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Aqueous Chlorination of D-Limonene [Elektronski vir]Lebedev, Albert T. ...Limonene (1-methyl-4-(1-methylethenyl)-cyclohexene) is one of the most widespread monocyclic terpenes, being both a natural and industrial compound. It is widely present in the environment, including ... in water supplies. Therefore, it may be subjected to aqueous chlorination at water treatment stations during drinking water preparation. Besides, being a component of numerous body care and cosmetic products, it may present at high levels in swimming pool waters and could also be subjected to aqueous chlorination. Laboratory experiments with aqueous chlorination of D-limonene demonstrated the prevalence of the conjugated electrophilic addition of HOCl molecule to the double bonds of the parent molecule as the primary reaction. The reaction obeys the Markovnikov rule, as the levels of the corresponding products were higher than those of the alternative ones. Fragmentation pattern in conditions of electron ionization enabled the assigning of the structures for four primary products. The major products of the chlorination are formed by the addition of two HOCl molecules to limonene. The reactions of electrophilic addition are usually accompanied by the reactions of elimination. Thus, the loss of water molecules from the products of various generations results in the reproduction of the double bond, which immediately reacts further. Thus, a cascade of addition-elimination reactions brings the most various isomeric polychlorinated species. At a ratio of limonene/active chlorine higher than 1:10, the final products of aqueous chlorination (haloforms) start forming, while brominated haloforms represent a notable portion of these products due to the presence of bromine impurities in the used NaOCl. It is worth mentioning that the bulk products of aqueous chlorination are less toxic in the bioluminescence test on V. fischeri than the parent limonene.Source: Molecules [Elektronski vir]. - ISSN 1420-3049 (Vol. 27, issue 9, [article no.] 2988, 2022, str. 1-14)Type of material - e-article ; adult, seriousPublish date - 2022Language - englishCOBISS.SI-ID - 107060739
Author
Lebedev, Albert T. |
Detenchuk, Elena Andreevna |
Latkin, Tomas B. |
Bavcon Kralj, Mojca |
Trebše, Polonca
Topics
limonene |
aqueous chlorination |
GC-HRMS |
haloforms |
electrophilic addition |
disinfection by-products |
limonen |
vodno kloriranje |
GC-HRMS |
haloforme |
elektrofilni dodatek |
stranski proizvodi dezinfekcije
Author | Lebedev, Albert T. ... |
Title | Aqueous Chlorination of D-Limonene [Elektronski vir] |
Publication date | 2022-05-06 |
COBISS.SI-ID | 107060739 |
Publication version in repository | Publisher's version |
Publication licence | Creative Commons Attribution 4.0 International |
Embargo | Immediate publication for public |
Project(s) from which the publication was funded
Title | Acronym | Project ID | Funder |
---|---|---|---|
Mehanizmi varovanja zdravja | P3-0388-2022 |
Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije |
|
Russian Foundation for Basic Research | RFBR | 19-33-90042 |
Files that belong to the publication
Link |
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https://www.mdpi.com/1420-3049/27/9/2988 |
https://d.cobiss.net/repository/si/files/107060739/99401/Limonene.pdf |
https://repozitorij.uni-lj.si/IzpisGradiva.php?id=136502 |
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Database name | Field | Year |
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Lebedev, Albert T. | |
Detenchuk, Elena Andreevna | |
Latkin, Tomas B. | |
Bavcon Kralj, Mojca | 22304 |
Trebše, Polonca | 11539 |
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