Highly Oxidized Multifunctional Organic Compounds Observed in Tropospheric Particles: A Field and Laboratory Study

Environmental Science and Technology

Volumn 49, Issue 13, 2015, Pages 7754-7761

  Mutzel, Anke ^a   Poulain, Laurent ^a   Berndt, Torsten ^a   Iinuma, Yoshiteru ^a   Rodigast, Maria ^a   Böge, Olaf ^a   Richters, Stefanie ^a   Spindler, Gerald ^a   Sipilä, Mikko ^b   Jokinen, Tuija ^b   Kulmala, Markku ^b   Herrmann, Hartmut ^a  

^a LEIBNIZ INSTITUTE FOR TROPOSPHERIC RESEARCH   (Germany)

^b UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

AEROSOLS; ATMOSPHERIC MOVEMENTS; FIBER OPTICS; OZONE; TROPOSPHERE; VOLATILE ORGANIC COMPOUNDS;

CHEMICAL CHARACTERIZATION; CONTINUOUS FLOW REACTORS; LABORATORY STUDIES; LOW VAPOR PRESSURES; MEASUREMENT CAMPAIGN; OXIDATION PRODUCTS; PRECURSOR CONCENTRATION; RESEARCH STATIONS;

OXIDATION;

CARBONYL DERIVATIVE; HIGHLY OXIDIZED MULTIFUNCTIONAL ORGANIC COMPOUND; ORGANIC COMPOUND; PINENE; UNCLASSIFIED DRUG; AEROSOL; ALPHA-PINENE; OZONE; TERPENE; VOLATILE ORGANIC COMPOUND;

AEROSOL; CONCENTRATION (COMPOSITION); FIELDWORK; LABORATORY METHOD; OXIDATION; RESEARCH INSTITUTION; TROPOSPHERE; VAPOR PRESSURE; VOLATILE ORGANIC COMPOUND;

AEROSOL; ARTICLE; CONCENTRATION (PARAMETERS); CONTINUOUS FLOW REACTOR; DECOMPOSITION; GAS; OXIDATION; OZONOLYSIS; PARTICLE SIZE; TROPOSPHERE; ANALYSIS; ATMOSPHERE; CHEMISTRY; ENVIRONMENTAL MONITORING; OXIDATION REDUCTION REACTION; PROCEDURES;

AEROSOLS; ATMOSPHERE; ENVIRONMENTAL MONITORING; MONOTERPENES; OXIDATION-REDUCTION; OZONE; VOLATILE ORGANIC COMPOUNDS;

EID: 84936818414     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/acs.est.5b00885     Document Type: Article

References (37)

