Secondary formation of nitrated phenols: Insights from observations during the Uintah Basin Winter Ozone Study (UBWOS) 2014

Atmospheric Chemistry and Physics

Volumn 16, Issue 4, 2016, Pages 2139-2153

  Yuan, Bin ^a,b   Liggio, John ^c   Wentzell, Jeremy ^c   Li, Shao Meng ^c   Stark, Harald ^b,d   Roberts, James M ^a   Gilman, Jessica ^a,b   Lerner, Brian ^a,b   Warneke, Carsten ^a,b   Li, Rui ^a,b   Leithead, Amy ^c   Osthoff, Hans D ^e   Wild, Robert ^a,b   Brown, Steven S ^a,b   De Gouw, Joost A ^a,b  

^a NOAA EARTH SYSTEM RESEARCH LABORATORY   (United States)

^b UNIVERSITY OF COLORADO   (United States)

^c ENVIRONMENT CANADA   (Canada)

^d AERODYNE RESEARCH INC   (United States)

^e UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC CHEMISTRY; DIURNAL VARIATION; MASS SPECTROMETRY; NITRATE; OXIDATION; PHENOL; VOLATILE ORGANIC COMPOUND;

UINTAH BASIN; UNITED STATES;

EID: 84959419172     PISSN: 16807316     EISSN: 16807324     Source Type: Journal    
DOI: 10.5194/acp-16-2139-2016     Document Type: Article

References (67)

