Study of the Synchrotron Photoionization Oxidation of Alpha-Angelica Lactone (AAL) Initiated by O(3P) at 298, 550, and 700 K

Rezaei, Golbon; Meloni, Giovanni

doi:10.3390/molecules26134070

Study of the Synchrotron Photoionization Oxidation of Alpha-Angelica Lactone (AAL) Initiated by O(³P) at 298, 550, and 700 K

Journal Article · Sat Jul 03 00:00:00 EDT 2021 · Molecules

DOI:https://doi.org/10.3390/molecules26134070· OSTI ID:1849947

Rezaei, Golbon ^[1]; ^[2]

Univ. of California, San Francisco, CA (United States). Dept. of Chemistry; Univ. of California, San Francisco, CA (United States)
Univ. of California, San Francisco, CA (United States). Dept. of Chemistry; Università degli Studi de L’Aquila (Italy). Dept. of Physical and Chemical Sciences

In recent years, biofuels have been receiving significant attention because of their potential for decreasing carbon emissions and providing a long-term renewable solution to unsustainable fossil fuels. Currently, lactones are some of the alternatives being produced. Many lactones occur in a range of natural substances and have many advantages over bioethanol. In this study, the oxidation of alpha-angelica lactone initiated by ground-state atomic oxygen, O(³P), was studied at 298, 550, and 700 K using synchrotron radiation coupled with multiplexed photoionization mass spectrometry at the Lawrence Berkeley National Lab (LBNL). Photoionization spectra and kinetic time traces were measured to identify the primary products. Ketene, acetaldehyde, methyl vinyl ketone, methylglyoxal, dimethyl glyoxal, and 5-methyl-2,4-furandione were characterized as major reaction products, with ketene being the most abundant at all three temperatures. Possible reaction pathways for the formation of the observed primary products were computed using the CBS–QB3 composite method.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, Oakland, CA (United States); Univ. of Pennsylvania, Philadelphia, PA (United States)

Sponsoring Organization:: American Chemical Society; USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231; FG02-87ER13792

OSTI ID:: 1849947

Journal Information:: Molecules, Journal Name: Molecules Journal Issue: 13 Vol. 26; ISSN MOLEFW; ISSN 1420-3049

Publisher:: MDPICopyright Statement

Country of Publication:: United States

Language:: English

References (64)

