Kinetic and chemical assessment of the UV/H2O2 treatment of antiepileptic drug carbamazepine.
The UV/H2O2-induced degradation of carbamazepine, a worldwide used antiepileptic drug, recently found as contaminant in many municipal sewage treatment plant (STP) effluents and other aquatic environments, is investigated. The oxidation treatment caused an effective removal of the drug. At complete abatement of the substrate after 4 min treatment, a 35% value of removed total organic carbon (TOC) was obtained. A kinetic constant of (2.05+/-0.14) x 10(9) lmol(-1)s(-1) was determined for OH radical attack to carbamazepine in the UV/H2O2 process. Preparative TLC of the reaction mixture led to the isolation of acridine-9-carboxaldehyde as a reaction intermediate. HPLC and GC/MS analysis indicated formation of small amounts of acridine, salicylic acid, catechol and anthranilic acid among the reaction products. Under the same reaction conditions, synthetically prepared 10,11-epoxycarbamazepine was easily degraded to acridine as main product, suggesting that this epoxide is a likely intermediate in the oxidative conversion of carbamazepine to acridine. Under sunlight irradiation, carbamazepine in water underwent slow degradation to afford likewise acridine as main product. In view of the mutagenic properties of acridine, these results would raise important issues concerning the possible environmental impact of carbamazepine release through domestic wastewaters and support the importance of prolonged oxidation treatments to ensure complete degradation of aromatic intermediates.
Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario M.S. Angelo, via Cinthia 4, I-80126 Naples, Italy.
Davide
D
Vogna
Raffaele
R
Marotta
Roberto
R
Andreozzi
Alessandra
A
Napolitano
Marco
M
d'Ischia
D000166:Acridines / Q000737:chemistry; D000927:Anticonvulsants / Q000737:chemistry / Q000528:radiation effects*; D002220:Carbamazepine / Q000737:chemistry* / Q000528:radiation effects*; D002244:Carbon / Q000737:chemistry / Q000302:isolation & purification; D004784:Environmental Monitoring; D008401:Gas Chromatography-Mass Spectrometry; D006812:Humic Substances; D006861:Hydrogen Peroxide / Q000737:chemistry*; D007700:Kinetics; D009566:Nitrates / Q000737:chemistry; D010083:Oxidants, Photochemical / Q000737:chemistry; D010777:Photochemistry; D013472:Sunlight; D014466:Ultraviolet Rays
D000166:Acridines; D000927:Anticonvulsants; D006812:Humic Substances; D009566:Nitrates; D010083:Oxidants, Photochemical; D002220:Carbamazepine; D002244:Carbon; D006861:Hydrogen Peroxide