Citation:
PAN Shan-Shan, WANG Li-Ming. The Atmospheric Oxidation Mechanism of o-Xylene Initiated by Hydroxyl Radicals[J]. Acta Physico-Chimica Sinica,
;2015, 31(12): 2259-2268.
doi:
10.3866/PKU.WHXB201510152
-
The atmospheric oxidation mechanism of o-xylene (oX) initiated by hydroxyl (OH) radicals has been investigated by using quantum chemistry, transition state theory, and unimolecular theory (RRKMME) calculations. Molecular structures of reactants, transition states, and products are optimized at M06- 2X/6-311++G(2df, 2p) level, and the electronic energies are calculated at the ROCBS-QB3 level. The classical transition state theory is employed to predict the rates or rate constants for all the reaction steps as well as the branching ratios of the reaction pathways. RRKM-ME calculations are employed to explore the pressure-dependence of the reaction kinetics. Under atmospheric conditions, the oxidation of o-Xylene is dominated by OH addition to the C1 and C3 positions, forming adducts oX-1-OH (R1) and oX-3-OH (R3), which will readily react with atmospheric oxygen. The reactions of R1 and R3 with O2 can proceed by irreversible H-abstraction to dimethylphenols (R3 only), or by reversible addition to form bicyclic radicals,which recombine with atmospheric oxygen to form bicyclic peroxy radicals (BPRs). BPRs will react with NO and/or HO2 in the atmosphere, forming organonitrate, hydroperoxides (ROOH), and bicyclic alkoxy radicals (BARs), of which the BARs eventually transfer to the final products, including biacetyl, butenedial, methylglyoxal, 4-oxo-2-pentenal, epoxy-2,3-butenedial, and a small amount of glyoxal. The products ROOH and methylglyoxal are considered to contribute to the formation of secondary organic aerosols. A new oxidation mechanism of oX in the atmosphere is proposed, based on the current theoretical predictions and previous experimental measurements, and the predicted product yields under high NO conditions are compared with previous experimental measurements. The effect of temperature on the oxidation mechanism is also discussed.
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[1]
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[1]
(1) Huang, C.; Chen, C. H.; Li, L.; Cheng, Z.; Wang, H. L.; Huang, H. Y.; Streets, D. G.; Wang, Y. J.; Zhang, G. F.; Chen, Y. R. Atmos. Chem. Phys. 2011, 11, 4105.
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[2]
(2) Zheng, J.; Shao, M.; Che, W.; Zhang, L.; Zhong, L.; Zhang, Y.; Street, D. Environ. Sci. Technol. 2009, 43, 8580. doi: 10.1021/es901688e
-
[3]
(3) Li, L.; Wang, X. M. Int. J. Environ. Res. Public Health 2012, 9, 1859. doi: 10.3390/ijerph9051859
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[4]
(4) Izumi, K.; Fukuyama, T. Atmos. Environ. A 1990, 24, 1433. doi: 10.1016/0960-1686(90)90052-O
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[5]
(5) Odum, J. R.; Jungkamp, T. P. W.; Griffin, R. J.; Flagan, R. C.; Seinfeld, J. H. Science 1997, 276, 96. doi: 10.1126/science.276.5309.96
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[6]
(6) Borras, E.; Tortajada-Genaro, L. A. Atmospheric Environment 2012, 47, 154. doi: 10.1016/j.atmosenv.2011.11.020
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[7]
(7) Martin-Reviejo, M.; Wirtz, K. Environ. Sci. Technol. 2005, 39, 1045. doi: 10.1021/es049802a
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[8]
(8) Derwent, R. G.; Jenkin, M. E.; Passant, N. R.; Pilling, M. J. Environ. Sci. Policy 2007, 10, 445. doi: 10.1016/j.envsci.2007.01.005
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[9]
(9) Carter, W. P. L. J. Air Waste Manage. Assoc. 1994, 44, 881.
