Contributions of organic peroxides to secondary aerosol formed from reactions of monoterpenes with O 3

Environmental Science and Technology

Volumn 39, Issue 11, 2005, Pages 4049-4059

  Docherty, Kenneth S ^a,b   Wu, Wilbur ^a,c   Lim, Yong Bin ^a,c   Ziemann, Paul J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Environmental Toxicology Graduate Program   (United States)

^c Department of Biology ^*

Author keywords

[No Author keywords available]

Indexed keywords

HYDROPEROXIDES; ORGANIC AEROSOLS; ORGANIC PEROXIDES; RADICAL SCAVENGERS;

ALCOHOLS; ENVIRONMENTAL CHAMBERS; HYDROCARBONS; OLEFINS; PEROXIDES; PROPANE; SCAVENGING; SPECTROPHOTOMETRY;

AEROSOLS;

3 CARENE; ACETAL DERIVATIVE; ACID; ALDEHYDE; ALKENE; CYCLOHEXANE; FORMALDEHYDE; HYDROXYL RADICAL; OLIGOMER; OXYGEN DERIVATIVE; OZONE; PEROXIDE; PEROXYHEMIACETAL DERIVATIVE; PINENE; PINIC ACID; PROPANOL; SABINENE; SCAVENGER; TERPENE; UNCLASSIFIED DRUG;

AEROSOL; FORMATION MECHANISM; OZONE;

AEROSOL; ANALYTIC METHOD; ARTICLE; ATMOSPHERE; CHEMICAL REACTION; DESORPTION; HUMIDITY; IODOMETRY; MASS; MASS SPECTROMETRY; REACTION ANALYSIS; SPECTROPHOTOMETRY; STOICHIOMETRY; VAPOR PRESSURE; VOLATILIZATION;

AEROSOLS; AIR; AIR POLLUTANTS; BICYCLO COMPOUNDS; CYCLOHEXANES; CYCLOHEXENES; HUMANS; HUMIDITY; HYDROXYL RADICAL; MASS SPECTROMETRY; MONOTERPENES; ORGANIC CHEMICALS; OZONE; PEROXIDES; TEMPERATURE; VOLATILIZATION;

LETHRINIDAE;

EID: 20044369192     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es050228s     Document Type: Article

References (64)