1. Atkinson, R., Aschmann, S. M., and Arey, J.: Reactions of hydroxyl and nitrogen trioxide radicals with phenol, cresols, and 2-nitrophenol at 296-2 K, Environ. Sci. Technol., 26, 1397-1403, doi:10.1021/es00031a018, 1992.
2. Bardini, P.: Atmospheric Chemistry of Dimethylphenols & Nitrophenols, PhD, University College Cork, Corcaigh, 1-156, 2006.
3. Bartmess, J. E.: Negative Ion Energetics Data, NIST Chemistry WebBook, NIST Standard Reference Database Number 69, edited by: Linstrom, P. J. and Mallard, W. G., National Institute of Standards and Technology, Gaithersburg MD, 20899, available at: http://webbook.nist.gov, last access: 28 August 2015.
4. Bejan, I., Abd El Aal, Y., Barnes, I., Benter, T., Bohn, B.,Wiesen, P., and Kleffmann, J.: The photolysis of ortho-nitrophenols: a new gas phase source of HONO, Phys. Chem. Chem. Phys., 8, 2028-2035, 2006.
5. Bejan, I., Barnes, I., Olariu, R., Zhou, S., Wiesen, P., and Benter, T.: Investigations on the gas-phase photolysis and OH radical kinetics of methyl-2-nitrophenols, Phys. Chem. Chem. Phys., 9, 5686-5692, doi:10.1039/B709464G, 2007.
6. Bejan, I., Duncianu, M., Olariu, R., Barnes, I., Seakins, P. W., and Wiesen, P.: Kinetic Study of the Gas-Phase Reactions of Chlorine Atoms with 2-Chlorophenol, 2-Nitrophenol, and Four Methyl-2-nitrophenol Isomers, The J. Phys. Chem. A, 119, 4735-4745, doi:10.1021/acs.jpca.5b02392, 2015.
7. Berndt, T. and Boge, O.: Gas-phase reaction of OH radicals with phenol, Phys. Chem. Chem. Phys., 5, 342-350, doi:10.1039/B208187C, 2003.
8. Bertram, T. H., Kimmel, J. R., Crisp, T. A., Ryder, O. S., Yatavelli, R. L. N., Thornton, J. A., Cubison, M. J., Gonin, M., and Worsnop, D. R.: A field-deployable, chemical ionization timeof-flight mass spectrometer, Atmos. Meas. Tech., 4, 1471-1479, doi:10.5194/amt-4-1471-2011, 2011.
9. 3, Environ. Sci. Technol., 35, 1791-1797, doi:10.1021/es001290m, 2001.
10. 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, doi:10.1016/S1352-2310(97)00245-8, 1997.
11. Brophy, P. and Farmer, D. K.: A switchable reagent ion high resolution time-of-flight chemical ionization mass spectrometer for real-time measurement of gas phase oxidized species: characterization from the 2013 southern oxidant and aerosol study, Atmos. Meas. Tech., 8, 2945-2959, doi:10.5194/amt-8-2945-2015, 2015.
12. Cappellin, L., Karl, T., Probst, M., Ismailova, O., Winkler, P. M., Soukoulis, C., Aprea, E., Mark, T. D., Gasperi, F., and Biasioli, F.: On quantitative determination of volatile organic compound concentrations using proton transfer reaction time-offlight mass spectrometry, Environ. Sci. Technol., 46, 2283-2290, doi:10.1021/es203985t, 2012.
13. 2 radical, Phys. Chem. Chem. Phys., 1, 3509-3517, doi:10.1039/A903088C, 1999.
14. Cecinato, A., Di Palo, V., Pomata, D., Tomasi Scianò, M. C., and Possanzini, M.: Measurement of phase-distributed nitrophenols in Rome ambient air, Chemosphere, 59, 679-683, doi:10.1016/j.chemosphere.2004.10.045, 2005.
15. Chen, J., Wenger, J. C., and Venables, D. S.: Near-Ultraviolet Absorption Cross Sections of Nitrophenols and Their Potential Influence on Tropospheric Oxidation Capacity, The J. Phys. Chem. A, 115, 12235-12242, doi:10.1021/jp206929r, 2011.
16. Cheng, S.-B., Zhou, C.-H., Yin, H.-M., Sun, J.-L., and Han, K.-L.: OH produced from o-nitrophenol photolysis: A combined experimental and theoretical investigation, The Journal of Chemical Physics, 130, 234311, doi:10.1063/1.3152635, 2009.
