Products and mechanism of the gas phase reaction of ozone with β-pinene

Journal of Atmospheric Chemistry

Volumn 35, Issue 2, 2000, Pages 165-197

  Winterhalter, Richard ^a,b   Neeb, Peter ^a   Grossmann, Dirk ^a   Kolloff, Antje ^a   Horie, Osamu ^a   Moortgat, Geert ^a  

^a MAX PLANCK INSTITUTE FOR CHEMISTRY   (Germany)

^b JOINT RESEARCH CENTRE   (Italy)

Author keywords

cis pinic acid; Criegee intermediates; Dicarboxylic acid; Gas to particle conversion; H2O2; Nopinone; Nucleation; Secondary organic aerosol; Secondary ozonide

Indexed keywords

ALCOHOL; CYCLOHEXANE; DICARBOXYLIC ACID; HYDROPEROXIDE; HYDROXYL RADICAL; METHANOL; OZONE; PINENE; SCAVENGER;

GAS PHASE REACTION; OZONE; SCAVENGING;

AIR ANALYSIS; AIR POLLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY;

EID: 0033961057     PISSN: 01677764     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1006257800929     Document Type: Article

References (74)

1. 3 with alpha-pinene and 1,2-dimethyl-1-cyclohexene, J. Geophys. Res. 103, 25541-25551.
2. Andrews, E., Kreidenweis, S. M., Penner, J. E., and Larson, S. M., 1997: Potential origin of organic cloud condensation nuclei observed at marine site, J. Geophys. Res. 102, 21997-22012.
3. Arey, J., Winer, A. M., Atkinson, R., Aschmann, S. M., Long, W. D., Morrison, C. L., and Olszyk, D. M., 1991: Terpenes emitted from agricultural species found in California's central valley, J. Geophys. Res. 96, 9329-9336.
4. Arora, P. K., Chatha, J. P. S., and Vohra, K. G., 1983: Gas-phase chemiluminescent reactions of ozone with monoterpenes, Chem. Phys. Lett. 100, 93-98.
5. Atkinson, R., 1994: Gas-phase tropospheric chemistry of organic compounds, J. Phys. Chem. Ref. Data, Monograph 2, pp. 1-216.
6. Atkinson, R., 1997: Gas-phase tropospheric chemistry of volatile organic compounds: 1. Alkanes and alkenes, J. Phys. Chem. Ref. Data 26, 215-290.
7. 3 with a series of terpenes, J. Geophys. Res. 97, 6065-6073.
8. 3 with a series of alkenes, Int. J. Chem. Kin. 26, 945-950.
9. Bach, R. D., Ayala, P. Y., and Schlegel, H. B., 1996: A reassessment of the bond dissociation energies of peroxides, An ab initio study, J. Am. Chem. Soc. 118, 12758-12765.
10. 2 in the ozonolysis of alkenes, Atmos. Environ. 27A, 57-61.
11. Becker, K. H., Brockmann, K. J., and Bechara, J., 1990: Production of hydrogen peroxide in forest air by reaction of ozone with terpenes, Nature 346, 256-258.
12. Bertin, N., Staudt, M., Hansen, U., Seufert, G., Ciccioli, P., Foster, P., Fugit, J. L., and Torres, L., 1997: Diurnal and seasonal course of monoterpene emissions from Quercus Ilex (L.) under natural conditions - Applications of light and temperature algorithms, Atmos. Environ. 31, 135-144.
13. Burrows, J. P., Moortgat, G. K., Tyndall, G. S., Cox, R. A., Jenkin, M. E., Hayman, G. D., and Veyret, B., 1989: Kinetics and mechanism of the photooxidation of formaldehyde. 2. Molecular modulation studies, J. Phys. Chem. 93, 2375-2382.
14. Christoffersen, T. S., Hjorth, J., Horie, O., Jensen, N. R., Kotzias, D., Molander, L. L., Neeb, P., Ruppert, L., Winterhalter, R., Virkkula, A., Wirtz, K., and Larsen, B. R., 1998: cis-Pinic acid, a possible precursor for organic aerosol formation from ozonolysis of alpha-pinene, Atmos. Environ. 32, 1657-1661.
