Influence of molecular structure and chemical functionality on the heterogeneous OH-initiated oxidation of unsaturated organic particles

Journal of Physical Chemistry A

Volumn 118, Issue 23, 2014, Pages 4106-4119

  Nah, Theodora ^a,b   Kessler, Sean H ^c   Daumit, Kelly E ^c   Kroll, Jesse H ^c   Leone, Stephen R ^a,b   Wilson, Kevin R ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^c Massachusetts Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AEROSOLS; CHAINS; CHEMICAL BONDS; MOLECULAR STRUCTURE; OXIDATION;

CHAIN PROPAGATION; CHAIN TERMINATIONS; CHEMICAL FUNCTIONALITY; FRAGMENTATION REACTIONS; MEASUREMENTS OF; ORGANIC AEROSOL; ORGANIC PARTICLES; UPTAKE COEFFICIENTS;

LINOLEIC ACID;

EID: 84902489067     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp502666g     Document Type: Article

References (55)

1. Finlayson-Pitts, B. J.; Pitts, J. N. Chemistry of the Upper and Lower Atmosphere: Theory, Experiments, and Applications; Academic Press: San Diego, 2000.
2. Hallquist, M.; Wenger, J. C.; Baltensperger, U.; Rudich, Y.; Simpson, D.; Claeys, M.; Dommen, J.; Donahue, N. M.; George, C.; Goldstein, A. H. The Formation, Properties and Impact of Secondary Organic Aerosol: Current and Emerging Issues Atmos. Chem. Phys. 2009, 9, 5155-5236
3. Rudich, Y. Laboratory Perspectives on the Chemical Transformations of Organic Matter in Atmospheric Particles Chem. Rev. 2003, 103, 5097-5124
4. Jimenez, J. L.; Canagaratna, M. R.; Donahue, N. M.; Prevot, A. S. H.; Zhang, Q.; Kroll, J. H.; DeCarlo, P. F.; Allan, J. D.; Coe, H.; Ng, N. L. Evolution of Organic Aerosols in the Atmosphere Science 2009, 326, 1525-1529
5. Ng, N. L.; Canagaratna, M. R.; Zhang, Q.; Jimenez, J. L.; Tian, J.; Ulbrich, I. M.; Kroll, J. H.; Docherty, K. S.; Chhabra, P. S.; Bahreini, R. Organic Aerosol Components Observed in Northern Hemispheric Datasets from Aerosol Mass Spectrometry Atmos. Chem. Phys. 2010, 10, 4625-4641
6. Robinson, A. L.; Donahue, N. M.; Rogge, W. F. Photochemical Oxidation and Changes in Molecular Composition of Organic Aerosol in the Regional Context J. Geophys. Res, D: Atmos. 2006, 111, D03302
7. Atkinson, R. Gas-Phase Tropospheric Chemistry of Organic-Compounds J. Phys. Chem. Ref. Data 1994, R1-R216
8. Atkinson, R. Gas-Phase Tropospheric Chemistry of Volatile Organic Compounds 0.1. Alkanes and Alkenes J. Phys. Chem. Ref. Data 1997, 26, 215-290
9. Atkinson, R. Kinetics of the Gas-Phase Reactions of OH Radicals with Alkanes and Cycloalkanes Atmos. Chem. Phys. 2003, 3, 2233-2307
10. Atkinson, R.; Arey, J. Atmospheric Degradation of Volatile Organic Compounds Chem. Rev. 2003, 103, 4605-4638
11. Kwok, E. S. C.; Atkinson, R. Estimation of Hydroxyl Radical Reaction-Rate Constants for Gas-Phase Organic-Compounds Using a Structure-Reactivity Relationship-An Update Atmos. Environ. 1995, 29, 1685-1695
12. Peeters, J.; Boullart, W.; Pultau, V.; Vandenberk, S.; Vereecken, L. Structure-Activity Relationship for the Addition of OH to (Poly)Alkenes: Site-Specific and Total Rate Constants J. Phys. Chem. A 2007, 111, 1618-1631