17. Corbin, J. C., Othman, A., D. Allan, J., R.Worsnop, D., D. Haskins, J., Sierau, B., Lohmann, U., and A. Mensah, A.: Peak-fitting and integration imprecision in the Aerodyne aerosol mass spectrometer: effects of mass accuracy on location-constrained fits, Atmos. Meas. Tech., 8, 4615-4636, doi:10.5194/amt-8-4615-2015, 2015.
18. Cubison, M. J. and Jimenez, J. L.: Statistical precision of the intensities retrieved from constrained fitting of overlapping peaks in high-resolution mass spectra, Atmos. Meas. Tech., 8, 2333-2345, doi:10.5194/amt-8-2333-2015, 2015.
19. de Gouw, J. and Warneke, C.: Measurements of volatile organic compounds in the earth's atmosphere using proton-transferreaction mass spectrometry, Mass Spectrom. Rev., 26, 223-257, 2007.
20. Delhomme, O., Morville, S., and Millet, M.: Seasonal and diurnal variations of atmospheric concentrations of phenols and nitrophenols measured in the Strasbourg area, France, Atmospheric Pollution Research, 16-22, doi:10.5094/APR.2010.003, 2010.
21. Desyaterik, Y., Sun, Y., Shen, X., Lee, T., Wang, X., Wang, T., and Collett, J. L.: Speciation of "brown" carbon in cloud water impacted by agricultural biomass burning in eastern China, J. Geophys. Res.-Atmos., 118, 7389-7399, doi:10.1002/jgrd.50561, 2013.
22. Donahue, N. M., Robinson, A. L., Stanier, C. O., and Pandis, S. N.: Coupled Partitioning, Dilution, and Chemical Aging of Semivolatile Organics, Environ. Sci. Technol., 40, 2635-2643, doi:10.1021/es052297c, 2006.
23. 2O5 via pulsed cavity ring-down spectroscopy, Rev. Sci. Instrum., 77, 034101, doi:10.1063/1.2176058, 2006.
24. Edwards, P. M., Brown, S. S., Roberts, J. M., Ahmadov, R., Banta, R. M., deGouw, J. A., Dube, W. P., Field, R. A., Flynn, J. H., Gilman, J. B., Graus, M., Helmig, D., Koss, A., Langford, A. O., Lefer, B. L., Lerner, B. M., Li, R., Li, S. M., McKeen, S. A., Murphy, S. M., Parrish, D. D., Senff, C. J., Soltis, J., Stutz, J., Sweeney, C., Thompson, C. R., Trainer, M. K., Tsai, C., Veres, P. R., Washenfelder, R. A., Warneke, C., Wild, R. J., Young, C. J., Yuan, B., and Zamora, R.: High winter ozone pollution from carbonyl photolysis in an oil and gas basin, Nature, 514, 351-354, doi:10.1038/nature13767, 2014.
25. Fernandez, P., Grifoll, M., Solanas, A. M., Bayona, J. M., and Albaiges, J.: Bioassay-directed chemical analysis of genotoxic components in coastal sediments, Environ. Sci. Technol., 26, 817-829, doi:10.1021/es00028a024, 1992.
26. 2O aerosols, Atmos. Chem. Phys., 7, 4639-4659, doi:10.5194/acp-7-4639-2007, 2007.
27. Gilman, J. B., Lerner, B. M., Kuster, W. C., and de Gouw, J. A.: Source signature of volatile organic compounds from oil and natural gas operations in northeastern Colorado, Environ. Sci. Technol., 47, 1297-1305, 10.1021/es304119a, 2013.
28. Harrison, M. A. J., Barra, S., Borghesi, D., Vione, D., Arsene, C., and Iulian Olariu, R.: Nitrated phenols in the atmosphere: a review, Atmos. Environ., 39, 231-248, doi:10.1016/j.atmosenv.2004.09.044, 2005a.
29. Harrison, M. A. J., Heal, M. R., and Cape, J. N.: Evaluation of the pathways of tropospheric nitrophenol formation from benzene and phenol using a multiphase model, Atmos. Chem. Phys., 5, 1679-1695, doi:10.5194/acp-5-1679-2005, 2005b.
30. 2, Atmos. Environ., 41, 3515-3520, doi:10.1016/j.atmosenv.2007.02.003, 2007.
31. Herterich, R. and Herrmann, R.: Comparing the distribution of nitrated phenols in the atmosphere of two German hill sites, Environ. Technol., 11, 961-972, doi:10.1080/09593339009384948, 1990.
