Low-Temperature Oxidation of Ethylene by Ozone in a Jet-Stirred Reactor

Rousso, Aric C.; Hansen, Nils; Jasper, Ahren W.; Ju, Yiguang

doi:10.1021/acs.jpca.8b06556

Title: Low-Temperature Oxidation of Ethylene by Ozone in a Jet-Stirred Reactor

Journal Article · Sun Oct 07 00:00:00 EDT 2018 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.8b06556· OSTI ID:1487124

Rousso, Aric C. ^[1];

^[2];

^[3]; Ju, Yiguang ^[1]

Princeton Univ., NJ (United States). Dept. of Mechanical and Aerospace Engineering
Sandia National Lab. (SNL-CA), Livermore, CA (United States). Combustion Research Facility
Argonne National Lab. (ANL), Argonne, IL (United States). Chemical Sciences and Engineering Division

Ethylene oxidation initiated by ozone addition (ozonolysis) is carried out in a jet-stirred reactor from 300-1000 K to explore the kinetic pathways relevant to low-temperature oxidation. The temperature dependencies of species’ mole fractions are quantified using molecular-beam mass spectrometry with electron ionization and single-photon ionization employing tunable synchrotron-generated vacuum-ultraviolet radiation. Upon ozone addition, significant ethylene oxidation is found in the low-temperature regime from 300-600 K. Here, we provide new insights into the ethylene ozonolysis reaction network via identification and quantification of previously elusive intermediates by combining experimental photoionization energy scans and ab initio threshold energy calculations for isomer identification. Specifically, the C₂H₄+O₃ adduct C₂H₄O₃ is identified as a keto-hydroperoxide (hydroperoxy-acetaldehyde, HOOCH₂CHO) based on the calculated and experimentally observed ionization energy of 9.80 (±0.05) eV. Quantification using a photoionization cross-section of 5 Mb at 10.5 eV results in 5 ppm at atmospheric conditions which decreases monotonically with temperature until 550 K. Other hydroperoxide species, that contribute in larger amounts to the low-temperature oxidation of C₂H₄, like H₂O₂, CH₃OOH, and C₂H₅OOH, are identified and their temperature-dependent mole fractions are reported. The experimental evidence for additional oxygenated species such as methanol, ketene, acetaldehyde, and hydroxy-acetaldehyde suggest multiple active oxidation routes. This experimental investigation closes the gap between ozonolysis at atmospheric and elevated temperature conditions and provides a database for future modeling.

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Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Workforce Development for Teachers and Scientists (WDTS)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1487124

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 122, Issue 43; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 36 works

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References (62)