1. Singh, H. B.; Salas, L.; Viezee, W.; Sitton, B.; Ferek, R. Measurement of volatile organic chemicals at selected sites in California. Atmos. Environ. A 1992, 26, 2929-2946.
2. Guenther, A.; Geron, C.; Pierce, T.; Lamb, B.; Harley, P.; Fall, R. Natural emissions of nonmethane volatile organic compounds, carbon monoxide, and oxides of nitrogen from North America. Atmos. Environ. 2000, 34, 2205-2230.
3. Atkinson, R. Gas-phase tropospheric chemistry of volatile organic compounds. 1. Alkanes and alkenes. J. Phys. Chem. Ref. Data 1997, 26, 215-290.
4. Calvert, J. G.; Atkinson, R.; Kerr, J. A.; Madronich, S.; Moortgat, G. K.; Wallington, T. J.; Yarwood, G. The Mechanisms of Atmospheric Oxidation of the Alkenes; Oxford University Press: Oxford, 2000.
5. Griffin, R. J.; Cocker III, D. R.; Flagan, R. C.; Seinfeld, J. H. Organic aerosol formation from the oxidation of biogenic hydrocarbons J. Geophys. Res. 1999, 104, 3555-3567.
6. Seinfeld, J. H.; Pandis, S. N. Atmospheric Chemistry and Physics; John Wiley & Sons: New York, 1998.
7. Englert, N. Fine Particle and Human Health - A review of epidemiological studies. Toxicol. Lett. 2004, 149, 235-242.
8. Yu, J.; Cocker, D. R., III; Griffin, R. J.; Flagan, R. C.; Seinfeld, J. H. Gas-phase ozone oxidation of monoterpenes: gaseous and particulate products. J. Atmos. Chem. 1999, 34, 207-258.
9. x/air in the presence of natural sunlight. J. Atmos. Chem. 2003, 44, 259-297.
10. 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, 1428-1434.
11. 3 reaction, influence of particle acidity on aerosol yields and products. Atmos. Environ. 2004, 38, 761-773.
12. Gao, S.; Keywood, M.; Ng, N. L.; Surratt, J.; Varutbangkul, V.; Bahreini, R.; Flagan, R. C.; Seinfeld, J. H. Low-molecular weight and oligomeric components in secondary organic aerosol from the ozonolysis of cycloalkenes and α-pinene. J. Phys. Chem. A 2004, 108, 10147-10164.
13. Gao, S.; Ng, N. L.; Varutbangkul, V.; Behreini, R.; Nenes, A.; He, J.; Yoo, K. Y.; Beauchamp, J. L.; Hodyss, R. P.; Flagan, R. C.; Seinfeld, J. H. Particle phase acidity and oligomer formation in secondary organic aerosol. Environ. Sci. Technol. 2004, 38, 6582-6589.
14. Jang, M.; Czoschke, N. M.; Lee, S.; Kamens, R. M. Heterogeneous atmospheric aerosol production by acid-catalyzed particle-phase reactions. Science 2002, 298, 814-817.
15. 3 in the presence of alcohols and carboxylic acids. Environ. Sci. Technol. 2000, 34, 2105-2115.
16. 3. Environ. Sci. Technol. 2000, 34, 2116-2125.
17. Paulson, S. E.; Chung, M. Y.; Hasson, A. S. OH Radical formation from the gas-phase reaction of ozone with terminal alkenes and the relationship between structure and mechanism. J. Phys. Chem. A 1999, 103, 8125-8138.
18. Neeb, P.; Horie, O.; Moortgat, G. K. Gas-phase ozonolysis of ethene in the presence of hydroxylic compounds. Int. J. Chem. Kinet. 1996, 28, 721-730.
19. Neeb, P.; Horie, O.; Moortgat, G. K. The ethene-ozone reaction in the gas phase. J. Phys. Chem. A 1998, 34, 6778-6785.
20. 3 with selected alkenes. Int. J. Chem. Kinet. 2002, 34, 73-85.
21. Winterhalter, R.; Neeb, P.; Grassmann, D.; Kolloff, A.; Horie, O.; Moortgat, G. Products and mechanism of the gas-phase reaction of ozone with β-pinene. J. Atmos. Chem. 2000, 35, 165-197.
22. 3 in the presence of alcohols. J. Phys. Chem. A 2003, 107, 2048-2060.
23. 3. Aerosol Sci. Technol. 2003, 37, 877-891.
