Formation of PAHs, phenol, benzofuran, and dibenzofuran in a flow reactor from the oxidation of ethylene, toluene, and n-decane

Suzuki, Shunsuke; Kukkadapu, Goutham; Kiuchi, Shota; Wagnon, Scott W.; Kinoshita, Koichi; Takeda, Yoshinaka; Sakaida, Satoshi; Konno, Mitsuru; Tanaka, Kotaro; Oguma, Mitsuharu; Pitz, William J.

doi:10.1016/j.combustflame.2022.112136

Cited by 14 publications

(3 citation statements)

References 81 publications

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“…Oxygenated rings, in turn, can participate in char formation and generation/growth of soot particles. Oxygenated soot/aromatic rings and their formation mechanisms (e.g., ref ) are in a current focus of the combustion community (e.g., ref ).…”

Section: Resultsmentioning

confidence: 99%

Intramolecular Catalytic Hydrogen Atom Transfer (CHAT)

Asatryan,

Hudzik,

Swihart

2024

J. Phys. Chem. A

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Intramolecular catalysis (IntraCat) is the acceleration of a process at one site of a molecule catalyzed by a functional group in the same molecule; an external agent such as a solvent typically facilitates it. Here, we report a general first-principles-based IntraCat mechanism, which strictly occurs within a single molecule with no coreagent being involved�we call it intramolecular catalytic transfer of hydrogen atoms (CHAT). A reactive part of a molecule (chat catalyst moiety or chat agent, represented by −OOH, −COOH, −SH, −CH 2 OH, −HPO 4 , or another bifunctional Hdonor/acceptor group) catalyzes an interconversion process, such as keto−enol or amino−imino tautomerization, and cyclization in the same molecule, while being regenerated in the process. It can thus be regarded as an intramolecular version of the intermolecular H atom transfer processes mediated by an external molecular catalyst, e.g., dihydrogen, water, or a carboxylic acid. Earlier, we proposed a general mechanistic systematization of intermolecular processes, illustrated in the simplest case of the H 2 -mediated reactions classified as dihydrogen catalysis [

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Section: Resultsmentioning

confidence: 99%

Intramolecular Catalytic Hydrogen Atom Transfer (CHAT)

Asatryan,

Hudzik,

Swihart

2024

J. Phys. Chem. A

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“…However, other formation routes cannot be excluded, e.g., pathways involving PAHs, because the formation of OPAHs from classical PAHs could also be relevant. For example, the formation of dibenzofuran from biphenyl could also be possible. , However, this contribution could be less significant as compared to the direct formation pathways via anisole as none of the OPAHs were observed in detectable amounts in another flame that we studied without anisole addition (refer to the Supporting Information, Figure S4, for details). Thus, straight thinking implies that the formation of OPAHs detected in the anisole-doped flame is mainly controlled by the presence of anisole.…”

Section: Results and Discussionmentioning

confidence: 99%

Experimental Detection of Oxygenated Aromatics in an Anisole-Blended Flame

Sood,

Gosselin,

Seifali Abbas-Abadi

et al. 2024

Energy Fuels

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Anisole serves as a pivotal constituent in the model for ligninderived biofuels. Despite considerable interest in these biofuels, their combustion processes have the potential to increase the formation of aromatic compounds, particularly oxygenated aromatics. These oxygen-containing aromatics, known for their increased toxicity compared to conventional aromatics, can significantly impact the characteristics of soot particles and exhaust gas emissions. Recent research efforts have delved into the formation of oxygenated aromatics during combustion. However, our understanding of the kinetics governing the production of these aromatics remains limited, primarily due to a scarcity of experimental data for their identification. This study addresses this gap by investigating a fuel-rich hydrocarbon flame enriched with 10% anisole at an equivalence ratio of 1.90 and atmospheric pressure. Chemical products sampled from the flame underwent analysis using one-dimensional (1D) and two-dimensional (2D) gas chromatography−mass spectrometry setups. The results facilitated the separation and identification of over 100 aromatic species, encompassing approximately 80 oxygenated variants with diverse functional groups, such as alcohols, ethers, carbonyls (aldehydes, ketones), and esters. The molecular weights of these species ranged from 94 (phenol) to 224 (9-fluorenyl acetate). Surprisingly, only a fraction of the identified species have been considered in the existing literature models. Notably, alcohol and ether functional groups emerged as the most prevalent among the detected aromatics, hinting at their crucial roles in the reaction mechanisms involving anisole. The dominant reaction paths are identified and discussed in detail, offering valuable insights for future enhancements of kinetic models pertaining to "lignin-based biofuel and oxygenated aromatics".

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“…For example, naphthalene sublimes at room temperature. However, the rest of the listed PAHs are stable under standard laboratory conditions, but all PAHs can be oxidized [ 16 ]. Some PAHs, such as perylene and benzo[a]pyrene, undergo photo-oxidation after sun or ultraviolet light irradiation.…”

Section: Introductionmentioning

confidence: 99%

Automotive Diesel Fuel Internal Stability Testing with the Use of UV and Temperature as Degradation Factors

2022

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Diesel fuel stability can be considered from many points of view, of which the two considered most important are stability in contact with the environment and internal stability. Fuel stability in touch with the environment is often defined as oxidation stability, of which measurement procedures are well developed. The presented paper shows that fuel’s internal stability can also be important. The internal stability of diesel fuel with the local use of thermal and ultraviolet radiation (UV) as degradation factors and fluorescence signals as a probe is presented in this paper. We show that the internal degradation of fuel with temperature use differs from that with UV and simultaneous both factors use. Our study shows that using temperature as a degradation factor introduces significant fluorescence fading. Moreover, the fluorescence signal restores significantly later than the sample stabilizes at room temperature. The novelty proposed based on examination is hybrid degradation and an examination cycle that enables the simultaneous use of degradation factors and fluorescence reading. For this purpose, a dedicated measurement setup of signal control and processing was constructed and programmed. The measurement procedure of the data series for specific wavelength enables calculation of signal shifts that allow the internal stability classification of diesel fuel samples in less than 30 min with the cost of a single disposable capillary probe and one polymer plug. Premium and regular fuel examination results show that internal fuel stability can be related to polycyclic aromatic hydrocarbons (PAH) concentrations and can be modified with dedicated additives.

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Formation of PAHs, phenol, benzofuran, and dibenzofuran in a flow reactor from the oxidation of ethylene, toluene, and n-decane

Cited by 14 publications

References 81 publications

Intramolecular Catalytic Hydrogen Atom Transfer (CHAT)

Intramolecular Catalytic Hydrogen Atom Transfer (CHAT)

Experimental Detection of Oxygenated Aromatics in an Anisole-Blended Flame

Automotive Diesel Fuel Internal Stability Testing with the Use of UV and Temperature as Degradation Factors

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