Identification of the molecular-weight growth reaction network in counterflow flames of the C3H4 isomers allene and propyne

Kukkadapu, G.; Wagnon, S. W.; Pitz, W. J.; Hansen, N.

doi:10.1016/j.proci.2020.07.130

Identification of the molecular-weight growth reaction network in counterflow flames of the C₃H₄ isomers allene and propyne

Journal Article · Tue Oct 27 00:00:00 EDT 2020 · Proceedings of the Combustion Institute

DOI:https://doi.org/10.1016/j.proci.2020.07.130· OSTI ID:1671188

^[1]; ^[1]; Pitz, W. J. ^[1]; ^[2]

Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sandia National Lab. (SNL-CA), Livermore, CA (United States)

The reaction networks responsible for aromatics formation in counterflow flames of the C₃H₄ isomers allene and propyne are identified through a combined experimental and modeling study. Mole fraction profiles of near-atmospheric pressure (933 mbar) diffusion flames fueled by the C₃H₄ isomers are analyzed by means of a newly assembled, chemically detailed kinetic mechanism. The experiment consists of a counterflow burner system that is coupled to a high-resolution time-of-flight molecular-beam mass spectrometer with single-photon ionization via synchrotron-generated vacuum-ultraviolet photons. Flame-sampled, mass-specific photoionization efficiency curves are used to identify the presence of aliphatically substituted aromatic species in addition to the commonly considered pericondensed ring structures. The new mechanism describes the formation and growth of aromatics through repetitive sequences of radical–radical and radical–molecule reactions that include C₁₆ intermediates. Higher concentrations of aromatic species are observed in the allene flame and the new mechanism captures the observed experimental trends very accurately. The results indicate the importance of the aliphatically substituted aromatics and of ring-enlargement reactions for the growth reactions. According to the model simulations, radical+radical recombination and PAH-radical+molecule reactions play an important role in PAH growth.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)

Sponsoring Organization:: USDOE; USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: AC52-07NA27344

OSTI ID:: 1671188

Alternate ID(s):: OSTI ID: 1777053

Report Number(s):: LLNL-JRNL--796421; 997350

Journal Information:: Proceedings of the Combustion Institute, Journal Name: Proceedings of the Combustion Institute Vol. vol. 38; ISSN 1540-7489

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (50)

HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars Yang, Tao; Kaiser, Ralf I.; Troy, Tyler P. Angewandte Chemie, Vol. 129, Issue 16 https://doi.org/10.1002/ange.201701259	journal	March 2017
Computational study on the recombination reaction between benzyl and propargyl radicals Matsugi, Akira; Miyoshi, Akira International Journal of Chemical Kinetics, Vol. 44, Issue 3 https://doi.org/10.1002/kin.20625	journal	January 2012
Further studies on effects of thermophoresis on seeding particles in LDV measurements of strained flames Sung, C. J.; Kistler, J. S.; Nishioka, M. Combustion and Flame, Vol. 105, Issue 1-2 https://doi.org/10.1016/0010-2180(95)00189-1	journal	April 1996
A new path to benzene in flames Stein, Stephen E.; Walker, James A.; Suryan, Mahendra M. Symposium (International) on Combustion, Vol. 23, Issue 1 https://doi.org/10.1016/S0082-0784(06)80245-6	journal	January 1991
Experimental and kinetic modeling study of butene isomer pyrolysis: Part I. 1- and 2-Butene Wang, Kun; Villano, Stephanie M.; Dean, Anthony M. Combustion and Flame, Vol. 173 https://doi.org/10.1016/j.combustflame.2016.07.037	journal	November 2016
Investigating repetitive reaction pathways for the formation of polycyclic aromatic hydrocarbons in combustion processes Hansen, Nils; Schenk, Marina; Moshammer, Kai Combustion and Flame, Vol. 180 https://doi.org/10.1016/j.combustflame.2016.09.013	journal	June 2017
2D-imaging of sampling-probe perturbations in laminar premixed flames using Kr X-ray fluorescence Hansen, Nils; Tranter, Robert S.; Moshammer, Kai Combustion and Flame, Vol. 181 https://doi.org/10.1016/j.combustflame.2017.03.024	journal	July 2017
Reaction mechanism, rate constants, and product yields for unimolecular and H-assisted decomposition of 2,4-cyclopentadienone and oxidation of cyclopentadienyl with atomic oxygen Ghildina, A. R.; Oleinikov, A. D.; Azyazov, V. N. Combustion and Flame, Vol. 183 https://doi.org/10.1016/j.combustflame.2017.05.015	journal	September 2017
Reaction mechanism, rate constants, and product yields for the oxidation of Cyclopentadienyl and embedded five-member ring radicals with hydroxyl Galimova, G. R.; Azyazov, V. N.; Mebel, A. M. Combustion and Flame, Vol. 187 https://doi.org/10.1016/j.combustflame.2017.09.005	journal	January 2018
On the formation of ethynylbiphenyl (C14D5H5; C6D5C6H4CCH) isomers in the reaction of D5-phenyl radicals (C6D5; X2A1) with phenylacetylene (C6H5C2H; X1A1) under single collision conditions Parker, Dorian S. N.; Yang, Tao; Kaiser, Ralf I. Chemical Physics Letters, Vol. 595-596 https://doi.org/10.1016/j.cplett.2014.02.013	journal	March 2014
Near-threshold photoionization mass spectra of combustion-generated high-molecular-weight soot precursors Skeen, Scott A.; Michelsen, Hope A.; Wilson, Kevin R. Journal of Aerosol Science, Vol. 58 https://doi.org/10.1016/j.jaerosci.2012.12.008	journal	April 2013
Studies of aromatic hydrocarbon formation mechanisms in flames: Progress towards closing the fuel gap McEnally, Charles S.; Pfefferle, Lisa D.; Atakan, Burak Progress in Energy and Combustion Science, Vol. 32, Issue 3 https://doi.org/10.1016/j.pecs.2005.11.003	journal	January 2006
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
Photoionization mass spectrometric studies and modeling of fuel-rich allene and propyne flames Hansen, Nils; Miller, James A.; Taatjes, Craig A. Proceedings of the Combustion Institute, Vol. 31, Issue 1 https://doi.org/10.1016/j.proci.2006.07.045	journal	January 2007
Formation of nascent soot and other condensed-phase materials in flames Wang, Hai Proceedings of the Combustion Institute, Vol. 33, Issue 1 https://doi.org/10.1016/j.proci.2010.09.009	journal	January 2011
Soot precursor formation and limitations of the stabilomer grid Johansson, K. O.; Lai, J. Y. W.; Skeen, S. A. Proceedings of the Combustion Institute, Vol. 35, Issue 2 https://doi.org/10.1016/j.proci.2014.05.033	journal	January 2015
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
Temperature- and pressure-dependent rate coefficients for the HACA pathways from benzene to naphthalene Mebel, Alexander M.; Georgievskii, Yuri; Jasper, Ahren W. Proceedings of the Combustion Institute, Vol. 36, Issue 1 https://doi.org/10.1016/j.proci.2016.07.013	journal	January 2017
Aromatic ring formation in opposed-flow diffusive 1,3-butadiene flames Moshammer, Kai; Seidel, Lars; Wang, Yu Proceedings of the Combustion Institute, Vol. 36, Issue 1 https://doi.org/10.1016/j.proci.2016.09.010	journal	January 2017