32. Inomata, S., Tanimoto, H., Fujitani, Y., Sekimoto, K., Sato, K., Fushimi, A., Yamada, H., Hori, S., Kumazawa, Y., Shimono, A., and Hikida, T.: On-line measurements of gaseous nitroorganic compounds in diesel vehicle exhaust by proton-transferreaction mass spectrometry, Atmos. Environ., 73, 195-203, doi:10.1016/j.atmosenv.2013.03.035, 2013.
33. Jacob, D. J.: Heterogeneous chemistry and tropospheric ozone, Atmos. Environ., 34, 2131-2159, doi:10.1016/S1352-2310(99)00462-8, 2000.
34. Jenkin, M. E., Saunders, S. M., Wagner, V., and Pilling, M. J.: Protocol for the development of the Master Chemical Mechanism, MCM v3 (Part B): tropospheric degradation of aromatic volatile organic compounds, Atmos. Chem. Phys., 3, 181-193, doi:10.5194/acp-3-181-2003, 2003.
35. Jenkin, M. E., Wyche, K. P., Evans, C. J., Carr, T., Monks, P. S., Alfarra, M. R., Barley, M. H., McFiggans, G. B., Young, J. C., and Rickard, A. R.: Development and chamber evaluation of the MCM v3.2 degradation scheme for caryophyllene, Atmos. Chem. Phys., 12, 5275-5308, doi:10.5194/acp-12-5275-2012, 2012.
36. Karl, T. G., Christian, T. J., Yokelson, R. J., Artaxo, P., Hao, W. M., and Guenther, A.: The Tropical Forest and Fire Emissions Experiment: method evaluation of volatile organic compound emissions measured by PTR-MS, FTIR, and GC from tropical biomass burning, Atmos. Chem. Phys., 7, 5883-5897, doi:10.5194/acp-7-5883-2007, 2007.
37. Kaser, L., Karl, T., Guenther, A., Graus, M., Schnitzhofer, R., Turnipseed, A., Fischer, L., Harley, P., Madronich, M., Gochis, D., Keutsch, F. N., and Hansel, A.: Undisturbed and disturbed above canopy ponderosa pine emissions: PTR-TOF-MS measurements and MEGAN 2.1 model results, Atmos. Chem. Phys., 13, 11935-11947, doi:10.5194/acp-13-11935-2013, 2013.
38. Kitanovski, Z., Grgić, I., Yasmeen, F., Claeys, M., and Čusak, A.: Development of a liquid chromatographic method based on ultraviolet-visible and electrospray ionization mass spectrometric detection for the identification of nitrocatechols and related tracers in biomass burning atmospheric organic aerosol, Rapid Commun. Mass Sp., 26, 793-804, doi:10.1002/rcm.6170, 2012.
39. Lauraguais, A., Coeur-Tourneur, C., Cassez, A., Deboudt, K., Fourmentin, M., and Choël, M.: Atmospheric reactivity of hydroxyl radicals with guaiacol (2-methoxyphenol), a biomass burning emitted compound: Secondary organic aerosol formation and gas-phase oxidation products, Atmos. Environ., 86, 155-163, doi:10.1016/j.atmosenv.2013.11.074, 2014.
40. Lee, B. H., Lopez-Hilfiker, F., Mohr, C., Kurtén, T. C.,Worsnop, D., and Thornton, J. A.: An Iodide-Adduct High-Resolution Timeof-Flight Chemical-Ionization Mass Spectrometer: Application to Atmospheric Inorganic and Organic Compounds, Environ. Sci. Technol., 48, 6309-6317, doi:10.1021/es500362a, 2014.
41. Lin, P., Liu, J., Shilling, J. E., Kathmann, S., Laskin, J., and Laskin, A.: Molecular Characterization of Brown Carbon (BrC) Chromophores in Secondary Organic Aerosol Generated From Photo-Oxidation of Toluene, Phys. Chem. Chem. Phys., 17, 23312-23325, doi:10.1039/C5CP02563J, 2015.
42. Mohr, C., Lopez-Hilfiker, F. D., Zotter, P., Prévôt, A. S. H., Xu, L., Ng, N. L., Herndon, S. C., Williams, L. R., Franklin, J. P., Zahniser, M. S., Worsnop, D. R., Knighton, W. B., Aiken, A. C., Gorkowski, K. J., Dubey, M. K., Allan, J. D., and Thornton, J. A.: Contribution of Nitrated Phenols to Wood Burning Brown Carbon Light Absorption in Detling, United Kingdom during Winter Time, Environ. Sci. Technol., 47, 6316-6324, doi:10.1021/es400683v, 2013.