13. Moise, T.; Rudich, Y. Uptake of Cl and Br by Organic-A Perspective on Organic Aerosols Processing by Tropospheric Oxidants Geophys. Res. Lett. 2001, 28, 4083-4086
14. Liu, C. L.; Smith, J. D.; Che, D. L.; Ahmed, M.; Leone, S. R.; Wilson, K. R. The Direct Observation of Secondary Radical Chain Chemistry in the Heterogeneous Reaction of Chlorine Atoms with Submicron Squalane Droplets Phys. Chem. Chem. Phys. 2011, 13, 8993-9007
15. Ruehl, C. R.; Nah, T.; Isaacman, G.; Worton, D. R.; Chan, A. W. H.; Kolesar, K. R.; Cappa, C. D.; Goldstein, A. H.; Wilson, K. R. The Influence of Molecular Structure and Aerosol Phase on the Heterogeneous Oxidation of Normal and Branched Alkanes by OH J. Phys. Chem. A 2013, 117, 3990-4000
16. Kroll, J. H.; Donahue, N. M.; Jimenez, J. L.; Kessler, S. H.; Canagaratna, M. R.; Wilson, K. R.; Altieri, K. E.; Mazzoleni, L. R.; Wozniak, A. S.; Bluhm, H. Carbon Oxidation State as a Metric for Describing the Chemistry of Atmospheric Organic Aerosol Nat. Chem. 2011, 3, 133-139
17. Kroll, J. H.; Smith, J. D.; Che, D. L.; Kessler, S. H.; Worsnop, D. R.; Wilson, K. R. Measurement of Fragmentation and Functionalization Pathways in the Heterogeneous Oxidation of Oxidized Organic Aerosol Phys. Chem. Chem. Phys. 2009, 11, 8005-8014
18. Wilson, K. R.; Smith, J. D.; Kessler, S. H.; Kroll, J. H. The Statistical Evolution of Multiple Generations of Oxidation Products in the Photochemical Aging of Chemically Reduced Organic Aerosol Phys. Chem. Chem. Phys. 2012, 14, 1468-1479
19. Kessler, S. H.; Smith, J. D.; Che, D. L.; Worsnop, D. R.; Wilson, K. R.; Kroll, J. H. Chemical Sinks of Organic Aerosol: Kinetics and Products of the Heterogeneous Oxidation of Erythritol and Levoglucosan Environ. Sci. Technol. 2010, 44, 7005-7010
20. Isaacman, G.; Chan, A. W. H.; Nah, T.; Worton, D. R.; Ruehl, C. R.; Wilson, K. R.; Goldstein, A. H. Heterogeneous OH Oxidation of Motor Oil Particles Causes Selective Depletion of Branched and Less Cyclic Hydrocarbons Environ. Sci. Technol. 2012, 46, 10632-10640
21. Nah, T.; Kessler, S. H.; Daumit, K. E.; Kroll, J. H.; Leone, S. R.; Wilson, K. R. OH-Initiated Oxidation of Sub-Micron Unsaturated Fatty Acid Particles Phys. Chem. Chem. Phys. 2013, 15, 18649-18663
22. Gloaguen, E.; Mysak, E. R.; Leone, S. R.; Ahmed, M.; Wilson, K. R. Investigating the Chemical Composition of Mixed Organic-Inorganic Particles by Soft Vacuum Ultraviolet Photoionization: The Reaction of Ozone with Anthracene on Sodium Chloride Particles Int. J. Mass Spectrom. 2006, 258, 74-85
23. Aiken, A. C.; DeCarlo, P. F.; Jimenez, J. L. Elemental Analysis of Organic Species with Electron Ionization High-Resolution Mass Spectrometry Anal. Chem. 2007, 79, 8350-8358
24. Aiken, A. C.; Decarlo, P. F.; Kroll, J. H.; Worsnop, D. R.; Huffman, J. A.; Docherty, K. S.; Ulbrich, I. M.; Mohr, C.; Kimmel, J. R.; Sueper, D. O/C and Om/Oc Ratios of Primary, Secondary, and Ambient Organic Aerosols with High-Resolution Time-of-Flight Aerosol Mass Spectrometry Environ. Sci. Technol. 2008, 42, 4478-4485
