.1016/j.atmosenv.2015.09.050
  3. Albinet, A., Garziandia, E.L., Budzinski, H., Villenave, E. (2007) Polycyclic aromatic hydrocarbons (PAHs), nitrated PAHs and oxygenated PAHs in ambient air of the Marseilles area (South of France): Concentrations and sources, Science of the Total Environment, 384, 280-292. https://doi.org/10.1016/j.scitotenv.2007.04.028
  4. Alves, C.A., Vicente, A.M., Custodio, D., Cerqueira, M., Nunes, T., Pio, C., Lucarelli, F., Calzolai, G., Nava, S., Diapouli, E., Eleftheriadis, K., Querol, X., Bandowe, B.A.M. (2017) Polycyclic aromatic hydrocarbons and their derivatives (nitro-PAHs, oxygented PAHs, and azaarenes) in $PM_{2.5}$ from Southern European cities, Science of the Total Environment, 595, 494-504.
  5. Aragon, M., Marce, R.M., Borrull, F. (2013) Determination of N-nitrosamines and nicotine in air particulate matter samples by pressurised liquid extraction and gas chromatography-ion trap tandem mass spectrometry, Talanta, 115, 896-901. https://doi.org/10.1016/j.talanta.2013.07.010
  6. Bamford, H.A., Bezabeh, D.Z., Schantz, M.M., Wise, S.A., Baker, J.E. (2003) Determination and comparison of nitrated-polycyclic aromatic hydrocarbons measured in air and diesel particulate reference materials, Chemosphere, 50, 575-587. https://doi.org/10.1016/S0045-6535(02)00667-7
  7. Barrado, A.I., Garcia, S., Sevillano, M.L., Rodriguez, J.A., Barrado, E. (2013) Vapor-phase concentrations of PAHs and their derivatives determined in a large city: Correlations with their atmospheric aerosol concentrations, Chemosphere, 93, 1678-1684. https://doi.org/10.1016/j.chemosphere.2013.05.031
  8. Carter, W.P.L. (1994) Development of ozone reactivity scales for volatile orgnaic compounds, Journal of Air and Waste Management Association, 44, 881-899.
  9. Choi, N.R., Lee, S.P., Lee, J.Y., Jung, C.H., Kim, Y.P. (2016a) Speciation and source identification of organic compounds in $PM_{10}$ over Seoul, South Korea, Chemosphere, 144, 1589-1596. https://doi.org/10.1016/j.chemosphere.2015.10.041
  10. Choi, N.R., Kim, Y.P., Ji, W.H., Hwang, G.-S., Ahn, Y.G. (2016b) Identification and quantification of seven volatile n-nitrosamines in cosmetics using gas chromatography/chemical ionization-mass spectrometry coupled with head space-solid phase microextraction, Talanta, 148, 69-74. https://doi.org/10.1016/j.talanta.2015.10.045
  11. Chuesaard, T., Chetiyanukornkul, T., Kameda, T., Hayakawa, K., Toriba, A. (2014) Influence of biomass burning on the levels of atmospheric polycyclic aromatic hydrocarbons and their nitro derivatives in Chiang Mai, Thailand, Aerosol and Air Quality Research, 14, 1247-1257.
  12. Dye, C., Fjellsbo, L.M.B., Dusinska, M. (2011) Nitramine analysis procedures development and screening toxicity study, Norwegian Institute for Air Research, Scientific Report (OR 15/2011).
  13. Erupe, M.E., Price, D.J., Silva, P.J., Malloy, Q.G.J., Qi, L., Warren, B., Cocker Iii, D.R. (2008) Secondary organic aerosol formation from reaction of tertiary amines with nitrate radical, Atmosheric Chemistry and Physics Discussion, 8, 16585-16608. https://doi.org/10.5194/acpd-8-16585-2008
  14. European Community (EC) (1993) Directive 93/11/EEC. http://eur-lex.europa.eu/legal-content/en/ALL/?uri=CELEX:31993L0011. Accessed on 2018.02.02.
  15. Fajen, J.M., Carson, G.A., Roundehler, D.P., Vita, T.Y., Goff, U.E., Wolf, M.H., Edwards, G.S., Fine, D.H. (1979) N-nitrosamines in the rubber and tire industry, Science, 205, 1262-1264.
