Production of stabilized Criegee intermediates and peroxides in the gas phase ozonolysis of alkenes 1. Ethene, trans-2-butene, and 2,3-dimethyl-2-butene

Journal of Geophysical Research Atmospheres

Volumn 106, Issue D24, 2001, Pages 34131-34142

  Hasson, Alam S ^a,b   Orzechowska, Grazyna ^a   Paulson, Suzanne E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ATMOSPHERIC CHEMISTRY; CHEMICAL REACTION; HYDROGEN PEROXIDE; OZONE;

EID: 0035728341     PISSN: 01480227     EISSN: None     Source Type: Journal    
DOI: 10.1029/2001JD000597     Document Type: Article

References (53)

1. Atkinson, R., Gas-phase tropospheric chemistry of volatile organic compounds: 1. Alkanes and alkenes, J. Phys. Chem. Ref. Data, 26(2), 215-290, 1997.
2. 3 with a series of terpenes, J. Geophys. Res. D, 97(D5), 6065-6073, 1992.
3. Bach, R., A. Owensby, J. Andres, and H. Schlegel, Electronic structure and reactivity of dioxirane and carbonyl oxide, J. Am. Chem. Soc., 114, 7207-7217, 1992.
4. Becker, K. H., J. Bechara, and K. J. Brockmann, Studies of the formation of H2O2 in the ozonolysis of alkenes, Atmos. Environ. Part A, 27, 57-61, 1993.
5. 2 diluent, J. Phys. Chem., 99(12), 4071-4077, 1995.
6. 2, and OH from carbonyl oxide in the presence of water vapor: A theoretical study of the reaction mechanism, Chem. Eur. J., 7(10), 2227-2235, 2001.
7. Criegee, R., Mechanism of ozonolysis, Agew. Chem. Int. Ed., 14, 745-752, 1975.
8. Criegee, R., and G. Wenner, Liebigs. Ann. Chem., 564, 9, 1949.
9. Donahue, N. M., J. H. Kroll, J. G. Anderson, and K. L. Demerjian, Direct observation of OH production from the ozonolysis of olefins, Geophys. Res. Lett., 25(1), 59-62, 1998.
10. 3CHOO generated by the trans-2-butene reaction with ozone in the gas-phase, J. Phys. Chem. A, 104(44), 9921-9932, 2000a.
11. Fenske, J. D., A. S. Hasson, S. E. Paulson, K. T. Kuwata, A. Ho, and K. N. Houk, Pressure dependence of the OH yield from ozone-alkene aeactions, J. Phys. Chem. A, 104(33), 7821-7833, 2000b.
12. Friedlander, S. K., and E. K. Yeh, The submicron atmospheric aerosol as a carrier of reactive chemical species: Case of peroxides, Appl. Occup. Environ. Hyg., 13(6), 416-420, 1998.
13. Gab, S., E. Hellpointner, W. V. Turner, and F. Korte, Hydroxymethyl hydroperoxide and bis(hydroxymethyl) peroxide from gas phase ozonolysis of naturally-occurring Alkenes, Nature, 316, 535-536, 1985.
14. Greenspan, F. P., The convenient preparation of peracids, J. Am. Chem. Soc., 907, 1946.
15. Gunz, D. W., and M. R. Hoffmann, Atmospheric chemistry of peroxides: A review, Atmos. Environ., Part A, 24(7), 1601-1633, 1990.
16. Gutbrod, R., R. N. Schindler, E. Kraka, and D. Cremer, Formation of OH radicals in the gas phase ozonolysis of alkenes, the unexpected role of carbonyl oxides, Chem. Phys. Lett., 252, 221-229, 1996.
17. Hartkamp, H., and P. Bachhausen, A method for the determination of hydrogen peroxide in air, Atmos. Environ., 21(10), 2207-2213, 1987.
18. Hasson, A. S., A. .W. Ho, K. T. Kuwata, and S. E. Paulson, Production of stabilized Criegee intermediates and peroxides in the gas phase ozonolysis of alkenes, 2, Asymmetric and biogenic alkenes, J. Geophys. Res., this issue.