24. Warscheid, B.; Hoffmann, T. On-line measurements of α-pinene ozonolysis products using an atmospheric pressure chemical ionization ion-trap mass spectrometer. Atmos. Environ. 2001, 35, 2927-2940.
25. 13 stabilized Criegee intermediate formed from ozonolysis of 1-tetradecene. J. Phys. Chem. A 2001, 105, 6129-6135.
26. Hasson, A. S.; Ho, A. W.; Kuwata, K. T.; Paulson, S. E. Production of stabilized Criegee intermediates and peroxides in the gas-phase ozonolysis of alkenes. 2. Asymmetric and biogenic alkenes. J. Geophys. Res. 2001, 106, 34, 143-34, 153.
27. 3 with a series of terpenes. Atmos. Environ. 2002, 36, 4347-4355.
28. Jenkin, M. E. Modeling the formation and composition of secondary organic aerosol from α- and β-pinene ozonolysis using MCM v3. Atmos. Chem. Phys. 2004, 4, 1741-1757.
29. Bonn, B.; Kuhlmann, R. v.; Lawrence, M. G. High contribution of biogenic hydroperoxides to secondary organic aerosol formation. Geophys. Res. Lett. 2004, 31, L10108.
30. Tobias, H. J.; Kooiman, P. M.; Docherty, K. S.; Ziemann, P. J. Real-time chemical analysis of organic aerosols using a thermal desorption particle beam mass spectrometer. Aerosol Sci. 2000, 33, 170-190.
31. 3 with a series of terpenes. J. Geophys. Res. 1992, 97, 6065-6073.
32. Tobias, H. J.; Ziemann, P. J. Compound identification in organic aerosols using temperature-programmed thermal desorption particle beam mass spectrometry. Anal. Chem. 1999, 71, 3428-3435.
33. Liu, P.; Ziemann, P. J.; Kittelson, D. B.; McMurry, P. H. Generating particle beams of controlled dimension and divergence: 1. Theory of particle motion in aerodynamic lenses and nozzle expansions. Aerosol Sci. Technol. 1995, 22, 293-313.
34. Liu, P.; Ziemann, P. J.; Kittelson, D. B.; McMurry, P. H. Generating particle beams of controlled dimensions and divergence. II. Experimental evaluation of particle motion in aerodynamic lenses and nozzle expansions. Aerosol Sci. Technol. 1995, 22, 314-324.
35. Wang, S. C.; Flagan, R. C. Scanning electrical mobility analyzer. Aerosol Sci. Technol. 1990, 13, 230-240.
36. Odum, J. R.; Hoffmann, T.; Bowman, F.; Collins, D.; Flagan, R. C.; Seinfeld, J. H. Gas/particle partitioning and secondary organic aerosol yields. Environ. Sci. Technol. 1996, 30, 2580-2585.
37. 3 reactions. J. Chromatogr. A 2004, 1029, 205-215.
38. Banerjee, D. K.; Budke, C. C. Spectrophotometric determination of traces of peroxides in organic solvents. Anal. Chem. 1964, 36, 792-796.
39. Crable, G. F.; Coggeshall, N. D. Application of total ionization principles to mass spectrometric analysis. Anal. Chem. 1958, 30, 310-313.
40. Chattopadhyay, S.; Tobias, H. J.; Ziemann, P. J. A method for measuring vapor pressures of low-volatility organic aerosol compounds using a thermal desorption particle beam mass spectrometer. Anal. Chem. 2001, 73, 3797-3803.
41. Bilde, M.; Pandis, S. N. Evaporation rates and vapor pressures of individual aerosol species formed in the atmospheric oxidation of α- and β-pinene. Environ. Sci. Technol. 2001, 35, 3344-3349.
42. McLafferty, F. W.; Turecek, F. Interpretation of Mass Spectra, 4th ed.; University Science Books: Sausalito, CA, 1993.
43. Lazrus, A. L.; Kok, G. L.; Gitlin, S. N.; Lind, J. A.; McLaren, S. E. Automated fluorometric method for hydrogen peroxide in atmospheric precipitation. Anal. Chem. 1985, 57, 917-922.
44. Lee, J. H.; Tang, I. N.; Weinstein-Lloyd, J. B. Nonenzymatic method for the determination of hydrogen peroxide in atmospheric samples. Anal. Chem. 1990, 62, 2381-2384.
