Oligomeric products and formation mechanisms from acid-catalyzed reactions of methyl vinyl ketone on acidic sulfate particles

Journal of Atmospheric Chemistry

Volumn 70, Issue 1, 2013, Pages 1-18

  Chan, Ka Man ^a   Huang, Dan Dan ^a   Li, Yong Jie ^a   Chan, Man Nin ^b,d   Seinfeld, John H ^b,c   Chan, Chak K ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b California Institute of Technology   (United States)

^c California Institute of Technology   (United States)

^d LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

Acid catalyzed reaction; Aldol reaction; Methyl vinyl ketone; Oligomerization; Secondary organic aerosols

Indexed keywords

AMMONIUM BISULFATE; AMMONIUM SULFATE; DIMER; INORGANIC COMPOUND; KETONE; METHYLVINYL KETONE; OLIGOMER; SULFURIC ACID; TETRAMER; UNCLASSIFIED DRUG;

ACIDITY; ATMOSPHERIC CHEMISTRY; DEHYDRATION; GAS CHROMATOGRAPHY; HYDRATION; IONIZATION; KETONE; LIQUID CHROMATOGRAPHY;

ALDOL REACTION; ARTICLE; CATALYSIS; HUMIDITY; HYDRATION; MASS FRAGMENTOGRAPHY; OLIGOMERIZATION; TIME OF FLIGHT MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84873357446     PISSN: 01677764     EISSN: 15730662     Source Type: Journal    
DOI: 10.1007/s10874-013-9248-7     Document Type: Article

References (60)