Direct, High-Yield Conversion of Cellulose into Biofuel Mascal, Mark; Nikitin, Edward B. Angewandte Chemie International Edition, Vol. 47, Issue 41 https://doi.org/10.1002/anie.200801594	journal	September 2008
Recursion relations for multi-dimensional Franck-Condon overlap integrals Ruhoff, Peder Thusgaard Chemical Physics, Vol. 186, Issue 2-3 https://doi.org/10.1016/0301-0104(94)00173-1	journal	September 1994
Catalytic etherification of glycerol to produce biofuels over novel spherical silica supported Hyflon® catalysts Frusteri, Francesco; Frusteri, Leone; Cannilla, Catia Bioresource Technology, Vol. 118 https://doi.org/10.1016/j.biortech.2012.04.103	journal	August 2012
Human health effects of air pollution Kampa, Marilena; Castanas, Elias Environmental Pollution, Vol. 151, Issue 2 https://doi.org/10.1016/j.envpol.2007.06.012	journal	January 2008
Synchrotron Photoionization Investigation of the Oxidation of Ethyl tert -Butyl Ether Winfough, Matthew; Yao, Rong; Ng, Martin The Journal of Physical Chemistry A, Vol. 121, Issue 7 https://doi.org/10.1021/acs.jpca.6b11507	journal	February 2017
Computational Kinetic Study for the Unimolecular Decomposition Pathways of Cyclohexanone Zaras, Aristotelis M.; Dagaut, Philippe; Serinyel, Zeynep The Journal of Physical Chemistry A, Vol. 119, Issue 28 https://doi.org/10.1021/jp506227w	journal	November 2014
Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates Román-Leshkov, Yuriy; Barrett, Christopher J.; Liu, Zhen Y. Nature, Vol. 447, Issue 7147, p. 982-985 https://doi.org/10.1038/nature05923	journal	June 2007
Formation of dimethylketene and methacrolein by reaction of the CH radical with acetone Goulay, Fabien; Derakhshan, Adeeb; Maher, Eamonn Physical Chemistry Chemical Physics, Vol. 15, Issue 11 https://doi.org/10.1039/c3cp43829e	journal	January 2013
Absolute photoionization cross-section of the propargyl radical Savee, John D.; Soorkia, Satchin; Welz, Oliver The Journal of Chemical Physics, Vol. 136, Issue 13 https://doi.org/10.1063/1.3698282	journal	April 2012
Transesterification of vegetable oils: a review Schuchardt, Ulf; Sercheli, Ricardo; Vargas, Rogério Matheus Journal of the Brazilian Chemical Society, Vol. 9, Issue 3 https://doi.org/10.1590/s0103-50531998000300002	journal	January 1998
Biofuel Combustion Chemistry: From Ethanol to Biodiesel Kohse-Höinghaus, Katharina; Oßwald, Patrick; Cool, Terrill A. Angewandte Chemie International Edition, Vol. 49, Issue 21 https://doi.org/10.1002/anie.200905335	journal	May 2010
Synchrotron Photoionization Study of the Diisopropyl Ether Oxidation Giustini, Andrea; Meloni, Giovanni ChemPhysChem, Vol. 21, Issue 9 https://doi.org/10.1002/cphc.201901134	journal	April 2020
Angelica Lactones: From Biomass-Derived Platform Chemicals to Value-Added Products Lima, Carolina G. S.; Monteiro, Julia L.; de Melo Lima, Thiago ChemSusChem, Vol. 11, Issue 1 https://doi.org/10.1002/cssc.201701469	journal	October 2017
Bacterial production of free fatty acids from freshwater macroalgal cellulose Hoover, Spencer W.; Marner, Wesley D.; Brownson, Amy K. Applied Microbiology and Biotechnology, Vol. 91, Issue 2 https://doi.org/10.1007/s00253-011-3344-x	journal	June 2011
Integration of Homogeneous and Heterogeneous Catalytic Processes for a Multi-step Conversion of Biomass: From Sucrose to Levulinic Acid, γ-Valerolactone, 1,4-Pentanediol, 2-Methyl-tetrahydrofuran, and Alkanes Mehdi, Hasan; Fábos, Viktória; Tuba, Róbert Topics in Catalysis, Vol. 48, Issue 1-4 https://doi.org/10.1007/s11244-008-9047-6	journal	April 2008
Iterative methods to compute one- and two-dimensional Franck-Condon factors. Tests of accuracy and application to study indirect molecular transitions Lermé, J. Chemical Physics, Vol. 145, Issue 1 https://doi.org/10.1016/0301-0104(90)80119-I	journal	August 1990
