Radiolysis of paracetamol in dilute aqueous solution

Szabó, László; Tóth, Tünde; Homlok, Renáta; Takács, Erzsébet; Wojnárovits, László

doi:10.1016/j.radphyschem.2011.11.036

Cited by 27 publications

(9 citation statements)

References 17 publications

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“…The absorbance above 400 nm can be attributed to reactions on the 4-aminophenol part of AQ in agreement with results on 4-aminophenol and acetaminophen [2,8,14]. OH reaction in these molecules produces 4-aminophenoxy radical with k max % 440 nm and e max % 5000 mol À1 dm 3 cm À1 [7,8].…”

Section: Uv-vis Absorption Spectra Of Amodiaquine In C-radiolysis and Pulse Radiolysis Experimentssupporting

confidence: 88%

“…In OH reaction the 450 nm absorbance was also attributed to the aminophenoxy radical forming in dehydration of the hydroxycyclohexadienyl intermediate. The dehydration is fast process taking place on the few ms timescale [10,14,19]. Bisby [2] suggested a similar mechanism for the OH þ AQ reaction:…”

Section: Introductionmentioning

confidence: 98%

“…Using pulse radiolysis technique, the radical reactions of AQ were studied by Bisby [2]. However, the radical reactions of its structural unit 4-aminophenol [7,8] and also of the analgesic and antipyretic type drug molecule acetaminophen (paracetamol) [9][10][11][12][13][14] were investigated by several research groups. The hydroxyl radicals in their reactions with the aromatic molecules generally add to the conjugated ring, direct oxidation (i.e.…”

Section: Introductionmentioning

confidence: 99%

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High-energy ionizing radiation-induced degradation of amodiaquine in dilute aqueous solution: radical reactions and kinetics

Kovács

Simon

Balogh

et al. 2020

Free Radical Research

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The widely used antimalarial drug amodiaquine (AQ) contains a 7-Cl-quinoline unit, a substituted 4-aminophenol part connected through the amino group and a tertiary amine part. The 4-aminophenol unit can be easily oxidized through radical intermediates to iminoquinone. This reaction also takes place in vitro and in vivo enzymatic reactions. The reaction is expected to have an important role in degradation of AQ in surface waters and also during degradation in advanced oxidation processes. In this paper by means of radiation chemical techniques the one-electron oxidation and reduction of AQ were studied using transient kinetics, kinetics of AQ degradation, formation and decay of end-products of radical reactions. The hydroxyl radicals were shown to add both to the quinoline ($ 38%) and aminophenol ($ 50%) parts via formation of hydroxycyclohexadienyl radicals and by H-abstraction or by an electron removal from the tertiary amine part of the molecule ($ 12%). The dihydroxycyclohexadienyl radical formed on the aminophenol part is suggested to transform to aminophenoxy radical. The hydrated electrons can also effectively contribute to AQ degradation. Chemical oxygen demand and total organic carbon content investigations were also made in order to characterize the ionizing radiation-induced oxidation and mineralization. In aerated 0.1 mmol dm À3 solution, at 2.5 kGy absorbed dose AQ and its higher molecular mass degradation products demolished completely. Ionizing irradiation is a capable technique for degradation of AQ under both oxidative and reductive circumstances.

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Section: Uv-vis Absorption Spectra Of Amodiaquine In C-radiolysis and Pulse Radiolysis Experimentssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

High-energy ionizing radiation-induced degradation of amodiaquine in dilute aqueous solution: radical reactions and kinetics

Kovács

Simon

Balogh

et al. 2020

Free Radical Research

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“…The reaction rate constant of paracetamol with hydroxyl radical ( . OH) is determined as 5.6 × 10 9 mol −1 dm 3 s −1 , [68] [68] although e − aq reacts with oxygen at a rate constant of 1.2 × 10 10 mol −1 dm 3 s −1 [39,42,43] in which e − aq is scavenged by dissolved oxygen for aerated solutions that makes the presence of e − aq unimportant for degradation of paracetamol in aerated solutions.…”

Section: Degradation Of Paracetamolmentioning

confidence: 99%

Mineralization of paracetamol in aqueous solution with advanced oxidation processes

Torun

Gültekin

Şolpan

et al. 2014

Environmental Technology

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Paracetamol is a common analgesic drug widely used in all regions of the world more than hundred tonnes per year and it poses a great problem for the aquatic environment. Its phenolic intermediates are classified as persistent organic pollutants and toxic for the environment as well as human beings. In the present study, the irradiation of aqueous solutions of paracetamol with 60Co gamma-rays was examined on a laboratory scale and its degradation path was suggested with detected radiolysis products. The synergic effect of ozone on gamma-irradiation was investigated by preliminary ozonation before irradiation which reduced the irradiation dose from 5 to 3 kGy to completely remove paracetamol and its toxic intermediate hydroquinone from 6 to 4 kGy as well as increasing the radiation chemical yield (Gi values 1.36 and 1.66 in the absence and presence of ozone, respectively). The observed amount of formed hydroquinone was also decreased in the presence of ozone. There is a decrease in pH from 6.4 to 5.2 and dissolved oxygen consumed, which is up to 0.8 mg l(-1), to form some peroxyl radicals used for oxidation. Analytical measurements were carried out with gas chromatography/mass spectrometry and ion chromatography (IC) both qualitatively and quantitatively. Amounts of paracetamol and hydroquinone were measured with gas chromatography after trimethylsilane derivatization. Small aliphatic acids, such as acetic acid, formic acid and oxalic acid, were measured quantitatively with IC as well as inorganic ions (nitrite and nitrate) in which their yields increase with irradiation.

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“…It has been found in European Sewage Treatment Plants in concentrations around 6 µg L -1 (Ternes 1998) and several studies have demonstrated AOPs capability to degrade PCT from different matrixes, more specifically, ozonation (Andreozzi et al 2003), radiolysis (Szabó et al 2003), photolysis and UV/H 2 O 2 (Kim et al 2009), heterogeneous photocatalysis (Yang et al 2008) and Fenton and related process (Trovó et al 2008;Santos-Juanes et al 2011a and2011b;Durán et al 2011;De Luna et al 2012;Li et al 2012) have been used to degrade this EC at a wide range of concentrations (from 1x10 -6 to 25 mM). These investigations have confirmed that sole UV irradiation above 254 nm does not degrade PCT or mineralize samples, but the presence of H 2 O 2 may lead to total degradation and partial mineralization of the samples (Kim et al 2009;Trovó et al 2008;Yang et al 2008).…”

Section: Introductionmentioning

confidence: 99%

Photonic efficiency of the photodegradation of paracetamol in water by the photo-Fenton process

Yamal-Turbay

Ortega

Conte

et al. 2014

Environ Sci Pollut Res

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Radiolysis of paracetamol in dilute aqueous solution

Cited by 27 publications

References 17 publications

High-energy ionizing radiation-induced degradation of amodiaquine in dilute aqueous solution: radical reactions and kinetics

High-energy ionizing radiation-induced degradation of amodiaquine in dilute aqueous solution: radical reactions and kinetics

Mineralization of paracetamol in aqueous solution with advanced oxidation processes

Photonic efficiency of the photodegradation of paracetamol in water by the photo-Fenton process

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