1. Ehn, M.; Kleist, E.; Junninen, H.; Petaja, T.; Lonn, G.; Schobesberger, S.; Dal Maso, M.; Trimborn, A.; Kulmala, M.; Worsnop, D. R.; Wahner, A.; Wildt, J.; Mentel, T. F. Gas phase formation of extremely oxidized pinene reaction products in chamber and ambient air Atmos. Chem. Phys. 2012, 12 (11) 5113-5127 10.5194/acp-12-5113-2012
2. Ehn, M.; Thornton, J. A.; Kleist, E.; Sipila, M.; Junninen, H.; Pullinen, I.; Springer, M.; Rubach, F.; Tillmann, R.; Lee, B.; Lopez-Hilfiker, F.; Andres, S.; Acir, I. H.; Rissanen, M.; Jokinen, T.; Schobesberger, S.; Kangasluoma, J.; Kontkanen, J.; Nieminen, T.; Kurten, T.; Nielsen, L. B.; Jorgensen, S.; Kjaergaard, H. G.; Canagaratna, M.; Dal Maso, M.; Berndt, T.; Petaja, T.; Wahner, A.; Kerminen, V. M.; Kulmala, M.; Worsnop, D. R.; Wildt, J.; Mentel, T. F. A large source of low-volatility secondary organic aerosol Nature 2014, 506 (7489) 476-479 10.1038/nature13032
3. Mentel, T. F.; Springer, M.; Ehn, M.; Kleist, E.; Pullinen, I.; Kurtén, T.; Rissanen, M.; Wahner, A.; Wildt, J. Formation of highly oxidized multifunctional compounds: Autoxidation of peroxy radicals formed in the ozonolysis of alkenes-Deduced from structure-product relationships Atmos. Chem. Phys. Discuss. 2015, 15 (2) 2791-2851 10.5194/acpd-15-2791-2015
4. Zhao, J.; Ortega, J.; Chen, M.; McMurry, P. H.; Smith, J. N. Dependence of particle nucleation and growth on high-molecular-weight gas-phase products during ozonolysis of α-pinene Atmos. Chem. Phys. 2013, 13 (15) 7631-7644 10.5194/acp-13-7631-2013
5. Jokinen, T.; Sipila¨, M.; Richters, S.; Kerminen, V. M.; Paasonen, P.; Stratmann, F.; Worsnop, D. R.; Kulmala, M.; Ehn, M.; Herrmann, H.; Berndt, T. Rapid autoxidation forming highly oxidized RO2 radicals in the atmosphere Angew. Chem., Int. Ed. 2014, 125 (25) 14825-14829
6. Kulmala, M.; Toivonen, A.; Makela, J. M.; Laaksonen, A. Analysis of the growth of nucleation mode particles observed in Boreal forest Tellus, Ser. B 1998, 50 (5) 449-462 10.1034/j.1600-0889.1998.t01-4-00004.x
7. Donahue, N. M.; Ortega, I. K.; Chuang, W.; Riipinen, I.; Riccobono, F.; Schobesberger, S.; Dommen, J.; Baltensperger, U.; Kulmala, M.; Worsnop, D. R.; Vehkamaki, H. How do organic vapors contribute to new-particle formation? Faraday Discuss. 2013, 165 (0) 91-104 10.1039/C3FD00046J
8. Riipinen, I.; Pierce, J. R.; Yli-Juuti, T.; Nieminen, T.; Hakkinen, S.; Ehn, M.; Junninen, H.; Lehtipalo, K.; Petaja, T.; Slowik, J.; Chang, R.; Shantz, N. C.; Abbatt, J.; Leaitch, W. R.; Kerminen, V. M.; Worsnop, D. R.; Pandis, S. N.; Donahue, N. M.; Kulmala, M. Organic condensation: A vital link connecting aerosol formation to cloud condensation nuclei (CCN) concentrations Atmos. Chem. Phys. 2011, 11 (8) 3865-3878 10.5194/acp-11-3865-2011
9. Riipinen, I.; Yli-Juuti, T.; Pierce, J. R.; Petaja, T.; Worsnop, D. R.; Kulmala, M.; Donahue, N. M. The contribution of organics to atmospheric nanoparticle growth Nat. Geosci. 2012, 5 (7) 453-458 10.1038/ngeo1499
10. Donahue, N. M.; Kroll, J. H.; Pandis, S. N.; Robinson, A. L. A two-dimensional volatility basis set-Part 2: Diagnostics of organic-aerosol evolution Atmos. Chem. Phys. 2012, 12 (2) 615-634 10.5194/acp-12-615-2012
11. Rissanen, M. P.; Kurtén, T.; Sipila¨, M.; Thornton, J. A.; Kangasluoma, J.; Sarnela, N.; Junninen, H.; Jørgensen, S.; Schallhart, S.; Kajos, M. K.; Taipale, R.; Springer, M.; Mentel, T. F.; Ruuskanen, T.; Peta¨ja¨, T.; Worsnop, D. R.; Kjaergaard, H. G.; Ehn, M. The formation of highly oxidized multifunctional products in the ozonolysis of cyclohexene J. Am. Chem. Soc. 2014, 136 (44) 15596-15606 10.1021/ja507146s
