Thermal Decomposition of 2-Cyclopentenone

Narkin, Kathryn; Legg, Heather R.; Brown, Glenna J.; El-Shazly, Khaled; Martin, Thaddeus D.; Jarrell, Mia; McCunn, Laura R.; Chen, Zhijian; Parish, Carol A.

doi:10.1021/acs.jpca.4c05532

Title: Thermal Decomposition of 2-Cyclopentenone

Journal Article · 15 October 2024 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI: https://doi.org/10.1021/acs.jpca.4c05532 · OSTI ID:2468729

Narkin, Kathryn ^[1]; Legg, Heather R. ^[1]; Brown, Glenna J. ^[1]; El-Shazly, Khaled ^[1]; Martin, Thaddeus D. ^[1]; Jarrell, Mia ^[1];

^[1];

^[2];

^[2]

Department of Chemistry, Marshall University, 1 John Marshall Dr., Huntington, West Virginia 25755, United States
Department of Chemistry, University of Richmond, Gottwald Center for the Sciences, Richmond, Virginia 23173, United States

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Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0019732

OSTI ID:: 2468729

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 42 Vol. 128; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (62)

Bio-oil, solid and gaseous biofuels from biomass pyrolysis processes-An overview Vamvuka, D. International Journal of Energy Research, Vol. 35, Issue 10 https://doi.org/10.1002/er.1804	journal	January 2011
Computational Kinetic Study for the Unimolecular Decomposition of Cyclopentanone: KINETIC STUDY FOR THE UNIMOLECULAR DECOMPOSITION OF CYCLOPENTANONE Zaras, Aristotelis M.; Thion, Sebastien; Dagaut, Philippe International Journal of Chemical Kinetics, Vol. 47, Issue 7 https://doi.org/10.1002/kin.20921	journal	April 2015
Boundary-Layer Model to Predict Chemically Reacting Flow within Heated, High-Speed, Microtubular Reactors: PREDICTING CHEMICALLY REACTING FLOW WITHIN HEATED, MICROTUBULAR REACTORS Weddle, Peter J.; Karakaya, Canan; Zhu, Huayang International Journal of Chemical Kinetics, Vol. 50, Issue 7 https://doi.org/10.1002/kin.21173	journal	April 2018
S-trans and S-cis acrolein: trapping from thermal molecular beams and uv-induced isomerization in argon matrices Blom, C. E.; Müller, R. P.; Günthard, Hs. H. Chemical Physics Letters, Vol. 73, Issue 3 https://doi.org/10.1016/0009-2614(80)80700-7	journal	August 1980
Kinetic and thermodynamic issues in the formation of aromatic compounds in flames of aliphatic fuels Miller, James A.; Melius, Carl F. Combustion and Flame, Vol. 91, Issue 1 https://doi.org/10.1016/0010-2180(92)90124-8	journal	October 1992
Co-pyrolysis of rice straw and water hyacinth: Characterization of products, yields and biomass interaction effect Jin, Xu; Chen-yang, Niu; Deng-yin, Zhang Biomass and Bioenergy, Vol. 127 https://doi.org/10.1016/j.biombioe.2019.105281	journal	August 2019
Pyrolysis mechanism study of minimally damaged hemicellulose polymers isolated from agricultural waste straw samples Wang, Shurong; Ru, Bin; Dai, Gongxin Bioresource Technology, Vol. 190 https://doi.org/10.1016/j.biortech.2015.04.098	journal	August 2015
Hydrothermal liquefaction of biogenic municipal solid waste under reduced H2 atmosphere in biorefinery format Katakojwala, Ranaprathap; Kopperi, Harishankar; Kumar, Sunil Bioresource Technology, Vol. 310 https://doi.org/10.1016/j.biortech.2020.123369	journal	August 2020
Pyrolysis of oil extracted safflower seeds: Product evaluation, kinetic and thermodynamic studies Tahir, Mudassir Hussain; Mahmood, Marwan A.; Çakman, Gülce Bioresource Technology, Vol. 314 https://doi.org/10.1016/j.biortech.2020.123699	journal	October 2020
Reaction kinetics and characterisation of species in renewable crude from hydrothermal liquefaction of monomers to represent organic fractions of biomass feedstocks Obeid, Reem; Lewis, David M.; Smith, Neil Chemical Engineering Journal, Vol. 389 https://doi.org/10.1016/j.cej.2020.124397	journal	June 2020