15. Criegee, R., 1975: Mechanismus der Ozonolyse, Angew. Chem. 87, 765-771.
16. Dallwigk, E., Susz, B., and Briner, E., 1952: Recherches sur les spectres d'absorption infrarouges des ozonides. III. Détermination des spectres d' absorption infrarouges des ozonides de l'anéthol, du méthylisoeugénol, du benzène, du naphtalène, du cyclohèxene, du limonène, du caryophyllène, du nopinène et des maléate et fumarate d'éthyle, Helv. Chim. Acta 35, 353-362.
17. DeMore, W. B., Sander, S. P., Howard, C. J., Ravishankara, A. R., Golden, D. M., Kolb, C. E., Hampson, R. F., Kurylo, M. J., and Molina, M. J., 1997: Chemical Kinetics and photochemical data for use in stratospheric modelling, JPL Publication, 97-4.
18. Finkbeiner, M., Neeb, P., Horie, O., and Moortgat, G. K., 1995: A method of calibration of the formic acid monomer concentration in the gas phase, Fresenius J. Anal. Chem. 351, 521-525.
19. François, H. and Josien, M. L., 1959: Étude par spectroscopie infrarouge des vibrations de valence des groupements carbonyles et hydroxyles des acides dl-pinanique, dl-pinolique, dl-pinonique, dl-pinique et de leurs esters, Bull. Soc. Chim. Fr., 1606-1609.
20. Gab, S., Turner, W. V., Wolff, S., Becker, K. H., Ruppert, L., and Brockmann, K. J., 1995: Formation of alkyl and hydroxyalkyl hydroperoxides on ozonolysis in water and in air, Atmos. Environ. 29, 2401-2407.
21. 3 and OH oxidation of cyclic monoterpenes, in P. M. Borrell and P. Borrell, EUROTRAC-2 Symposium 1998, Garmisch-Partenkirchen, Germany.
22. Griesbaum, K., Hilß, M., and Bosch, J., 1996: Ozonides of mono-, bi- and tricyclic terpenes, Tetrahedron 52, 14813-14826.
23. Griesbaum, K., Miclaus, V., and Jung, I. C., 1998: Isolation of ozonides from gas-phase ozonolyses of terpenes, Environ. Sci. Technol. 32, 647-649.
24. Grosjean, D., Williams, E. L., II, Grosjean, E., Andino, J. M., and Seinfeld, J. H., 1993: Atmospheric oxidation of biogenic hydrocarbons: Reactions of ozone with β-pinene, d-limonene and transcaryophyllene, Environ. Sci. Technol. 27, 2754-2758.
25. Guenther, A., Hewitt, N. C., Erickson, D., Fall, R., Geron, C., Graedel, T., Harley, P., Klinger, L., Lerdau, M., McKay, W. A., Pierce, T., Scholes, B., Steinbrecher, R., Tallamraju, R., Taylor, J., and Zimmerman, P., 1995: A global model of natural volatile organic compound emissions, J. Geophys. Res. 100, 8873-8892.
26. Gutbrod, R., Schindler, R. N., Kraka, E., and Cremer, D., 1996: Formation of OH radicals in the gas phase ozonolysis of alkenes: The unexpected role of carbonyl oxides, Chem. Phys. Lett. 252, 221-229.
27. 3 with a series of monoterpenes, J. Atmos. Chem. 18, 75-102.
28. Hatakeyama, S., Izumi, K., Fukuyama, T., and Akimoto, H., 1989: Reactions of ozone with alpha-pinene and beta-pinene in air: Yields of gaseous and particulate products, J. Geophys. Res. 94, 13013-13024.
29. Hatakeyama, S., Izumi, K., Fukuyama, T., Akimoto, H., and Washida, N., 1991: Reactions of OH with alpha-pinene and beta-pinene in air: Estimate of global CO production from the atmospheric oxidation of terpenes, J. Geophys. Res. 96, 947-958.
30. 2 in the ozone-olefin reactions, J. Phys. Chem. 88, 4736-4739.
31. Hatakeyama, S., Tanonaka, T., Weng, H. H., Bandow, H., Takagi, H., and Akimoto, H., 1985: Ozone-cyclohexene reaction in air: Quantitative analysis of particulate products and the reaction mechanism, Environ. Sci. Technol. 19, 935-942.
