On the mechanism of phenol ozonolysis

Комиссаров, В. Д.; Zimin, Yu. S.; Хурсан, С. Л.

doi:10.1134/s0023158406060061

Cited by 14 publications

(9 citation statements)

References 9 publications

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“…Similarly, oxidation of humic substances, showed an increase of the O/C ratio and formation of aliphatic and aromatic carboxylic acids. 40,41 This functionalization pattern would render HULIS T more hydrophilic.…”

Section: Hulis T Initial Characterization and Aging Experimentmentioning

confidence: 99%

Oxidation of Atmospheric Humic Like Substances by Ozone: A Kinetic and Structural Analysis Approach

Baduel

Monge

Voisin

et al. 2011

Environ. Sci. Technol.

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This work explores the heterogeneous reaction between HUmic-LIke Substances (so-called HULIS) and ozone. Genuine atmospheric HULIS were extracted from aerosol samples collected in Chamonix (France) in winter and used in coated flow tube experiments to evaluate heterogeneous uptake of O₃ on such mixtures. The uptake coefficient (γ) was investigated as a function of pH (from 2.5 to 10), O₃ concentration (from 8 to 33 × 10¹¹ molecules cm⁻³), relative humidity (20 to 65%) and photon flux (from 0 to 1.66 × 10¹⁵ photons cm⁻² s⁻¹). Reactive uptake was found to increase in the irradiated experiment with pH, humidity and photon flux. The extract was characterized before and after exposure to O₃ and/or UV light in the attempt to elucidate the effect of the photochemical aging. Carbon content measurements, UV-vis spectroscopy and functional groups analysis revealed a decrease of the UV absorbance as well as of the carbon mass content, while the functionalization rate (COOH and C═O) and therefore the polarity increased during the simulated photochemical exposure.

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Section: Hulis T Initial Characterization and Aging Experimentmentioning

confidence: 99%

Oxidation of Atmospheric Humic Like Substances by Ozone: A Kinetic and Structural Analysis Approach

Baduel

Monge

Voisin

et al. 2011

Environ. Sci. Technol.

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“…For the E2 and E1 byproducts with m/z 277 and m/z 275, respectively, the pathway of degradation based on the mechanism of phenol ozonolysis (Komissarov et al, 2006) is suggested. This pathway is illustrated in Figure 5 for E2.…”

Section: (Figure 4)mentioning

confidence: 99%

Identification of new ozonation disinfection byproducts of 17β-estradiol and estrone in water

et al. 2011

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Estrogens are a class of micro-pollutants found in water at low concentrations (in the ng L(-1) range), but often sufficient to exert estrogenic effects due to their high estrogenic potency. Disinfection of waters containing estrogens through oxidative processes has been shown to lead to the formation of disinfection byproducts, which may also be estrogenic. The present work investigates the formation of disinfection byproducts of 17β-estradiol (E2) and estrone (E1) in the treatment of water with ozone. Experiments have been carried out at two different concentrations of the estrogens in ground water (100 ng L(-1) and 100 μg L(-1)) and at varying ozone dosages (0-30 mg L(-1)). Detection of the estrogens and their disinfection byproducts in the water samples has been performed by means of ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) with a triple quadrupole (QqQ) and a quadrupole-time of flight (QqTOF) instrument. Both E2 and E1 have been found to form two main byproducts, with molecular mass (MM) 288 and 278 in the case of E2, and 286 and 276 in the case of E1, following presumably the same reaction pathways. The E2 byproduct with MM 288 has been identified as 10 epsilon-17beta-dihydroxy-1,4-estradieno-3-one (DEO), in agreement with previously published results. The molecular structures and the formation pathways of the other three newly identified byproducts have been suggested. These byproducts have been found to be formed at both high and low concentrations of the estrogens and to be persistent even after application of high ozone dosages.

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“…Numerous oxidation products and reaction pathways of the ozonation of phenol solutions have been reported. ,,,, Phenol oxidation can take place at para or ortho -positions. The oxidation of phenol at the para -position generates p- benzoquinone which can be further oxidized to give 2,5-dioxo-3-hexenedioic acid; then, the oxidation and decarboxylation of this acid gives maleic acid (C 4 H 4 O 4 ) .…”

Section: Resultsmentioning

confidence: 99%

Monitoring the Ozonation of Phenol Solutions at Constant pH by Different Methods

Contreras

Bértola

Zaritzky

2011

Ind. Eng. Chem. Res.

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In this study the oxidation–reduction potential (ORP) and the proton production (Hp) profiles as a function of time were proposed as indicators to monitor the ozonation of phenol solutions at constant pH. Analysis of the ozone gas outlet stream (X O3), COD, and phenol measurements in the aqueous phase confirm the reliability of the proposed indicators. Results show that the derivative with respect to time of the normalized ozone gas outlet concentration ((1/X O30)dX O3/dt), of the oxidation–reduction potential (dORP/dt) or of its logarithmic value (dLog(ORP)/dt), and of the proton production rate (dHp/dt) exhibited maximum values that were close to the critical ozonation time (t c) determined by X O3, COD, and phenol measurements. Additionally, ORP and X O3 measurements were useful to determine t c for all the tested pHs (5 to 11); however, Hp was useful only for pH values higher than 9. The indicators of the ozonation process proposed in the present work (ORP, Hp) as alternatives of X O3 may be useful to control the addition of ozone, minimizing the ozonation process costs.

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On the mechanism of phenol ozonolysis

Cited by 14 publications

References 9 publications

Oxidation of Atmospheric Humic Like Substances by Ozone: A Kinetic and Structural Analysis Approach

Oxidation of Atmospheric Humic Like Substances by Ozone: A Kinetic and Structural Analysis Approach

Identification of new ozonation disinfection byproducts of 17β-estradiol and estrone in water

Monitoring the Ozonation of Phenol Solutions at Constant pH by Different Methods

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