Abstract
Because of the high occupant density in aircraft, the surface chemistry of ozone and squalene, an important component of skin oil, was evaluated. A reaction probability of (45±14)×10−5 was determined for the reaction of squalene (2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene) with ozone (50 parts per billion (ppb)) on a glass plate surface using the Field and Laboratory Emission Cell (FLEC) Automation and Control System (FACS). To more clearly define part of squalene’s indoor environment degradation mechanism, gas-phase and surface-bound products of the squalene+O3 reaction were also investigated. Emitted products were captured in solution, derivatized with O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine (PFBHA), and analyzed by gas chromatography and ion trap mass spectroscopy. The identified squalene+O3 reaction products were: 6-methyl-5-hepten-2-one (6MHO, ((CH3)2CCH(CH2)2 C(O)CH3)), glyoxal (ethanedial, HC(O)C(O)H), 4-oxopentanal (4OPA, CH3C(O)CH2CH2 CH(O)), and 6,10-dimethylundeca-5,9-dien-2-one (geranyl acetone). The compound 5,9,13-trimethyltetradeca-4,8,12-trienal is proposed as the other major squalene+O3 reaction product. This compound was determined from mass spectrometry coupled with plausible squalene+O3 reaction mechanisms based on previously published volatile organic compound+O3 gas-phase reaction mechanisms.
Issue Section:
Research Papers
References
1.
Weschler
, C. J.
, Wisthaler
, A.
, Cowlin
, S.
, Tamas
, G.
, Strom-Tejsen
, P.
, Hodgson
, A. T.
, Destaillats
, H.
, Herrington
, J.
, Zhang
, J. J.
, and Nazaroff
, W. W.
, “Ozone-Initiated Chemistry in an Occupied Simulated Aircraft Cabin
,” Environ. Sci. Technol.
0013-936X, Vol. 41
, No. 17
, 2007
, pp. 6177
–6184
.2.
Coleman
, B. K.
, Destaillats
, H.
, Hodgson
, A. T.
, and Nazaroff
, W. W.
, “Ozone Consumption and Volatile Byproduct Formation from Surface Reactions with Aircraft Cabin Materials and Clothing Fabrics
,” Atmos. Environ.
1352-2310, Vol. 42
, 2008
, pp. 642
–654
.3.
Tamas
, G.
, Weschler
, C. J.
, Bako-Biro
, Z.
, Wyon
, D. P.
, and Strom-Tejsen
, P.
, “Factors Affecting Ozone Removal Rates in a Simulated Aircraft Cabin Environment
,” Atmos. Environ.
1352-2310, Vol. 40
, No. 32
, 2006
, pp. 6122
–6133
.4.
Wisthaler
, A.
, Tamas
, G.
, Wyon
, D. P.
, Strom-Tejsen
, P.
, Space
, D.
, Beauchamp
, J.
, Hansel
, A.
, Mark
, T. D.
, and Weschler
, C. J.
, “Products of ozone-initiated chemistry in a Simulated Aircraft Environment
,” Environ. Sci. Technol.
0013-936X, Vol. 39
, No. 13
, 2005
, pp. 4823
–4832
.5.
Spengler
, J. D.
, Ludwig
, S.
, and Weker
, R. A.
, “Ozone Exposures During Trans-Continental and Trans-Pacific Flights
,” Indoor Air
0905-6947, Vol. 14
, 2004
, pp. 67
–73
.6.
Wisthaler
, A.
, Strom-Tejsen
, P.
, Fang
, L.
, Arnaud
, T. J.
, Hansel
, A.
, Mark
, T. D.
, and Wyon
, D. P.
, “PTR-MS Assessment of Photocatalytic and Sorption-Based Purification of Recirculated Cabin Air During Simulated 7-h Flights with High Passenger Density
,” Environ. Sci. Technol.
0013-936X, Vol. 41
, No. 1
, 2007
, pp. 229
–234
.7.
Greene
, R. S.
, Downing
, D. T.
, Pochi
, P. E.
, and Strauss
, J. S.
, “Anatomical Variation in the Amount and Composition of Human Skin Surface Lipid
,” J. Invest. Dermatol.
0022-202X, Vol. 54
, No. 3
, 1970
, pp. 240
–247
.8.
Atkinson
, R.
and Arey
, J.
“Atmospheric Degradation of Volatile Organic Compounds
,” Chem. Rev. (Washington, D.C.)
0009-2665 https://doi.org/10.1021/cr0206420, Vol. 103
, No. 12
, 2003
, pp. 4605
–4638
.9.
Fruekilde
, P.
, Hjorth
, J.
, Jensen
, N. R.
, Kotzias
, D.
, and Larsen
, B.
“Ozonolysis at Vegetation Surfaces: A Source of Acetone, 4-oxopentanal, 6-methyl-5-hepten-2-one, and Geranyl Acetone in the Troposphere
,” Atmos. Environ.
1352-2310, Vol. 32
, No. 11
, 1998
, pp. 1893
–1902
.10.
Flemmer
, M. M.
, Ham
, J. E.
, and Wells
, J. R.
, “Field and Laboratory Emission Cell Automation and Control System for Investigating Surface Chemistry Reactions
,” Rev. Sci. Instrum.