C.—The oxidation of hydrocarbons by ozone at low temperatures Drugman, Julien J. Chem. Soc., Trans., Vol. 89, Issue 0 https://doi.org/10.1039/CT9068900939	journal	January 1906
Measurement and modelling of air pollution and atmospheric chemistry in the U.K. West Midlands conurbation: Overview of the PUMA Consortium project Harrison, R. M.; Yin, J.; Tilling, R. M. Science of The Total Environment, Vol. 360, Issue 1-3 https://doi.org/10.1016/j.scitotenv.2005.08.053	journal	May 2006
Energetics, Kinetics, and Product Distributions of the Reactions of Ozone with Ethene and 2,3-Dimethyl-2-butene Olzmann, M.; Kraka, E.; Cremer, D. The Journal of Physical Chemistry A, Vol. 101, Issue 49 https://doi.org/10.1021/jp971663e	journal	December 1997
Highly Oxygenated Molecules from Atmospheric Autoxidation of Hydrocarbons: A Prominent Challenge for Chemical Kinetics Studies: HIGHLY OXYGENATED MOLECULES FROM ATMOSPHERIC AUTOXIDATION OF HYDROCARBONS Ehn, Mikael; Berndt, Torsten; Wildt, Jürgen International Journal of Chemical Kinetics, Vol. 49, Issue 11 https://doi.org/10.1002/kin.21130	journal	September 2017
The Formation of Highly Oxidized Multifunctional Products in the Ozonolysis of Cyclohexene Rissanen, Matti P.; Kurtén, Theo; Sipilä, Mikko Journal of the American Chemical Society, Vol. 136, Issue 44 https://doi.org/10.1021/ja507146s	journal	October 2014
Observation of the simplest Criegee intermediate CH ₂ OO in the gas-phase ozonolysis of ethylene Womack, Caroline C.; Martin-Drumel, Marie-Aline; Brown, Gordon G. Science Advances, Vol. 1, Issue 2 https://doi.org/10.1126/sciadv.1400105	journal	March 2015
Oligomerization Reaction of the Criegee Intermediate Leads to Secondary Organic Aerosol Formation in Ethylene Ozonolysis Sakamoto, Yosuke; Inomata, Satoshi; Hirokawa, Jun The Journal of Physical Chemistry A, Vol. 117, Issue 48 https://doi.org/10.1021/jp408672m	journal	November 2013
Water vapour effects on secondary organic aerosol formation in isoprene ozonolysis Sakamoto, Yosuke; Yajima, Ryoji; Inomata, Satoshi Physical Chemistry Chemical Physics, Vol. 19, Issue 4 https://doi.org/10.1039/C6CP04521A	journal	January 2017
The physical chemistry of Criegee intermediates in the gas phase Osborn, David L.; Taatjes, Craig A. International Reviews in Physical Chemistry, Vol. 34, Issue 3 https://doi.org/10.1080/0144235X.2015.1055676	journal	July 2015
Criegee Intermediates: What Direct Production and Detection Can Teach Us About Reactions of Carbonyl Oxides Taatjes, Craig A. Annual Review of Physical Chemistry, Vol. 68, Issue 1 https://doi.org/10.1146/annurev-physchem-052516-050739	journal	May 2017
Die Ozonisierung des 9,10-Oktalins Criegee, Rudolf; Wenner, Gotthilf Justus Liebigs Annalen der Chemie, Vol. 564, Issue 1 https://doi.org/10.1002/jlac.19495640103	journal	July 1949
Quantum Chemical Study of the Initial Step of Ozone Addition to the Double Bond of Ethylene Gadzhiev, Oleg B.; Ignatov, Stanislav K.; Krisyuk, Boris E. The Journal of Physical Chemistry A, Vol. 116, Issue 42 https://doi.org/10.1021/jp307738p	journal	October 2012
Kinetics of CH ₂ OO reactions with SO ₂ , NO ₂ , NO, H ₂ O and CH ₃ CHO as a function of pressure Stone, Daniel; Blitz, Mark; Daubney, Laura Phys. Chem. Chem. Phys., Vol. 16, Issue 3 https://doi.org/10.1039/C3CP54391A	journal	January 2014
The reactions of Criegee intermediates with alkenes, ozone, and carbonyl oxides Vereecken, L.; Harder, H.; Novelli, A. Physical Chemistry Chemical Physics, Vol. 16, Issue 9 https://doi.org/10.1039/c3cp54514h	journal	January 2014
Nascent energy distribution of the Criegee intermediate CH ₂ OO from direct dynamics calculations of primary ozonide dissociation Pfeifle, Mark; Ma, Yong-Tao; Jasper, Ahren W. The Journal of Chemical Physics, Vol. 148, Issue 17 https://doi.org/10.1063/1.5028117	journal	May 2018
