Radical product yields from the ozonolysis of short chain alkenes under atmospheric boundary layer conditions

Journal of Physical Chemistry A

Volumn 117, Issue 47, 2013, Pages 12468-12483

  Alam, Mohammed S ^a   Rickard, Andrew R ^b,d   Camredon, Marie ^a,e   Wyche, Kevin P ^c,f   Carr, Timo ^c   Hornsby, Karen E ^c,g   Monks, Paul S ^c   Bloss, William J ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY OF LEEDS   (United Kingdom)

^c UNIVERSITY OF LEICESTER   (United Kingdom)

^d UNIVERSITY OF YORK   (United Kingdom)

^e STATION DE RADIOASTRONOMIE DE NANÇAY   (France)

^f UNIVERSITY OF BRIGHTON   (United Kingdom)

^g INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ,3-DIMETHYL-2-BUTENE; ALKENE OZONOLYSIS; ATMOSPHERIC OXIDANTS; ATMOSPHERIC SIMULATIONS; CHEMICAL AMPLIFICATION; EXPERIMENTAL DETERMINATION; GAS-PHASE REACTIONS; LASER INDUCED FLUORESCENCE;

ATMOSPHERIC BOUNDARY LAYER; ATMOSPHERIC CHEMISTRY; ATMOSPHERIC HUMIDITY; ATMOSPHERIC PRESSURE; BUTENES; ETHYLENE; OZONE; PHASE INTERFACES; VOLATILE ORGANIC COMPOUNDS;

HYDROCARBONS;

ALKENE; HYDROXYL RADICAL; OZONE; PERHYDROXYL RADICAL; PEROXIDE;

ARTICLE; ATMOSPHERE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKENES; ATMOSPHERE; HYDROXYL RADICAL; MOLECULAR STRUCTURE; OZONE; PEROXIDES;

EID: 84889064084     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp408745h     Document Type: Article

References (74)