On the low-temperature limit of HACA Frenklach, Michael; Singh, Ravi I.; Mebel, Alexander M. Proceedings of the Combustion Institute, Vol. 37, Issue 1 https://doi.org/10.1016/j.proci.2018.05.068	journal	January 2019
Knowledge generation through data research: New validation targets for the refinement of kinetic mechanisms Hansen, N.; He, X.; Griggs, R. Proceedings of the Combustion Institute, Vol. 37, Issue 1 https://doi.org/10.1016/j.proci.2018.07.023	journal	January 2019
Kinetic modeling study of surrogate components for gasoline, jet and diesel fuels: C7-C11 methylated aromatics Kukkadapu, Goutham; Kang, Dongil; Wagnon, Scott W. Proceedings of the Combustion Institute, Vol. 37, Issue 1 https://doi.org/10.1016/j.proci.2018.08.016	journal	January 2019
Oxidation of Graphene-Edge Six- and Five-Member Rings by Molecular Oxygen Singh, Ravi I.; Mebel, Alexander M.; Frenklach, Michael The Journal of Physical Chemistry A, Vol. 119, Issue 28 https://doi.org/10.1021/acs.jpca.5b00868	journal	February 2015
Mystery of 1-Vinylpropargyl Formation from Acetylene Addition to the Propargyl Radical: An Open-and-Shut Case da Silva, Gabriel The Journal of Physical Chemistry A, Vol. 121, Issue 10 https://doi.org/10.1021/acs.jpca.6b12996	journal	March 2017
Detection of Aliphatically Bridged Multi-Core Polycyclic Aromatic Hydrocarbons in Sooting Flames with Atmospheric-Sampling High-Resolution Tandem Mass Spectrometry Adamson, B. D.; Skeen, S. A.; Ahmed, M. The Journal of Physical Chemistry A, Vol. 122, Issue 48 https://doi.org/10.1021/acs.jpca.8b08947	journal	November 2018
VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C ₁₀ H ₈ ) Zhao, Long; Kaiser, Ralf I.; Xu, Bo The Journal of Physical Chemistry Letters, Vol. 9, Issue 10 https://doi.org/10.1021/acs.jpclett.8b01020	journal	May 2018
Density Functional Theory Study of the Formation of Naphthalene and Phenanthrene from Reactions of Phenyl with Vinyl- and Phenylacetylene Aguilera-Iparraguirre, Jorge; Klopper, Wim Journal of Chemical Theory and Computation, Vol. 3, Issue 1 https://doi.org/10.1021/ct600255u	journal	December 2006
High-temperature stabilities of hydrocarbons Stein, Stephen E.; Fahr, A. The Journal of Physical Chemistry, Vol. 89, Issue 17 https://doi.org/10.1021/j100263a027	journal	August 1985
The Recombination of Propargyl Radicals and Other Reactions on a C ₆ H ₆ Potential Miller, James A.; Klippenstein, Stephen J. The Journal of Physical Chemistry A, Vol. 107, Issue 39 https://doi.org/10.1021/jp030375h	journal	October 2003
Quantum Chemistry Investigation of Key Reactions Involved in the Formation of Naphthalene and Indene Fascella, S.; Cavallotti, C.; Rota, R. The Journal of Physical Chemistry A, Vol. 108, Issue 17 https://doi.org/10.1021/jp037518k	journal	April 2004
The Reaction of n - and i -C ₄ H ₅ Radicals with Acetylene ^† Senosiain, Juan P.; Miller, James A. The Journal of Physical Chemistry A, Vol. 111, Issue 19 https://doi.org/10.1021/jp0675126	journal	May 2007
Experimental and Theoretical Investigation of the Self-Reaction of Phenyl Radicals Tranter, Robert S.; Klippenstein, Stephen J.; Harding, Lawrence B. The Journal of Physical Chemistry A, Vol. 114, Issue 32 https://doi.org/10.1021/jp1031064	journal	August 2010
Theoretical Study of the Formation of Naphthalene from the Radical/π-Bond Addition between Single-Ring Aromatic Hydrocarbons Comandini, Andrea; Brezinsky, Kenneth The Journal of Physical Chemistry A, Vol. 115, Issue 22 https://doi.org/10.1021/jp200201c	journal	June 2011
Analysis of Some Reaction Pathways Active during Cyclopentadiene Pyrolysis Cavallotti, Carlo; Polino, Daniela; Frassoldati, Alessio The Journal of Physical Chemistry A, Vol. 116, Issue 13 https://doi.org/10.1021/jp212151p	journal	March 2012
Reaction of Phenyl Radical with Propylene as a Possible Source of Indene and Other Polycyclic Aromatic Hydrocarbons: An Ab Initio/RRKM-ME Study Kislov, V. V.; Mebel, A. M.; Aguilera-Iparraguirre, J. The Journal of Physical Chemistry A, Vol. 116, Issue 16 https://doi.org/10.1021/jp212338g	journal	April 2012
Formation Mechanism of Polycyclic Aromatic Hydrocarbons beyond the Second Aromatic Ring Kislov, V. V.; Sadovnikov, A. I.; Mebel, A. M. The Journal of Physical Chemistry A, Vol. 117, Issue 23 https://doi.org/10.1021/jp402481y	journal	May 2013