1. Blank, I., Milo, C., Lin, J.M., Fay, L.B.: Quantification of aroma-impact components by isotope dilution assay - recent developments. Flavor chemistry: 30 years of progress. Kluwer Academic / Plenum Publishers, New York (1999)
2. Budzikiewicz, H., Drabner, G., Hammes, C.: Rearrangements accompanying the fragmentation of ionized 1-Phenylalkan-1-Ols. Org. Mass Spectrom. 28(11), 1326-1328 (1993)
3. Carlton, A.G., Wiedinmyer, C., Kroll, J.H.: A review of secondary organic aerosol (SOA) formation from isoprene. Atmos. Chem. Phys. 9(14), 4987-5005 (2009). doi: 10.5194/acp-9-4987-2009
4. Chan, L.P., Chan, C.K.: Enhanced reactive uptake of nonanal by acidic aerosols in the presence of particle-phase organics. Aerosol Sci. Technol. 45(7), 872-883 (2011). doi: 10.1080/02786826.2011.567314
5. Chan, A.W.H., Chan, M.N., Surratt, J.D., Chhabra, P.S., Loza, C.L., Crounse, J.D., Yee, L.D., Flagan, R.C., Wennberg, P.O., Seinfeld, J.H.: Role of aldehyde chemistry and NOx concentrations in secondary organic aerosol formation. Atmos. Chem. Phys. 10(15), 7169-7188 (2010). doi: 10.5194/acp-10-7169-2010
6. Chen, Z.M., Jie, C.Y., Li, S., Wang, H.L., Wang, C.X., Xu, J.R., Hua, W.: Heterogeneous reactions of methacrolein and methyl vinyl ketone: kinetics and mechanisms of uptake and ozonolysis on silicon dioxide. J. Geophys. Res.-Atmos. 113(D22) (2008). doi: 10.1029/2007jd009754
7. Chiavarino, B., Crestoni, M.E., Fornarini, S., Dopfer, O., Lemaire, J., Maitre, P.: Ir spectroscopic features of gaseous C7h7o+ ions: benzylium versus tropylium ion structures. J. Phys. Chem. A 110(30), 9352-9360 (2006). doi: 10.1021/Jp0628380 (Pubitemid 44325001)
8. Claeys, M., Wang, W., Ion, A.C., Kourtchev, I., Gelencser, A., Maenhaut, W.: Formation of secondary organic aerosols from isoprene and its gas-phase oxidation products through reaction with hydrogen peroxide. Atmos. Environ. 38(25), 4093-4098 (2004). doi: 10.1016/j.atmosenv.2004.06.001 (Pubitemid 38844701)
9. de Gouw, J.A., Middlebrook, A.M., Warneke, C., Goldan, P.D., Kuster, W.C., Roberts, J.M., Fehsenfeld, F.C., Worsnop, D.R., Canagaratna, M.R., Pszenny, A.A.P., Keene, W.C., Marchewka, M., Bertman, S.B., Bates, T.S.: Budget of organic carbon in a polluted atmosphere: results from the new England air quality study in 2002. J. Geophys. Res.-Atmos. 110(D16) (2005). doi: 10.1029/2004jd005623 (Pubitemid 41431133)
10. Drexler, E.J., Field, K.W.: Nmr-study of keto-enol tautomerism in beta-dicarbonyl compounds. J. Chem. Educ. 53(6), 392-393 (1976)
11. Duncan, J.L., Schindler, L.R., Roberts, J.T.: A new sulfate-mediated reaction: conversion of acetone to trimethylbenzene in the presence of liquid sulfuric acid. Geophys. Res. Lett. 25(5), 631-634 (1998). doi: 10.1029/98gl00250
12. Duncan, J.L., Schindler, L.R., Roberts, J.T.: Chemistry at and near the surface of liquid sulfuric acid: a kinetic, thermodynamic, and mechanistic analysis of heterogeneous reactions of acetone. J. Phys. Chem. B 103(34), 7247-7259 (1999). doi: 10.1021/jp991322w (Pubitemid 129702671)
13. Ervens, B., Turpin, B.J., Weber, R.J.: Secondary organic aerosol formation in cloud droplets and aqueous particles (aqSOA): a review of laboratory, field and model studies. Atmos. Chem. Phys. 11(21), 11069-11102 (2011). doi: 10.5194/acp-11-11069-2011
14. Galloway, M.M., Chhabra, P.S., Chan, A.W.H., Surratt, J.D., Flagan, R.C., Seinfeld, J.H., Keutsch, F.N.: Glyoxal uptake on ammonium sulphate seed aerosol: reaction products and reversibility of uptake under dark and irradiated conditions. Atmos. Chem. Phys. 9(10), 3331-3345 (2009)
