FTIR product distribution study of the Cl and OH initiated degradation of methyl acrylate at atmospheric pressure

Environmental Science and Technology

Volumn 44, Issue 18, 2010, Pages 7031-7036

  Blanco, María B ^a   Bejan, Iustinian ^b,c   Barnes, Ian ^b   Wiesen, Peter ^b   Teruel, Mariano A ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

^b UNIVERSITY OF WUPPERTAL   (Germany)

^c ALEXANDRU IOAN CUZA UNIVERSITY OF IASI   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC DEGRADATION; CL ATOMS; CONCENTRATION-TIME; COPRODUCT; FORMYL CHLORIDE; FTIR; GAS-PHASE REACTIONS; GLASS CHAMBERS; GLYOXYLATE; IN-SITU FT-IR; LONG-PATH; METHYL ACRYLATES; OH RADICAL; OH REACTION; PRODUCT DISTRIBUTIONS; PRODUCT STUDIES; RESIDUAL PRODUCTS; SECONDARY PRODUCT; SIMULATED SPECTRA; SYNTHETIC AIR;

ATMOSPHERIC PRESSURE; CHLORINE COMPOUNDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FREE RADICALS; PHASE INTERFACES; QUARTZ;

DEGRADATION;

ACRYLIC ACID METHYL ESTER; CARBON MONOXIDE; CHLORINE; FORMALDEHYDE; HYDROCHLORIC ACID; HYDROXIDE; METHYLGLYOXAL;

ATMOSPHERIC PRESSURE; CHLORINE; DEGRADATION; ESTER; EXPERIMENTAL STUDY; FORMALDEHYDE; FTIR SPECTROSCOPY; GAS PHASE REACTION; HYDROXYL RADICAL; REACTION KINETICS;

ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEGRADATION; INFRARED SPECTROSCOPY; SIMULATION;

ACRYLATES; ATMOSPHERIC PRESSURE; CHLORINE; HYDROXYL RADICAL; OXIDATION-REDUCTION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 77956541800     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es101831r     Document Type: Article

References (37)

