Ozonation of polycyclic aromatic hydrocarbon in hexane and water: Identification of intermediates and pathway

Youngik, Choi; Hong, Andrew

doi:10.1007/s11814-007-0111-x

Cited by 10 publications

(4 citation statements)

References 15 publications

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“…3). previously identified as a product of pyrene ozonation in aqueous solution [5,38], to our knowledge, it has never been reported in heterogeneous ozonation reactions. We were not able to unequivocally identify the last of the m/z 205 peaks; however, this compound is likely to be another isomer of phenanthrenecarboxylic acid.…”

Section: Products From the Heterogeneous Ozonation Of Pahsmentioning

confidence: 83%

“…The major PAH derivatives previously reported are those functionalized with carbonyl (oxo-PAHs), nitro (nitro-PAHs), hydroxyl (hydroxy-PAHs), and carboxyl (carboxy-PAHs) groups [3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Nevertheless, due to the difficulty in their analysis, PAH derivatives have been reported to a lesser extent than their PAH precursors, with studies targeting either selected classes of compounds or specific chemicals [12,[17][18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

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Detection of nitrated and oxygenated polycyclic aromatic hydrocarbons using atmospheric pressure chemical ionization high resolution mass spectrometry

Cochran

Smoliakova

Kubátová

2016

International Journal of Mass Spectrometry

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Polycyclic aromatic hydrocarbons (PAHs) are common pollutants in the atmosphere and have long been recognized to be toxic to humans. These PAHs can be oxidized into more toxic products in both the gas and condensed (on the surface of suspended particulate matter) phases. In this work, we report fragmentation patterns observed atmospheric pressure chemical ionization with high resolution mass spectrometry (APCI-HRMS) for PAH oxidation products. A representative group of 18 PAH derivatives containing carbonyl (oxo-PAHs), hydroxyl (hydroxy-PAHs), carboxyl (carboxy-PAHs), and/or nitro (nitro-PAHs) groups was studied. Ionization of carboxy-RAHs in negative mode yielded common fragments of [M-H]-, [M-H-CO]-, and [M-H-CO 2 ]-. Oxo-PAHs provided common fragments of [M+H] + , [M+H-CO] + and [M+H-2CO] + in positive mode and [M+e-]in negative mode. Mass spectra of aldehydes exhibited common fragments of [M+H] + , [M+H-CO] + , and [M+H-O] + in positive mode and [M+e-]and [M-H+O]in negative mode. For all nitro-PAHs, [M+H] + , [M+H-O] + and [M+3H-O 2 ] + ions were observed in positive mode. On the basis of the APCI-HRMS analysis of standards, eight reaction products of pyrene oxidation under heterogeneous conditions were characterized. HRMS data, specific fragments and common ions such as that of 205 m/z, characteristic for carbonyl phenanthrene, enabled the identification of the oxidation products.

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Section: Products From the Heterogeneous Ozonation Of Pahsmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Detection of nitrated and oxygenated polycyclic aromatic hydrocarbons using atmospheric pressure chemical ionization high resolution mass spectrometry

Cochran

Smoliakova

Kubátová

2016

International Journal of Mass Spectrometry

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“…In pyrene, the ozone attack starts preferentially through the 4,5-and 9,10-bonds (called the K region), since these bonds have a higher double-bond character and, as consequence, they are more reactive [41,43,44]. According to the literature, phenanthrene-4,5-dicarboxaldehyde (m/z 234) is one of the first pyrene degradation intermediates, while cyclopenta[def]phenanthren-4-one (m/z 204) [43], and 4-oxapyren-5-one (m/z 220) [39,41] are produced by the subsequent ozonolysis of the former.…”

Section: Homogeneous Experimentsmentioning

confidence: 99%

Evaluation of an Ozone Chamber as a Routine Method to Decontaminate Firefighters’ PPE

