Photolytic and photocatalytic degradation of nitrofurantoin and its photohydrolytic products

Erzsébet Szabó-Bárdos, Andrea Cafuta, Péter Hegedűs, Orsolya Fónagy, G. Kiss, Sandra Babić, Irena Škorić, O. Horváth

Research output: Contribution to journalArticle

Abstract

TiO2 based photocatalytic degradation of nitrofurantion (NFT), a widely used drug, and its primary decomposition products, nitrofuraldehyde (NFA) and aminohydantoin (AHD) was investigated and compared to their photolysis in aerobic systems. UV–vis spectrophotometry, pH, IC, and HPLC measurements were applied to follow the changes during the irradiations and subsequently, in the dark. After a fast anti→syn (or trans→cis) photoisomerization of NFT (giving i-NFT), a slower photohydrolysis of both isomers took place upon UV excitation, leading to the formation of NFA and AHD. i-NFT proved to be more reactive than NFT; it underwent hydrolysis in the dark, too. While photolysis could not totally convert NFT and i-NFT within 120 min, they disappeared within 90 min during the photocatalysis under the same irradiation conditions, along with the degradation of NFA and AHD, and the accumulation of a rather stable intermediate identified as 5-hydroxyfuran-2-carbaldehyde, formed from NFA. The direct photolysis of NFA also gave this characteristic intermediate along with its several derivatives formed via addition or condensation then redox transformations. They very slowly decomposed in photolysis, while totally disappeared during photocatalysis of NFA, producing polar aliphatic intermediates. Direct irradiation could not convert AHD, while photocatalysis led to its significant degradation in aerobic system. These results indicate that TiO2 based photocatalysis is suitable for the efficient decomposition of NFT and their photoderivatives.

Original languageEnglish
Article number112093
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume386
DOIs
Publication statusPublished - Jan 1 2020

Fingerprint

Nitrofurantoin
Photocatalysis
Photolysis
photolysis
degradation
Degradation
Irradiation
products
irradiation
Decomposition
decomposition
Photoisomerization
Spectrophotometry
spectrophotometry
Isomers
hydrolysis
Condensation
Hydrolysis
drugs
isomers

Keywords

  • Intermediates
  • Nitrofurantoin derivatives
  • Photocatalysis
  • Photolysis
  • Thermal instability

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

Cite this

Photolytic and photocatalytic degradation of nitrofurantoin and its photohydrolytic products. / Szabó-Bárdos, Erzsébet; Cafuta, Andrea; Hegedűs, Péter; Fónagy, Orsolya; Kiss, G.; Babić, Sandra; Škorić, Irena; Horváth, O.

In: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 386, 112093, 01.01.2020.

Research output: Contribution to journalArticle

Szabó-Bárdos, Erzsébet ; Cafuta, Andrea ; Hegedűs, Péter ; Fónagy, Orsolya ; Kiss, G. ; Babić, Sandra ; Škorić, Irena ; Horváth, O. / Photolytic and photocatalytic degradation of nitrofurantoin and its photohydrolytic products. In: Journal of Photochemistry and Photobiology A: Chemistry. 2020 ; Vol. 386.
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AB - TiO2 based photocatalytic degradation of nitrofurantion (NFT), a widely used drug, and its primary decomposition products, nitrofuraldehyde (NFA) and aminohydantoin (AHD) was investigated and compared to their photolysis in aerobic systems. UV–vis spectrophotometry, pH, IC, and HPLC measurements were applied to follow the changes during the irradiations and subsequently, in the dark. After a fast anti→syn (or trans→cis) photoisomerization of NFT (giving i-NFT), a slower photohydrolysis of both isomers took place upon UV excitation, leading to the formation of NFA and AHD. i-NFT proved to be more reactive than NFT; it underwent hydrolysis in the dark, too. While photolysis could not totally convert NFT and i-NFT within 120 min, they disappeared within 90 min during the photocatalysis under the same irradiation conditions, along with the degradation of NFA and AHD, and the accumulation of a rather stable intermediate identified as 5-hydroxyfuran-2-carbaldehyde, formed from NFA. The direct photolysis of NFA also gave this characteristic intermediate along with its several derivatives formed via addition or condensation then redox transformations. They very slowly decomposed in photolysis, while totally disappeared during photocatalysis of NFA, producing polar aliphatic intermediates. Direct irradiation could not convert AHD, while photocatalysis led to its significant degradation in aerobic system. These results indicate that TiO2 based photocatalysis is suitable for the efficient decomposition of NFT and their photoderivatives.

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