Heterogeneous reactions of methylglyoxal in acidic media: Implications for secondary organic aerosol formation

Environmental Science and Technology

Volumn 40, Issue 24, 2006, Pages 7682-7687

  Zhao, Jun ^a   Levitt, Nicholas P ^a   Zhang, Renyi ^a   Chen, Jianmin ^b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC RANGE; HENRY'S LAW; ORGANIC AEROSOL;

ACIDITY; CATALYSIS; ENVIRONMENTAL CHAMBERS; ESTERS; POLYMERIZATION; SOLUBILITY;

AEROSOLS;

CARBONYL DERIVATIVE; GLYOXAL DERIVATIVE; METHYGLYOXAL; SULFURIC ACID; UNCLASSIFIED DRUG; VOLATILE ORGANIC COMPOUND;

ACIDITY; AEROSOLS; CATALYSIS; ENVIRONMENTAL CHAMBERS; ESTERS; POLYMERIZATION; SOLUBILITY;

ACIDITY; AEROSOL FORMATION; CARBONYL COMPOUND; CATALYSIS; HETEROGENEITY; HYGROSCOPICITY; SULFURIC ACID;

ACIDITY; AEROSOL; ARTICLE; ATMOSPHERE; CHEMICAL REACTION; GAS; MASS SPECTROMETER; MASS SPECTROMETRY; PHYSICAL PHASE;

ACIDS; AEROSOLS; CATALYSIS; ESTERIFICATION; PYRUVALDEHYDE; SULFURIC ACIDS;

EID: 33845793577     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es060610k     Document Type: Article

References (36)