43. Morville, S., Scheyer, A., Mirabel, P., and Millet, M.: Spatial and Geographical Variations of Urban, Suburban and Rural Atmospheric Concentrations of Phenols and Nitrophenols, Environ. Sci. Pollut. R, 13, 83-89, doi:10.1065/espr2005.06.264, 2006.
44. Müller, M., George, C., and D'Anna, B.: Enhanced spectral analysis of C-TOF Aerosol Mass Spectrometer data: Iterative residual analysis and cumulative peak fitting, Int. J. Mass Spectrom., 306, 1-8, doi:10.1016/j.ijms.2011.04.007, 2011.
45. Natangelo, M., Mangiapan, S., Bagnati, R., Benfenati, E., and Fanelli, R.: Increased concentrations of nitrophenols in leaves from a damaged forestal site, Chemosphere, 38, 1495-1503, doi:10.1016/S0045-6535(98)00370-1, 1999.
46. Olariu, R. I., Klotz, B., Barnes, I., Becker, K. H., and Mocanu, R.: FT-IR study of the ring-retaining products from the reaction of OH radicals with phenol, o-, m-, and p-cresol, Atmos. Environ., 36, 3685-3697, doi:10.1016/S1352-2310(02)00202-9, 2002.
47. Pankow, J. F.: An absorption model of the gas/aerosol partitioning involved in the formation of secondary organic aerosol, Atmos. Environ., 28, 189-193, doi:10.1016/1352-2310(94)90094-9, 1994.
48. 2, The J. Phys. Chem. A, 102, 7964-7974, doi:10.1021/jp982221l, 1998.
49. Rippen, G., Zietz, E., Frank, R., Knacker, T., and Klöpffer, W.: Do airborne nitrophenols contribute to forest decline?, Environ. Technol. Lett., 8, 475-482, doi:10.1080/09593338709384508, 1987.
50. Rubio, M. A., Lissi, E., Herrera, N., Pérez, V., and Fuentes, N.: Phenol and nitrophenols in the air and dew waters of Santiago de Chile, Chemosphere, 86, 1035-1039,doi:10.1016/j.chemosphere.2011.11.046, 2012.
51. Sander, R.: Compilation of Henry's law constants (version 4.0) for water as solvent, Atmos. Chem. Phys., 15, 4399-4981, doi:10.5194/acp-15-4399-2015, 2015.
52. Schwarzenbach, R. P., Stierli, R., Folsom, B. R., and Zeyer, J.: Compound properties relevant for assessing the environmental partitioning of nitrophenols, Environ. Sci. Technol., 22, 83-92, doi:10.1021/es00166a009, 1988.
53. Sekimoto, K., Inomata, S., Tanimoto, H., Fushimi, A., Fujitani, Y., Sato, K., and Yamada, H.: Characterization of nitromethane emission from automotive exhaust, Atmos. Environ., 81, 523-531, doi:10.1016/j.atmosenv.2013.09.031, 2013.
54. Stark, H., Yatavelli, R. L. N., Kimmel, J. R., Bertram, T. H., Thornton, J. A., Jimenez, J. L., and Worsnop, D. R.: Cluster Formation and Ion Chemistry in the High Pressure Inlet of a Chemical Ionization Mass Spectrometer: Lessons learned from Field and Laboratory Studies, 22nd International Symposium on Gas Kinetics, 18-22 June 2012, Boulder, CO, 2012.
55. Stark, H., Yatavelli, R. L. N., Thompson, S. L., Kimmel, J. R., Cubison, M. J., Chhabra, P. S., Canagaratna, M. R., Jayne, J. T., Worsnop, D. R., and Jimenez, J. L.: Methods to extract molecular and bulk chemical information from series of complex mass spectra with limited mass resolution, Int. J. Mass Spectrom., 389, 26-38, doi:10.1016/j.ijms.2015.08.011, 2015.
56. Stockwell, C. E., Veres, P. R., Williams, J., and Yokelson, R. J.: Characterization of biomass burning emissions from cooking fires, peat, crop residue, and other fuels with high-resolution proton-transfer-reaction time-of-flight mass spectrometry, Atmos. Chem. Phys., 15, 845-865, doi:10.5194/acp-15-845-2015, 2015.