45. Lee, M.; Heikes, B. G.; O'Sullivan, D. W. Hydrogen peroxide and organic hydroperoxide in the troposphere: a review. Atmos. Environ. 2000, 34, 3475-3494.
46. Hung, H.; Wang, C. Experimental determination of reactive oxygen species in Taipei aerosols. J. Aerosol Sci. 2002, 32, 1201-1211.
47. Hewitt, C. N.; Kok, G. L. Formation and occurrence of organic hydroperoxides in the troposphere: laboratory and field observations. J. Atmos. Chem. 1991, 12, 181-194.
48. Parker, W. E.; Witnauer, L. P.; Swern, D. Peroxides. V. Kinetics and products of decomposition of perlauric acid. J. Am. Chem. Soc. 1958, 80, 323-327.
49. Wurster, C. F., Jr.; Durham, L. J.; Mosher, H. S. Peroxides. VII. The thermal decomposition of primary hydroperoxides. J. Am. Chem. Soc. 1958, 80, 327-331.
50. Wurster, C. F., Jr.; Durham, L. J.; Mosher, H. S. Peroxides. VIII. The mechanism for the thermal decomposition of n-butyl hydroperoxides and n-butyl-1-hydroxybutyl peroxide. J. Am. Chem. Soc. 1958, 80, 327-331.
51. Hasson, A. S.; Paulson, S. E. An investigation of the relationship between gas-phase and aerosol-borne hydroperoxides in urban air. J. Aerosol Sci. 2003, 34, 459-468.
52. Keywood, M. D.; Kroll, J. H.; Varutbangkul, V.; Bahreini, R.; Flagan, R. C.; Seinfeld, J. H. Secondary organic aerosol formation from cyclohexene ozonolysis: effect of OH scavenger and the role of radical chemistry. Environ. Sci. Technol. 2004, 38, 3343-3350.
53. 2 in the ozone-olefin reactions. J. Phys. Chem. 1984, 88, 4736-4739.
54. Atkinson, R. personal communication.
55. Antonovskii, V. L.; Terent'ev, V. A. Effect of the structure of hydroperoxides and some aldehydes on the kinetics of the noncatalytic formation of α-hydroxy peroxides. J. Org. Chem. U.S.S.R. (Engl. Transl.) 1967, 3, 972-976.
56. Dickey, F. H.; Rust, F. F.; Vaughan, R. E. Some t-butyl hydroperoxide derivatives of aldehydes and ketones. J. Am. Chem. Soc. 1949, 71, 1432-1434.
57. 3 radical with organic compounds. J. Phys. Chem. Ref. Data 1991, 20, 459-507.
58. Wayne, R. P.; Barnes, I.; Biggs, P.; Burrows, J. P.; Canosa-Mas, C. E.; Hjorth, J.; Le Bras, G.; Moortgat, G. K.; Perner, D.; Poulet, G.; Restelli, G.; Sidebottom, H. The nitrate radical: physics, chemistry, and the atmosphere. Atmos. Environ. 1991, 25A, 1-206.
59. Fuentes, J. D.; Lerdau, M.; Atkinson, R.; Baldocchi, D.; Bottenheim, J. W.; Ciccioli, P.; Lamb, B.; Geron, C.; Gu, L.; Guenther, A.; Sharkey, T. D.; Stockwell, W. Biogenic hydrocarbons in the atmospheric boundary layer: a review. Bull. Am. Meteor. Soc. 2000, 81, 1537-1575.
60. Orlando, J. J.; Tyndall, G. S.; Moortgat, G. K.; Calvert, J. G. Quantum yields for nitrate radical photolysis between 570 and 635 nm. J. Phys. Chem. 1993, 97, 10996-11000.
61. x, and hydrocarbons in urban and polluted rural environments. Atmos. Environ. 1999, 33, 1821-1845.
62. Makar, P. A.; Fuentes, J. D.; Wang, D.; Staebler, R. M.; Wiebe, H. A. Chemical processing of biogenic hydrocarbons within and above a temperate deciduous forest. J. Geophys. Res. 1999, 104, 3581-3603.
63. Ziemann, P. J. Aerosol products, mechanisms, and kinetics of heterogeneous reactions of ozone with oleic acid in pure and mixed particles. Faraday Discuss. 2005, 130, in press.
64. Warscheid, B.; Hoffmann, T. Direct analysis of highly oxidized organic aerosol constituents by on-line ion trap mass spectrometry in the negative ion mode. Rapid Commun. Mass Spectrom. 2002, 16, 496-504.