Lucena

Zapata

Mauricio

et al. 2021

IJERPH

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Ozone chambers have emerged as an alternative method to decontaminate firefighters’ Personal Protective Equipment (PPE) from toxic fire residues. This work evaluated the efficiency of using an ozone chamber to clean firefighters’ PPE. This was achieved by studying the degradation of pyrene and 9-methylanthracene polycyclic aromatic hydrocarbons (PAHs). The following experiments were performed: (i) insufflating ozone into PAH solutions (homogeneous setup), and (ii) exposing pieces of PPE impregnated with the PAHs to an ozone atmosphere for up to one hour (heterogeneous setup). The ozonolysis products were assessed by Fourier Transform Infrared Spectroscopy (FTIR), Thin-Layer Chromatography (TLC), and Mass Spectrometry (MS) analysis. In the homogeneous experiments, compounds of a higher molecular weight were produced due to the incorporation of oxygen into the PAH structures. Some of these new compounds included 4-oxapyren-5-one (m/z 220) and phenanthrene-4,5-dicarboxaldehyde (m/z 234) from pyrene; or 9-anthracenecarboxaldehyde (m/z 207) and hydroxy-9,10-anthracenedione (m/z 225) from 9-methylanthracene. In the heterogeneous experiments, a lower oxidation was revealed, since no byproducts were detected using FTIR and TLC, but only using MS. However, in both experiments, significant amounts of the original PAHs were still present even after one hour of ozone treatment. Thus, although some partial chemical degradation was observed, the remaining PAH and the new oxygenated-PAH compounds (equally or more toxic than the initial molecules) alerted us of the risks to firefighters’ health when using an ozone chamber as a unique decontamination method. These results do not prove the ozone-advertised efficiency of the ozone chambers for decontaminating (degrading the toxic combustion residues into innocuous compounds) firefighters’ PPE.

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“…Ozone as an effective oxidizing agent is widely used in the oxidation of organic and inorganic compounds [1−5] . As a rule, oxidation reactions are performed in solutions of the starting compounds in organic or aqueous media depending on the kind of the substrate being oxidized [6−8] . To intensify the oxidation, it is necessary to create the optimum conditions ensuring the stability of the reaction medium and the sufficient concentrations of ozone and the substrate being oxidized in the reaction zone.…”

Section: Introductionmentioning

confidence: 99%

Ozone in Polar (Acetonitrile) and Nonpolar (Carbon Tetrachloride) Organic Liquids: Optical Absorption, Solubility, and Stability

Ершов

Panich

2022

ChemistrySelect

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The optical characteristics, solubility, and decomposition kinetics of ozone in polar (acetonitrile, CH 3 CN) and nonpolar (carbon tetrachloride, CCl 4 ) liquids in the temperature range 233.15-295.15 K were studied. The rate constants of the O 3 decomposition at 295.15 K in CH 3 CN and CCl 4 are 3.3 × 10 À 5 and 5.0 × 10 À 5 s À 1 , respectively. At low temperatures, ozone solu-tions are practically stable. The solubility coefficients at 295.15 K are 2.6 in CH 3 CN and 2.9 in CCl 4 ; at 233.15 K, they increase to approximately 7.0. Thus, these two liquids have a set of properties making them optimum for studying the ozonolysis in polar and nonpolar media.

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Ozonation of polycyclic aromatic hydrocarbon in hexane and water: Identification of intermediates and pathway

Cited by 10 publications

References 15 publications

Detection of nitrated and oxygenated polycyclic aromatic hydrocarbons using atmospheric pressure chemical ionization high resolution mass spectrometry

Detection of nitrated and oxygenated polycyclic aromatic hydrocarbons using atmospheric pressure chemical ionization high resolution mass spectrometry

Evaluation of an Ozone Chamber as a Routine Method to Decontaminate Firefighters’ PPE

Ozone in Polar (Acetonitrile) and Nonpolar (Carbon Tetrachloride) Organic Liquids: Optical Absorption, Solubility, and Stability

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