57. Tremp, J., Mattrel, P., Fingler, S., and Giger, W.: Phenols and nitrophenols as tropospheric pollutants: Emissions from automobile exhausts and phase transfer in the atmosphere, Water Air Soil Pollut, 68, 113-123, doi:10.1007/BF00479396, 1993.
58. Veres, P., Roberts, J. M., Warneke, C., Welsh-Bon, D., Zahniser, M., Herndon, S., Fall, R., and de Gouw, J.: Development of negative-ion proton-transfer chemical-ionization mass spectrometry (NI-PT-CIMS) for the measurement of gas-phase organic acids in the atmosphere, Int. J. Mass Spectrom., 274, 48-55, doi:10.1016/j.ijms.2008.04.032, 2008.
59. Vione, D., Maurino, V., Minero, C., and Pelizzetti, E.: Phenol photonitration upon UV irradiation of nitrite in aqueous solution I: Effects of oxygen and 2-propanol, Chemosphere, 45, 893-902, doi:10.1016/S0045-6535(01)00035-2, 2001.
60. Vione, D., Maurino, V., Minero, C., and Pelizzetti, E.: Aqueous Atmospheric Chemistry:? Formation of 2,4-Dinitrophenol upon Nitration of 2-Nitrophenol and 4-Nitrophenol in Solution, Environ. Sci. Technol., 39, 7921-7931, doi:10.1021/es050824m, 2005.
61. Vione, D., Maurino, V., Minero, C., Duncianu, M., Olariu, R.-I., Arsene, C., Sarakha, M., and Mailhot, G.: Assessing the transformation kinetics of 2-and 4-nitrophenol in the atmospheric aqueous phase. Implications for the distribution of both nitroisomers in the atmosphere, Atmos. Environ., 43, 2321-2327, doi:10.1016/j.atmosenv.2009.01.025, 2009.
62. Warneke, C., Geiger, F., Edwards, P. M., Dube, W., Pétron, G., Kofler, J., Zahn, A., Brown, S. S., Graus, M., Gilman, J. B., Lerner, B. M., Peischl, J., Ryerson, T. B., de Gouw, J. A., and Roberts, J. M.: Volatile organic compound emissions from the oil and natural gas industry in the Uintah Basin, Utah: oil and gas well pad emissions compared to ambient air composition, Atmos. Chem. Phys., 14, 10977-10988, doi:10.5194/acp-14-10977-2014, 2014.
63. Warneke, C., Veres, P., Murphy, S. M., Soltis, J., Field, R. A., Graus, M. G., Koss, A., Li, S.-M., Li, R., Yuan, B., Roberts, J. M., and de Gouw, J. A.: PTR-QMS versus PTR-TOF comparison in a region with oil and natural gas extraction industry in the Uintah Basin in 2013, Atmos. Meas. Tech., 8, 411-420, doi:10.5194/amt-8-411-2015, 2015.
64. 3 via Cavity Ring-down Spectroscopy, Environ. Sci. Technol., 48, 9609-9615, doi:10.1021/es501896w, 2014.
65. Yatavelli, R. L. N., Stark, H., Thompson, S. L., Kimmel, J. R., Cubison, M. J., Day, D. A., Campuzano-Jost, P., Palm, B. B., Hodzic, A., Thornton, J. A., Jayne, J. T., Worsnop, D. R., and Jimenez, J. L.: Semicontinuous measurements of gas-particle partitioning of organic acids in a ponderosa pine forest using a MOVI-HRToFCIMS, Atmos. Chem. Phys., 14, 1527-1546, doi:10.5194/acp-14-1527-2014, 2014.
66. Yuan, B., Veres, P. R., Warneke, C., Roberts, J. M., Gilman, J. B., Koss, A., Edwards, P. M., Graus, M., Kuster, W. C., Li, S.-M., Wild, R. J., Brown, S. S., Dubé, W. P., Lerner, B. M., Williams, E. J., Johnson, J. E., Quinn, P. K., Bates, T. S., Lefer, B., Hayes, P. L., Jimenez, J. L., Weber, R. J., Zamora, R., Ervens, B., Millet, D. B., Rappenglück, B., and de Gouw, J. A.: Investigation of secondary formation of formic acid: urban environment vs. oil and gas producing region, Atmos. Chem. Phys., 15, 1975-1993, doi:10.5194/acp-15-1975-2015, 2015.
67. Zhang, X., Lin, Y.-H., Surratt, J. D., and Weber, R. J.: Sources, Composition and Absorption Ångström Exponent of Lightabsorbing Organic Components in Aerosol Extracts from the Los Angeles Basin, Environ. Sci. Technol., 47, 3685-3693, doi:10.1021/es305047b, 2013.