Role of ring-enlargement reactions in the formation of aromatic hydrocarbons
Literature Information
Martina Baroncelli, Qian Mao, Simon Galle, Nils Hansen, Heinz Pitsch
Ring-enlargement reactions can provide a fast route towards the formation of six-membered single-ring or polycyclic aromatic hydrocarbons (PAHs). To investigate the participation of the cyclopentadienyl (C5H5) radical in ring-enlargement reactions in high-temperature environments, a mass-spectrometric study was conducted. Experimental access to the C5H5 high-temperature chemistry was provided by two counterflow diffusion flames. Cyclopentene was chosen as a primary fuel given the large amount of resonantly stabilized cyclopentadienyl radicals produced by its decomposition and its high tendency to form PAHs. In a second experiment, methane was added to the fuel stream to promote methyl addition pathways and to assess the importance of ring-enlargement reactions for PAH growth. The experimental dataset includes mole fraction profiles of small intermediate hydrocarbons and of several larger species featuring up to four condensed aromatic rings. Results show that, while the addition of methane enhances the production of methylcyclopentadiene and benzene, the concentration of larger polycyclic hydrocarbons is reduced. The increase of benzene is probably attributable to the interaction between the methyl and the cyclopentadienyl radicals. However, the formation of larger aromatics seems to be dominated only by the cyclopentadienyl driven molecular-growth routes which are hampered by the addition of methane. In addition to the experimental work, two chemical mechanisms were tested and newly calculated reaction rates for cyclopentadiene reactions were included. In an attempt to assess the impact of cyclopentadienyl ring-enlargement chemistry on the mechanisms’ predictivity, pathways to form benzene, toluene, and ethylbenzene were investigated. Results show that the updated mechanism provides an improved agreement between the computed and measured aromatics concentrations. Nevertheless, a detailed study of the single reaction steps leading to toluene, styrene, and ethylbenzene would be certainly beneficial.
Recommended Journals
Related Literature
A novel Kolbe reaction pathway for a selective one- and two-electron reduction of azo compounds
Huifang-Jie Li, De-Hui Wang, Liang-Jun Zhou, Li Li, Xin Gan, Quan-Qing Xu, Hai-Bin Song
DOI: 10.1039/B906910K
Control and modulation of chirality for azobenzene-substituted polydiacetylene LB films with circularly polarized light
Gang Zou, Hao Jiang, Hideki Kohn, Takaaki Manaka, Mitsumasa Iwamoto
DOI: 10.1039/B909085A
Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction
Michael M. Madden, Claudia I. Rivera Vera, Wenjiao Song, Qing Lin
DOI: 10.1039/B912094G
Saturation transfer difference NMR reveals functionally essential kinetic differences for a sugar-binding repressor protein
Ignacio Pérez-Victoria, Sebastian Kemper, Mitul K. Patel, John M. Edwards, James C. Errey, Lucia F. Primavesi, Matthew J. Paul, Timothy D. W. Claridge, Benjamin G. Davis
DOI: 10.1039/B913489A
Direct assessment of molecular transport in mordenite: dominance of surface resistances
Lei Zhang, Christian Chmelik, Adri N. C. van Laak, Jörg Kärger, Petra E. de Jongh, Krijn P. de Jong
DOI: 10.1039/B914391B
Intramolecular base-accelerated radical-scavenging reaction of a planar catechin derivative bearing a lysine moiety
Kiyoshi Fukuhara, Kei Ohkubo, Yoshinori Obara, Ayako Tada, Kohei Imai, Akiko Ohno, Asao Nakamura, Shiro Urano, Shinichi Saito, Shunichi Fukuzumi, Kazunori Anzai, Haruhiro Okuda
DOI: 10.1039/B913714A
Dialysis process for the removal of surfactants to form colloidal mesoporous silica nanoparticles
Chihiro Urata, Yuko Aoyama, Akihisa Tonegawa, Kazuyuki Kuroda
DOI: 10.1039/B908625K
Pronounced effects of substituents on the iridium-catalyzed borylation of aryl C–H bonds‡
Carl W. Liskey, Carolyn S. Wei, Dale R. Pahls, John F. Hartwig
DOI: 10.1039/B913949D
Ionic nano-convection in anodisation of aluminium plate
Shijing Lu, Zixue Su, Jian Sha, Wuzong Zhou
DOI: 10.1039/B909256K
You might also like
What precautions should be taken when handling lithium chloride hydrate (1:1:1) (CAS: 16712-20-2)?
When handling lithium chloride hydrate (1:1:1) (CAS: 16712-20-2), it is importan...
Is 4-(4H-1,2,4-Triazol-4-yl)piperidine (CAS: 690261-92-8) safe?
4-(4H-1,2,4-Triazol-4-yl)piperidine is generally considered safe for use in phar...
How should waste containing 1,3-Thiazole-2-carboxamide (CAS: 16733-85-0) be handled?
Waste containing 1,3-Thiazole-2-carboxamide (CAS: 16733-85-0) should be collecte...
What regulatory guidelines apply to 5-(Difluoromethyl)-2-fluorobenzonitrile (CAS: 934175-58-3)?
5-(Difluoromethyl)-2-fluorobenzonitrile (CAS: 934175-58-3) is subject to regulat...
How is Methyl 3-acetamido-2-thiophenecarboxylate (CAS: 22288-79-5) typically synthesized?
Methyl 3-acetamido-2-thiophenecarboxylate can be synthesized by the reaction of ...
What is 4-Isoquinolinecarbonitrile (CAS: 34846-65-6)?
4-Isoquinolinecarbonitrile is a chemical compound with the CAS number 34846-65-6...
How should Methyl 1H-1,2,3-triazole-4-carboxylate (CAS: 877309-59-6) be stored?
Store Methyl 1H-1,2,3-triazole-4-carboxylate (CAS: 877309-59-6) in a cool, dry p...
What regulatory guidelines apply to 6-Bromo[1,3]thiazolo[5,4-b]pyridin-2-amine (CAS: 1160791-13-8)?
6-Bromo[1,3]thiazolo[5,4-b]pyridin-2-amine (CAS: 1160791-13-8) is subject to the...
Is (2S,3S)-2-Ammonio-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate (CAS: 23651-95-8) safe?
(2S,3S)-2-Ammonio-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate (CAS: 23651-95-8) ...
What are the physical and chemical properties of 7-bromo-3-methyl-3,4-dihydroquinazolin-4-one (CAS: 1293987-84-4)?
7-Bromo-3-methyl-3,4-dihydroquinazolin-4-one is a solid with a crystalline form....
Source Journal
Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.












![6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde structure 6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde structure](https://static.chemtradehub.com/structs/564/564-94-3-e746.webp)
![6-(Benzyloxy)-8-(2-bromoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one structure 6-(Benzyloxy)-8-(2-bromoacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one structure](https://static.chemtradehub.com/structs/926/926319-53-1-2287.webp)