  16. Farren, N.J., Ramirez, N., Lee, J.D., Finessi, E., Lewis, A.C., Hamilton, J.F. (2015) Estimated exposure risks from carcinogenic nitrosamines in urban airborne particulate matter, Environmental science & technology, 49, 9648-9656. https://doi.org/10.1021/acs.est.5b01620
  17. Fine, D., Rounbehler, D.P., Belcher, N. (1976) N-Nitroso compounds: detection in ambient air, Science, 192, 1328-1330. https://doi.org/10.1126/science.192.4246.1328
  18. Fischer, C., Maurice, C., Lagerkvist, A. (1999) Gas emission from landfills. An overview of issues and research needs, Swedish Environmental Protection Agency, Stockholm, Sweden.
  19. Ge, X., Wexler, A.S., Clegg, S.L. (2011a) Atmospheric amines - Part I. A review, Atmospheric Environment, 45, 524-546. https://doi.org/10.1016/j.atmosenv.2010.10.012
  20. Ge, X., Wexler, A.S., Clegg, S.L. (2011b) Atmospheric amines-Part II. Thermodynamic properties and gas/particle partitioning, Atmospheric Environment, 45, 561-577. https://doi.org/10.1016/j.atmosenv.2010.10.013
  21. Grosjean, D. (1991) Atmospheric chemistry of toxic contaminants. 6. Nitrosamines: dialkyl nitrosamines and nitrosomorpholine, Journal of the Air & Waste Management Association, 41, 306-311. https://doi.org/10.1080/10473289.1991.10466847
  22. Hernandez, B.S.V., Alvarez, V.M., Talavera, E.S., Munoz, O.A., Tovar, M.A.M., Pietrini, R.V., Ruiz, A.D.V. (2010) Temporal variation of nitro-polycyclic aromatic hydrocarbons in $PM_{10}$ and $PM_{2.5}$ collected in Northern Mexico City, Science of the Total Environment, 408, 5429-5438. https://doi.org/10.1016/j.scitotenv.2010.07.065
  23. Hong, Y., Kim, K.H., Sang, B.-I., Kim, H. (2017) Simple quantification method for N-nitrosamines in atmospheric particulates based on facile pretreatment and GC-MS/MS, Environmental Pollution, 226, 324-334.
  24. Hutchings, J.W., Ervens, B., Straub, D., Herckes, P. (2010) N-nitrosodimethylamine occurrence, formation and cycling in clouds and fogs, Environmental science & technology, 44, 8128-8133. https://doi.org/10.1021/es101698q
  25. International Agency for Research on Cancer (IARC) (2008) IARC monographs on the evaluation of carcinogenic risks to human, IARC. http://monographs. iarc.fr/ENG/Classification/. Accessed on 2017.09.13.
  26. Kim, S., Lee, G., Kim, K.-R. (2001) Measurements of Peroxyacetyl Nitrates at an Urban and a Rural Site in Korea, Journal of Korean Society for Atmospheric Environment, 17, 157-167. (in Korean with English abstract)
  27. Lafontaine, S., Schrlau, J., Butler, J., Jia, Y., Harper, B., Harris, S., Bramer, L.M., Waters, K.M., Hardig, A., Simonich, S.L.M. (2015) Relative influence of tanspacific and regional atmospheric transport of PAHs in the Pacific Northwest, U.S., Environmental Science and Technology, 49, 13807-13816. https://doi.org/10.1021/acs.est.5b00800
  28. Lee, D.Y., Wexler, A.S. (2013) Atmospheirc amines-Part III: Photochemistry and toxicity, Atmospheric Environment, 71, 95-103. https://doi.org/10.1016/j.atmosenv.2013.01.058
  29. Lewtas, J., Nishioka, M., Peterson, B. (1990) Bioassay directed fractionation of the organic extract of SRM 1649 urban air particulate and ambient matter, International Journal of Environmental Analytical Chemistry, 39, 245-256. https://doi.org/10.1080/03067319008032068
  30. Li, W., Shen, G., Yuan, C., Wang, C., Shen, H., Jiang, H., Zhang, Y., Chen, Y., Su, S., Lin, N., Tao, S. (2016) The gas/particle partitioning of nitro- and oxy-polycyclic aromatic hydrocarbons in the atmsophere of northern China, Atmospheric Research, 172-173, 66-73. https://doi.org/10.1016/j.atmosres.2015.12.008
  31. Lindahl, S., Gundersen, C.B., Lundanes, E. (2014) A review of available analytical technologies for qualitative and quantitative determination of nitramines, Royal Society of Chemistry, 16, 1825-1840.
