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Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor

The enantiospecific fate of three common pharmaceuticals was monitored in a laboratory�scale membrane bioreactor (MBR). The MBR was operated with a hydraulic retention time of 24 h and a mixed liquor suspended solids concentration of 8.6e10 g/L. Standard solu�tions of ibuprofen, ketoprofen and napr...

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Main Authors: Hashim, N. H., Nghiem, L. D., Stuetz, R. M., Khan, S. J.
Format: Article
Language:English
Published: Elsevier 2011
Subjects:
T Technology (General)
Online Access:http://eprints.uthm.edu.my/7989/1/J5715_26d79197079a86179031e8c7682a7d91.pdf
http://eprints.uthm.edu.my/7989/
https://doi.org/10.1016/j.watres.2011.09.020
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spelling my.uthm.eprints.79892022-11-08T01:37:39Z http://eprints.uthm.edu.my/7989/ Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor Hashim, N. H. Nghiem, L. D. Stuetz, R. M. Khan, S. J. T Technology (General) The enantiospecific fate of three common pharmaceuticals was monitored in a laboratory�scale membrane bioreactor (MBR). The MBR was operated with a hydraulic retention time of 24 h and a mixed liquor suspended solids concentration of 8.6e10 g/L. Standard solu�tions of ibuprofen, ketoprofen and naproxen were dosed into the synthetic feed of the MBR. Influent and permeate samples were then collected for enantiospecific analysis. The individual (R)- and (S )-enantiomers of the three pharmaceuticals were derivatised using a chiral derivatizing agent to form pairs of diastereomers, which could then be separated and analysed by gas chromatographyetandem mass spectrometry (GCeMS/MS). Accurate quantitation of individual enantiomers was undertaken by an isotope dilution process. By comparing the total concentration (as the sum of the two enantiomers) in the MBR influent and permeate, ibuprofen, ketoprofen and naproxen concentrations were observed to have been reduced as much as 99%, 43% and 68%, respectively. Furthermore, evidence of enantioselective biodegradation was observed for all three pharmaceuticals. (S )-Ibuprofen was shown to be preferentially degraded compared to (R)-ibuprofen with an average decrease in enantiomeric fraction (EF ) from 0.52 to 0.39. In contrast, (R)-ketoprofen was preferentially degraded compared to (S )-ketoprofen with a relatively minor increase in EF from 0.52 to 0.63. The use of a relatively pure enantiomeric solution of (S )-naproxen resulted in a significant change in EF from 0.99 to 0.65. However, this experiment consis�tently revealed significantly increased concentrations of (R)-naproxen during MBR treat�ment. It is hypothesised that the source of this (R)-naproxen was the enantiomeric inversion of (S )-naproxen. Such enantiomeric inversion of chiral pharmaceuticals during wastewater treatment processes has not previously been reported. Elsevier 2011 Article PeerReviewed text en http://eprints.uthm.edu.my/7989/1/J5715_26d79197079a86179031e8c7682a7d91.pdf Hashim, N. H. and Nghiem, L. D. and Stuetz, R. M. and Khan, S. J. (2011) Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor. Water Research, 45. pp. 6429-6258. https://doi.org/10.1016/j.watres.2011.09.020
institution Universiti Tun Hussein Onn Malaysia
building UTHM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Tun Hussein Onn Malaysia
content_source UTHM Institutional Repository
url_provider http://eprints.uthm.edu.my/
language English
topic T Technology (General)
spellingShingle T Technology (General)
Hashim, N. H.
Nghiem, L. D.
Stuetz, R. M.
Khan, S. J.
Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor
description The enantiospecific fate of three common pharmaceuticals was monitored in a laboratory�scale membrane bioreactor (MBR). The MBR was operated with a hydraulic retention time of 24 h and a mixed liquor suspended solids concentration of 8.6e10 g/L. Standard solu�tions of ibuprofen, ketoprofen and naproxen were dosed into the synthetic feed of the MBR. Influent and permeate samples were then collected for enantiospecific analysis. The individual (R)- and (S )-enantiomers of the three pharmaceuticals were derivatised using a chiral derivatizing agent to form pairs of diastereomers, which could then be separated and analysed by gas chromatographyetandem mass spectrometry (GCeMS/MS). Accurate quantitation of individual enantiomers was undertaken by an isotope dilution process. By comparing the total concentration (as the sum of the two enantiomers) in the MBR influent and permeate, ibuprofen, ketoprofen and naproxen concentrations were observed to have been reduced as much as 99%, 43% and 68%, respectively. Furthermore, evidence of enantioselective biodegradation was observed for all three pharmaceuticals. (S )-Ibuprofen was shown to be preferentially degraded compared to (R)-ibuprofen with an average decrease in enantiomeric fraction (EF ) from 0.52 to 0.39. In contrast, (R)-ketoprofen was preferentially degraded compared to (S )-ketoprofen with a relatively minor increase in EF from 0.52 to 0.63. The use of a relatively pure enantiomeric solution of (S )-naproxen resulted in a significant change in EF from 0.99 to 0.65. However, this experiment consis�tently revealed significantly increased concentrations of (R)-naproxen during MBR treat�ment. It is hypothesised that the source of this (R)-naproxen was the enantiomeric inversion of (S )-naproxen. Such enantiomeric inversion of chiral pharmaceuticals during wastewater treatment processes has not previously been reported.
format Article
author Hashim, N. H.
Nghiem, L. D.
Stuetz, R. M.
Khan, S. J.
author_facet Hashim, N. H.
Nghiem, L. D.
Stuetz, R. M.
Khan, S. J.
author_sort Hashim, N. H.
title Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor
title_short Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor
title_full Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor
title_fullStr Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor
title_full_unstemmed Enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor
title_sort enantiospecific fate of ibuprofen, ketoprofen and naproxen in a laboratory-scale membrane bioreactor
publisher Elsevier
publishDate 2011
url http://eprints.uthm.edu.my/7989/1/J5715_26d79197079a86179031e8c7682a7d91.pdf
http://eprints.uthm.edu.my/7989/
https://doi.org/10.1016/j.watres.2011.09.020
_version_ 1751538643041779712
score 13.211869

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