Stabilization of the Simplest Criegee Intermediate from the Reaction between Ozone and Ethylene: A High-Level Quantum Chemical and Kinetic Analysis of Ozonolysis Nguyen, Thanh Lam; Lee, Hyunwoo; Matthews, Devin A. The Journal of Physical Chemistry A, Vol. 119, Issue 22 https://doi.org/10.1021/acs.jpca.5b02088	journal	May 2015
Identification of dioxirane (H2COO) in ozone-olefin reactions via microwave spectroscopy Lovas, F. J.; Suenram, R. D. Chemical Physics Letters, Vol. 51, Issue 3 https://doi.org/10.1016/0009-2614(77)85398-0	journal	November 1977
Formation of hydroxymethyl hydroperoxide and formic acid in alkene ozonolysis in the presence of water vapour Neeb, Peter; Sauer, Frank; Horie, Osamu Atmospheric Environment, Vol. 31, Issue 10 https://doi.org/10.1016/S1352-2310(96)00322-6	journal	May 1997
First-principles-derived kinetics of the reactions involved in low-temperature dimethyl ether oxidation Andersen, Amity; Carter, Emily A. Molecular Physics, Vol. 106, Issue 2-4 https://doi.org/10.1080/00268970701837008	journal	February 2008
Plasma assisted combustion: Dynamics and chemistry Ju, Yiguang; Sun, Wenting Progress in Energy and Combustion Science, Vol. 48 https://doi.org/10.1016/j.pecs.2014.12.002	journal	June 2015
The effect of ozone addition on laminar flame speed Gao, Xiang; Zhang, Yao; Adusumilli, Sampath Combustion and Flame, Vol. 162, Issue 10 https://doi.org/10.1016/j.combustflame.2015.07.028	journal	October 2015
Kinetic studies of ozone assisted low temperature oxidation of dimethyl ether in a flow reactor using molecular-beam mass spectrometry Zhao, Hao; Yang, Xueliang; Ju, Yiguang Combustion and Flame, Vol. 173 https://doi.org/10.1016/j.combustflame.2016.08.008	journal	November 2016
Spark ignition of methane and methanol in ozonized air Nomaguchi, T.; Koda, S. Symposium (International) on Combustion, Vol. 22, Issue 1 https://doi.org/10.1016/S0082-0784(89)80180-8	journal	January 1989
Flame propagation enhancement by plasma excitation of oxygen. Part I: Effects of O3 Ombrello, Timothy; Won, Sang Hee; Ju, Yiguang Combustion and Flame, Vol. 157, Issue 10 https://doi.org/10.1016/j.combustflame.2010.02.005	journal	October 2010
Quantification of the Keto-Hydroperoxide (HOOCH ₂ OCHO) and Other Elusive Intermediates during Low-Temperature Oxidation of Dimethyl Ether Moshammer, Kai; Jasper, Ahren W.; Popolan-Vaida, Denisia M. The Journal of Physical Chemistry A, Vol. 120, Issue 40 https://doi.org/10.1021/acs.jpca.6b06634	journal	September 2016
Detection and Identification of the Keto-Hydroperoxide (HOOCH ₂ OCHO) and Other Intermediates during Low-Temperature Oxidation of Dimethyl Ether Moshammer, Kai; Jasper, Ahren W.; Popolan-Vaida, Denisia M. The Journal of Physical Chemistry A, Vol. 119, Issue 28 https://doi.org/10.1021/acs.jpca.5b00101	journal	February 2015
New insights into the low-temperature oxidation of 2-methylhexane Wang, Zhandong; Mohamed, Samah Y.; Zhang, Lidong Proceedings of the Combustion Institute, Vol. 36, Issue 1 https://doi.org/10.1016/j.proci.2016.06.085	journal	January 2017
Absorption cross-sections of ozone in the ultraviolet and visible spectral regions: Status report 2015 Orphal, Johannes; Staehelin, Johannes; Tamminen, Johanna Journal of Molecular Spectroscopy, Vol. 327 https://doi.org/10.1016/j.jms.2016.07.007	journal	September 2016
Kinetic modeling of ethylene oxidation Dagaut, P. Combustion and Flame, Vol. 71, Issue 3 https://doi.org/10.1016/0010-2180(88)90065-X	journal	March 1988
Chemical dynamics, molecular energetics, and kinetics at the synchrotron Leone, Stephen R.; Ahmed, Musahid; Wilson, Kevin R. Physical Chemistry Chemical Physics, Vol. 12, Issue 25 https://doi.org/10.1039/c001707h	journal	January 2010
Advances and challenges in laminar flame experiments and implications for combustion chemistry Egolfopoulos, F. N.; Hansen, N.; Ju, Y. Progress in Energy and Combustion Science, Vol. 43 https://doi.org/10.1016/j.pecs.2014.04.004	journal	August 2014
