Photochemical transformation of ibuprofen into harmful 4-isobutylacetophenone: Pathways, kinetics, and significance for surface waters
Articolo
Data di Pubblicazione:
2013
Abstract:
The harmful compound 4-isobutylacetophenone (IBAP) can be formed photochemically
from the anti-inflammatory drug ibuprofen (IBP), upon direct photolysis (yield 25 7%,
m s), reaction with OH (yield 2.3 0.1%) and reaction with triplet states of chromophoric
dissolved organic matter, 3CDOM* (yield 31 4%). In the latter case, anthraquinone-2-
sulphonate was used as CDOM proxy. The three processes would account for most of
the photochemical transformation of IBP and IBAP in surface waters. IBAP formation from
IBP involves the propanoic acid chain, which is more reactive than the aromatic ring as
shown by quantum mechanical calculations. IBAP is expected to undergo slightly faster
photochemical transformation than IBP in surface waters, with a modelled pseudo-first
order rate constant that is higher by 1.5e1.9 times compared to IBP. Due to fairly high
formation yields and depending on IBP emission scenarios, photochemical modelling
suggests that IBAP could reach concentration values up to w15% of IBP in surface waters,
thus being a potentially important transformation intermediate. This issue prompts for the
need of field studies that provide information on IBAP environmental occurrence, which is
virtually unknown at the present moment.
Tipologia CRIS:
03A-Articolo su Rivista
Keywords:
Surface-water photochemistry; Photosensitised transformation; Transformation by-products and intermediates; Non-steroidal anti-inflammatory drugs; Radical reactions
Elenco autori:
Giulia Ruggeri; Giovanni Ghigo; Valter Maurino; Claudio Minero;
Davide Vione
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