25. DeCarlo, P. F.; Kimmel, J. R.; Trimborn, A.; Northway, M. J.; Jayne, J. T.; Aiken, A. C.; Gonin, M.; Fuhrer, K.; Horvath, T.; Docherty, K. S. Field-Deployable, High-Resolution, Time-of-Flight Aerosol Mass Spectrometer Anal. Chem. 2006, 78, 8281-8289
26. Jayne, J. T.; Leard, D. C.; Zhang, X. F.; Davidovits, P.; Smith, K. A.; Kolb, C. E.; Worsnop, D. R. Development of an Aerosol Mass Spectrometer for Size and Composition Analysis of Submicron Particles Aerosol Sci. Technol. 2000, 33, 49-70
27. Smith, J. D.; Kroll, J. H.; Cappa, C. D.; Che, D. L.; Liu, C. L.; Ahmed, M.; Leone, S. R.; Worsnop, D. R.; Wilson, K. R. The Heterogeneous Reaction of Hydroxyl Radicals with Sub-Micron Squalane Particles: A Model System for Understanding the Oxidative Aging of Ambient Aerosols Atmos. Chem. Phys. 2009, 9, 3209-3222
28. Hearn, J. D.; Smith, G. D.; Mixed-Phase, A. Relative Rates Technique for Measuring Aerosol Reaction Kinetics Geophys. Res. Lett. 2006, 33, L17895
29. 3 Radicals: Products, Mechanism, and Implications for Radical-Initiated Organic Aerosol Oxidation J. Phys. Chem. A 2006, 110, 3567-3577
30. George, I. J.; Abbatt, J. P. D. Heterogeneous Oxidation of Atmospheric Aerosol Particles by Gas-Phase Radicals Nat. Chem. 2010, 2, 713-722
31. George, I. J.; Vlasenko, A.; Slowik, J. G.; Broekhuizen, K.; Abbatt, J. P. D. Heterogeneous Oxidation of Saturated Organic Aerosols by Hydroxyl Radicals: Uptake Kinetics, Condensed-Phase Products, and Particle Size Change Atmos. Chem. Phys. 2007, 7, 4187-4201
32. McNeill, V. F.; Yatavelli, R. L. N.; Thornton, J. A.; Stipe, C. B.; Landgrebe, O. Heterogeneous OH Oxidation of Palmitic Acid in Single Component and Internally Mixed Aerosol Particles: Vaporization and the Role of Particle Phase Atmos. Chem. Phys. 2008, 8, 5465-5476
33. Atkinson, R.; Tuazon, E. C.; Aschmann, S. M. Products of the Gas-Phase Reaction of the OH Radical with 3-Methyl-1-Butene in the Presence of NO Int. J. Chem. Kinet. 1998, 30, 577-587
34. Atkinson, R.; Tuazon, E. C.; Carter, W. P. L. Extent of H-Atom Abstraction from the Reaction of the OH Radical with 1-Butene under Atmospheric Conditions Int. J. Chem. Kinet. 1985, 17, 725-734
35. D'andrea, T. M.; Zhang, X.; Jochnowitz, E. B.; Lindeman, T. G.; Simpson, C. J. S. M.; David, D. E.; Curtiss, T. J.; Morris, J. R.; Ellison, G. B. Oxidation of Organic Films by Beams of Hydroxyl Radicals J. Phys. Chem. B 2008, 112, 535-544
36. Moussa, S. G.; Finlayson-Pitts, B. J. Reaction of Gas Phase OH with Unsaturated Self-Assembled Monolayers and Relevance to Atmospheric Organic Oxidations Phys. Chem. Chem. Phys. 2010, 12, 9419-9428
37. 2: A Model for Radical-Initiated Oxidation of Organic Aerosols Phys. Chem. Chem. Phys. 2007, 9, 4803-4813
38. Ingold, K. U. Peroxy Radicals Acc. Chem. Res. 1969, 2, 1-9
39. von Sonntag, C.; Dowideit, P.; Fang, X. W.; Mertens, R.; Pan, X. M.; Schuchmann, M. N.; Schuchmann, H. P. The Fate of Peroxyl Radicals in Aqueous Solution Water Sci. Technol. 1997, 35, 9-15