1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry: Part A Structure and Mechanisms, 4th ed.; Plenum Press: New York, 2000.
2. Barton, D. in Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds; Ollis, W. D., Ed.; Pergamon Press; New York, 1979; pp 960-1013.
3. Jang, M.; Czoschke, N. M.; Lee, S.; Kamens, R. M. Heterogeneous atmospheric aerosol production by acid-catalyzed particle-phase reactions. Science 2002, 298, 814-817.
4. Kalberer, M.; Poulsen, D.; Sax, M.; Steinbacher, M.; Dommen, J.; Prevot, A. S. H.; Fisseha, R.; Weingartner, E.; Frankevich, V.; Zenobi, R.; Baltensperger, U. Identification of polymers as major components of atmospheric organic aerosols. Science 2004, 303, 1659-1662.
5. Andreae, M. O.; Crutzen, P. J. Atmospheric aerosols: Biogeochemical sources and role in atmospheric chemistry. Science 1997, 276, 1052-1058.
6. Zhang, R.; Suh, I.; Zhao, J.; Zhang, D.; Fortner, E. C.; Tie, X.; Molina, L. T.; Molina, M. J. Atmospheric new particle formation enhanced by organic acids. Science 2004, 304, 1487-1490.
7. Fan, J.; Zhang, R. Atmospheric oxidation mechanism of p-Xylene: A density functional theory study. J. Phys. Chem. A 2006, 110, 7728-7737.
8. Suh, I.; Zhang, R.; Molina, L. T.; Molina, M. J. Oxidation mechanism of aromatic peroxy and bicyclic radicals from OH-toluene reactions. J. Am. Chem. Soc. 2003, 125, 12655-12665.
9. Zhao, J.; Zhang, R.; Misawa, K.; Shibuya, K. Experimental product study of the OH-initiated oxidation of m-xylene. J. Photochem. Photobiol. A 2005, 176, 199-207.
10. Grosjean, E.; Grosjean, D.; Fraser, M. P.; Cass, G. R. Air quality model evaluation data for organics .2. C-1-C-14 carbonyls in Los Angeles air. Environ. Sci. Technol. 1996, 30, 2687-2703.
11. Chen, Y.; Wang, W.; Zhu, L. Wavelength-dependent photolysis of methylglyoxal in the 290-440 nm region. J. Phys. Chem. A 2000, 104, 11126-11131.
12. Zhao, J.; Levitt, N. P.; Zhang, R. Heterogeneous chemistry of octanal and 2,4-hexadienal with sulfuric acid. Geophys. Res. Lett. 2005, 32, L09802, doi:10.1029/2004GL022200.
13. Zhang, R.; Wooldridge, P. J.; Abbatt, J. P. D.; Molina, M. J. Physical chemistry of the sulfuric acid/water binary system at low temperatures: stratospheric implications. J. Phys. Chem. 1993, 97, 7351-7358.
14. Zhang, R.; Wooldridge, P. J.; Molina, M. J. Vapor pressure measurements for sulfuric acid/nitric acid/water and sulfuric acid/hydrochloric acid/water systems: incorporation of stratospheric acids into background sulfate aerosols. J. Phys. Chem. 1993, 97, 8541-8548.
15. Gurnick, M.; Chaiken, J.; Benson, T.; McDonald, J. D. Vibrational and rotational spectroscopy of the first electronically allowed transition of α-dicarbonyls. J. Chem. Phys. 1981, 74, 99-105.
16. Mackay, D.; Bobra, A.; Chan, D. W.; Shiu, W. Y. Vapor-pressure correlations for low-volatility environmental chemicals. Environ. Sci. Technol. 1982, 16, 645-649.
17. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry; Wiley: New York, 1993.
18. Zhao, L.; Ni, N.; Yalkowsky, S. H. A modification of Trouton's rule by simple molecular parameters for hydrocarbon compounds. Ind. Eng. Chem. Res. 1999, 38, 324-327.
19. Zhao, L.; Ni, N.; Yalkowsky, S. H. Predicting the entropy of boiling for organic compounds. J. Chem. Inf. Comput. Sci. 1999, 39, 1112-1116.
20. Handbook of Chemistry and Physics, 83rd ed.; Lide, D. R., Ed.; CRC press: New York, 2002-2003.
21. Fortner, E. C.; Zhao, J.; Zhang, R. Development of ion drift-chemical ionization mass spectrometry. Anal. Chem. 2004, 76, 5436-5440.
22. Zhao, J.; Fortner, E. C.; Zhang, R. Quantification of hydroxycarbonyls from OH-isoprene reactions. J. Am. Chem. Soc. 2004, 126, 2686-2687.
23. Timonen, R. S.;Chu, L. T.; Leu, M. T.; Keyser, L. F. Heterogeneous reaction of ClONO2(g) + NaCl(s) .fwdarw. Cl2(g) + NaNO3(s). J. Phys. Chem. 1994, 98, 9509-9517.
24. Jayne, J. T.; Worsnop, D. R.; Kolb, C. E.; Swartz, E.; Davidovits, P. Uptake of Gas-Phase Formaldehyde by Aqueous Acid Surfaces. J. Phys. Chem. 1996, 100, 8015-8022.
25. Zhang, D.; Zhang, R. Laboratory investigation of heterogeneous interaction of sulfuric acid with soot. Environ. Sci. Technol. 2005, 39, 5722-5728.
26. Klassen, J. K.; Lynton, J.; Golden, D. M.; Williams, L. R. Solubility of acetone in low-temperature (210-240 K) sulfuric acid solutions. J. Geophy. Res. 1999, 104, 26355-26361.
27. Betterton, E. A.; Hoffmann, M. R. Henry's law constants of some environmentally important aldehydes. Environ. Sci. Technol. 1988, 22, 1415-1418.
28. Liggio, J.; Li, S. M.; McLaren, R. Reactive uptake of glyoxal by particulate matter. J. Geophys. Res. 2005, 110, D10304, doi: 10.1029/2004JD005113.
29. Nemet, I.; Drazen, V. T.; Varga-Defterdarovic, L. Spectroscopic studies of methylglyoxal in water and dimethylsulfoxide. Bioorg. Chem. 2004, 32, 560-570.
30. Whipple, E. B. Structure of glyoxal in water. J. Am. Chem. Soc. 1970, 92, 7183-7186.
31. Garner, H. K.; Lucas, H. J. Preparation and hydrolysis of some acetals and esters of D(-)-2,3-butanediol. J. Am. Chem. Soc. 1950, 72, 5497-5501.
32. Deno, N. C.; Newman, M. S. Mechanism of sulfation of alcohols. J. Am. Chem. Soc. 1950, 72, 3852-3856.
33. Clark, D. J.; Williams, G. Esterification by sulphuric acid .2. alcohol. J. Chem. Soc. 1957, 4218-4221.
34. Liggio, J.; Li, S. M.; McLaren, R. Heterogeneous reactions of glyoxal on particulate matter: Identification of acetals and sulfate esters. Environ. Sci. Technol. 2005, 39, 1532-1541.
35. Iraci, L. T.; Tolbert, M. A. Heterogeneous interaction of formaldehyde with cold sulfuric acid: Implications for the upper troposphere and lower stratosphere. J. Geophys. Res. 1997, 102, 16099-16107.
36. Kroll, J. H.; Ng, N. L.; Murphy, S. M.; Varubangkul, V.; Flagan, R. C.; Seinfeld, J. H. Chamber studies of secondary organic aerosol growth by reactive uptake of simple carbonyl compounds. J. Geophys. Res. 2005, 110, D23207, doi:10.1029/2005JD006004.