0034-6748 https://doi.org/10.1063/1.2432243, Vol. 78
, No. 1
, 2007
, p. 014101.11.
Yu
, J. Z.
, Flagan
, R. C.
, and Seinfeld
, J. H.
, “Identification of Products Containing −COOH, −OH, and −CO in Atmospheric Oxidation of Hydrocarbons
,” Environ. Sci. Technol.
0013-936X https://doi.org/10.1021/es980129x, Vol. 32
, No. 16
, 1998
, pp. 2357
–2370
.12.
EPA
, (2000
), AOPWIN v1.91, U.S. Environmental Protection Agency
, Washington D.C.
, 2000
.13.
Matsunaga
, S.
, Mochida
, M.
, and Kawamura
, K.
, “High Abundance of Gaseous and Particulate 4-oxopentanal in the Forestal Atmosphere
,” Chemosphere
0045-6535, Vol. 55
, No. 8
, 2004
, pp. 1143
–1147
.14.
Hagvall
, L.
, Backtorp
, C.
, Svensson
, S.
, Nyman
, G.
, Borje
, A.
, and Karlberg
, A. T.
, “Fragrance Compound Geraniol Forms Contact Allergens on Air Exposure. Identification and Quantification of Oxidation Products and Effect on Skin Sensitization
,” Chem. Res. Toxicol.
0893-228X, Vol. 20
, No. 5
, 2007
, pp. 807
–814
.15.
Matura
, M.
, Skold
, M.
, Borje
, A.
, Andersen
, K. E.
, Bruze
, M.
, Frosch
, P.
, Goossens
, A.
, Johansen
, J. D.
, Svedman
, C.
, White
, I. R.
, and Karlberg
, A. T.
, “Selected Oxidized Fragrance Terpenes are Common Contact Allergens
,” Contact Dermatitis
0105-1873, Vol. 52
, No. 6
, 2005
, pp. 320
–328
.16.
Matura
, M.
, Goossens
, A.
, Bordalo
, O.
, Garcia-Bravo
, B.
, Magnusson
, K.
, Wrangsjo
, K.
, and Karlberg
, A. T.
, “Patch Testing with Oxidized r-(+)-Limonene and Its Hydroperoxide Fraction
,” Contact Dermatitis
0105-1873, Vol. 49
, No. 1
, 2003
, pp. 15
–21
.17.
Karlberg
, A. T.
, Shao
, L. P.
, Nilsson
, U.
, Gafvert
, E.
, and Nilsson
, J. L. G.
, “Hydroperoxides in Oxidized d-Limonene Identified as Potent Contact Allergens
,” Arch. Dermatol. Res.
0340-3696, Vol. 286
, No. 2
, 1994
, pp. 97
–103
.18.
Atkinson
, R.
and Arey
, J.
, “Gas-Phase Tropospheric Chemistry of Biogenic Volatile Organic Compounds: A Review
,” Atmos. Environ.
1352-2310, Vol. 37
, Supplement 2
, 2003
, pp. 197
–219
.19.
Atkinson
, R.
, Hasegawa
, D.
, and Aschmann
, S. M.
, “Rate Constants for the Gas-Phase Reactions of O-3 with a Series of Monoterpenes and Related Compounds at 296-k +/−2-K
,” Int. J. Chem. Kinet.
0538-8066 https://doi.org/10.1002/kin.550220807, Vol. 22
, No. 8
, 1990
, pp. 871
–887
.20.
Moise
, T.
and Rudich
, Y.
, “Reactive Uptake of Ozone by Aerosol-Associated Unsaturated Fatty Acids: Kinetics, Mechanism, and Products
,” J. Phys. Chem. A
1089-5639, Vol. 106
, No. 27
, 2002
, pp. 6469
–6476
.21.
Bird
, R. B.
, Stewart
, W. E.
, and Lightfoot
, E. N.
, Transport Phenomena
, John Wiley & Sons, Inc.
, New York
, 1960
.22.
McQuarrie
, D. A.
and Simon
, J. D.
, Physical Chemistry: A Molecular Approach
, Viva Books
, New York
, 2008
.23.
CRC Handbook of Chemistry and Physics
, D. R.
Lide
, Ed., CRC Press
, New York
, 2007–2008.24.
Zhang
, L. Z.
and Niu
, J. L.
, “Laminar Fluid Flow and Mass Transfer in a Standard Field and Laboratory Emission Cell
,” Int. J. Heat Mass Transfer
0017-9310, Vol. 46
, No. 1
, 2003
, pp. 91
–100
.25.
Anderson
, S. E.
, Wells
, J. R.
, Fedorowicz
, A.
, Butterworth
, L. F.
, Meade
, B. J.
, and Munson
, A. E.
, “Evaluation of the Contact and Respiratory Sensitization Potential of Volatile Organic Compounds Generated by Simulated Indoor Air Chemistry
,” Toxicol. Sci.
1096-6080, Vol. 97
, No. 2
, 2007
, pp. 355
–363
.26.
Pandrangi
, L.
and Morrison
, G. C.
, “Ozone Interactions with Human Hair: Ozone Uptake Rates and Product Formation
,” Atmos. Environ.
1352-2310, Vol. 42
, 2008
, pp. 5079
–5089
.
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