  32. Lindley, C.R.C., Calvert, J.C., Shaw, J.H. (1979) Rate studies of the reactions of the ($CH_3$)N radical with $O_2$, NO and $NO_2$, Chemical Physics Letters, 67, 57-62. https://doi.org/10.1016/0009-2614(79)87105-5
  33. Maguta, M.M. (2014) Environmental impact of amines emitted to the atmosphere, Disserattion for the degree of Philosophiae Doctor (PhD), Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Oslo, Norway (January, 2014).
  34. Masuda, M., Mower, H.F., Brigitte, P., Celan, I., Friesen, M.D., Nishino, H., Ohshima, H. (2000) Formation of n-nitrosamines and n-nitramines by the reaction of secondary amines with peroxynitrite and other reactive nitrogen species: Comparison with nitrotyrosine formation, Chemical Research in Toxicology, 13, 301-308. https://doi.org/10.1021/tx990120o
  35. Ministry of Food and Drug Safety (MFDS) (2013) Criteria for the equipment, containers and package (2013-246). Korea Ministry of Food and Drug Safety. (MFDS) http://www.lawnb.com/data/Focuslawdata/lawnbfocusB00029494540.pdf. Accessed on 2017.06.23 (Written in Korean).
  36. National Toxicology Program (NTP) (2016) 14th Report on Carcinogens (RoC), National Toxicology Program (NTP), US Department of Health and Human Services. https://ntp.niehs.nih.gov/pubhealth/roc/index-1.html. Accessed on 2017.07.20.
  37. Nerin, C., Aznar, M., Carrizo, D. (2016) Food contamination during food process, Trends in Food Science & Technology, 48, 63-68. https://doi.org/10.1016/j.tifs.2015.12.004
  38. Nielsen, C., D'Anna, B., Bossi, R., Bunkan, A.J.C., Dithmer, L., Glasius, M., Hallquist, M., Hansen, A.M.K., Luts, A., Salo, K., Maguta, M.M., Nguyen, Q., Mikoviny, T., Mueller, M., Skov, H., Sarrasin, E., Stenstrom, Y., Tang, Y., Westerlund, J., Wisthaler, A. (2012) Atmospheric Degradation of Amines (ADA)-Summary report from atmospheric chemistry studies of amines, nitrosaimes, nitramines and amides, CLIMIT prject no. 208122, University of Oslo, Norway.
  39. Nielsen, C.J., D'Anna, B., Dye, C., Graus, M., Karl, M., King, S., Maguto, M.M., Mueller, M., Schmidbauer, N., Stenstrom, Y., Wisthaler, A., Pedersen, S. (2011) Atmospheric chemistry of 2-aminoethanol (MEA), Energy Porcedia, 4, 2245-2252. https://doi.org/10.1016/j.egypro.2011.02.113
  40. Park, J., Lee, S.B., Kim, M.J., Kim, J.C., Lee, S.J. (2010) Analysis of PAHs and Nitro-PAHs in stationary emissions, Proceeding of the 50th Meeting of Korean Society for Atmospheric Environment, 427-428.
  41. Pitts, J.N., Grosjean, D., Cauwenberghe, K.V., Schmid, J.P., Dennis, R.F. (1976) Photooxidation of aliphatic amines under simulated atmospheric conditions: Formation o fnitrosamines, nitramines, amides, and photochemical oxidant, Environmental Science and Technology, 12, 946-953.
  42. Pliss, G.B., Zabezhinski, M.A., Petrov, A.S., Khudoley, V.V. (1982) Peculiarities of N-nitramines carcinogenic action, Arch Geschwulstjbrsch, 52, 629-634.