19. Hatakeyama, S., and H. Akimoto, Reactions of Criegee intermediates in the gas phase, Res. Chem. Intermed., 20, 503-524, 1994.
20. Hatakeyama, S., H. Lai, and K. Murano, Formation of 2-hydroxyethyl hydroperoxide in an OH-initiated reaction of ethylene in air in the absence of NO, Environ. Sci. Technol., 29(3), 833-835, 1995.
21. Hewitt, C.N. and G.L. Kok, Formation and occurrence of organic hydroperoxides in the troposphere: Laboratory and field observations, J. Atmos. Chem., 12, 181-194, 1991.
22. Horie, O., and G. K. Moortgat, Gas-phase ozonolysis of alkenes: Recent advances in mechanistic investigations, Acc. Chem. Res., 31, 387-396, 1998.
23. Horie, O., P. Neeb, S. Limbach, and G. K. Moortgat, Formation of formic acid and organic peroxides in the ozonolysis of ethene with added water vapor, Geophys. Res. Lett., 21(14), 1523-1526, 1994.
24. Horie, O., C. Schafer, and G. K. Moortgat, High reactivity of hexafluoro acetone toward Criegee intermediates in the gas-phase ozonolysis of simple alkenes, Int. J. Chem. Kinet., 31(4), 261-269, 1999.
25. Jackson, A. V., and C. N. Hewitt, Atmosphere hydrogen peroxide and organic hydroperoxides: A review, Critical Rev. in Environ. Sci. Technol., 29(2), 175-228, 1999.
26. Jeffries, H. E., Composition, Chemistry and Climate of the Atmosphere, Van Nostrand Reinhold, New York, 1995.
27. Jenkin, M. E., R. A. Cox, M. Emrich, and G. K. Moortgat, Mechanisms of the Cl-atom-initiated oxidation of acetone and hydroxyacetone in Air, J. Chem. Soc. Faraday Trans., 89(16), 2983-2991, 1993.
28. Johnson, D., A. G. Lewin, and G. Marston, The Effect of Criegee-intermediate scavengers on the OH yield from the reaction of ozone with 2-methylbut-2-ene, J. Phys. Chem. A, 105(13), 2933-2935, 2001.
29. Kan, C., F. Su, J. G. Calvert, and J. H. Shaw, Mechanism of the ozone-ethene reaction in dilute N2/O2 mixtures near 1-atm pressure, J. Phys. Chem., 85, 2359-2363, 1981.
30. Khare, P., N. Kumar, K. M. Kumari, and S. S. Srivastava, Atmospheric formic and acetic acids: An overview, Rev. Geophys., 37(2), 227-248, 1999.
31. Kok, G. L., S. E. McLaren, and T. A. Staffelbach, HPLC determination of atmospheric organic hydroperoxides, J. Atmos. Oceanic Technol., 12, 282-289, 1995.
32. x formation in the gas-phase ozone-alkene reaction. 1. Direct, pressure dependent measurement of prompt OH yields., J. Phys. Chem. A, 105(9), 1554-1560, 2001a.
33. x formation in the gas-phase ozone-alkene reaction. 2. Prompt versus thermal decomposition of carbonyl oxides to form OH., J. Phys. Chem. A, 105(18), 4446-4457, 2001b.
34. Lee, M., B. G. Heikes, and D. W. O'Sullivan, Hydrogen peroxide and organic hydroperoxide in the troposphere: a review, Atmos. Environ., 34, 3475-3494, 2000.
35. Mihelcic, D., M. Heitlinger, D. Kley, P. Musgen, and A. Volz-Thomas, Formation of hydroxyl and hydroperoxy radicals in the gas-phase ozonolysis of ethene, Chem. Phys. Lett., 301, 559-564, 1999.
36. Neeb, P., O. Horie, and G. K. Moortgat, Gas phase ozonolysis of ethene in the presence of hydroxylic compounds, Int. J. Chem. Kinet., 28, 721-730, 1996.