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[10]
(10) Carter, W. P. L.; Pierce, J. R.; Luo, D.; Malkina, I. L. Atmos. Environ. 1995, 29, 2499. doi: 10.1016/1352-2310(95)00149-S
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(11) Hao, J. M.; Lü , Z. F.; Chu, B. W.; Wu, S.; Zhao, Z. Characterization, Experimental Study, and Modeling of Atmospheric Secondary Organic Aerosol; Science Press: Beijing, 2015. [郝吉明, 吕子峰, 楚碧武, 武山, 赵喆. 大气二次有机气溶胶污染特征及模拟研究. 北京: 科学出版社, 2015.]
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[12]
(12) Henze, D. K.; Seinfeld, J. H.; Ng, N. L.; Kroll, J. H.; Fu, T. M.; Jacob, D. J.; Heald, C. L. Atmos. Chem. Phys. 2008, 8, 2405.
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[13]
(13) Atkinson, R.; Aschmann, S. M. Int. J. Chem. Kinet. 1989, 21, 355.
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[14]
(14) Anderson, R. S.; Czuba, E.; Ernst, D.; Huang, L.; Thompson, A. E.; Rudolph, J. J. Phys. Chem. A 2003, 107, 6191. doi: 10.1021/jp034256d
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[15]
(15) Mehta, D.; Nguyen, A.; Montenegro, A.; Li, Z. J. Phys. Chem. A 2009, 113, 12942. doi: 10.1021/jp905074j
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[16]
(16) Atkinson, R.; Aschmann, S. M.; Arey, J. Int. J. Chem. Kinet. 1991, 23, 77.
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[17]
(17) Koch, R.; Knispel, R.; Elend, M.; Siese, M.; Zetzsch, C. Atmos. Chem. Phys. 2007, 7, 2057. doi: 10.5194/acp-7-2057-2007
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[18]
(18) Nishino, N.; Arey, J.; Atkinson, R. J. Phys. Chem. A 2010, 114, 10140. doi: 10.1021/jp105112h
-
[19]
(19) Bloss, C.; Wagner, V.; Jenkin, M. E.; Volkamer, R.; Bloss, W. J.; Lee, J. D.; Heard, D. E.; Wirtz, K.; Martin-Reviejo, M.; Rea, G.; Wenger, J. C.; Pilling, M. J. Atmos. Chem. Phys. 2005, 5, 641. doi: 10.5194/acp-5-641-2005
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[20]
(20) Carter, W. P. L. Atmos. Environ. 2007, 44, 5324.
-
[21]
(21) Carter, W. P. L.; Heo, G. Atmos. Environ. 2013, 77, 404. doi: 10.1016/j.atmosenv.2013.05.021
-
[22]
(22) Bandow, H.; Washida, N.; Akimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2531. doi: 10.1246/bcsj.58.2531
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[23]
(23) Tuazon, E. C.; Leod, H. M.; Atkinson, R.; Carter, W. P. L. Environ. Sci. Technol. 1986, 20, 383. doi: 10.1021/es00146a010
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[24]
(24) Arey, J.; Obermeyer, G.; Aschmann, S. M.; Chattopadhyay, S.; Cusick, R. D.; Atkinson, R. Environ. Sci. Technol. 2009, 43, 683. doi: 10.1021/es8019098
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[25]
(25) Shepson, P. B.; Edney, E. O.; Corse, E. W. J. Phys. Chem. 1984, 88, 4122. doi: 10.1021/j150662a053
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[26]
(26) Huang, M.; Zhang, W.; Wang, Z.; Hao, L.; Zhao, W.; Liu, X.; Long, B.; Fang, L. Int. J. Quantum Chem. 2008, 108, 954.
-
[27]
(27) Glowacki, D. R.; Wang, L.; Pilling, M. J. J. Phys. Chem. A 2009, 113, 5385. doi: 10.1021/jp9001466
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[28]
(28) Wang, L.; Wu, R.; Xu, C. J. Phys. Chem. A 2013, 117, 14163.
