Mechanism of the photochemical transformation of naphthalene in water

Vialaton, Delphine; Richard, Claire; Baglio, Daniela; Paya-Perez, Ana-Beatriz

doi:10.1016/s1010-6030(99)00044-1

Cited by 42 publications

(30 citation statements)

References 11 publications

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“…This remaining loss under N 2 -purging could be due to a number of factors, including the presence of O 2 -independent pathways, such as photoionization or PAH self reactions, or through reaction of the long-lived PAH triplet states ( 3 P*) with residual O 2 . By employing sacrificial electron donors to reduce the cation radical intermediate (P + ) and thus to regenerate the PAH, we showed however, that P + is not produced substantially at low O 2 concentrations, thus excluding photoionization (Zepp and Schlotzhauer, 1979;Vialaton et al, 1999). Further, reaction of PAH excited states (P*), either singlet or triplet, with ground state PAH is also unlikely in our experiments, owing to the very low PAH concentrations employed (£25 nM), the relatively high O 2 concentrations likely to be remaining in our N 2 -purged solutions (probably on the order of micromolar), and the large rate constants for O 2 quenching of P* (k > 10 9 M -1 s -1 ) (AbdelShafi and Wilkinson, 2000).…”

Section: Introductionmentioning

confidence: 91%

Kinetic analysis of the photodegradation of polycyclic aromatic hydrocarbons in aqueous solution

Fasnacht

Blough

2003

Aquatic Sciences - Research Across Boundaries

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The mechanisms by which polycyclic aromatic hydrocarbons (PAHs) photodegrade in dilute (£25 nM) aqueous solutions under varying O 2 concentrations were examined. Employing previously measured photodegradation quantum yields (acquired in the absence and presence of electron donors to the PAH cation radicals, P + ), excited singlet state ( 1 P*) lifetimes, 1 P*/O 2 quenching rate constants and other parameters from the literature, a kinetic model was developed to analyze the fraction of PAH photodegradation that proceeds via the 1 P* or excited triplet state ( 3 P*), as well as to determine the relative contribution of electron transfer to O 2 versus the direct reaction with O 2 from each state. The analysis supports the Aquatic Sciences following conclusions: 1) 1 P* is more reactive with O 2 than 3 P*; 2) reaction via 1 P* proceeds predominantly through electron transfer to produce the P + intermediate, whereas reaction via 3 P* proceeds primarily through direct reaction with O 2 within the collision complex, consistent with the thermodynamic driving forces for electron transfer from these states; 3) although 3 P* is involved significantly in the degradation of many PAHs, such as anthracene, 9-methylanthracene, acenaphthene, and perylene, it is not involved in the degradation of others such as pyrene and benzo[a]pyrene. Under aerobic conditions, photodegradation is likely to be controlled largely by 1 P* lifetime and reactivity.

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Section: Introductionmentioning

confidence: 91%

Kinetic analysis of the photodegradation of polycyclic aromatic hydrocarbons in aqueous solution

Fasnacht

Blough

2003

Aquatic Sciences - Research Across Boundaries

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“…This oxidative process is one of the chief degradation pathways for PAHs in the natural aquatic environment. Photodegradation products of the following PAHs are characterized: naphthalene in vapor (51)(52)(53), phenanthrene in silica-air inter-phase (54,55), anthracene in aqueous and organic solvents (56)(57)(58)(59)(60), pyrene in soil surface or on carbon (61-64), benzo[a]pyrene in aqueous media (65,66), and some heterocyclic compounds in solutions or on solid surfaces. Since then, characterization of photoproducts of some PAH in aqueous or water/organic solvent mixtures are available: naphthalene (53), pyrene (67,68), benz [a]anthracene (57,69,70), methyl substituted BAs (69), 1-hydroxypyrene (71), and 1-aminopyrene (AP).…”

Section: Pah Photochemistrymentioning

confidence: 99%

“…Photolysis of naphthalene in aqueous solutions yields 7-hydroxy-1,4-naphthoquinone (I), 2-formylcinnamaldehyde (II), and 2-carboxycinnamaldehyde (III) (53) (Figure 3). The authors suggested that compound I be formed via the 1,4-naphthoquinone intermediate, and compounds II and III be from the breaking of the C1-C2 bond in naphthalene.…”

