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Ozonation of Carbamazepine in Drinking Water: Identification and Kinetic Study of Major Oxidation Products
Open accessAbstract
Kinetics and product formation of the anti-epileptic drug carbamazepine (CBZ) were investigated in lab-scale experiments during reactions with ozone and OH radicals. Ozone reacts rapidly with the double bond in CBZ, yielding several ozonation products containing quinazoline-based functional groups. The structures for three new oxidation products were elucidated using a combination of mass spectrometric and NMR techniques. The three products were determined to be 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one (BQM), 1-(2-benzaldehyde)-(1H,3H)-quinazoline-2,4-dione (BQD), and 1-(2-benzoic acid)-(1H,3H)-quinazoline-2,4-dione (BaQD). Additional kinetic studies of the ozonation products showed very slow subsequent oxidation kinetics with ozone (second-order rate constants, kO3 = approximately 7 M(-1)s(-1) and approximately 1 M(-1)s(-1) at pH = 6 for BQM and BQD, respectively). Rate constants for reactions with OH radicals, kOH, were determined as approximately 7 x 10(9) M(-1)s(-1) for BQM and approximately 5 x 10(9)M(-1)s(-1) for BQD. Thus, mainly reactions with OH radicals lead to their further oxidation. A kinetic model including ozone and OH radical reactions allows a prediction of the time-dependent product distribution during ozonation of natural waters. In Rhine River water, CBZ spiked at 500 ng/L was completely oxidized by ozone with applied doses > or =0.3 mg/L. To confirm that the two major ozonation products BQM and BQD are produced as a result of the ozonation of a CBZ-containing natural water, Lake Zurich water samples were spiked with CBZ (1 microM, 236 microg/L). The oxidation products were identified via LC-UV. Concentrations of 0.48 and 0.15 microM for BQM and BQD, respectively, were measured for an ozone dose of 1.9 mg/L. BQM and BQD were also identified in ozonated water from a German waterworks containing CBZ in its raw water with 0.07-0.20 microg/L. Currently, there are no data available on the biological effects of the formed oxidation products.
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Buxton, G. V., Greenstock, C. L., Helman, W. P., & Ross, A. B. (1988) · Journal of Physical and Chemical Reference Data · doi:10.1063/1.555805 · Cited by 12,332
Cited by
RICHARDSON, S., PLEWA, M., WAGNER, E., SCHOENY, R., & DEMARINI, D. (2007) · Mutation Research/Reviews in Mutation Research · doi:10.1016/j.mrrev.2007.09.001 · Cited by 3,317
Water Analysis: Emerging Contaminants and Current Issues
Richardson, S. D., & Ternes, T. A. (2014) · Analytical Chemistry · doi:10.1021/ac500508t · Cited by 2,144
Self-citationFarré, M. L., Pérez, S., Kantiani, L., & Barceló, D. (2008) · TrAC Trends in Analytical Chemistry · doi:10.1016/j.trac.2008.09.010 · Cited by 1,009
Hollender, J., Zimmermann, S. G., Koepke, S., Krauss, M., McArdell, C. S., Ort, C., Singer, H., von Gunten, U., & Siegrist, H. (2009) · Environmental Science & Technology · doi:10.1021/es9014629 · Cited by 870
Self-citationOxidation of Pharmaceuticals during Ozonation of Municipal Wastewater Effluents: A Pilot Study
Huber, M. M., GÖbel, A., Joss, A., Hermann, N., LÖffler, D., McArdell, C. S., Ried, A., Siegrist, H., Ternes, T. A., & von Gunten, U. (2005) · Environmental Science & Technology · doi:10.1021/es048396s · Cited by 830
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Metadata
- Authors
- McDowell, D. C., Huber, M. M., Wagner, M., von Gunten, U., & Ternes, T. A.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-09-08
- Volume
- 39
- Issue
- 20
- Pages
- 8014-8022
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2077471442
- Cited by
- 291
- References
- 1
- FWCI
- 16.01
- Type
- journal article
- Language
- en
- Open access
- green
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