Formation of ring‐retaining products from the OH radical‐initiated reactions of benzene and toluene

Atkinson, Roger; Aschmann, Sara M.; Arey, Janet; Carter, William

doi:10.1002/kin.550210907

Cited by 176 publications

(221 citation statements)

References 44 publications

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“…It is important to note that the majority of the OH radical-initiated reaction products of the PAH remain unidentified. While there are uncertainties about the reaction mechanisms, a recently postulated mechanism (60) that is consistent with our product data (9,14) is shown below for the reaction of the OH radical with fluoranthene in the presence of NOX. The nitroarenes formed from the OH radical-initiated reactions of the PAH (Table 3) those observed in direct emissions such as diesel exhaust particles.…”

Section: H-chohsupporting

confidence: 84%

Atmospheric Chemistry of Gas-Phase Polycyclic Aromatic Hydrocarbons: Formation of Atmospheric Mutagens

Atkinson¹,

Arey²

1994

Environmental Health Perspectives

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129

150

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The atmospheric chemistry of the 2-to 4-ring polycyclic aromatic hydrocarbons (PAH), which exist mainly in the gas phase in the atmosphere, is discussed. The dominant loss process for the gas-phase PAH is by reaction with the hydroxyl radical, resulting in calculated lifetimes in the atmosphere of generally less than one day. The hydroxyl (OH) radical-initiated reactions and nitrate (NO3) radical-initiated reactions often lead to the formation of mutagenic nitro-PAH and other nitropolycyclic aromatic compounds, including nitrodibenzopyranones. These atmospheric reactions have a significant effect on ambient mutagenic activity, indicating that health risk assessments of combustion emissions should include atmospheric transformation products. -Environ Health Perspect 102(Suppl 4): 117-126 (1994).

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Section: H-chohsupporting

confidence: 84%

Atmospheric Chemistry of Gas-Phase Polycyclic Aromatic Hydrocarbons: Formation of Atmospheric Mutagens

Atkinson¹,

Arey²

1994

Environmental Health Perspectives

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129

150

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“…Though product data for this reaction are not available, it is assumed that high NO 2 concentrations lead to higher yields of the cresol isomers. 9,11,22 In this study, the yields of the ring-retaining products benzaldehyde and o-, m-, and p-cresol have been determined by an in situ method at NO x concentrations close to those observed in the troposphere of urban areas. This, in conjunction with the facts that real sunlight could be used for the photooxidation and that the experiments were conducted in a largevolume chamber, has resulted in a reliable determination of the ring-retaining products from the oxidation of toluene which can be used in chemical models used to describe tropospheric photooxidation formation.…”

Section: Introductionmentioning

confidence: 90%

Atmospheric Oxidation of Toluene in a Large-Volume Outdoor Photoreactor: In Situ Determination of Ring-Retaining Product Yields

Klotz¹,

Sørensen²,

Barnes³

et al. 1998

J. Phys. Chem. A

156

150

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Experiments on the photooxidation of toluene/NO x /air mixtures were performed in the European Photoreactor (EUPHORE), a large-scale outdoor reaction chamber located in Valencia/Spain. The objective of the study was the in situ determination of the yields of ring-retaining products by differential optical absorption spectroscopy (DOAS) and the elucidation of their formation pathways. The experiments were performed with toluene concentrations between 0.68 and 3.85 ppm and initial NO x concentrations ranging from 3 to 300 ppb, i.e., down to the range actually observed in the lower atmosphere. The ring-retaining product yields were found to be 5.8 ( 0.8%, 12.0 ( 1.4%, 2.7 ( 0.7%, and 3.2 ( 0.6% for benzaldehyde, o-cresol, m-cresol, and p-cresol, respectively. Under the experimental conditions, no dependency of the yields on the NO x concentration or the toluene/NO x ratio could be found. The formation kinetics of the cresols are in line with a "prompt" formation mechanism, i.e., abstraction of a hydrogen atom from the toluene-OH adduct (toluene-OH + O 2 f cresols + HO 2 ). In addition, substantial evidence was found that reaction with NO 3 radicals represents an important sink for cresols in smog chamber studies conducted under conditions of NO x concentrations above the range observed in the troposphere, possibly also under tropospheric conditions.

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“…In urban settings, hydrocarbons released from natural combustion processes and the incomplete combustion of fossil fuels serve as substrates for nitration with atmospheric nitrogen dioxide. Through a hydroxy radical-initiated mechanism, nitrobenzene, 3-nitrotoluene, 1-and 2-nitronaphthalene, 3-nitrobiphenyl, and mixtures of many other nitro-polyaromatic hydrocarbons (nitro-PAHs) can be produced (3,4,128,152,165). In aqueous environments, sunlight catalyzes nitration and halogenation reactions of naturally occurring or anthropogenic compounds in a similar fashion.…”

Section: Naturally Occurring Nitroaromatic Compoundsmentioning

confidence: 99%

Nitroaromatic Compounds, from Synthesis to Biodegradation

Parales

2010

Microbiol Mol Biol Rev

734

470

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SUMMARY Nitroaromatic compounds are relatively rare in nature and have been introduced into the environment mainly by human activities. This important class of industrial chemicals is widely used in the synthesis of many diverse products, including dyes, polymers, pesticides, and explosives. Unfortunately, their extensive use has led to environmental contamination of soil and groundwater. The nitro group, which provides chemical and functional diversity in these molecules, also contributes to the recalcitrance of these compounds to biodegradation. The electron-withdrawing nature of the nitro group, in concert with the stability of the benzene ring, makes nitroaromatic compounds resistant to oxidative degradation. Recalcitrance is further compounded by their acute toxicity, mutagenicity, and easy reduction into carcinogenic aromatic amines. Nitroaromatic compounds are hazardous to human health and are registered on the U.S. Environmental Protection Agency's list of priority pollutants for environmental remediation. Although the majority of these compounds are synthetic in nature, microorganisms in contaminated environments have rapidly adapted to their presence by evolving new biodegradation pathways that take advantage of them as sources of carbon, nitrogen, and energy. This review provides an overview of the synthesis of both man-made and biogenic nitroaromatic compounds, the bacteria that have been identified to grow on and completely mineralize nitroaromatic compounds, and the pathways that are present in these strains. The possible evolutionary origins of the newly evolved pathways are also discussed.

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Formation of ring‐retaining products from the OH radical‐initiated reactions of benzene and toluene

Cited by 176 publications

References 44 publications

Atmospheric Chemistry of Gas-Phase Polycyclic Aromatic Hydrocarbons: Formation of Atmospheric Mutagens

Atmospheric Chemistry of Gas-Phase Polycyclic Aromatic Hydrocarbons: Formation of Atmospheric Mutagens

Atmospheric Oxidation of Toluene in a Large-Volume Outdoor Photoreactor: In Situ Determination of Ring-Retaining Product Yields

Nitroaromatic Compounds, from Synthesis to Biodegradation

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