1. Calvert, J. G.; Atkinson, R.; Kerr, J. A.; Madronich, S.; Moortgat, G. K.; Wallington, T. J.; Yarwood, G. The Mechanism of Atmospheric Oxidation of the Alkenes; Oxford University Press: New York, 2000.
2. Di Carlo, P.; Brune, W. H.; Martinez, M.; Harder, H.; Lesher, R.; Ren, X.; Thornberry, T.; Carroll, M. A.; Young, V.; Shepson, P. B. Missing OH Reactivity in a Forest: Evidence for Unknown Reactive Biogenic VOCs Science 2004, 302, 722-725
3. Johnson, D.; Marston, G. The Gas-Phase Ozonolysis of Unsaturated Volatile Organic Compounds in the Troposphere Chem. Soc. Rev. 2008, 37, 699-716
4. Emmerson, K. M.; Carslaw, N.; Carslaw, D. C.; Lee, J. D.; McFiggans, G.; Bloss, W. J.; Gravestock, T.; Heard, D. E.; Hopkins, J.; Ingham, T. Free Radical Modelling Studies during the UK TORCH Campaign in Summer 2003 Atmos. Chem. Phys. 2007, 7, 167-181
5. Criegee, R. Mechanism of Ozonolysis Angew. Chem., Int. Ed. 1975, 14, 745-752
6. Rathman, W. C. D.; Claxton, T. A.; Rickard, A. R.; Marston, G. A Theoretical Investigation of OH Formation in the Gas-Phase Ozonolysis of E -but-2-ene and Z -but-2-ene Phys. Chem. Chem. Phys. 1999, 1, 3981-3985
7. Niki, H.; Maker, P. D.; Savage, C. M.; Breitenbach, L. P.; Hurley, M. FTIR Spectroscopic Study of the Mechanism for the Gas-Phase Reaction between Ozone and Tetramethylethylene J. Phys. Chem. 1987, 91, 941-946
8. Drozd, G. T.; Kroll, J.; Donahue, N. M. 2,3-Dimethyl-2-butene (TME) Ozonolysis: Pressure Dependence of Stabilized Criegee Intermediates and Evidence of Stabilized Vinyl Hydroperoxides J. Phys. Chem. A 2011, 115, 161-166
9. Kuwata, K. T.; Hasson, A. S.; Dickinson, R. V.; Petersen, E. B.; Valin, L. C. Quantum Chemical and Master Equation Simulations of the Oxidation and Isomerization of Vinoxy Radicals J. Phys. Chem. A 2005, 109, 2514-2524
10. Fenske, D.; Hasson, A. S.; Paulson, S. E.; Kuwata, K. T.; Ho, A.; Houk, A. N. The Pressure Dependence of the OH Radical Yield from Ozone-Alkene Reactions J. Phys. Chem. A 2000, 104, 7821-7833
11. Olzmann, M.; Kraka, E.; Cremer, D.; Gutbrod, R.; Andersson, S. Energetics, Kinetics, and Product Distributions of the Reactions of Ozone with Ethene and 2,3-Dimethyl-2-butene J. Phys. Chem. A 1997, 101, 9421-9429
12. 2CHOOH: There Is a Saddle Point J. Phys. Chem. A 2012, 116, 6823-6830
13. Hatakeyama, S.; Akimoto, H. Reactions of Criegee Intermediates in the Gas Phase Res. Chem. Intermed. 1994, 20, 503-524
14. Johnson, D.; Lewin, A. G.; Marston, G. The Effect of Criegee-Intermediate Scavengers on the OH Yield from the Reaction of Ozone with 2-Methylbut-2-ene J. Phys. Chem. A 2001, 105, 2933-2935
15. 2 Science 2012, 335, 204-207
16. Mauldin, R. L., III; Berndt, T.; Sipilä, M.; Paasonen, P.; Petäjä, T.; Kim, S.; Kurtén, T.; Stratmann, F.; Kerminen, V.-M.; Kulmala, M. A New Atmospherically Relevant Oxidant of Sulphur Dioxide Nature 2012, 488, 193-197
17. 2 Phys. Chem. Chem. Phys. 2013, 15, 17070-17075
18. Finlayson, B. J.; Pitts, J. N.; Atkinson, R. Low-Pressure Gas Phase Ozone-Olefin Reactions: Chemiluminescence, Kinetics and Mechanisms J. Am. Chem. Soc. 1974, 96, 5356-5367
19. Herron, J. T.; Huie, R. E. Stopped-Flow Studies of the Mechanisms of Ozone-Alkene Reactions in the Gas Phase Propene and Isobutene Int. J. Chem. Kinet. 1978, 10, 1019-1041
20. Martinez, R. I.; Herron, J. T.; Huie, R. E. The Mechanism of Ozone-Alkene Reactions in the Gas Phase. A Mass Spectrometric Study of the Reactions of Eight Linear and Branched-Chain Alkenes J. Am. Chem. Soc. 1981, 103, 3807-3820
21. 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
22. Rickard, A. R.; Johnson, D.; McGill, C. D.; Marston, G. OH Yields in the Gas-Phase Reactions of Ozone with Alkenes J. Phys. Chem. A 1999, 103, 7656-7664
23. 3 with a Series of Terpenes J. Geophys. Res. 1992, 97, 6065-6073
24. 2 Yields from the Gas Phase Ozonolysis of Isoprene Atmos. Chem. Phys. 2010, 10, 1441-1459
25. Donahue, N. M.; Kroll, J. H.; Anderson, J. G.; Demerjian, K. L. Direct Observation of OH Production from the Ozonolysis of Olefins Geophys. Res. Lett. 1998, 25, 59-62