-
[29]
(29) Wu, R.; Pan, S.; Li, Y.; Wang, L. J. Phys. Chem. A 2014, 118, 4533. doi: 10.1021/jp500077f
-
[30]
(30) Li, Y.; Wang, L. Phys. Chem. Chem. Phys. 2014, 16, 17908. doi: 10.1039/C4CP02027H
-
[31]
(31) Pan, S.; Wang, L. J. Phys. Chem. A 2014, 118, 10778. doi: 10.1021/jp506815v
-
[32]
(32) Wang, L. ChemPhysChem 2015, 16, 1542. doi: 10.1002/cphc.201500012
-
[33]
(33) Wu, R.; Wang, S.; Wang, L. Chemosphere 2014, 111, 537. doi: 10.1016/j.chemosphere.2014.04.067
-
[34]
(34) Wood, G. P. F.; Radom, L.; Petersson, G. A.; Barnes, E. C.; Frisch, M. J.; Montgomery, J., J. A. J. Chem. Phys. 2006, 125, 094106.
-
[35]
(35) Jensen, F. Introduction to Computational Chemistry, 2nd ed.; John Wiley & Sons, Ltd: WestSussex, 2007.
-
[36]
(36) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 09, Revision A.1; Gaussian Inc.: Wallingford CT, 2009.
-
[37]
(37) Fernandez-Ramos, A.; Ellingson, B. A.; Meana-Paneda, R.; Marques, J. M. C.; Truhlar, D. G. Theor. Chem. Acc. 2007, 118, 813. doi: 10.1007/s00214-007-0328-0
-
[38]
(38) Alvarez-Idaboy, J. R.; Mora-Diez, N.; Boyd, R. J.; Vivier-Bunge, A. J. Am. Chem. Soc. 2001, 123, 2018. doi: 10.1021/ja003372g
-
[39]
(39) Pilling, M. J.; Seakins, P. W. Reaction Kinetics; Oxford University Press Inc.: New York, 1999.
-
[40]
(40) Johnson, H. S.; Heicklen, J. J. Phys. Chem. 1962, 66, 532. doi: 10.1021/j100809a040
-
[41]
(41) Forst, W. Unimolecular Reactions: a Concise Introduction; Cambridge University Press: Cambridge, 2003.
-
[42]
(42) Holbrook, K. A.; Pilling, M. J.; Robertson, S. H.; Robinson, P. J. Unimolecular Reactions, 2nd ed.; Wiley: New York, 1996.
-
[43]
(43) Glowacki, D. R.; Liang, C. H.; Morley, C.; Pilling, M. J.; Robertson, S. H. J. Phys. Chem. A 2012, 116, 9545. doi: 10.1021/jp3051033
-
[44]
(44) Miller, W. H. J. Am. Chem. Soc. 1979, 101, 6810. doi: 10.1021/ja00517a004
-
[45]
(45) Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; BlackwellScientific Publications: Boston, 1990.
-
[46]
(46) Malick, D. K.; Petersson, G. A.; Montgomery, J., J. A. J. Chem. Phys. 1998, 108, 5703.
-
[47]
(47) Birdsall, A. W.; Andreoni, J. F.; Elrod, M. J. J. Phys. Chem. A 2010, 114, 10655. doi: 10.1021/jp105467e
-
[48]
(48) Carlton, A. G.; Bhave, P. V.; Napelenok, S. L.; Edney, E. O.; Sarwar, G.; Pinder, R. W.; Pouliot, G.A.; Houyoux, M. Environ. Sci. Technol. 2010, 44, 8553. doi: 10.1021/es100636q
-
[49]
(49) Ng, N. L.; Kroll, J. H.; Chan, A. W. H.; Chhabra, P. S.; Flagan, R. C.; Seinfeld, J. H. Atmos. Chem. Phys. 2007, 7, 3909.
-
[50]
(50) Orlando, J. J.; Tyndall, G. S. Chem. Soc. Rev. 2012, 41, 6294. doi: 10.1039/c2cs35166h
-
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