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J Hazard Mater. 2015 Apr 28;287:133-41. doi: 10.1016/j.jhazmat.2015.01.045. Epub 2015 Jan 21.

TiO2 photocatalytic degradation and transformation of oxazaphosphorine drugs in an aqueous environment.

Author information

1
Graduate Institute of Environmental Engineering, National Taiwan University, 71-Chou-shan Road, Taipei 106, Taiwan, ROC.
2
Graduate Institute of Environmental Engineering, National Taiwan University, 71-Chou-shan Road, Taipei 106, Taiwan, ROC. Electronic address: yuchenlin@ntu.edu.tw.

Abstract

This study investigated the TiO2 photocatalytic degradation and transformation of the oxazaphosphorines ifosfamide (IFO), cyclophosphamide (CP) and trofosfamide (TRO). Under the optimum conditions of TiO2=100mg/L, IFO=100μg/L and solution pH=5.5, IFO was completely removed within 10min (k=0.433min(-1)). The results indicated that OHfree radicals generated by valence holes in the bulk solution were the predominant species for the degradation of IFO. At higher initial concentrations of oxazaphosphorines (20mg/L), >50% of TOC remained after 6h of reaction time, indicating that parent compounds were transformed to byproducts, which exhibit higher Microtox acute toxicities; chlorinated byproducts were likely the source of toxicity. Photocatalytic degradation pathways of the three oxazaphosphorines were proposed. IFO, CP and TRO follow very similar pathways and bond-breaking processes: ketonization and breaking of the CCl bond, the PN bond and the CN bond (N-dechloroethylation). Chloride (Cl(-)) release is likely the first and primary step in the decomposition process. Several of the identified byproducts were also metabolites, which implies that photocatalytic oxidation proceeds through pathways that are similar to metabolic pathways.

KEYWORDS:

Oxazaphosphorine drugs; Photocatalytic degradation; Titanium dioxide; Toxicity

PMID:
25644030
DOI:
10.1016/j.jhazmat.2015.01.045
[Indexed for MEDLINE]

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