Disinfection by-products from halogenation of aqueous solutions of terpenoids
We report the formation of trihalomethanes and other disinfection by-products from four polyfunctional terpenoids during simulated chlorination of natural waters. Complex suites of products were identified by closed loop stripping analysis (CLSA)/gas chromatography-mass spectrometry (GC-MS) from hal...
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| Format: | Journal Article |
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Elsevier Science Ltd
2010
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| Online Access: | http://hdl.handle.net/20.500.11937/34129 |
| _version_ | 1848754138436861952 |
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| author | Joll, Cynthia Alessandrino, Michael Heitz, Anna |
| author_facet | Joll, Cynthia Alessandrino, Michael Heitz, Anna |
| author_sort | Joll, Cynthia |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | We report the formation of trihalomethanes and other disinfection by-products from four polyfunctional terpenoids during simulated chlorination of natural waters. Complex suites of products were identified by closed loop stripping analysis (CLSA)/gas chromatography-mass spectrometry (GC-MS) from halogenation of b-carotene and retinol. b-Ionone appeared to be a key intermediate in the halogenation of b-carotene and retinol, reacting further under the reaction conditions to produce trans-b-ionone-5,6-epoxide and b-cyclocitral. Halogenation of the four terpenoids also produced trihalomethanes (THMs), most likely through haloform reaction on methyl ketone groups within many of the intermediates. Since halogenation of retinol produced a significant quantity of THMs at a slow reaction rate, retinol-based structures may possibly contribute to the slow reacting phase of THM formation in natural waters. Two polyhydroxyphenol model compounds were halogenated for comparison. The only products identified by CLSA/GC-MS from halogenation of 40,5,7- trihydroxyflavanone and ellagic acid were THMs. 40,5,7-Trihydroxyflavanone rapidly produced THMs, with an extremely high molar yield (94%) at pH 7. Terpenoids of the b-ionone and retinol type should be considered to be significant THM precursors, while 40,5,7-trihydroxyflavanone has been shown to be an extremely significant THM precursor, potentially present within natural organic matter in water treatment processes and distribution systems |
| first_indexed | 2025-11-14T08:35:39Z |
| format | Journal Article |
| id | curtin-20.500.11937-34129 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:35:39Z |
| publishDate | 2010 |
| publisher | Elsevier Science Ltd |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-341292017-09-13T15:53:17Z Disinfection by-products from halogenation of aqueous solutions of terpenoids Joll, Cynthia Alessandrino, Michael Heitz, Anna Disinfection by-products Polyhydroxyphenols Trihalomethanes Chlorine Terpenoids Drinking water We report the formation of trihalomethanes and other disinfection by-products from four polyfunctional terpenoids during simulated chlorination of natural waters. Complex suites of products were identified by closed loop stripping analysis (CLSA)/gas chromatography-mass spectrometry (GC-MS) from halogenation of b-carotene and retinol. b-Ionone appeared to be a key intermediate in the halogenation of b-carotene and retinol, reacting further under the reaction conditions to produce trans-b-ionone-5,6-epoxide and b-cyclocitral. Halogenation of the four terpenoids also produced trihalomethanes (THMs), most likely through haloform reaction on methyl ketone groups within many of the intermediates. Since halogenation of retinol produced a significant quantity of THMs at a slow reaction rate, retinol-based structures may possibly contribute to the slow reacting phase of THM formation in natural waters. Two polyhydroxyphenol model compounds were halogenated for comparison. The only products identified by CLSA/GC-MS from halogenation of 40,5,7- trihydroxyflavanone and ellagic acid were THMs. 40,5,7-Trihydroxyflavanone rapidly produced THMs, with an extremely high molar yield (94%) at pH 7. Terpenoids of the b-ionone and retinol type should be considered to be significant THM precursors, while 40,5,7-trihydroxyflavanone has been shown to be an extremely significant THM precursor, potentially present within natural organic matter in water treatment processes and distribution systems 2010 Journal Article http://hdl.handle.net/20.500.11937/34129 10.1016/j.watres.2009.09.003 Elsevier Science Ltd fulltext |
| spellingShingle | Disinfection by-products Polyhydroxyphenols Trihalomethanes Chlorine Terpenoids Drinking water Joll, Cynthia Alessandrino, Michael Heitz, Anna Disinfection by-products from halogenation of aqueous solutions of terpenoids |
| title | Disinfection by-products from halogenation of aqueous solutions of terpenoids |
| title_full | Disinfection by-products from halogenation of aqueous solutions of terpenoids |
| title_fullStr | Disinfection by-products from halogenation of aqueous solutions of terpenoids |
| title_full_unstemmed | Disinfection by-products from halogenation of aqueous solutions of terpenoids |
| title_short | Disinfection by-products from halogenation of aqueous solutions of terpenoids |
| title_sort | disinfection by-products from halogenation of aqueous solutions of terpenoids |
| topic | Disinfection by-products Polyhydroxyphenols Trihalomethanes Chlorine Terpenoids Drinking water |
| url | http://hdl.handle.net/20.500.11937/34129 |