Section: Pah Photochemistrymentioning

confidence: 99%

“…Photo-oxidation of some nitro (56,82,84,86,(88)(89)(90)146), amino (94)(95)(96)102), and hydroxy (71) PAHs also lead to quinones. In addition to quinones, hydroxy (53,65,67,93), carboxy (53), hydroxymethyl and formyl-PAHs for methyl substituted PAHs (70) are also detected among the photolysis products. Quinones are known reactive oxygen species sensitizers (28,31,147,148).…”

Section: Perspectivesmentioning

confidence: 99%

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Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

2002

Journal of Environmental Science and Health, Part C

341

252

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“…Indeed, irradiation of benzo [a]pyrene or DMBA inside the cells tends to lower the amount of covalent DNA adducts formed by enzymatic activation (Prodi et al, 1984), an effect that was mainly attributed to photodegradation of the PAHs. Photo-oxidation of the unsubstituted PAHs -two-ring naphthalene (Vialaton et al, 1999); three-ring anthracene (Mallakin et al, 2000) and phenanthrene (Wen et al, 2002); four-ring benz [a]anthracene (Dong et al, 2002) and pyrene (Sigman et al, 1998); and five-ring benzo [a]pyrene (Lee-Ruff et al, 1988) -can produce respective quinones, ring-open products or hydroxy-substituted products. In addition to quinones, hydroxy- (Koizumi et al, 1994), carboxy- (Zeng et al, 2002), hydroxymethyl-and formyl-PAHs or methyl-substituted PAHs are also detected among the photoproducts.…”

Section: Phototoxicitymentioning

confidence: 99%

Integrating Field Analyses with Laboratory Exposures to Assess Ecosystems Health

Hellou¹,

Beach²,

Leonard³

et al. 2012

Polycyclic Aromatic Compounds

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initiated a programme on the evaluation of the carcinogenic risk of chemicals to humans involving the production of critically evaluated monographs on individual chemicals. The programme was subsequently expanded to include evaluations of carcinogenic risks associated with exposures to complex mixtures, life-style factors and biological and physical agents, as well as those in specific occupations. The objective of the programme is to elaborate and publish in the form of monographs critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations; to evaluate these data in terms of human risk with the help of international working groups of experts in chemical carcinogenesis Publications of the World Health Organization enjoy copyright protection in accordance with the provisions of Protocol 2 of the Universal Copyright Convention. All rights reserved.The International Agency for Research on Cancer welcomes requests for permission to reproduce or translate its publications, in part or in full. Requests for permission to reproduce or translate IARC publications -whether for sale or for noncommercial distribution -should be addressed to WHO Press, at the above address (fax: +41 22 791 4806; email: permissions@who.int).The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the World Health Organization concerning the legal status of any country, territory, city, or area or of its authorities, or concerning the delimitation of its frontiers or boundaries.The mention of specific companies or of certain manufacturers' products does not imply that they are endorsed or recommended by the World Health Organization in preference to others of a similar nature that are not mentioned. Errors and omissions excepted, the names of proprietary products are distinguished by initial capital letters.The IARC Monographs Working Group alone is responsible for the views expressed in this publication. IARC Library Cataloguing in Publication Data NOTE TO THE READERThe term 'carcinogenic risk' in the IARC Monographs series is taken to mean that an agent is capable of causing cancer under some circumstances. The Monographs evaluate cancer hazards, despite the historical presence of the word 'risks' in the title.Inclusion of an agent in the Monographs does not imply that it is a carcinogen, only that the published data have been examined. Equally, the fact that an agent has not yet been evaluated in a Monograph does not mean that it is not carcinogenic.The evaluations of carcinogenic risk are made by international working groups of independent scientists and are qualitative in nature. No recommendation is given for regulation or legislation.Anyone who is aware of published data that may alter the evaluation of the carcinogenic risk of an agent to humans is encouraged to make this information available to the Section of IARC Monographs, International Agency for...

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Mechanism of the photochemical transformation of naphthalene in water

Cited by 42 publications

References 11 publications

Kinetic analysis of the photodegradation of polycyclic aromatic hydrocarbons in aqueous solution

Kinetic analysis of the photodegradation of polycyclic aromatic hydrocarbons in aqueous solution

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

Integrating Field Analyses with Laboratory Exposures to Assess Ecosystems Health

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