40. von Sonntag, C.; Schuchmann, H. P. The Elucidation of Peroxyl Radical Reactions in Aqueous Solution with the Help of Radiation-Chemical Methods Angew. Chem., Int. Ed. Engl. 1991, 30, 1229-1253
41. Waring, C.; King, K. L.; Bagot, P. A. J.; Costen, M. L.; McKendrick, K. G. Collision Dynamics and Reactive Uptake of Oh Radicals at Liquid Surfaces of Atmospheric Interest Phys. Chem. Chem. Phys. 2011, 13, 8457-8469
42. Lide, D. R. CRC Handbook of Chemistry and Physics, 85 th ed.; CRC Press Inc LLC: 2004.
43. Tesa-Serrate, M. A.; King, K. L.; Paterson, G.; Costen, M. L.; McKendrick, K. G. Site and Bond-Specific Dynamics of Reactions at the Gas-Liquid Interface Phys. Chem. Chem. Phys. 2014, 16, 173-183
44. Renbaum, L. H.; Smith, G. D. Artifacts in Measuring Aerosol Uptake Kinetics: The Roles of Time, Concentration and Adsorption Atmos. Chem. Phys. 2011, 11, 6881-6893
45. DeCarlo, P. F.; Slowik, J. G.; Worsnop, D. R.; Davidovits, P.; Jimenez, J. L. Particle Morphology and Density Characterization by Combined Mobility and Aerodynamic Diameter Measurements. Part 1: Theory Aerosol Sci. Technol. 2004, 38, 1185-1205
46. Hearn, J. D.; Lovett, A. J.; Smith, G. D. Ozonolysis of Oleic Acid Particles: Evidence for a Surface Reaction and Secondary Reactions Involving Criegee Intermediates Phys. Chem. Chem. Phys. 2005, 7, 501-511
47. Iwahashi, M.; Kasahara, Y. Dynamic Molecular Movements and Aggregation Structures of Lipids in a Liquid State Curr. Opin. Colloid Interface Sci. 2011, 16, 359-366
48. Iwahashi, M.; Kasahara, Y.; Matsuzawa, H.; Yagi, K.; Nomura, K.; Terauchi, H.; Ozaki, Y.; Suzuki, M. Self-Diffusion, Dynamical Molecular Conformation, and Liquid Structures of N-Saturated and Unsaturated Fatty Acids J. Phys. Chem. B 2000, 104, 6186-6194
49. King, K. L.; Paterson, G.; Rossi, G. E.; Iljina, M.; Westacott, R. E.; Costen, M. L.; McKendrick, K. G. Inelastic Scattering of OH Radicals from Organic Liquids: Isolating the Thermal Desorption Channel Phys. Chem. Chem. Phys. 2013, 15, 12852-12863
50. Banco, M. B.; Barnes, I.; Wiesen, P. Kinetic Investigation of the OH Radical and Cl Atom Initiated Degradation of Unsaturated Ketones at Atmospheric Pressure and 298 K J. Phys. Chem. A 2012, 116, 6033-6040
51. Smith, I. W. M.; Ravishankara, A. R. Role of Hydrogen-Bonded Intermediates in the Bimolecular Reactions of the Hydroxyl Radical J. Phys. Chem. A 2002, 106, 4798-4807
52. Mellouki, A.; Le Bras, G.; Sidebottom, H. Kinetics and Mechanisms of the Oxidation of Oxygenated Organic Compounds in the Gas Phase Chem. Rev. 2003, 103, 5077-5096
53. Orlando, J. J.; Tyndall, G. S.; Ceazan, N. Rate Coefficients and Product Yields from Reaction of Oh with 1-Penten-3-ol, (Z)-2-Penten-1-ol, and Allyl Alcohol (2-Propen-1-ol) J. Phys. Chem. A 2001, 105, 3564-3569
54. Papagni, C.; Arey, J.; Atkinson, R. Rate Constants for the Gas-Phase Reactions of Oh Radicals with a Series of Unsaturated Alcohols Int. J. Chem. Kinet. 2001, 33, 142-147
55. Ziemann, P. J. Effects of Molecular Structure on the Chemistry of Aerosol Formation from the Oh-Radical-Initiated Oxidation of Alkanes and Alkenes Int. Rev. Phys. Chem. 2011, 30, 161-195