Catalytic ozonation of the antibiotic sulfadiazine: reaction kinetics and transformation mechanisms

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

doi:10.1016/j.chemosphere.2020.125853

Catalytic ozonation of the antibiotic sulfadiazine: reaction kinetics and transformation mechanisms

Matilda Kråkström, Soudabeh Saeid, Pasi Tolvanen, Tapio Salmi, Patrik Christoffer Eklund, Leif Kronberg

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Abstract

In this work, ozone has been used to study the transformation of the antibiotic sulfadiazine (SDZ). SDZ and its transformation products was investigated using liquid chromatography coupled to mass spectrometry and using NMR. The results revealed that 6% of SDZ is transformed into 2-aminopyrimidine. A significant amount of SDZ undergoes a rearrangement reaction followed by ring-closing reactions. One of these products, SDZ-P15, is the main product after 240 min of ozonation. Almost 30% of SDZ transforms into SDZ-P15. SDZ was also transformed via the addition of one or more hydroxyl groups, via the oxidation of an amine group to a nitro group as well as via a bond cleavage reaction. Most of the intermediate products presented in this study have not previously been reported as SDZ transformation products formed using ozonation technology.

Original language	English
Article number	125853
Pages (from-to)	–
Journal	Chemosphere
Volume	247
DOIs	https://doi.org/10.1016/j.chemosphere.2020.125853
Publication status	Published - May 2020
MoE publication type	A1 Journal article-refereed

Keywords

Chemical Engineering

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Catalytic ozonation of the antibiotic sulfadiazine_ reaction kinetics and transformation mechanisms.pdfAccepted author manuscript, 1.54 MBLicence: CC BY-NC-ND

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abstract = "In this work, ozone has been used to study the transformation of the antibiotic sulfadiazine (SDZ). SDZ and its transformation products was investigated using liquid chromatography coupled to mass spectrometry and using NMR. The results revealed that 6% of SDZ is transformed into 2-aminopyrimidine. A significant amount of SDZ undergoes a rearrangement reaction followed by ring-closing reactions. One of these products, SDZ-P15, is the main product after 240 min of ozonation. Almost 30% of SDZ transforms into SDZ-P15. SDZ was also transformed via the addition of one or more hydroxyl groups, via the oxidation of an amine group to a nitro group as well as via a bond cleavage reaction. Most of the intermediate products presented in this study have not previously been reported as SDZ transformation products formed using ozonation technology.",

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AU - Kråkström, Matilda

AU - Saeid, Soudabeh

AU - Tolvanen, Pasi

AU - Salmi, Tapio

AU - Eklund, Patrik Christoffer

AU - Kronberg, Leif

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PY - 2020/5

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N2 - In this work, ozone has been used to study the transformation of the antibiotic sulfadiazine (SDZ). SDZ and its transformation products was investigated using liquid chromatography coupled to mass spectrometry and using NMR. The results revealed that 6% of SDZ is transformed into 2-aminopyrimidine. A significant amount of SDZ undergoes a rearrangement reaction followed by ring-closing reactions. One of these products, SDZ-P15, is the main product after 240 min of ozonation. Almost 30% of SDZ transforms into SDZ-P15. SDZ was also transformed via the addition of one or more hydroxyl groups, via the oxidation of an amine group to a nitro group as well as via a bond cleavage reaction. Most of the intermediate products presented in this study have not previously been reported as SDZ transformation products formed using ozonation technology.

AB - In this work, ozone has been used to study the transformation of the antibiotic sulfadiazine (SDZ). SDZ and its transformation products was investigated using liquid chromatography coupled to mass spectrometry and using NMR. The results revealed that 6% of SDZ is transformed into 2-aminopyrimidine. A significant amount of SDZ undergoes a rearrangement reaction followed by ring-closing reactions. One of these products, SDZ-P15, is the main product after 240 min of ozonation. Almost 30% of SDZ transforms into SDZ-P15. SDZ was also transformed via the addition of one or more hydroxyl groups, via the oxidation of an amine group to a nitro group as well as via a bond cleavage reaction. Most of the intermediate products presented in this study have not previously been reported as SDZ transformation products formed using ozonation technology.

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Catalytic ozonation of the antibiotic sulfadiazine: reaction kinetics and transformation mechanisms

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