Simple models for the calculation of photoionization and electron impact ionization cross sections of polyatomic molecules Bobeldijk, M.; van der Zande, W. J.; Kistemaker, P. G. Chemical Physics, Vol. 179, Issue 2 https://doi.org/10.1016/0301-0104(93)E0376-7	journal	January 1994
Measurements of the NO2 absorption cross-section from 42 000 cm−1 to 10 000 cm−1 (238–1000 nm) at 220 K and 294 K Vandaele, A. C.; Hermans, C.; Simon, P. C. Journal of Quantitative Spectroscopy and Radiative Transfer, Vol. 59, Issue 3-5 https://doi.org/10.1016/S0022-4073(97)00168-4	journal	March 1998
Detailed chemical kinetic models for the combustion of hydrocarbon fuels Simmie, John M. Progress in Energy and Combustion Science, Vol. 29, Issue 6 https://doi.org/10.1016/S0360-1285(03)00060-1	journal	January 2003
Production of jet and diesel biofuels from renewable lignocellulosic biomass Zhang, Yajing; Bi, Peiyan; Wang, Jicong Applied Energy, Vol. 150 https://doi.org/10.1016/j.apenergy.2015.04.023	journal	July 2015
Air pollution, greenhouse gases and climate change: Global and regional perspectives Ramanathan, V.; Feng, Y. Atmospheric Environment, Vol. 43, Issue 1 https://doi.org/10.1016/j.atmosenv.2008.09.063	journal	January 2009
Cyclopentanone: A raw material for production of C15 and C17 fuel precursors Hronec, Milan; Fulajtárova, Katarína; Liptaj, Tibor Biomass and Bioenergy, Vol. 63 https://doi.org/10.1016/j.biombioe.2014.02.025	journal	April 2014
Enzymes for second generation biofuels: Recent developments and future perspectives Binod, Parameswaran; Gnansounou, Edgard; Sindhu, Raveendran Bioresource Technology Reports, Vol. 5 https://doi.org/10.1016/j.biteb.2018.06.005	journal	February 2019
Fatty acid methyl ester production using lipase-immobilizing silica particles with different particle sizes and different specific surface areas Park, Enoch Y.; Sato, Masayasu; Kojima, Seiji Enzyme and Microbial Technology, Vol. 39, Issue 4 https://doi.org/10.1016/j.enzmictec.2006.01.022	journal	August 2006
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
Absolute photoionization cross-sections of selected furanic and lactonic potential biofuels Czekner, Joseph; Taatjes, Craig A.; Osborn, David L. International Journal of Mass Spectrometry, Vol. 348 https://doi.org/10.1016/j.ijms.2013.04.020	journal	August 2013
Microwave-assisted organosolv extraction of coconut shell lignin by Brønsted and Lewis acids catalysts Avelino, Francisco; Silva, Kássia Teixeira da; de Souza Filho, Men de Sá Moreira Journal of Cleaner Production, Vol. 189 https://doi.org/10.1016/j.jclepro.2018.04.126	journal	July 2018
Biofuels (alcohols and biodiesel) applications as fuels for internal combustion engines Agarwal, Avinash Kumar Progress in Energy and Combustion Science, Vol. 33, Issue 3 https://doi.org/10.1016/j.pecs.2006.08.003	journal	June 2007
Kinetics of elementary reactions in low-temperature autoignition chemistry Zádor, Judit; Taatjes, Craig A.; Fernandes, Ravi X. Progress in Energy and Combustion Science, Vol. 37, Issue 4 https://doi.org/10.1016/j.pecs.2010.06.006	journal	August 2011
Low temperature autoignition of conventional jet fuels and surrogate jet fuels with targeted properties in a rapid compression machine Valco, Daniel J.; Min, Kyungwook; Oldani, Anna Proceedings of the Combustion Institute, Vol. 36, Issue 3 https://doi.org/10.1016/j.proci.2016.05.032	journal	January 2017
Biofuels: Environment, technology and food security Escobar, José C.; Lora, Electo S.; Venturini, Osvaldo J. Renewable and Sustainable Energy Reviews, Vol. 13, Issue 6-7 https://doi.org/10.1016/j.rser.2008.08.014	journal	August 2009
Classification of Diesel Fuel Using Two-Dimensional Fluorescence Spectroscopy Ranzan, Lucas; Ranzan, Cassiano; Trierweiler, Luciane F. Energy & Fuels, Vol. 31, Issue 9 https://doi.org/10.1021/acs.energyfuels.7b00954	journal	August 2017