1. Atkinson, R. Gas-Phase Tropospheric Chemistry of Organic Compounds J. Phys. Chem. Ref. Data 1994, Monograph No. 2
2. Thornton, J. A.; Kercher, J. P.; Riedel, T. P.; Wagner, N. L.; Cozic, J.; Holloway, J. S.; Dubé, W. P.; Wolfe, G. M.; Quinn, P. K.; Middlebrook, A. M.; Alexander, B.; Brown, S. S. A large atomic chlorine source inferred from mid-continental reactive nitrogen chemistry Nature? 2010, 464, 271-274 doi:10.1038/nature08905
3. Ullmannâs Encyclopedia of Industrial Chemistry, 6th ed. Electronic Release; Wiley-VCH Verlag Gmbh: Weinheim, Germany, 2001.
4. Graedel, T. E.; Hawkins, D. T.; Claxton, L. D. Atmospheric Compounds: Sources, Occurrence, and Bioassay; Academic Press: Orlando, FL, 1986.
5. Blanco, M. B.; Taccone, R. A.; Lane, S. I.; Teruel, M. A. On the OH-initiated degradation of methacrylates in the troposphere: gas-phase kinetics and formation of pyruvates Chem. Phys. Lett. 2006, 429 (4-6) 389-394
6. Teruel, M. A.; Lane, S. I.; Mellouki, A.; Solignac, G.; Le Bras, G. OH reaction rate constants and UV absorption cross-sections of unsaturated esters Atmos. Environ. 2006, 40 (20) 3764-3772
7. Blanco, M. B.; Teruel, M. A. Photodegradation of n -butyl acrylate in the troposphere by OH radicals: Kinetics and fate of 1,2-hydroxyalcoxy radicals J. Org. Chem. 2008, 21, 397-401
8. Blanco, M. B.; Bejan, I.; Barnes, I.; Wiesen, P.; Teruel, M. A. OH-Initiated Degradation of Unsaturated Esters in the Atmosphere: Kinetics in the Temperature Range of 287-313 K J. Phys. Chem. A 2009, 113, 5958-5965
9. 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
10. 3 radicals with a series of alkynes, haloalkenes, and alpha, beta unsaturated-aldehydes Int. J. Chem. Kinet. 1987, 19, 299-307
11. 3 in the troposphere Environ. Sci. Pollut. Res. 2009, 16, 641-648
12. Blanco, M. B.; Bejan, I.; Barnes, I.; Wiesen, P.; Teruel, M. A. Temperature-dependent rate coefficients for the reactions of Cl atoms with methyl methacrylate, methyl acrylate and butyl methacrylate at atmospheric pressure Atmos. Environ. 2009, 43, 5996-6002
13. Martín, M. P.; Gallego-Iniesta, M. P.; Espinosa, J. L.; Tapia, A.; Cabañas, B.; Salgado, M. S. Gas phase reactions of unsaturated esters with Cl atoms. Environ. Sci. Pollut. Res. 2010, 17, 539 - 546.
14. 3 with methyl vinyl ketone, methacrolein, acrolein, methyl acrylate and methyl methacrylate Phys. Chem. Chem. Phys. 1999, 1, 4195-4202
15. 2]: Kinetics, mechanisms, and products of chlorine-atom-and OH-radical-initiated oxidation J. Phys.Chem. A 2009, 113 (13) 3155-3161
16. Barnes, I.; Becker, K. H. An FTIR Product Study of the Photooxidation of Dimethyl Disulfide J. Atmos. Chem. 1994, 18, 267-289
17. Atkinson, R.; Arey, J. Atmospheric degradation of volatile organic compounds Chem. Rev. 2003, 103, 4605-4638
18. Lightfoot, P. D.; Cox, R. A.; Crowley, J. N.; Destriau, M.; Hayman, G. D.; Jenkin, M. E.; Moortgat, G. K.; Zabel, F. Organic peroxy radicals: kinetics, spectroscopy and tropospheric chemistry Atmos. Environ. 1992, 26A, 1805-1964
19. Ifang, S. Kinetische Untersuchungen an organischen Estern. Diplom Thesis, University of Wuppertal, Germany, 2010.
20. 3Cl in the present of NO J. Phys. Chem. A 1999, 103, 3963-3968
21. Cavalli, F. Atmospheric oxidation of selected alcohols and esters. PhD thesis, University of Wuppertal, Germany, 2000.
22. 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 (Pubitemid 44369557)
23. 8 n -alkanes J. Phys. Chem. 1982, 86, 4563-4569
24. x-air photooxidations of a series of aromatic hydrocarbons in air Environ. Sci. Technol. 1986, 20, 383-387
25. 2O Chem. Phys. Lett. 1980, 75, 533-535
26. Su, F.; Calvert, J. G.; Shaw, J. H.; Niki, H.; Maker, P. D.; Savage, C. M.; Breitenbach, L. P. Spectroscopic and kinetic studies of a new metastable species in the photooxidation of gaseosus formaldehyde Chem. Phys. Lett. 1979, 65, 221-225
27. Sidebottom, H.; Morris, R.; Viero, L.; Mellouki, A.; Le Bras, G.; Vera, T.; Muñoz, A. Poster; EUROCHAMP Meeting, Binz/Rügen, Germany, May 13-15, 2009.
28. Orlando, J. J.; Tyndall, G. S. Mechanisms for the reactions of OH with two unsaturated aldehydes: Crotonaldehyde and acrolein J. Phys. Chem. A 2002, 106, 122252-12259
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T., Jr.; Kudin, N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian Inc., Wallingford, CT, 2004.
30. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
31. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev., B. 1988, 37, 785-789
32. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Results obtained with the correlation energy density functionals of Becke and Lee, Yang and Parr Chem. Phys. Lett. 1989, 157, 200-206
33. Canosa-Mas, C. E.; Cotter, E. S. N.; Duffy, J.; Thompson, K. C.; Wayne, R. P. The reactions of atomic chlorine with acrolein, methacrolein and methyl vinyl ketone Phys. Chem. Chem. Phys. 2001, 3, 3075-3084
34. Orlando, J. J.; Tyndall, G. S.; Paulson, S. E. Mechanism of the OH-initiated oxidation of methacrolein Geophys. Res. Lett. 1999, 26, 2191-2194
35. Spicer, C. W.; Chapman, E. G.; Finlayson-Pitts, B. J.; Plastidge, R. A.; Hubbe, J. M.; Fast, J. D.; Berkowitz, C. M. Observations of molecular chlorine in coastal air Nature 1998, 394, 353-356
36. Ezell, M. J.; Wang, W.; Ezell, A. A.; Soskin, G.; Finlayson-Pitts, B. J. Kinetics of reactions of chlorine atoms with a series of alkenes at 1 atm and 298 K: structure and reactivity Phys. Chem. Chem. Phys. 2002, 4, 5813-5820
37. Yasmeen, F.; Sauret, N.; Gal, J.-F.; Maria, P.-C.; Massi, L.; Maenhaut, W.; Claeys, M. Characterization of oligomers from methylglyoxal under dark conditions: a pathway to produce secondary organic aerosol through cloud processing during nighttime Atmos. Chem. Phys. 2010, 10, 3803-3812