Kinetics and Products of Vinyl + 1,3-Butadiene, a Potential Route to Benzene Buras, Zachary J.; Dames, Enoch E.; Merchant, Shamel S. The Journal of Physical Chemistry A, Vol. 119, Issue 28 https://doi.org/10.1021/jp512705r	journal	February 2015
Role of Phenyl Radicals in the Growth of Polycyclic Aromatic Hydrocarbons Shukla, Bikau; Susa, Akio; Miyoshi, Akira The Journal of Physical Chemistry A, Vol. 112, Issue 11 https://doi.org/10.1021/jp7098398	journal	March 2008
Computed Rate Coefficients and Product Yields for c -C ₅ H ₅ + CH ₃ → Products Sharma, Sandeep; Green, William H. The Journal of Physical Chemistry A, Vol. 113, Issue 31 https://doi.org/10.1021/jp900679t	journal	August 2009
The C ₇ H ₅ Fulvenallenyl Radical as a Combustion Intermediate: Potential New Pathways to Two- and Three-Ring PAHs da Silva, Gabriel; Bozzelli, Joseph W. The Journal of Physical Chemistry A, Vol. 113, Issue 44 https://doi.org/10.1021/jp907230b	journal	November 2009
Reactions between Resonance-Stabilized Radicals: Propargyl + Allyl ^† Miller, James A.; Klippenstein, Stephen J.; Georgievskii, Yuri The Journal of Physical Chemistry A, Vol. 114, Issue 14 https://doi.org/10.1021/jp910604b	journal	April 2010
Experimental and Theoretical Studies of the C ₆ H ₅ + C ₆ H ₆ Reaction Park, J.; Burova, S.; Rodgers, A. S. The Journal of Physical Chemistry A, Vol. 103, Issue 45 https://doi.org/10.1021/jp9920592	journal	November 1999
Double-slit photoelectron interference in strong-field ionization of the neon dimer Kunitski, Maksim; Eicke, Nicolas; Huber, Pia Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-018-07882-8	journal	January 2019
Pressure-dependent rate constants for PAH growth: formation of indene and its conversion to naphthalene Mebel, Alexander M.; Georgievskii, Yuri; Jasper, Ahren W. Faraday Discussions, Vol. 195 https://doi.org/10.1039/C6FD00111D	journal	January 2016
Influences of the molecular fuel structure on combustion reactions towards soot precursors in selected alkane and alkene flames Ruwe, Lena; Moshammer, Kai; Hansen, Nils Physical Chemistry Chemical Physics, Vol. 20, Issue 16 https://doi.org/10.1039/C7CP07743B	journal	January 2018
How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C 10 H 7 ) to benzindenes (C 13 H 10 ) as a case study Zhao, Long; Prendergast, Matthew; Kaiser, Ralf I. Physical Chemistry Chemical Physics, Vol. 21, Issue 30 https://doi.org/10.1039/C9CP02930C	journal	January 2019
Theoretical study of the reaction mechanism and kinetics of the phenyl + propargyl association Morozov, Alexander N.; Mebel, Alexander M. Physical Chemistry Chemical Physics, Vol. 22, Issue 13 https://doi.org/10.1039/D0CP00306A	journal	January 2020
Association rate constants for reactions between resonance-stabilized radicals: C3H3 + C3H3, C3H3 + C3H5, and C3H5 + C3H5 Georgievskii, Yuri; Miller, James A.; Klippenstein, Stephen J. Physical Chemistry Chemical Physics, Vol. 9, Issue 31 https://doi.org/10.1039/b703261g	journal	January 2007
Resonance-stabilized hydrocarbon-radical chain reactions may explain soot inception and growth Johansson, K. O.; Head-Gordon, M. P.; Schrader, P. E. Science, Vol. 361, Issue 6406 https://doi.org/10.1126/science.aat3417	journal	September 2018
Exploring formation pathways of aromatic compounds in laboratory-based model flames of aliphatic fuels Hansen, N.; Miller, J. A.; Klippenstein, S. J. Combustion, Explosion, and Shock Waves, Vol. 48, Issue 5 https://doi.org/10.1134/S0010508212050024	journal	September 2012

Similar Records

Isomer-specific combustion chemistry in allene and propyne flames

Journal Article · Sat Nov 14 23:00:00 EST 2009 · Combustion and Flame · OSTI ID:21235982

Isomer-specific combustion chemistry in allene and propyne flames

Journal Article · Sun Nov 01 00:00:00 EDT 2009 · Combustion and Flame · OSTI ID:1060504

An experimental and detailed kinetic modeling study of the pyrolysis and oxidation of allene and propyne over a wide range of conditions

Journal Article · Mon Jul 26 20:00:00 EDT 2021 · Combustion and Flame · OSTI ID:1976986

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Energy
PAH formation
allene
chemical modeling
counterflow flames
propyne

Identification of the molecular-weight growth reaction network in counterflow flames of the C3H4 isomers allene and propyne

Citation Formats

References (50)

Similar Records

Related Subjects

Identification of the molecular-weight growth reaction network in counterflow flames of the C₃H₄ isomers allene and propyne