32. Hellpointner, E., and Gäb, S., 1989: Detection of methyl, hydroxymethyl and hydroxyethyl hydroperoxides in air and precipitation, Nature 337, 631-634.
33. Hewitt, C. N., and Kok, G. L., 1991: Formation and occurrence of organic hydroperoxides in the troposphere: Laboratory and field observations, J. Atmos. Chem. 12, 181-194.
34. 3 reaction: Implications for new particle formation processes, J. Geophys. Res. 103, 25569-25578.
35. Hoffmann, T., Odum, J., Bowman, F., Collins, D., Klockow, D., Flagan, R. C., and Seinfeld, J. H., 1997: Formation of organic aerosols from the oxidation of biogenic hydrocarbons, J. Atmos. Chem. 26, 189-222.
36. Hofmann, U., Weller, D., Ammann, C., Jork, E., and Kesselmeier, J., 1997: Cryogenic trapping of atmospheric organic acids under laboratory and field conditions, Atmos. Environ. 31, 1275-1284.
37. Horie, O. and Moortgat, G. K., 1991: Decomposition pathways of the excited Criegee intermediates in the ozonolysis of simple alkenes, Atmos. Environ. 25A, 1881-1896.
38. 3CHOO in the gas-phase ozonolysis of 2-butene isomers, Int. J. Chem. Kin. 29, 461-468.
39. Hull, L. A., 1981: Terpene ozonolysis products, in J. J. Bufalini and R. R. Arnts (eds), Atmospheric biogenic hydrocarbons, Ann Arbor Science, pp. 161-184.
40. Izumi, K., Murano, K., Mizuochi, M., and Fukuyama, T., 1988: Aerosol formation by the photooxidation of cyclohexene in the presence of nitrogen oxides, Environ. Sci. Technol. 22, 1207-1215.
41. 2), in P. Mathy, (ed.), Air Pollution and Ecosystems, 542-547.
42. 2, Atmos. Environ. 23, 1219-1221.
43. Jenkin, M. E., Cox, R. A., Emrich, M., and Moortgat, G. K., 1993: Mechanisms of the Cl-atom-initiated oxidation of acetone and hydroxyaxetone in air, J. Chem. Soc. Faraday Trans. 89, 2983-2991.
44. 2 and formation of sulphuric acid, Atmos. Environ. 24 A, 2127-2132.
45. Krc, J., 1953: dl-Pinic acid, Anal. Chem. 25, 1420-1521.
46. Lazrus, A. L., Kok, G. L., Lind, J. A., Gitlin, S. N., Heikes, B. G., and Shetter, R. E., 1986: Automated fluormetric method for hydrogen peroxide in air, Anal. Chem. 58, 594-597.
47. Mäkelä, J. M., Aalto, P., Jokinen, V., Phoja, T., Nissinen, A., Palmroth, S., Markkanen, T., Seitsonen, K., Lihavainen, H., and Kulmala, M., 1997: Observations of ultrafine aerosol particle formation and growth in boreal forest, Geophys. Res. Lett. 24, 1219-1222.
48. 2 and organic precursors, J. Geophys. Res. 102, 6331-6339.
49. Martinez, R. I. and Herron, J. T., 1987: Stopped-flow studies of the mechanisms of ozone-alkene reactions in the gas phase: Tetramethylethylene, J. Phys. Chem. 91, 946-53.
50. Moortgat, G. K., Veyret, B., and Lesclaux, R., 1989a: Absorption spectrum and kinetics of reactions of the acetylperoxy radical, J. Phys. Chem. 93, 2362-2368.
51. 2 in the temperature range 253-368 K, Chem. Phys. Lett. 160, 443-447.
52. Müller, J.-F., 1992: Geographical distribution and seasonal variation of surface emissions and deposition velocities of atmospheric trace gases, J. Geophys. Res. 97, 3787-3804.
53. Neeb, P., Horie, O., and Moortgat, G. K., 1996a: Formation of secondary ozonides in the gas-phase ozonolysis of simple alkenes, Tetrahedron Letters 37, 9297-9300.