Detailed mass spectrometric and modeling study of isomeric butene flames Schenk, Marina; Leon, Larisa; Moshammer, Kai Combustion and Flame, Vol. 160, Issue 3 https://doi.org/10.1016/j.combustflame.2012.10.023	journal	March 2013
Near-threshold absolute photoionization cross-sections of some reaction intermediates in combustion Wang, Juan; Yang, Bin; Cool, Terrill A. International Journal of Mass Spectrometry, Vol. 269, Issue 3 https://doi.org/10.1016/j.ijms.2007.10.013	journal	February 2008
Comprehensive kinetic modeling and experimental study of a fuel-rich, premixed n-heptane flame Seidel, Lars; Moshammer, Kai; Wang, Xiaoxiao Combustion and Flame, Vol. 162, Issue 5 https://doi.org/10.1016/j.combustflame.2015.01.002	journal	May 2015
Photoionization mass spectrometer for studies of flame chemistry with a synchrotron light source Cool, Terrill A.; McIlroy, Andrew; Qi, Fei Review of Scientific Instruments, Vol. 76, Issue 9 https://doi.org/10.1063/1.2010307	journal	September 2005
Selective detection of isomers with photoionization mass spectrometry for studies of hydrocarbon flame chemistry Cool, Terrill A.; Nakajima, Koichi; Mostefaoui, Toufik A. The Journal of Chemical Physics, Vol. 119, Issue 16 https://doi.org/10.1063/1.1611173	journal	October 2003
Recent contributions of flame-sampling molecular-beam mass spectrometry to a fundamental understanding of combustion chemistry Hansen, Nils; Cool, Terrill A.; Westmoreland, Phillip R. Progress in Energy and Combustion Science, Vol. 35, Issue 2 https://doi.org/10.1016/j.pecs.2008.10.001	journal	April 2009
“Imaging” combustion chemistry via multiplexed synchrotron-photoionization mass spectrometry Taatjes, Craig A.; Hansen, Nils; Osborn, David L. Phys. Chem. Chem. Phys., Vol. 10, Issue 1 https://doi.org/10.1039/B713460F	journal	January 2008
Studies of a fuel-rich propane flame with photoionization mass spectrometry Cool, Terrill A.; Nakajima, Koichi; Taatjes, Craig A. Proceedings of the Combustion Institute, Vol. 30, Issue 1 https://doi.org/10.1016/j.proci.2004.08.103	journal	January 2005
Ethylene pyrolysis and oxidation: A kinetic modeling study Dagaut, Philippe; Boettner, Jean-Claude; Cathonnet, Michel International Journal of Chemical Kinetics, Vol. 22, Issue 6 https://doi.org/10.1002/kin.550220608	journal	June 1990
Ethylene oxidation in a well-stirred reactor Marinov, Nick M.; Malte, Philip C. International Journal of Chemical Kinetics, Vol. 27, Issue 10 https://doi.org/10.1002/kin.550271003	journal	October 1995
The oxidation of 2-butene: A high pressure ignition delay, kinetic modeling study and reactivity comparison with isobutene and 1-butene Li, Yang; Zhou, Chong-Wen; Somers, Kieran P. Proceedings of the Combustion Institute, Vol. 36, Issue 1 https://doi.org/10.1016/j.proci.2016.05.052	journal	January 2017
A Hierarchical and Comparative Kinetic Modeling Study of C ₁ − C ₂ Hydrocarbon and Oxygenated Fuels : KINETIC STUDY OF C Metcalfe, Wayne K.; Burke, Sinéad M.; Ahmed, Syed S. International Journal of Chemical Kinetics, Vol. 45, Issue 10 https://doi.org/10.1002/kin.20802	journal	August 2013
Effect of prompt dissociation of formyl radical on 1,3,5-trioxane and CH2O laminar flame speeds with CO2 dilution at elevated pressure Zhao, Hao; Fu, Jiapeng; Haas, Francis M. Combustion and Flame, Vol. 183 https://doi.org/10.1016/j.combustflame.2017.05.005	journal	September 2017
An Experimental and Kinetic Study of Ethene Oxidation at a High Equivalence Ratio Jallais, S.; Bonneau, L.; Auzanneau, M. Industrial & Engineering Chemistry Research, Vol. 41, Issue 23 https://doi.org/10.1021/ie010568w	journal	October 2002
Experimental Confirmation of the Low-Temperature Oxidation Scheme of Alkanes Battin-Leclerc, Frédérique; Herbinet, Olivier; Glaude, Pierre-Alexandre Angewandte Chemie International Edition, Vol. 49, Issue 18 https://doi.org/10.1002/anie.200906850	journal	April 2010
The nature of the transitory product in the gas-phase ozonolysis of ethene Neeb, Peter; Horie, Osamu; Moortgat, Geert K. Chemical Physics Letters, Vol. 246, Issue 1-2 https://doi.org/10.1016/0009-2614(95)01073-I	journal	November 1995