Fast pyrolysis of coffee grounds: Characteristics of product yields and biocrude oil quality Bok, Jin Pil; Choi, Hang Seok; Choi, Yeon Seok Energy, Vol. 47, Issue 1 https://doi.org/10.1016/j.energy.2012.06.003	journal	November 2012
Products distribution of catalytic co-pyrolysis of greenhouse vegetable wastes and coal Merdun, Hasan; Sezgin, İsmail Veli Energy, Vol. 162 https://doi.org/10.1016/j.energy.2018.08.004	journal	November 2018
Pyrolysis of algal biomass Yanik, Jale; Stahl, Ralph; Troeger, Nicole Journal of Analytical and Applied Pyrolysis, Vol. 103 https://doi.org/10.1016/j.jaap.2012.08.016	journal	September 2013
Pyrolysis of switchgrass (Panicum virgatum L.) at low temperatures in N2 and CO2 environments; a study on chemical composition of chars extracts and bio-oils Pilon, Guillaume; Lavoie, Jean-Michel Journal of Analytical and Applied Pyrolysis, Vol. 101 https://doi.org/10.1016/j.jaap.2013.02.002	journal	May 2013
Autothermal and allothermal pyrolysis in a continuous fixed bed reactor Milhé, Mathieu; van de Steene, Laurent; Haube, Michaël Journal of Analytical and Applied Pyrolysis, Vol. 103 https://doi.org/10.1016/j.jaap.2013.03.011	journal	September 2013
Multi-technique characterization of fast pyrolysis oils Charon, Nadège; Ponthus, Jérémie; Espinat, Didier Journal of Analytical and Applied Pyrolysis, Vol. 116 https://doi.org/10.1016/j.jaap.2015.10.012	journal	November 2015
Study on two-step pyrolysis of soybean stalk by TG-FTIR and Py-GC/MS Zhang, Liqiang; Li, Kai; Zhu, Xifeng Journal of Analytical and Applied Pyrolysis, Vol. 127 https://doi.org/10.1016/j.jaap.2017.08.019	journal	September 2017
Changes in wood smoke volatile composition by manipulating the smoke generation conditions Zhang, Yuanyang; Silcock, Patrick; Jones, Jim R. Journal of Analytical and Applied Pyrolysis, Vol. 148 https://doi.org/10.1016/j.jaap.2019.104769	journal	June 2020
Classification of lignocellulosic matrix of spines in Cactaceae by Py-GC/MS combined with omic tools and multivariate analysis: A chemotaxonomic approach Reyes-Rivera, Jorge; Solano, Eloy; Terrazas, Teresa Journal of Analytical and Applied Pyrolysis, Vol. 148 https://doi.org/10.1016/j.jaap.2020.104796	journal	June 2020
Relative contribution of foliar and fine root pine litter to the molecular composition of soil organic matter after in situ degradation Mambelli, Stefania; Bird, Jeffrey A.; Gleixner, Gerd Organic Geochemistry https://doi.org/10.1016/j.orggeochem.2011.06.008	journal	June 2011
Reaction mechanisms and multi-scale modelling of lignocellulosic biomass pyrolysis Anca-Couce, Andrés Progress in Energy and Combustion Science, Vol. 53 https://doi.org/10.1016/j.pecs.2015.10.002	journal	March 2016
Comparative study of fast pyrolysis, hydropyrolysis and catalytic hydropyrolysis of poplar sawdust and rice husk in a modified Py-GC/MS microreactor system: Insights into product distribution, quantum description and reaction mechanism He, Yifeng; Zhao, Yingnan; Chai, Meiyun Renewable and Sustainable Energy Reviews, Vol. 119 https://doi.org/10.1016/j.rser.2019.109604	journal	March 2020
FT-Raman and FT-IR spectra, vibrational assignments and density functional studies of 5-bromo-2-nitropyridine Sundaraganesan, N.; Ilakiamani, S.; Saleem, H. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 61, Issue 13-14 https://doi.org/10.1016/j.saa.2004.11.016	journal	October 2005
Analytical approaches to characterizing pyrolysis oil from biomass Kanaujia, Pankaj K.; Sharma, Y. K.; Agrawal, U. C. TrAC Trends in Analytical Chemistry, Vol. 42 https://doi.org/10.1016/j.trac.2012.09.009	journal	January 2013
Fates of Chemical Elements in Biomass during Its Pyrolysis Liu, Wu-Jun; Li, Wen-Wei; Jiang, Hong Chemical Reviews, Vol. 117, Issue 9 https://doi.org/10.1021/acs.chemrev.6b00647	journal	March 2017
Experimental and Detailed Kinetic Modeling Study of Cyclopentanone Oxidation in a Jet-Stirred Reactor at 1 and 10 atm Thion, Sébastien; Togbé, Casimir; Dayma, Guillaume Energy & Fuels, Vol. 31, Issue 3 https://doi.org/10.1021/acs.energyfuels.6b02061	journal	October 2016