12. Crounse, J. D.; Nielsen, L. B.; Jorgensen, S.; Kjaergaard, H. G.; Wennberg, P. O. Autoxidation of organic compounds in the atmosphere J. Phys. Chem. Lett. 2013, 4 (20) 3513-3520 10.1021/jz4019207
13. Mutzel, A.; Rodigast, M.; Iinuma, Y.; Böge, O.; Herrmann, H. An improved method for the quantification of SOA bound peroxides Atmos. Environ. 2013, 67, 365-369 10.1016/j.atmosenv.2012.11.012
14. 3 Environ. Sci. Technol. 2005, 39 (11) 4049-4059 10.1021/es050228s
15. Mertes, P.; Pfaffenberger, L.; Dommen, J.; Kalberer, M.; Baltensperger, U. Development of a sensitive long pathlength absorbance photometer to quantify peroxides in aerosol particles (Peroxide-LOPAP) Atmos. Meas. Technol. Discuss. 2012, 5 (1) 1431-1457 10.5194/amtd-5-1431-2012
16. Chen, Q.; Liu, Y.; Donahue, N. M.; Shilling, J. E.; Martin, S. T. Particle-phase chemistry of secondary organic material: Modeled compared to measured O:C and H:C elemental ratios provide constraints Environ. Sci. Technol. 2011, 45 (11) 4763-4770 10.1021/es104398s
17. Surratt, J. D.; Murphy, S. M.; Kroll, J. H.; Ng, N. L.; Hildebrandt, L.; Sorooshian, A.; Szmigielski, R.; Vermeylen, R.; Maenhaut, W.; Claeys, M.; Flagan, R. C.; Seinfeld, J. H. Chemical composition of secondary organic aerosol formed from the photooxidation of isoprene J. Phys. Chem. A 2006, 110 (31) 9665-9690 10.1021/jp061734m
18. Jokinen, T.; Sipila, M.; Junninen, H.; Ehn, M.; Lonn, G.; Hakala, J.; Petaja, T.; Mauldin, R. L.; Kulmala, M.; Worsnop, D. R. Atmospheric sulphuric acid and neutral cluster measurements using CI-APi-TOF Atmos. Chem. Phys. 2012, 12 (9) 4117-4125 10.5194/acp-12-4117-2012
19. Kulmala, M.; Kontkanen, J.; Junninen, H.; Lehtipalo, K.; Manninen, H. E.; Nieminen, T.; Petaja, T.; Sipila, M.; Schobesberger, S.; Rantala, P.; Franchin, A.; Jokinen, T.; Jarvinen, E.; Aijala, M.; Kangasluoma, J.; Hakala, J.; Aalto, P. P.; Paasonen, P.; Mikkila, J.; Vanhanen, J.; Aalto, J.; Hakola, H.; Makkonen, U.; Ruuskanen, T.; Mauldin, R. L.; Duplissy, J.; Vehkamaki, H.; Back, J.; Kortelainen, A.; Riipinen, I.; Kurten, T.; Johnston, M. V.; Smith, J. N.; Ehn, M.; Mentel, T. F.; Lehtinen, K. E. J.; Laaksonen, A.; Kerminen, V. M.; Worsnop, D. R. Direct observations of atmospheric aerosol nucleation Science 2013, 339 (6122) 943-946 10.1126/science.1227385
20. Kahnt, A.; Iinuma, Y.; Böge, O.; Mutzel, A.; Herrmann, H. Denuder sampling techniques for the determination of gas-phase carbonyl compounds: A comparison and characterisation of in situ and ex situ derivatisation methods J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2011, 879 (17-18) 1402-1411 10.1016/j.jchromb.2011.02.028
21. Chi, Y. G.; Feng, Y. L.; Wen, S.; Lu, H. X.; Yu, Z. Q.; Zhang, W. B.; Sheng, G. Y.; Fu, J. M. Determination of carbonyl compounds in the atmosphere by DNPH derivatization and LC-ESI-MS/MS detection Talanta 2007, 72 (2) 539-545 10.1016/j.talanta.2006.11.018
22. Vairavamurthy, A.; Roberts, J. M.; Newman, L. Methods for the deteremination of low-molecular weight carbonyl compounds in the atmosphere Atmos. Environ., Part A 1992, 26 (11) 1965-1993 10.1016/0960-1686(92)90083-w
23. Vogel, M.; Buldt, A.; Karst, U. Hydrazine reagents as derivatizing agents in environmental analysis-A critical review Fresenius' J. Anal. Chem. 2000, 366 (8) 781-791 10.1007/s002160051572
24. Vereecken, L.; Müller, J. F.; Peeters, J. Low-volatility poly-oxygenates in the OH-initiated atmospheric oxidation of α-pinene: Impact of non-traditional peroxyl radical chemistry Phys. Chem. Chem. Phys. 2007, 9 (38) 5241-5248 10.1039/b708023a
25. Hamilton, E. J.; Korcek, S.; Mahoney, L. R.; Zinbo, M. Kinetics and mechanism of the autoxidation of pentaerythrityl tetraheptanoate at 180-220 °C Int. J. Chem. Kinet. 1980, 12 (9) 577-603 10.1002/kin.550120902