Synchrotron photoionization mass spectrometry study of intermediates in fuel-rich 1,2-dimethoxyethane flame Lin, Z. K.; Han, D. L.; Li, S. F. The Journal of Chemical Physics, Vol. 130, Issue 15 https://doi.org/10.1063/1.3109687	journal	April 2009
Direct Kinetic Measurements of Reactions between the Simplest Criegee Intermediate CH ₂ OO and Alkenes Buras, Zachary J.; Elsamra, Rehab M. I.; Jalan, Amrit The Journal of Physical Chemistry A, Vol. 118, Issue 11 https://doi.org/10.1021/jp4118985	journal	March 2014
Plasma supported combustion Starikovskii, A. Yu. Proceedings of the Combustion Institute, Vol. 30, Issue 2 https://doi.org/10.1016/j.proci.2004.08.272	journal	January 2005
Effect of ozone on combustion of compression ignition engines Tachibana, T.; Hirata, K.; Nishida, H. Combustion and Flame, Vol. 85, Issue 3-4 https://doi.org/10.1016/0010-2180(91)90154-4	journal	June 1991
Direct measurement of Criegee intermediate (CH2OO) reactions with acetone, acetaldehyde, and hexafluoroacetone Taatjes, Craig A.; Welz, Oliver; Eskola, Arkke J. Physical Chemistry Chemical Physics, Vol. 14, Issue 30 https://doi.org/10.1039/c2cp40294g	journal	January 2012
Formation of formic acid and organic peroxides in the ozonolysis of ethene with added water vapour Horie, Osamu; Neeb, Peter; Limbach, Stefan Geophysical Research Letters, Vol. 21, Issue 14 https://doi.org/10.1029/94GL01174	journal	July 1994
VUV Photoionization Cross Sections of HO ₂ , H ₂ O ₂ , and H ₂ CO Dodson, Leah G.; Shen, Linhan; Savee, John D. The Journal of Physical Chemistry A, Vol. 119, Issue 8 https://doi.org/10.1021/jp508942a	journal	February 2015
Photolysis of methane revisited at 121.6 nm and at 118.2 nm: quantum yields of the primary products, measured by mass spectrometry Gans, Bérenger; Boyé-Péronne, Séverine; Broquier, Michel Physical Chemistry Chemical Physics, Vol. 13, Issue 18 https://doi.org/10.1039/c0cp02627a	journal	January 2011
Calculation of low‐energy elastic cross sections for electron‐CF ₄ scattering Gianturco, F. A.; Lucchese, R. R.; Sanna, N. The Journal of Chemical Physics, Vol. 100, Issue 9 https://doi.org/10.1063/1.467237	journal	May 1994
A Near-Threshold Shape Resonance in the Valence-Shell Photoabsorption of Linear Alkynes Jacovella, U.; Holland, D. M. P.; Boyé-Péronne, S. The Journal of Physical Chemistry A, Vol. 119, Issue 50 https://doi.org/10.1021/acs.jpca.5b06949	journal	October 2015
High-resolution vacuum-ultraviolet photoabsorption spectra of 1-butyne and 2-butyne Jacovella, U.; Holland, D. M. P.; Boyé-Péronne, S. The Journal of Chemical Physics, Vol. 143, Issue 3 https://doi.org/10.1063/1.4926541	journal	July 2015
Cross section and asymmetry parameter calculation for sulfur 1s photoionization of SF6 Natalense, Alexandra P. P.; Lucchese, Robert R. The Journal of Chemical Physics, Vol. 111, Issue 12 https://doi.org/10.1063/1.479794	journal	September 1999
Developing detailed chemical kinetic mechanisms for fuel combustion Curran, Henry J. Proceedings of the Combustion Institute, Vol. 37, Issue 1 https://doi.org/10.1016/j.proci.2018.06.054	journal	January 2019
Photoionization cross sections for reaction intermediates in hydrocarbon combustion Cool, Terrill A.; Wang, Juan; Nakajima, Koichi International Journal of Mass Spectrometry, Vol. 247, Issue 1-3 https://doi.org/10.1016/j.ijms.2005.08.018	journal	December 2005
Absolute photoionization cross-sections of some combustion intermediates Yang, Bin; Wang, Juan; Cool, Terrill A. International Journal of Mass Spectrometry, Vol. 309 https://doi.org/10.1016/j.ijms.2011.09.006	journal	January 2012

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ethylene
jet-stirred reactor
keto-hydroperoxide
low-temperature chemistry
ozone

Title: Low-Temperature Oxidation of Ethylene by Ozone in a Jet-Stirred Reactor

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