Study of tert -Amyl Methyl Ether Low Temperature Oxidation Using Synchrotron Photoionization Mass Spectrometry Ng, Martin Y.; Bryan, Brittany M.; Nelson, Jordan The Journal of Physical Chemistry A, Vol. 119, Issue 32 https://doi.org/10.1021/acs.jpca.5b05223	journal	August 2015
Low-Temperature Synchrotron Photoionization Study of 2-Methyl-3-buten-2-ol (MBO) Oxidation Initiated by O( ³ P) Atoms in the 298–650 K Range Fathi, Yasmin; Price, Chelsea; Meloni, Giovanni The Journal of Physical Chemistry A, Vol. 121, Issue 15 https://doi.org/10.1021/acs.jpca.6b12421	journal	April 2017
Study of the Synchrotron Photoionization Oxidation of 2-Methylfuran Initiated by O( ³ P) under Low-Temperature Conditions at 550 and 650 K Fathi, Yasmin; Meloni, Giovanni The Journal of Physical Chemistry A, Vol. 121, Issue 37 https://doi.org/10.1021/acs.jpca.7b05561	journal	September 2017
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
Race To The Pump Ritter, Stephen Chemical & Engineering News https://doi.org/10.1021/cen020911090424	journal	February 2011
Transesterification Otera, Junzo. Chemical Reviews, Vol. 93, Issue 4 https://doi.org/10.1021/cr00020a004	journal	June 1993
Performance of B3LYP Density Functional Methods for a Large Set of Organic Molecules Tirado-Rives, Julian; Jorgensen, William L. Journal of Chemical Theory and Computation, Vol. 4, Issue 2 https://doi.org/10.1021/ct700248k	journal	January 2008
Automatic Chemistry Mechanism Reduction of Hydrocarbon Fuels for HCCI Engines Based on DRGEP and PCA Methods with Error Control Shi, Yu; Ge, Hai-Wen; Brakora, Jessica L. Energy & Fuels, Vol. 24, Issue 3 https://doi.org/10.1021/ef901469p	journal	February 2010
Synchrotron Photoionization Measurements of OH-Initiated Cyclohexene Oxidation: Ring-Preserving Products in OH + Cyclohexene and Hydroxycyclohexyl + O ₂ Reactions Ray, Amelia W.; Taatjes, Craig A.; Welz, Oliver The Journal of Physical Chemistry A, Vol. 116, Issue 25 https://doi.org/10.1021/jp3022437	journal	May 2012
Efficient Conversion of α-Angelica Lactone into γ-Valerolactone with Ionic Liquids at Room Temperature Cao, Ruimei; Xin, Jiayu; Zhang, Zhan ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 4 https://doi.org/10.1021/sc4005185	journal	January 2014
Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels Atsumi, Shota; Hanai, Taizo; Liao, James C. Nature, Vol. 451, Issue 7174, p. 86-89 https://doi.org/10.1038/nature06450	journal	January 2008
γ-Valerolactone—a sustainable liquid for energy and carbon-based chemicals Horváth, István T.; Mehdi, Hasan; Fábos, Viktória Green Chem., Vol. 10, Issue 2 https://doi.org/10.1039/B712863K	journal	January 2008
Electron impact studies. Part 4.—Glyoxal, methylglyoxal, and diacetyl Reed, R. I.; Brand, J. C. D. Trans. Faraday Soc., Vol. 54, Issue 0 https://doi.org/10.1039/TF9585400478	journal	January 1958
Low-temperature combustion chemistry of biofuels: pathways in the initial low-temperature (550 K–750 K) oxidation chemistry of isopentanol Welz, Oliver; Zádor, Judit; Savee, John D. Physical Chemistry Chemical Physics, Vol. 14, Issue 9 https://doi.org/10.1039/c2cp23248k	journal	January 2012
Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5-(alkoxymethyl)furfurals and 2,5-bis(alkoxymethyl)furans as potential bio-diesel candidates Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T. Green Chemistry, Vol. 14, Issue 6 https://doi.org/10.1039/c2gc35102a	journal	January 2012
Synthesis of renewable high-density fuels using cyclopentanone derived from lignocellulose Yang, Jinfan; Li, Ning; Li, Guangyi Chemical Communications, Vol. 50, Issue 20 https://doi.org/10.1039/c3cc46588h	journal	January 2014
Performance of the vacuum ultraviolet high-resolution and high-flux beamline for chemical dynamics studies at the Advanced Light Source Heimann, P. A.; Koike, M.; Hsu, C. W. Review of Scientific Instruments, Vol. 68, Issue 5 https://doi.org/10.1063/1.1148082	journal	May 1997
