Photochemical transformation of ibuprofen into harmful 4-isobutylacetophenone: Pathways, kinetics, and significance for surface waters

Ruggeri, Giulia; Ghigo, Giovanni; Maurino, Valter; Minero, Claudio; Vione, Davide

doi:10.1016/j.watres.2013.07.031

Cited by 81 publications

(59 citation statements)

References 62 publications

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“…Transformation products previously observed as the result of biodegradation of naproxen (Quintana et al, 2005;Wojcieszynska et al, 2014) and ibuprofen (Matamoros et al, 2008) were not observed in this study. IBP-T1 and NAP-T2 have been observed in other phototransformation studies (DellaGreca et al, 2003;Jacobs et al, 2011;Marotta et al, 2013;Ruggeri et al, 2013). Toxicity studies have shown these compounds, both aromatic ketones, to be more ecotoxic than the parent PhACs (DellaGreca et al, 2003;Ruggeri et al, 2013), raising concerns about their production during environmental processes.…”

Section: Transformation Products Formed During Soil Sorption Studiesmentioning

confidence: 93%

“…IBP-T1 and NAP-T2 have been observed in other phototransformation studies (DellaGreca et al, 2003;Jacobs et al, 2011;Marotta et al, 2013;Ruggeri et al, 2013). Toxicity studies have shown these compounds, both aromatic ketones, to be more ecotoxic than the parent PhACs (DellaGreca et al, 2003;Ruggeri et al, 2013), raising concerns about their production during environmental processes.…”

Section: Transformation Products Formed During Soil Sorption Studiesmentioning

confidence: 93%

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Sorption, photodegradation, and chemical transformation of naproxen and ibuprofen in soils and water

Vulava

Cory

Murphey

et al. 2016

Science of The Total Environment

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Pharmaceutically active compounds (PhACs) are released into the environment where they undergo soil sorption, photodegradation, and chemical transformation into structurally similar compounds. Here we report on studies of naproxen (NAP) and ibuprofen (IBP), two widely-used nonsteroidal anti-inflammatory drugs (NSAIDS), in soils and water. Organic matter (OM) was observed to play an important role in each of these processes. Sorption was observed to be stronger and nonlinear in higher OM soils while weaker but still significant in lower OM, higher clay soils; the amphiphilic nature of these two PhACs combined with the complex charged and nonpolar surfaces available in the soil was observed to control the sorption behavior. Simulated solar photodegradation rates of NAP and IBP in water were observed to change in the presence of humic acid or fulvic acid. Structural analogs of each compound were observed as the result of chemical transformation in both photoexposed aqueous solutions and non-photoexposed soil. Two of these transformation products were detected as both soil and photo transformation products for both PhACs. OM was observed to influence the chemical transformation of both pharmaceuticals.

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Section: Transformation Products Formed During Soil Sorption Studiesmentioning

confidence: 93%

Section: Transformation Products Formed During Soil Sorption Studiesmentioning

confidence: 93%

Sorption, photodegradation, and chemical transformation of naproxen and ibuprofen in soils and water

Vulava

Cory

Murphey

et al. 2016

Science of The Total Environment

View full text Add to dashboard Cite

show abstract

“…Three primary intermediates (compound 1, 2 and 19) were generated due to the attack of sulfate radicals and hydroxyl radicals on the two side chains of IBP at the first stage. The attack on the side chains is more favorable kinetically than that on the benzene ring, which may explain the lack of detection of ring-hydroxylated IBP intermediates at the initial stage [60]. Compound 1 (oxo-ibuprofen) derives from the attack of hydroxyl radicals or sulfate radicals on the secondary carbon of the isobutyl chain.…”

Section: åàmentioning

confidence: 99%

Degradation of ibuprofen by a synergistic UV/Fe(III)/Oxone process

Rao

Xue

Pan

et al. 2016

Chemical Engineering Journal

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“…where [MOBA] t is the concentration of MOBA at the time t and the other variables have been already defined (Ruggeri et al, 2014). It was also assumed that [MOBA] o = 0 M.…”

Section: Where [Ehmc] T Is the Concentration Of Ehmc At The Time Tmentioning

confidence: 99%

The role of direct photolysis and indirect photochemistry in the environmental fate of ethylhexyl methoxy cinnamate (EHMC) in surface waters

Vione

Calza

Galli

et al. 2015

Science of The Total Environment

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Photochemical transformation of ibuprofen into harmful 4-isobutylacetophenone: Pathways, kinetics, and significance for surface waters

Cited by 81 publications

References 62 publications

Sorption, photodegradation, and chemical transformation of naproxen and ibuprofen in soils and water

Sorption, photodegradation, and chemical transformation of naproxen and ibuprofen in soils and water

Degradation of ibuprofen by a synergistic UV/Fe(III)/Oxone process

The role of direct photolysis and indirect photochemistry in the environmental fate of ethylhexyl methoxy cinnamate (EHMC) in surface waters

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