Ozonation of carbamazepine and its main transformation products: Product determination and reaction mechanisms

Matilda Kråkström; Soudabeh Saeid; Pasi Tolvanen; Narendra Kumar; Tapio Salmi; Leif Kronberg; Patrik Eklund

doi:10.1007/s11356-020-08795-0

Ozonation of carbamazepine and its main transformation products: Product determination and reaction mechanisms

Matilda Kråkström^*
, Soudabeh Saeid
, Pasi Tolvanen
, Narendra Kumar
, Tapio Salmi
, Leif Kronberg
, Patrik Eklund

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

35 Citations (Scopus)

Abstract

Carbamazepine (CBZ) is a recalcitrant pharmaceutical often detected in wastewater and in the environment. CBZ can be removed from wastewater through advanced oxidation treatment methods such as ozonation. In this study, CBZ and its transformation product 1-(2-benzaldehyde)-(1H,3H)-quinazoline-2,4-dione (BQD) were ozonated, and the formation and transformation of their ozonation products were investigated using liquid chromatography coupled to ion trap mass spectrometry and high-resolution mass spectrometry as well as nuclear magnetic resonance (NMR). The main products, 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one (BQM) and BQD were quantified using isolated standards and LC-UV. Of the original CBZ concentration, 74% was transformed into BQM and 83% of BQM was further transformed into BQD. Both products are more stable than CBZ and could still be detected after 240 min of ozonation. Another major product, 2,2′-azanediyldibenzaldehyde (TP225) was for the first time identified using NMR. Twelve further CBZ products were identified.

Original language	English
Pages (from-to)	23258-23269
Number of pages	12
Journal	Environmental Science and Pollution Research
Volume	27
Issue number	18
DOIs	https://doi.org/10.1007/s11356-020-08795-0
Publication status	Published - 25 Apr 2020
MoE publication type	A1 Journal article-refereed

Funding

Open access funding provided by Abo Akademi University (ABO). This work is a part of the activities of the Johan Gadolin Process Chemistry Åbo Akademi University. This work was supported by Svenska Litteratursällskapet (SLS), Victoriastiftelsen and maa- ja vesitekniikan tuki is gratefully acknowledged.

Keywords

Carbamazepine
Ozonation
Pharmaceuticals
Product identification
Quantification
Transformation products
Wastewater treatment

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10.1007/s11356-020-08795-0

Cite this

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title = "Ozonation of carbamazepine and its main transformation products: Product determination and reaction mechanisms",

abstract = "Carbamazepine (CBZ) is a recalcitrant pharmaceutical often detected in wastewater and in the environment. CBZ can be removed from wastewater through advanced oxidation treatment methods such as ozonation. In this study, CBZ and its transformation product 1-(2-benzaldehyde)-(1H,3H)-quinazoline-2,4-dione (BQD) were ozonated, and the formation and transformation of their ozonation products were investigated using liquid chromatography coupled to ion trap mass spectrometry and high-resolution mass spectrometry as well as nuclear magnetic resonance (NMR). The main products, 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one (BQM) and BQD were quantified using isolated standards and LC-UV. Of the original CBZ concentration, 74\% was transformed into BQM and 83\% of BQM was further transformed into BQD. Both products are more stable than CBZ and could still be detected after 240 min of ozonation. Another major product, 2,2′-azanediyldibenzaldehyde (TP225) was for the first time identified using NMR. Twelve further CBZ products were identified.",

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AU - Kråkström, Matilda

AU - Saeid, Soudabeh

AU - Tolvanen, Pasi

AU - Kumar, Narendra

AU - Salmi, Tapio

AU - Kronberg, Leif

AU - Eklund, Patrik

PY - 2020/4/25

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N2 - Carbamazepine (CBZ) is a recalcitrant pharmaceutical often detected in wastewater and in the environment. CBZ can be removed from wastewater through advanced oxidation treatment methods such as ozonation. In this study, CBZ and its transformation product 1-(2-benzaldehyde)-(1H,3H)-quinazoline-2,4-dione (BQD) were ozonated, and the formation and transformation of their ozonation products were investigated using liquid chromatography coupled to ion trap mass spectrometry and high-resolution mass spectrometry as well as nuclear magnetic resonance (NMR). The main products, 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one (BQM) and BQD were quantified using isolated standards and LC-UV. Of the original CBZ concentration, 74% was transformed into BQM and 83% of BQM was further transformed into BQD. Both products are more stable than CBZ and could still be detected after 240 min of ozonation. Another major product, 2,2′-azanediyldibenzaldehyde (TP225) was for the first time identified using NMR. Twelve further CBZ products were identified.

AB - Carbamazepine (CBZ) is a recalcitrant pharmaceutical often detected in wastewater and in the environment. CBZ can be removed from wastewater through advanced oxidation treatment methods such as ozonation. In this study, CBZ and its transformation product 1-(2-benzaldehyde)-(1H,3H)-quinazoline-2,4-dione (BQD) were ozonated, and the formation and transformation of their ozonation products were investigated using liquid chromatography coupled to ion trap mass spectrometry and high-resolution mass spectrometry as well as nuclear magnetic resonance (NMR). The main products, 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one (BQM) and BQD were quantified using isolated standards and LC-UV. Of the original CBZ concentration, 74% was transformed into BQM and 83% of BQM was further transformed into BQD. Both products are more stable than CBZ and could still be detected after 240 min of ozonation. Another major product, 2,2′-azanediyldibenzaldehyde (TP225) was for the first time identified using NMR. Twelve further CBZ products were identified.

KW - Carbamazepine

KW - Ozonation

KW - Pharmaceuticals

KW - Product identification

KW - Quantification

KW - Transformation products

KW - Wastewater treatment

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ER -

Ozonation of carbamazepine and its main transformation products: Product determination and reaction mechanisms

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Removal of residual pharmaceuticals in waste water by catalytic ozonation technology

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Ozonation of carbamazepine and its main transformation products: Product determination and reaction mechanisms

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Removal of residual pharmaceuticals in waste water by catalytic ozonation technology

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