54. Neeb, P., Horie, O., and Moortgat, G. K., 1996b: Gas-phase ozonolysis of ethene in the presence of hydroxylic compounds, Int. J. Chem. Kin. 28, 721-730.
55. Neeb, P., Horie, O., and Moortgat, G. K., 1998: The ethene-ozone reaction in the gas phase, J. Phys. Chem. 102, 6778-6785.
56. Neeb, P., Sauer, F., Horie, O., and Moortgat, G. K., 1997: Formation of hydroxymethyl hydroperoxide and formic acid in alkene ozonolysis in the presence of water vapour, Atmos. Environ. 31, 1417-1423.
57. Niki, H., Maker, P. D., Savage, C. M., Breitenbach, L. P., and Hurley, M. D., 1987: FTIR spectroscopic study of the mechanism for the gas-phase reaction between ozone and tetramethyl-ethylene, J. Phys. Chem. 91, 941-946.
58. Novakov, T. and Penner, J. E., 1993: Large contribution of organic aerosols to cloud-condensation-nuclei concentrations, Nature 365, 823-826.
59. Owen, S., Boissard, C., Street, R. A., Duckham, S. C., Csiky, O., and Hewitt, C. N., 1997: Screening of 18 mediterranean plant species for volatile organic compound emissions, Atmos. Environ. 31, 101-117.
60. Palen, E. J., Allen, D. T., Pandis, S. N., Paulson, S. E., Seinfeld, J. H., and Flagan, R. C., 1992: Fourier transform infrared analysis of aerosol formed in the photooxidation of isoprene and β-pinene, Atmos. Environ. 26A, 1239-1251.
61. Phillips, B., Frostick, F. C., and Starcher, P. S., 1957: A new synthesis of peracetic acid, J. Am. Chem. Soc. 79, 5982-5986.
62. Rocklin, R. D., Pohl, C. A., and Schibler, J. A., 1987: Gradient elution in ion chromatography, J. Chromatogr. 411, 107-119.
63. Sauer, F., Schäfer, C., Neeb, P., Horie, O., and Moortgat, G. K., 1999: Formation of hydrogen peroxide in the ozonolysis of isoprene and simple alkenes under humid conditions, Atmos. Environ. 33, 229-241.
64. Schuetzle, D. and Rasmussen, R. A., 1978: The molecular composition of secondary aerosol particles formed from terpenes, J. Air Pollut. Control Assoc. 28, 236-240.
65. Simonaitis, R., Olszyna, K. J., and Meagher, J. F., 1991: Production of hydrogen peroxide and organic peroxides in the gas phase reactions of ozone with natural alkenes, Geophys. Res. Lett. 18, 9-12.
66. Street, R. A., Owen, S., Duckham, S. C., Boissard, C., and Hewitt, C. N., 1997: Effect of habitat and age on variations in volatile organic compound (VOC) emissions from Quercus Ilex and Pinus Pinea, Atmos. Environ. 31, 89-100.
67. 2-rich mixtures, J. Phys. Chem. 84, 239-246.
68. 6 dicarboxylic acids, Environ. Sci. Technol. 23, 1519-1523.
69. Veyret, B., Lesclaux, R., Rayez, M.-T., Tyndall, G. S., Cox, R. A., and Moortgat, G. K., 1989: Kinetics and mechanism of the photooxidation of formaldehyde. 1. Flash photolysis study, J. Phys. Chem. 93, 2368-2374.
70. Went, F. W., 1960: Blue hazes in the atmosphere, Nature 187, 641-643.
71. Went, F. W., 1966: On the nature of Aitken condensation nuclei, Tellus 18, 549-556.
72. Yokouchi, Y. and Ambe, Y., 1985: Aerosols formed from the chemical reaction of monoterpenes and ozone, Atmos. Environ. 19, 1271-1276.
73. Yu, J. Z., Flagan, R. C., and Seinfeld, J. H., 1998: Identification of products containing -COOH, -OH, and -C=O in atmospheric oxidation of hydrocarbons, Environ. Sci. Technol. 32, 2357-2370.
74. 2 from the oxidation of hydrocarbon emissions from vegetation, Geophys. Res. Lett. 5, 679-682.