26. Qi, B.; Sato, K.; Imarnura, T.; Takami, A.; Hatakeyama, S.; Ma, Y. Production of the Radicals in the Ozonolysis of Ethene: A Chamber Study by FT-IR and PERCA Chem. Phys. Lett. 2006, 427, 461-465
27. Mihelcic, D.; Heitlinger, M.; Kley, D.; Musgen, P.; Volz-Thomas, A. Formation of Hydroxyl and Hydroperoxy Radicals in the Gas-Phase Ozonolysis of Ethane Chem. Phys. Lett. 1999, 301, 559-564
28. Wegener, R.; Brauers, T.; Koppmann, R.; Bares, S. R.; Rohrer, F.; Tillmann, R.; Wahner, A.; Hansel, A.; Wisthaler, A. Simulation Chamber Investigation of the Reactions of Ozone with Short-Chained Alkenes J. Geophys. Res. 2007, 112, D13301
29. Alam, M. S.; Camredon, M.; Rickard, A. R.; Carr, T.; Wyche, K. P.; Hornsby, K. E.; Monks, P. S.; Bloss, W. J. Total Radical Yields from Tropospheric Ethene Ozonolysis Phys. Chem. Chem. Phys. 2011, 13, 11002-11015
30. 3 with Alkenes and Monoterpenes J. Geophys. Res. 1996, 101, 28649-28653
31. Gutbrod, R.; Meyer, S.; Rahman, M. M.; Schindler, R. N. On the Use of CO as Scavenger for OH Radicals in the Ozonolysis of Simple Alkenes and Isoprene Int. J. Chem. Kinet. 1997, 29, 717-723
32. Kroll, J. H.; Hanisco, T. F.; Donahue, N. M.; Demerjian, K. L.; Anderson, J. G. Accurate, Direct Measurements of OH Yields from Gas-Phase Ozone-Alkene Reactions using an in Situ LIF Instrument Geophys. Res. Lett. 2001, 28, 3863-3866
33. x Formation in the Gas-Phase Ozone-Alkene Reaction. 1. Direct, Pressure-Dependent Measurements of Prompt OH Yields J. Phys. Chem. A 2001, 105, 1554-1560
34. x Formation in the Gas-Phase Ozone-Alkene Reaction. 2. Prompt versus Thermal Dissociation of Carbonyl Oxides to form OH J. Phys. Chem. A 2001, 105, 4446-4457
35. Presto, A.; Donahue, N. Ozonolysis Fragment Quenching by Nitrate Formation: The Pressure Dependence of Prompt OH Radical Formation J. Phys. Chem. A 2004, 108, 9096-9104
36. Siese, M.; Becker, K. H.; Brockmann, K. J.; Geiger, H.; Hofzumahaus, A.; Holland, F.; Milhelcic, M.; Wirtz, K. Direct Measurement of OH Radicals from Ozonolysis of Selected Alkenes: A EUPHORE Simulation Chamber Study Environ. Sci. Technol. 2001, 35, 4660-4667
37. x in the Boundary Layer Geophys. Res. Lett. 1996, 23, 3727-3730
38. Qi, B.; Yang, B.; Wang, Z. Q.; Yang, H. Y.; Liu, L. Production of Radicals in the Ozonolysis of Propene in Air Sci. China, Ser. B: Chem. 2009, 52, 356-361
39. Jenkin, M. E.; Saunders, S. M.; Pilling, M. J. The Tropospheric Degradation of Volatile Organic Compounds: A Protocol for Mechanism Development Atmos. Environ. 1997, 31, 81-104
40. Becker, K. H. In Situ Euphore Radical Measurement (EUROPHAM): Report to the European Commission, Contract ENV4-CT95-0011; Bergische Universität Wuppertal: Germany, 1999.
41. Camredon, M.; Hamilton, J. F.; Alam, M. S.; Wyche, K. P.; Carr, T.; White, I. R.; Monks, P. S.; Rickard, A. R.; Bloss, W. J. Distribution of Gaseous and Particulate Organic Composition during Dark Alphapinene Ozonolysis Atmos. Chem. Phys. 2010, 10, 2893-2917
42. Bloss, W. J.; Lee, J. D.; Bloss, C.; Heard, D. E.; Pilling, M. J.; Wirtz, K.; Martin-Reviejo, M.; Siese, M. Validation of the Calibration of a Laser-Induced Fluorescence Instrument for the Measurement of OH Radicals in the Atmosphere Atmos. Chem. Phys. 2004, 4, 571-583
43. Green, T. J.; Reeves, C. E.; Fleming, Z. L.; Brough, N.; Rickard, A. R.; Bandy, B. J.; Monks, P. S.; Penkett, S. A. An Improved Dual Channel PERCA Instrument for Atmospheric Measurements of Peroxy Radicals J. Environ. Monit. 2006, 8, 530-536
44. Aschmutat, U.; Hessling, M.; Holland, F.; Hofzumahaus, A. Physico-Chemical Behaviour of Atmospheric Pollutants; Angeletti, G.; Restelli, C.; Proc. EUR 15609; Wiley: New York, 1994; pp 811-816.
45. 2 in the Troposphere by Laser-Induced Fluorescence J. Chem. Soc., Faraday Trans. 1997, 93, 2907-2913
46. Clemitshaw, K. C.; Carpenter, L. J.; Penket, S. A.; Jenkin, M. J. A Calibrated Peroxy Radical Chemical Amplifier for Ground-Based Tropospheric Measurements J. Geophys. Res. 1997, 102, 25405-25416