15. Heald, C.L., Jacob, D.J., Park, R.J., Russell, L.M., Huebert, B.J., Seinfeld, J.H., Liao, H., Weber, R.J.: A large organic aerosol source in the free troposphere missing from current models. Geophys. Res. Lett. 32(18) (2005). doi: 10.1029/2005gl023831 (Pubitemid 41582611)
16. Hennigan, C.J., Bergin, M.H., Dibb, J.E., Weber, R.J.: Enhanced secondary organic aerosol formation due to water uptake by fine particles. Geophys. Res. Lett. 35(18) (2008). doi: 10.1029/2008gl035046
17. Imamura, T., Akiyoshi, H.: Uptake of acetone into sulfuric-acid solutions. Geophys. Res. Lett. 27(9), 1419-1422 (2000). doi: 10.1029/1999gl011137 (Pubitemid 32040594)
18. 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.-Atmos. 102(D13), 16099-16107 (1997). doi: 10.1029/97jd01259
19. Jang, M.S., Kamens, R.M.: Atmospheric secondary aerosol formation by heterogeneous reactions of aldehydes in the presence of a sulfuric acid aerosol catalyst. Environ. Sci. Technol. 35(24), 4758-4766 (2001). doi: 10.1021/Es010790s (Pubitemid 33144338)
20. Jang, M.S., Czoschke, N.M., Lee, S., Kamens, R.M.: Heterogeneous atmospheric aerosol production by acid-catalyzed particle-phase reactions. Science 298(5594), 814-817 (2002) (Pubitemid 35231531)
21. Jang, M., Lee, S., Kamens, R.M.: Organic aerosol growth by acid-catalyzed heterogeneous reactions of octanal in a flow reactor. Atmos. Environ. 37(15), 2125-2138 (2003a). doi: 10.1016/S1352-2310(03)00077-3 (Pubitemid 36407476)
22. Jang, M.S., Carroll, B., Chandramouli, B., Kamens, R.M.: Particle growth by acid-catalyzed heterogeneous reactions of organic carbonyls on preexisting aerosols. Environ. Sci. Technol. 37(17), 3828-3837 (2003b). doi: 10.1021/Es021006u (Pubitemid 37071593)
23. Jang, M., Czoschke, N.M., Northcross, A.L.: Atmospheric organic aerosol production by heterogeneous acid-catalyzed reactions. Chemphyschem 5(11), 1647-1661 (2004). doi: 10.1002/cphc.200301077
24. Jaoui, M., Kleindienst, T.E., Lewandowski, M., Edney, E.O.: Identification and quantification of aerosol polar oxygenated compounds bearing carboxylic or hydroxyl groups. 1. Method development. Anal. Chem. 76(16), 4765-4778 (2004). doi: 10.1021/Ac049919h (Pubitemid 39079474)
25. Jaoui, M., Corse, E., Kleindienst, T.E., Offenberg, J.H., Lewandowski, M., Edney, E.O.: Analysis of secondary organic aerosol compounds from the photooxidation of D-limonene in the presence of NOx and their detection in ambient Pm2.5. Environ. Sci. Technol. 40(12), 3819-3828 (2006). doi: 10.1021/Es052566z (Pubitemid 43902380)
26. 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. 100(19), 8015-8022 (1996) (Pubitemid 126804537)
27. Kroll, J.H., Seinfeld, J.H.: Chemistry of secondary organic aerosol: formation and evolution of low-volatility organics in the atmosphere. Atmos. Environ. 42(16), 3593-3624 (2008). doi: 10.1016/j.atmosenv.2008.01.003
28. Kroll, J.H., Ng, N.L., Murphy, S.M., Varutbangkul, V., Flagan, R.C., Seinfeld, J.H.: Chamber studies of secondary organic aerosol growth by reactive uptake of simple carbonyl compounds. J. Geophys. Res.-Atmos. 110(D23) (2005). doi: 10.1029/2005jd006004 (Pubitemid 43141257)
29. Li, Y.J., Lee, A.K.Y., Lau, A.P.S., Chan, C.K.: Accretion reactions of octanal catalyzed by sulfuric acid: product identification, reaction pathways, and atmospheric implications. Environ. Sci. Technol. 42(19), 7138-7145 (2008). doi: 10.1021/Es7031373
30. Li, Y.J., Cheong, G.Y.L., Lau, A.P.S., Chan, C.K.: Acid-catalyzed condensed-phase reactions of limonene and terpineol and their impacts on gas-to-particle partitioning in the formation of organic aerosols. Environ. Sci. Technol. 44(14), 5483-5489 (2010). doi: 10.1021/Es101231m
