Literature DB >> 21964549

Structural elucidation of main ozonation products of the artificial sweeteners cyclamate and acesulfame.

Marco Scheurer1, Markus Godejohann, Arne Wick, Oliver Happel, Thomas A Ternes, Heinz-Jürgen Brauch, Wolfgang K L Ruck, Frank Thomas Lange.   

Abstract

PURPOSE: The two artificial sweeteners cyclamate (CYC) and acesulfame (ACE) have been detected in wastewater and drinking water treatment plants. As in both facilities ozonation might be applied, it is important to find out if undesired oxidation products (OPs) are formed.
METHODS: For the separation and detection of the OPs, several analytical techniques, including nuclear magnetic resonance experiments, were applied. In order to distinguish between direct ozone reaction and a radical mechanism, experiments were carried out at different pH values with and without scavenging OH radicals. Kinetic experiments were used for confirmation that the OPs are formed during short ozone contact time applied in waterworks. Samples from a waterworks using bank filtrate as raw water were analyzed in order to prove that the identified OPs are formed in real and full-scale ozone applications.
RESULTS: In the case of CYC, oxidation mainly occurs at the carbon atom, where the sulfonamide moiety is bound to the cyclohexyl ring. Consequently, amidosulfonic acid and cyclohexanone are formed as main OPs of CYC. When ozone reacts at another carbon atom of the ring a keto moiety is introduced into the CYC molecule. Acetic acid and the product ACE OP170, an anionic compound with m/z=170 and an aldehyde hydrate moiety, were identified as the main OPs for ACE. The observed reaction products suggest an ozone reaction according to the Criegee mechanism due to the presence of a C=C double bond. ACE OP170 was also detected after the ozonation unit of a full-scale drinking water treatment plant which uses surface water-influenced bank filtrate as raw water.
CONCLUSIONS: Acesulfame can be expected to be found in anthropogenic-influenced raw water used for drinking water production. However, when ACE OP170 is formed during ozonation, it is not expected to cause any problem for drinking water suppliers, because the primary findings suggest its removal in subsequent treatment steps, such as activated carbon filters.

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Year:  2011        PMID: 21964549     DOI: 10.1007/s11356-011-0618-x

Source DB:  PubMed          Journal:  Environ Sci Pollut Res Int        ISSN: 0944-1344            Impact factor:   4.223


  22 in total

1.  Ozonation: a tool for removal of pharmaceuticals, contrast media and musk fragrances from wastewater?

Authors:  Thomas A Ternes; Jeannette Stüber; Nadine Herrmann; Derek McDowell; Achim Ried; Martin Kampmann; Bernhard Teiser
Journal:  Water Res       Date:  2003-04       Impact factor: 11.236

2.  Partial oxidation by ozone to remove recalcitrance from wastewaters--a review.

Authors:  A B Alvares; C Diaper; S A Parsons
Journal:  Environ Technol       Date:  2001-04       Impact factor: 3.247

3.  Antiviral drugs in wastewater and surface waters: a new pharmaceutical class of environmental relevance?

Authors:  Carsten Prasse; Michael P Schlüsener; Ralf Schulz; Thomas A Ternes
Journal:  Environ Sci Technol       Date:  2010-03-01       Impact factor: 9.028

4.  Removal of estrogenic activity and formation of oxidation products during ozonation of 17alpha-ethinylestradiol.

Authors:  Marc M Huber; Thomas A Ternes; Urs von Gunten
Journal:  Environ Sci Technol       Date:  2004-10-01       Impact factor: 9.028

5.  Occurrence of emerging pollutants in urban wastewater and their removal through biological treatment followed by ozonation.

Authors:  Roberto Rosal; Antonio Rodríguez; José Antonio Perdigón-Melón; Alice Petre; Eloy García-Calvo; María José Gómez; Ana Agüera; Amadeo R Fernández-Alba
Journal:  Water Res       Date:  2009-07-09       Impact factor: 11.236

6.  Elimination of organic micropollutants in a municipal wastewater treatment plant upgraded with a full-scale post-ozonation followed by sand filtration.

Authors:  Juliane Hollender; Saskia G Zimmermann; Stephan Koepke; Martin Krauss; Christa S McArdell; Christoph Ort; Heinz Singer; Urs von Gunten; Hansruedi Siegrist
Journal:  Environ Sci Technol       Date:  2009-10-15       Impact factor: 9.028

7.  Analysis and occurrence of seven artificial sweeteners in German waste water and surface water and in soil aquifer treatment (SAT).

Authors:  Marco Scheurer; Heinz-J Brauch; Frank T Lange
Journal:  Anal Bioanal Chem       Date:  2009-06-16       Impact factor: 4.142

8.  Oxidation of antibacterial compounds by ozone and hydroxyl radical: elimination of biological activity during aqueous ozonation processes.

Authors:  Michael C Dodd; Hans-Peter E Kohler; Urs von Gunten
Journal:  Environ Sci Technol       Date:  2009-04-01       Impact factor: 9.028

9.  Ozonation of propranolol: formation of oxidation products.

Authors:  Jessica Benner; Thomas A Ternes
Journal:  Environ Sci Technol       Date:  2009-07-01       Impact factor: 9.028

10.  Pharmaceuticals and endocrine disrupting compounds in U.S. drinking water.

Authors:  Mark J Benotti; Rebecca A Trenholm; Brett J Vanderford; Janie C Holady; Benjamin D Stanford; Shane A Snyder
Journal:  Environ Sci Technol       Date:  2009-02-01       Impact factor: 9.028

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  5 in total

1.  A survey on trace organic chemicals in a German water protection area and the proposal of relevant indicators for anthropogenic influences.

Authors:  Wolfram Seitz; Rudi Winzenbacher
Journal:  Environ Monit Assess       Date:  2017-05-01       Impact factor: 2.513

2.  Biodegradation of the artificial sweetener acesulfame in biological wastewater treatment and sandfilters.

Authors:  Sandro Castronovo; Arne Wick; Marco Scheurer; Karsten Nödler; Manoj Schulz; Thomas A Ternes
Journal:  Water Res       Date:  2016-11-17       Impact factor: 11.236

3.  Efficient Degradation of Acesulfame by Ozone/Peroxymonosulfate Advanced Oxidation Process.

Authors:  Yu Shao; Zhicheng Pang; Lili Wang; Xiaowei Liu
Journal:  Molecules       Date:  2019-08-08       Impact factor: 4.411

Review 4.  A Review of the Environmental Fate and Effects of Acesulfame-Potassium.

Authors:  Kerry Belton; Edward Schaefer; Patrick D Guiney
Journal:  Integr Environ Assess Manag       Date:  2020-04-10       Impact factor: 2.992

5.  Dual-high-frequency from single-piezoelectric crystal for ACE degradation by hybrid advanced oxidation UV-sonochemistry process.

Authors:  Fabiola Mendez-Arriaga; Chad D Vecitis
Journal:  Ultrason Sonochem       Date:  2021-08-19       Impact factor: 7.491

  5 in total

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