47. Fleming, Z. L.; Monks, P. S.; Rickard, A. R.; Heard, D. E.; Bloss, W. J.; Seakins, P. W.; Still, T. J.; Sommariva, R.; Pilling, M. J.; Morgan, R. Peroxy Radical Chemistry and the Control of Ozone Photochemistry at Mace Head, Ireland during the Summer of 2002 Atmos. Chem. Phys. 2006, 6, 2193-2214
48. Saunders, S. M.; Jenkin, M. E.; Derwent, R. G.; Pilling, M. J. Protocol for the Development of the Master Chemical Mechanism, MCM v3 (Part A): Tropospheric Degradation of Non-Aromatic Volatile Organic Compounds Atmos. Chem. Phys. 2003, 3, 161-180
49. Curtis, A. R.; Sweetenham, W. P. Facsimile/Checkmat User's Manual; Harwell Laboratory: Oxfordshire, U.K., 1987.
50. IUPAC: Subcommittee for Gas Kinetic Data Evaluation, 1999. http://www.iupac-kinetic.ch.cam.ac.uk.
51. Alam, M. S. Ph.D. Thesis, University of Birmingham, 2011.
52. 2 and other Substituted Peroxy Radicals Atmos. Chem. Phys. 2008, 8, 4877-4889
53. 2) Radicals J. Phys. Chem. A 2004, 108, 5979-5989
54. 2 Reaction in the Gas Phase Phys. Chem. Chem. Phys. 2007, 9, 3149-3162
55. Atkinson, R.; Baulch, D. L.; Cox, R. A.; Crowley, J. N.; Hampson, R. F.; Hynes, R. G.; Jenkin, M. E.; Rossi, M. J.; Troe, J. Evaluated Kinetic and Photochemical Data for Atmospheric Chemistry: Volume II, Gas Phase Reactions of Organic Species Atmos. Chem. Phys. 2006, 6, 3625-4055
56. 3CHOO Science 2013, 340, 177-180
57. 2 in the Troposphere Chem. Rev. 2003, 103, 5163-5198
58. 2 Radicals Atmos. Meas. Tech. 2011, 4, 1209-1225
59. Atkinson, R. Gas-Phase Tropospheric Chemistry of Volatile Organic Compounds: 1. Alkanes and Alkenes J. Phys. Chem. Ref. Data 1997, 26, 215-290
60. 2 J. Phys. Chem. Lett. 2012, 3, 2892-2896
61. 2 from Alkene Ozonolysis under Humid Conditions ChemPhysChem 2002, 3, 215-221
62. Kuwata, K. T.; Hermes, M. R.; Carlson, M. J.; Zogg, C. K. Computational Studies of the Isomerization and Hydration Reactions of Acetaldehyde Oxide and Methyl Vinyl Carbonyl Oxide J. Phys. Chem. A 2010, 114, 9192-9204
63. Kroll, J. H.; Donahue, N. M.; Cee, V. J.; Demerjian, K. L.; Anderson, J. G. Gas-Phase Ozonolysis of Alkenes: Formation of OH from Anti Carbonyl Oxides J. Am. Chem. Soc. 2002, 124, 8518-8519
64. Tillmann, R.; Hallquist, M.; Jonsson, Å. M.; Kiendler-Scharr, A.; Saathoff, H.; Iinuma, Y.; Mentel, T. F. Influence of Relative Humidity and Temperature on the Production of Pinonaldehyde and OH Radicals from the Ozonolysis of Alpha-Pinene Atmos. Chem. Phys. 2010, 10, 7057-7072
65. n (n = 2,..., 4) in the Reaction of Criegee Intermediate with Water in the Atmosphere Chem. Phys. Lett. 2006, 419, 479-485
66. Lee, J. D.; Lewis, A. C.; Monks, P. S.; Jacob, M.; Hamilton, J. F.; Hopkins, J. R.; Watson, N. M.; Saxton, J. E.; Ennis, C.; Carpenter, L. J. Ozone Photochemistry and Elevated Isoprene during the UK Heatwave of August 2003 Atmos. Environ. 2006, 40, 7598-7613
67. 2 Chemistry in the Urban Atmosphere of New York City Atmos. Environ. 2003, 37, 3639-3651
68. 3 with a Series of Alkenes under Atmospheric Conditions Environ. Sci. Technol. 1993, 27, 1357-1363
69. 3: Yields and Mechanistic Implications J. Phys. Chem. A 1999, 103, 9003-9012
70. 3 with Cyclohexene J. Phys. Chem. A 2003, 107, 2247-2255
71. Horie, O.; Neep, P.; Moortgat, G. K. Ozonolysis of trans -2-Butenes and cis -2-Butenes in Low Parts-Per-Million Concentration Ranges Int. J. Chem. Kinet. 1994, 26, 1075-1094
72. McGill, D. D.; Rickard, A. R.; Johnson, D.; Marston, G. Product Yields in the Reactions of Ozone with Z -but-2-ene, E -but-2-ene and 2-Methylbut-2-ene Chemosphere 1999, 38, 1205-1212
73. Orzechowska, G. E.; Paulson, S. E. Production of OH Radicals from the Reactions of C4-C6 Internal Alkenes and Styrenes with Ozone in the Gas Phase Atmos. Environ. 2002, 36, 571-581
74. Hasson, A. S.; Chung, M. Y.; Kuwata, K. T.; Converse, A. D.; Krohn, D.; Paulson, S. E. Reaction of Criegee Intermediates with Water Vapor: An Additional Source of OH Radicals in Alkene Ozonolysis? J. Phys. Chem. A 2003, 107, 6176-6182