31. Li, Y.J., Chen, Q., Guzman, M.I., Chan, C.K., Martin, S.T.: Second-generation products contribute substantially to the particle-phase organic material produced by beta-caryophyllene ozonolysis. Atmos. Chem. Phys. 11(1), 121-132 (2011). doi: 10.5194/acp-11-121-2011
32. Liggio, J., Li, S.M.: Reversible and irreversible processing of biogenic olefins on acidic aerosols. Atmos. Chem. Phys. 8(7), 2039-2055 (2008)
33. Liggio, J., Li, S.M., McLaren, R.: Heterogeneous reactions of glyoxal on particulate matter: identification of acetals and sulfate esters. Environ. Sci. Technol. 39(6), 1532-1541 (2005) (Pubitemid 40387706)
34. Liggio, J., Li, S.M.: Organosulfate formation during the uptake of pinonaldehyde on acidic sulfate aerosols. Geophys. Res. Lett. 33(13) (2006). doi: 10.1029/2006gl026079 (Pubitemid 44945968)
35. Lim, Y.B., Tan, Y., Perri, M.J., Seitzinger, S.P., Turpin, B.J.: Aqueous chemistry and its role in secondary organic aerosol (SOA) formation. Atmos. Chem. Phys. 10(21), 10521-10539 (2010). doi: 10.5194/acp-10-10521-2010
36. Liu, P., Zhang, Y.: A computationally-efficient secondary organic aerosol module for three-dimensional air quality models. Atmos Chem. Phys. 8(14), 3985-3998 (2008)
37. Martin-Reviejo, M., Wirtz, K.: Is benzene a precursor for secondary organic aerosol? Environ. Sci. Technol. 39(4), 1045-1054 (2005). doi: 10.1021/Es049802a
38. McLafferty, F.W., Turecek, F.: Interpretation of Mass Spectra, 4th edn. University Science Books, Mill Valley (1993)
39. Michelsen, R.R., Ashbourn, S.F.M., Iraci, L.T.: Dissolution, speciation, and reaction of acetaldehyde in cold sulfuric acid. J. Geophys. Res.-Atmos. 109(D23) (2004). doi: 10.1029/2004jd005041 (Pubitemid 40318563)
40. Noziere, B., Voisin, D., Longfellow, C.A., Friedli, H., Henry, B.E., Hanson, D.R.: The uptake of methyl vinyl ketone, methacrolein, and 2-methyl-3-butene-2-ol onto sulfuric acid solutions. J. Phys. Chem. A 110(7), 2387-2395 (2006). doi: 10.1021/Jp055899
41. Noziere, B., Ekstrom, S., Alsberg, T., Holmstrom, S.: Radical-initiated formation of organosulfates and surfactants in atmospheric aerosols. Geophys. Res. Lett. 37 (2010). doi: 10.1029/2009gl041683
42. Pathak, R.K., Louie, P.K.K., Chan, C.K.: Characteristics of aerosol acidity in Hong Kong. Atmos. Environ. 38(19), 2965-2974 (2004). doi: 10.1016/j.atmosenv.2004.02.044 (Pubitemid 38591413)
43. Pathak, R.K., Wu, W.S., Wang, T.: Summertime Pm2.5 ionic species in four major cities of China: nitrate formation in an ammonia-deficient atmosphere. Atmos. Chem. Phys. 9(5), 1711-1722 (2009)
44. Perri, M.J., Lim, Y.B., Seitzinger, S.P., Turpin, B.J.: Organosulfates from glycolaldehyde in aqueous aerosols and clouds: laboratory studies. Atmos. Environ. 44(21-22), 2658-2664 (2010). doi: 10.1016/j.atmosenv.2010.03.031
45. Pun, B.K., Seigneur, C.: Investigative modeling of new pathways for secondary organic aerosol formation. Atmos. Chem. Phys. 7(9), 2199-2216 (2007) (Pubitemid 46707028)
46. Pun, B.K., Griffin, R.J., Seigneur, C., Seinfeld, J.H.: Secondary organic aerosol - 2. Thermodynamic model for gas/particle partitioning of molecular constituents. J. Geophys. Res.-Atmos. 107(D17) (2002). doi: 10.1029/2001jd000542 (Pubitemid 43206138)
47. Rudich, Y., Donahue, N.M., Mentel, T.F.: Aging of organic aerosol: bridging the gap between laboratory and field studies. Annu. Rev. Phys. Chem. 58, 321-352 (2007). doi: 10.1146/annurev.physchem.58.032806.104432 (Pubitemid 46877593)