Fast Pyrolysis of Dried Sugar Cane Vinasse at 400 and 500 °C: Product Distribution and Yield Dirbeba, Meheretu Jaleta; Aho, Atte; DeMartini, Nikolai Energy & Fuels, Vol. 33, Issue 2 https://doi.org/10.1021/acs.energyfuels.8b03757	journal	December 2018
The path of chemical reactions - the IRC approach Fukui, Kenichi Accounts of Chemical Research, Vol. 14, Issue 12 https://doi.org/10.1021/ar00072a001	journal	December 1981
Molecular characterization of the pyrolysis of biomass Evans, Robert J.; Milne, Thomas A. Energy & Fuels, Vol. 1, Issue 2 https://doi.org/10.1021/ef00002a001	journal	March 1987
Fast Pyrolysis of Forestry Residue. 2. Physicochemical Composition of Product Liquid Oasmaa, A.; Kuoppala, E.; Solantausta, Y. Energy & Fuels, Vol. 17, Issue 2 https://doi.org/10.1021/ef020206g	journal	March 2003
Primary Combustion Intermediates in Lean and Rich Low-Pressure Premixed Laminar 2-Methylfuran/Oxygen/Argon Flames Wei, Lixia; Li, Zheming; Tong, Laihui Energy & Fuels, Vol. 26, Issue 11 https://doi.org/10.1021/ef301173z	journal	October 2012
Overview of Analytical Methods Used for Chemical Characterization of Pyrolysis Bio-oil Staš, Martin; Kubička, David; Chudoba, Josef Energy & Fuels, Vol. 28, Issue 1 https://doi.org/10.1021/ef402047y	journal	November 2013
Chemical Composition of Bio-oils Produced by Fast Pyrolysis of Two Energy Crops ^† Mullen, Charles A.; Boateng, Akwasi A. Energy & Fuels, Vol. 22, Issue 3 https://doi.org/10.1021/ef700776w	journal	May 2008
Cyclic Oxygenates: A New Class of Second-Generation Biofuels for Diesel Engines? ^† Boot, Michael; Frijters, Peter; Luijten, Carlo Energy & Fuels, Vol. 23, Issue 4 https://doi.org/10.1021/ef8003637	journal	April 2009
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
Structure and Reactivity in the Vapor-Phase Photolysis of Ketones. IV. Cyclopropyl and Olefinic Cyclic Ketones Hess, L. D.; Pitts, J. N. Journal of the American Chemical Society, Vol. 89, Issue 9 https://doi.org/10.1021/ja00985a001	journal	April 1967
The Thermal Decomposition of Cyclopentanone ^1,2 Johnson, Everett R.; Walters, W. D. Journal of the American Chemical Society, Vol. 76, Issue 24 https://doi.org/10.1021/ja01653a012	journal	December 1954
The Pyrolysis of Cyclopentanone Delles, Frederick M.; Dodd, Louis T.; Lowden, Lefford F. Journal of the American Chemical Society, Vol. 91, Issue 27 https://doi.org/10.1021/ja50001a021	journal	December 1969
Quantum Monte Carlo and Density Functional Theory Characterization of 2-Cyclopentenone and 3-Cyclopentenone Formation from O(³P) + Cyclopentadiene Grossman, Jeffrey C.; Lester,, William A.; Louie, Steven G. Journal of the American Chemical Society, Vol. 122, Issue 4 https://doi.org/10.1021/ja983879f	journal	January 2000
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
Photoinduced Ethane Formation from Reaction of Ethene with Matrix-Isolated Ti, V, or Nb Atoms Thompson, Matthew G. K.; Parnis, J. Mark The Journal of Physical Chemistry A, Vol. 109, Issue 42 https://doi.org/10.1021/jp0447542	journal	October 2005
Radical Chemistry in the Thermal Decomposition of Anisole and Deuterated Anisoles: An Investigation of Aromatic Growth Scheer, Adam M.; Mukarakate, Calvin; Robichaud, David J. The Journal of Physical Chemistry A, Vol. 114, Issue 34 https://doi.org/10.1021/jp102046p	journal	September 2010
Products From Pyrolysis of Gas-Phase Propionaldehyde Warner, Brian J.; Wright, Emily M.; Foreman, Hannah E. The Journal of Physical Chemistry A, Vol. 119, Issue 1 https://doi.org/10.1021/jp5077802	journal	December 2014
FTIR Analysis of Dimethyl Ether Decomposition Products Following Charge Transfer Ionization with Ar⁺ under Matrix Isolation Conditions Thompson, Matthew G. K.; Parnis, J. Mark The Journal of Physical Chemistry A, Vol. 112, Issue 47 https://doi.org/10.1021/jp806689j	journal	November 2008