  43. Ramirez, N., Ozel, M.Z., Lezis, A., Marce, R.M., Borrull, F., Hamilton, J.F. (2012) Determination of nicotine and n-nitrosamines in house dust by pressurized liquid extraction and comprehensive gas chromatography-nitrogen chemiluminiscence detection, Journal of Chromatography A, 1219, 180-187. https://doi.org/10.1016/j.chroma.2011.11.017
  44. Ringuet, J., Albinet, A., Garziandia, E.L., Budzinski, H., Villenave, E. (2012) Diurnal/nocturnal concnetrations and sources of particulate-bound PAHs, OPAHs and NPAHs at traffic and suburban sites in the region of Paris (France), Sience of the Total Environment, 437, 297-305. https://doi.org/10.1016/j.scitotenv.2012.07.072
  45. Scherf, H.R., Frei, E., Wiessler, M. (1989) Carcinogenic properties of N-nitrodimethylamine and N-nitromethylamine in the rat, Carcinogenesis, 10, 1977-1981. https://doi.org/10.1093/carcin/10.11.1977
  46. Sen, N., Seaman, S., Miles, W. (1976) Dimethylnitrosamine and nitrosopyrrolidine in fumes produced during the frying of bacon, Food and Cosmetics Toxicology, 14, 167-170. https://doi.org/10.1016/S0015-6264(76)80417-8
  47. Shapley, D. (1976) Nitrosamines: scientists on the trail of prime suspect in urban cancer, Science, 191, 268-270. https://doi.org/10.1126/science.191.4224.268
  48. Simoneit, B.R.T., Rushdi, A.I., bin Abas, M.R., Didyk, B.M. (2002) Alkyl amides and nitriles as novel tracers for biomass burning, Environmental Science & Technology, 37, 16-21.
  49. Tang, N., Hattori, T., Taga, R., Igarashi, K., Yang, X., Tamura, K., Kakimoto, H., Mishukov, V.F., Toriba, A., Kizu, R., Hayakawa, K. (2005) Polycyclic aromatic hydrocarbons and nitropolycyclic aromatic hydrocarbons in urban air poarticulates and their relationship to emission sources in the Pan-Japan Sea countries, Atmopsheirc Environment, 39, 5817-5826. https://doi.org/10.1016/j.atmosenv.2005.06.018
  50. Tuazon, E.C., Atkinson, R., Aschmann, S.M., Arey, J. (1994) Kinetics and products of the gas-phase reactions of $O_3$ with amines and related-compounds, Research on Chemical Intermediates, 20, 303-320. https://doi.org/10.1163/156856794X00351
  51. U.S. Environmental Protection Agency (US EPA) (1972) Clean air act, United States Environmental Protection Agency (US EPA), https://www.epa.gov/laws-regulations/summary-clean-water-act. Accessed on 2017.06.23.
  52. U.S. Environmental Protection Agency (US EPA) (1976a) Resource Conservation and Recovery Act, United States Environmental Protection Agency (US EPA), https://www.epa.gov/laws-regulations/summary-resource-conservation-and-recovery-act. Accessed on 2017.06.23.
  53. U.S. Environmental Protection Agency (US EPA) (1976b) Toxic Substances Control Act. United States Environmental Protection Agency (US EPA), https://www.epa.gov/laws-regulations/summary-toxicsubstances-control-act. Accessed on 2017.06.23.
  54. U.S. Environmental Protection Agency (US EPA) (1980) Comprehensive Environmental Response, Compensation, and Liability Act, United States Environmental Protection Agency (US EPA), https://www.epa.gov/laws-regulations/summary-comprehensive-environmental-response-compensation-and-liability-act. Accessed on 2017.06.23.
  55. U.S. Food and Drug Administration (US FDA) (1984) CPG Sec. 500.450 Volatile N-Nitrosamines in Rubber Baby Bottle Nipples, United States Food and Drug Administration (US FDA), https://www.fda.gov/ICECI/ComplianceManuals/CompliancePolicyGuidanceManual/ucm074418.htm. Accessed on 2017.06.23.
  56. World Health Organization (WHO) (2008) N-Nitrosodimethylamine in Drinking-water. World Health Organization (WHO). http://www.who.int/water_sanitation_health/dwq/chemicals/ndma_2add_feb2008.pdf. Accessed on 2017.06.23.
  57. Yu, M.S., Kim, C., Yang, S.B., Han, J.S. (2006) Measurement of Atmospheric Concentrations of Aliphatic Amine Compounds by GC/FTD, Korean Society of Odor Research and Engineering, 5, 237-244 (in Korean with English abstract).