48. Seinfeld, J.H., Erdakos, G.B., Asher, W.E., Pankow, J.F.: Modeling the formation of secondary organic aerosol (SOA). 2. The predicted effects of relative humidity on aerosol formation in the alpha-pinene-, beta-pinene-, sabinene-, delta(3)-carene-, and cyclohexene-ozone systems. Environ. Sci. Technol. 35(9), 1806-1817 (2001). doi: 10.1021/Es001765+ (Pubitemid 32868205)
49. Stone, E.A., Yang, L.M., Yu, L.Y.E., Rupakheti, M.: Characterization of organosulfates in atmospheric aerosols at four Asian locations. Atmos. Environ. 47, 323-329 (2012). doi: 10.1016/j.atmosenv.2011.10.058
50. Surratt, J.D., Kroll, J.H., Kleindienst, T.E., Edney, E.O., Claeys, M., Sorooshian, A., Ng, N.L., Offenberg, J.H., Lewandowski, M., Jaoui, M., Flagan, R.C., Seinfeld, J.H.: Evidence for organosulfates in secondary organic aerosol. Environ. Sci. Technol. 41(2), 517-527 (2007). doi: 10.1021/es062081q (Pubitemid 46106285)
51. Surratt, J.D., Gomez-Gonzalez, Y., Chan, A.W.H., Vermeylen, R., Shahgholi, M., Kleindienst, T.E., Edney, E.O., Offenberg, J.H., Lewandowski, M., Jaoui, M., Maenhaut, W., Claeys, M., Flagan, R.C., Seinfeld, J.H.: Organosulfate formation in biogenic secondary organic aerosol. J. Phys. Chem. A 112(36), 8345-8378 (2008). doi: 10.1021/Jp802310p
52. Surratt, J.D., Chan, A.W.H., Eddingsaas, N.C., Chan, M.N., Loza, C.L., Kwan, A.J., Hersey, S.P., Flagan, R.C., Wennberg, P.O., Seinfeld, J.H.: Reactive intermediates revealed in secondary organic aerosol formation from isoprene. Proc. Natl. Acad. Sci. U.S.A. 107(15), 6640-6645 (2010). doi: 10.1073/pnas.0911114107
53. Szmigielski, R., Surratt, J.D., Vermeylen, R., Szmigielska, K., Kroll, J.H., Ng, N.L., Murphy, S.M., Sorooshian, A., Seinfeld, J.H., Claeys, M.: Characterization of 2-methylglyceric acid oligomers in secondary organic aerosol formed from the photooxidation of isoprene using trimethylsilylation and gas chromatography/ion trap mass spectrometry. J. Mass Spectrom. 42(1), 101-116 (2007). doi: 10.1002/Jms.1146 (Pubitemid 46173929)
54. Volkamer, R., Jimenez, J.L., San Martini, F., Dzepina, K., Zhang, Q., Salcedo, D., Molina, L.T., Worsnop, D.R., Molina, M.J.: Secondary organic aerosol formation from anthropogenic air pollution: rapid and higher than expected. Geophys. Res. Lett. 33(17) (2006). doi: 10.1029/2006gl026899 (Pubitemid 44945682)
55. Volkamer, R., Martini, F.S., Molina, L.T., Salcedo, D., Jimenez, J.L., Molina, M.J.: A missing sink for gas-phase glyoxal in Mexico City: formation of secondary organic aerosol. Geophys. Res. Lett. 34(19) (2007). doi: 10.1029/2007gl030752 (Pubitemid 350263040)
56. Volkamer, R., Ziemann, P.J., Molina, M.J.: Secondary organic aerosol formation from acetylene (C2h2): seed effect on SOA yields due to organic photochemistry in the aerosol aqueous phase. Atmos. Chem. Phys. 9(6), 1907-1928 (2009)
57. Wang, D.W., Guo, H., Chan, C.K.: Measuring ambient acidic ultrafine particles using iron nanofilm detectors: method development. Aerosol Sci. Technol. 46(5), 521-532 (2012). doi: 10.1080/02786826.2011.643258
58. Wexler, A.S., Clegg, S.L.: Atmospheric aerosol models for systems including the ions H+, Nh4+, Na+, So42-, No3-,Cl-, Br-, and H2o. J. Geophys. Res.-Atmos. 107(D14) (2002). doi: 10.1029/2001jd000451
59. Yu, J.Z., Flagan, R.C., Seinfeld, J.H.: Identification of products containing -Cooh, -OH, and -C=O in atmospheric oxidation of hydrocarbons. Environ. Sci. Technol. 32(16), 2357-2370 (1998) (Pubitemid 28374624)
60. Zhang, Q., Jimenez, J.L., Worsnop, D.R., Canagaratna, M.: A case study of urban particle acidity and its influence on secondary organic aerosol. Environ. Sci. Technol. 41(9), 3213-3219 (2007). doi: 10.1021/Es061812j (Pubitemid 46713382)