Thermal Decomposition of Furan Generates Propargyl Radicals Vasiliou, AnGayle; Nimlos, Mark R.; Daily, John W. The Journal of Physical Chemistry A, Vol. 113, Issue 30 https://doi.org/10.1021/jp903401h	journal	July 2009
UV Photodissociation of Matrix-Isolated Propionyl Chloride Winter, Paul R.; Rowland, Brad; Hess, Wayne P. The Journal of Physical Chemistry A, Vol. 102, Issue 19 https://doi.org/10.1021/jp980286i	journal	April 1998
Revealing pyrolysis chemistry for biofuels production: Conversion of cellulose to furans and small oxygenates Mettler, Matthew S.; Mushrif, Samir H.; Paulsen, Alex D. Energy Environ. Sci., Vol. 5, Issue 1 https://doi.org/10.1039/C1EE02743C	journal	January 2012
Infra-red cryogenic studies. Part 12.—Alkenes in argon matrices Barnes, A. J.; Howells, J. D. R. J. Chem. Soc., Faraday Trans. 2, Vol. 69, Issue 0 https://doi.org/10.1039/F29736900532	journal	January 1973
FTIR studies of CO–water complexes in argon matrices and in porous ices Givan, A.; Loewenschuss, A.; Nielsen, C. J. J. Chem. Soc., Faraday Trans., Vol. 92, Issue 24 https://doi.org/10.1039/FT9969204927	journal	January 1996
The spectroscopy of molecular reaction intermediates trapped in the solid rare gases Jacox, Marilyn E. Chemical Society Reviews, Vol. 31, Issue 2 https://doi.org/10.1039/b102907j	journal	January 2002
Intense, hyperthermal source of organic radicals for matrix-isolation spectroscopy Zhang, Xu; Friderichsen, Anders V.; Nandi, Sreela Review of Scientific Instruments, Vol. 74, Issue 6 https://doi.org/10.1063/1.1574397	journal	June 2003
Infrared Spectrum and Vibrational Potential Function of Ketene and the Deuterated Ketenes Moore, C. Bradley; Pimentel, George C. The Journal of Chemical Physics, Vol. 38, Issue 12 https://doi.org/10.1063/1.1733608	journal	June 1963
Unimolecular thermal decomposition of phenol and d ₅ -phenol: Direct observation of cyclopentadiene formation via cyclohexadienone Scheer, Adam M.; Mukarakate, Calvin; Robichaud, David J. The Journal of Chemical Physics, Vol. 136, Issue 4 https://doi.org/10.1063/1.3675902	journal	January 2012
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Thermal decomposition of CH ₃ CHO studied by matrix infrared spectroscopy and photoionization mass spectroscopy Vasiliou, AnGayle K.; Piech, Krzysztof M.; Reed, Beth The Journal of Chemical Physics, Vol. 137, Issue 16 https://doi.org/10.1063/1.4759050	journal	October 2012
6-31G ^* basis set for atoms K through Zn Rassolov, Vitaly A.; Pople, John A.; Ratner, Mark A. The Journal of Chemical Physics, Vol. 109, Issue 4 https://doi.org/10.1063/1.476673	journal	July 1998
Pyrolysis of furan in a microreactor Urness, Kimberly N.; Guan, Qi; Golan, Amir The Journal of Chemical Physics, Vol. 139, Issue 12 https://doi.org/10.1063/1.4821600	journal	September 2013
Primary Combustion Intermediates in Low-Pressure Premixed Laminar 2,5-Dimethylfuran/Oxygen/Argon Flames Wei, Lixia; Tong, Laihui; Xu, Jia Combustion Science and Technology, Vol. 186, Issue 3 https://doi.org/10.1080/00102202.2013.857666	journal	February 2014
The properties of a micro-reactor for the study of the unimolecular decomposition of large molecules Guan, Qi; Urness, Kimberly N.; Ormond, Thomas K. International Reviews in Physical Chemistry, Vol. 33, Issue 4 https://doi.org/10.1080/0144235X.2014.967951	journal	September 2014
Using pine and cocoa waste with pyrolysis technology by liquid smoke, charcoal and bio char Wijaya, M.; Wiharto, M.; Danial, M. Journal of Physics: Conference Series, Vol. 1321, Issue 2 https://doi.org/10.1088/1742-6596/1321/2/022031	journal	October 2019
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis Vosko, S. H.; Wilk, L.; Nusair, M. Canadian Journal of Physics, Vol. 58, Issue 8 https://doi.org/10.1139/p80-159	journal	August 1980

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