37. Neeb, P., F. Sauer, O. Horie, and G. K. Moortgat, Formation of hydroymethyl hydroperoxide and formic acid in alkene ozonolysis in the presence of water vapour, Atmos. Environ., 31(10), 1417-1423, 1997.
38. Niki, H., P. D. Maker, C. M. Savage, and L. P. Breitenbach, A FTIR study of a transitory product in the gas-phase ozone-ethylene reaction, J. Phys. Chem., 85, 1024-1027, 1981.
39. Olzmann, M., E. Kraka, D. Cremer, R. Gutbrod, and S. Anderson, Energetics, kinetics, and product distributions of the reactions of ozone with ethene and 2,3-dimethyl-2-butene, J. Phys. Chem. A, 101, 9421-9429, 1997.
40. Paulson, S. E., M. Y. Chung, and A. S. Hasson, OH Radical formation from the gas-phase reaction of ozone with terminal alkenes, and the relationship between structure and mechanism, J. Phys. Chem. A, 103(41), 8125-8138, 1999.
41. Paulson, S. E., R. C. Flagan, and J. H. Seinfeld, Atmospheric oxidation of isoprene. 2. The ozone-isoprene reaction, Int. J. Chem. Kinet., 24(1), 103-125, 1992.
42. Pun, B. K., C. Seigneur, D. Grosjean, and P. Saxena, Gas-phase formation of water soluble organic compounds in the atmosphere: A retrosynthetic analysis, J. Atmos. Chem., 35(2), 199-223, 2000.
43. Reiche, A., and F. Hitz, Monomethyl hydroperoxides, Ber. Bunsen Ges. Phys. Chem., 2458-2472, 1929.
44. Rickard, A. R., D. Johnston, C. D. McGill, and G. Marston, OH yields in the gas-phase reactions of ozone with alkenes, J. Phys. Chem. A, 103(38), 7656-7664, 1999.
45. 2 and organic peroxides in laboratory and field studies using reversed phase high performance liquid chromatography with enzymatic post-column derivatisation, Ph.D. thesis, Johannes-Gutenberg, Mainz, Germany, 1997.
46. Sauer, F., C. Schafer, P. Neeb, O. Horie, and G. K. Moortgat, Formation of hydrogen peroxide in the ozonolysis of isoprene and simple alkenes under humid conditions, Atmos. Environ., 33, 229-241, 1999.
47. Saxena, P., and L. M. Hildemann, Water soluble organics in atmospheric particles: A critical review of the literature and application of thermodynamics to identify candidate compounds J. Atmos. Chem., 24, 57-109, 1996.
48. Scanlon, J. T., and D. E. Willis, Calculation of flame ionization detector relative response factors using the effective carbon number concept, J. Chromatogr. Sci., 23, 333-340, 1985.
49. Simonaitis, R., K. L. Olszyna, and J. F. Meagher, Production of hydrogen peroxides and organic peroxides in the gas phase reactions of ozone with natural alkenes, Geophys. Res. Lett., 18(1), 9-12, 1991.
50. Williams, H. R., and H. S. Mosher, Peroxides. I n-Alkyl hydroperoxides, J. Am. Chem. Soc., 2984-2987, 1954.
51. Su, F., J. G. Calvert, and J. H. Shaw, A FTIR spectroscopic study of the ozone-ethene reaction mechanism in O2 rich mixtures, J. Phys. Chem., 84, 239-246, 1980.
52. Winterhalter, R., P. Neeb, D. Grossmann, A. Kolloff, O. Horie, and G. Moortgat, Products and Mechanism of the Gas Phase Reaction of Ozone with Beta-Pinene, J. Atmos. Chem., 35, 165-197, 2000.
53. Wolff, S., A. Boddenberg, J. Thamm, W. V. Turner, and S. Gab, Gas phase ozonolysis of ethene in the presence of carbonyl oxide scavengers, Atmos. Environ., 31(18), 2965-2969, 1997.