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
Franck—Condon Factors for Polyatomic Molecules Sharp, T. E.; Rosenstock, H. M. The Journal of Chemical Physics, Vol. 41, Issue 11 https://doi.org/10.1063/1.1725748	journal	December 1964
A complete basis set model chemistry. VI. Use of density functional geometries and frequencies Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W. The Journal of Chemical Physics, Vol. 110, Issue 6 https://doi.org/10.1063/1.477924	journal	February 1999
A complete basis set model chemistry. VII. Use of the minimum population localization method Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W. The Journal of Chemical Physics, Vol. 112, Issue 15 https://doi.org/10.1063/1.481224	journal	April 2000
The hydrogen abstraction reaction O( ³ P) + CH ₄ : A new analytical potential energy surface based on fit to ab initio calculations González-Lavado, Eloisa; Corchado, Jose C.; Espinosa-Garcia, Joaquin The Journal of Chemical Physics, Vol. 140, Issue 6 https://doi.org/10.1063/1.4864358	journal	February 2014
Evaluated Chemical Kinetic Data for the Reactions of Atomic Oxygen O( ³ P) with Unsaturated Hydrocarbons Cvetanović, R. J. Journal of Physical and Chemical Reference Data, Vol. 16, Issue 2 https://doi.org/10.1063/1.555783	journal	April 1987
Environmental, economic, and energetic costs and benefits of biodiesel and ethanol biofuels Hill, J.; Nelson, E.; Tilman, D. Proceedings of the National Academy of Sciences, Vol. 103, Issue 30 https://doi.org/10.1073/pnas.0604600103	journal	July 2006
Integrated Catalytic Conversion of γ-Valerolactone to Liquid Alkenes for Transportation Fuels Bond, J. Q.; Alonso, D. M.; Wang, D. Science, Vol. 327, Issue 5969, p. 1110-1114 https://doi.org/10.1126/science.1184362	journal	February 2010
Analysis of coumarin and angelica lactones in smokeless tobacco products McAdam, Kevin; Enos, Trevor; Goss, Carol Chemistry Central Journal, Vol. 12, Issue 1 https://doi.org/10.1186/s13065-018-0506-2	journal	December 2018
Absorption Coefficient and Photoionization Yield of NO in the Region 580–1350 Å Watanabe, K.; Matsunaga, Frederick M.; Sakai, Hajime Applied Optics, Vol. 6, Issue 3 https://doi.org/10.1364/AO.6.000391	journal	January 1967
Are Primary Quantum Yields of NO2 Photolysis at λ ≤ 398 nm Smaller than Unity? Troe, Jürgen Zeitschrift für Physikalische Chemie, Vol. 214, Issue 5 https://doi.org/10.1524/zpch.2000.214.5.573	journal	January 2000
Transesterification of vegetable oils: a review Schuchardt, Ulf; Sercheli, Ricardo; Vargas, Rogério Matheus Journal of the Brazilian Chemical Society, Vol. 9, Issue 3 https://doi.org/10.1590/S0103-50531998000300002	journal	January 1998
Synthetic Biology Approaches to Produce C3-C6 Alcohols from Microorganisms M. Rodriguez, Gabriel; Atsumi, Shota Current Chemical Biology, Vol. 6, Issue 1 https://doi.org/10.2174/187231312799984420	journal	March 2012
Ionisation Potentials in Tautomeric Analysis of 2-Hydroxy Derivatives of Thiophenes, Selenophenes, and Furans. Thorstad, Olav; Undheim, Kjell; Cederlund, Björn Acta Chemica Scandinavica, Vol. 29b https://doi.org/10.3891/acta.chem.scand.29b-0647	journal	January 1975

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09 BIOMASS FUELS
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multiplexed mass spectrometry
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synchrotron photoionization

Study of the Synchrotron Photoionization Oxidation of Alpha-Angelica Lactone (AAL) Initiated by O(3P) at 298, 550, and 700 K

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Study of the Synchrotron Photoionization Oxidation of Alpha-Angelica Lactone (AAL) Initiated by O(³P) at 298, 550, and 700 K