26. Jensen, R. K.; Korcek, S.; Mahoney, L. R.; Zinbo, M. Liquid-phase autoxidation of organic compounds at elevated temperatures. 1. The stirred flow reactor technique and analysis of primary products from n -hexadecane autoxidation at 120-180 °C J. Am. Chem. Soc. 1979, 101 (25) 7574-7584 10.1021/ja00519a018
27. Jensen, R. K.; Korcek, S.; Mahoney, L. R.; Zinbo, M. Liquid-phase autoxidation of organic compounds at elevated temperatures. 2. Kinetics and mechanisms of the formation of cleavage products in n-hexadecane autoxidation J. Am. Chem. Soc. 1981, 103 (7) 1742-1749 10.1021/ja00397a026
28. Jalan, A.; Alecu, I. M.; Meana-Paneda, R.; Aguilera-Iparraguirre, J.; Yang, K. R.; Merchant, S. S.; Truhlar, D. G.; Green, W. H. New pathways for formation of acids and carbonyl products in low-temperature oxidation: The Korcek decomposition of γ-ketohydroperoxides J. Am. Chem. Soc. 2013, 135 (30) 11100-11114 10.1021/ja4034439
29. Yasmeen, F.; Vermeylen, R.; Szmigielski, R.; Iinuma, Y.; Böge, O.; Herrmann, H.; Maenhaut, W.; Claeys, M. Terpenylic acid and related compounds: Precursors for dimers in secondary organic aerosol from the ozonolysis of α- and β-pinene Atmos. Chem. Phys. 2010, 10 (19) 9383-9392 10.5194/acp-10-9383-2010
30. Claeys, M.; Iinuma, Y.; Szmigielski, R.; Surratt, J. D.; Blockhuys, F.; Van Alsenoy, C.; Böge, O.; Sierau, B.; Gomez-Gonzalez, Y.; Vermeylen, R.; Van der Veken, P.; Shahgholi, M.; Chan, A. W. H.; Herrmann, H.; Seinfeld, J. H.; Maenhaut, W. Terpenylic acid and related compounds from the oxidation of α-pinene: Implications for new particle formation and growth above forests Environ. Sci. Technol. 2009, 43 (18) 6976-6982 10.1021/es9007596
31. Szmigielski, R.; Surratt, J. D.; Gomez-Gonzalez, Y.; Van der Veken, P.; Kourtchev, I.; Vermeylen, R.; Blockhuys, F.; Jaoui, M.; Kleindienst, T. E.; Lewandowski, M.; Offenberg, J. H.; Edney, E. O.; Seinfeld, J. H.; Maenhaut, W.; Claeys, M. 3-Methyl-1,2,3-butanetricarboxylic acid: An atmospheric tracer for terpene secondary organic aerosol Geophys. Res. Lett. 2007, 34 (24) L24811 10.1029/2007gl031338
32. Larsen, B. R.; Di Bella, D.; Glasius, M.; Winterhalter, R.; Jensen, N.; Hjorth, J. Gas-phase OH oxidation of monoterpenes: Gaseous and particulate products J. Atmos. Chem. 2001, 38 (3) 231-276 10.1023/A:1006487530903
33. Christoffersen, T. S.; Hjorth, J.; Horie, O.; Jensen, N. R.; Kotzias, D.; Molander, L. L.; Neeb, P.; Ruppert, L.; Winterhalter, R.; Virkkula, A.; Wirtz, K.; Larsen, B. R. cis-Pinic acid, a possible precursor for organic aerosol formation from ozonolysis of α-pinene Atmos. Environ. 1998, 32 (10) 1657-1661 10.1016/s1352-2310(97)00448-2
34. Müller, L.; Reinnig, M. C.; Naumann, K. H.; Saathoff, H.; Mentel, T. F.; Donahue, N. M.; Hoffmann, T. Formation of 3-methyl-1,2,3-butanetricarboxylic acid via gas phase oxidation of pinonic acid-A mass spectrometric study of SOA aging Atmos. Chem. Phys. 2012, 12 (3) 1483-1496 10.5194/acp-12-1483-2012
35. Winterhalter, R.; Neeb, P.; Grossmann, D.; Kolloff, A.; Horie, O.; Moortgat, G. Products and mechanism of the gas phase reaction of ozone with β-pinene J. Atmos. Chem. 2000, 35 (2) 165-197 10.1023/a:1006257800929
36. 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 2008, 112 (36) 8345-8378 10.1021/jp802310p
37. 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.; Mysak, E. R.; Smith, J. D.; Kolb, C. E.; Worsnop, D. R. Carbon oxidation state as a metric for describing the chemistry of atmospheric organic aerosol Nat. Chem. 2011, 3 (2) 133-139 10.1038/nchem.948