20.500.12556/RUL-136502 Aqueous Chlorination of D-Limonene 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. limonene aqueous chlorination GC-HRMS haloforms electrophilic addition disinfection by-products limonen vodno kloriranje GC-HRMS haloforme elektrofilni dodatek stranski proizvodi dezinfekcije true false true Angleški jezik Ni določen Članek v reviji 2022-05-09 13:40:06 2022-05-09 13:40:12 2022-09-15 04:13:57 0000-00-00 00:00:00 2022 0 0 14 str. iss. 9, art. 2988 Vol. 27 2022 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 2022-05-06 543.422.3 1420-3049 10.3390/molecules27092988 107060739 Limonene.pdf Limonene.pdf 1 DF4DA5FB84ECFA0E39525C3406F42561 18238f9d08208b1c2bc193540f4ef332878cd68cb78044300f284c6c600081f0 ba066fe9-cf8d-11ec-8aca-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=156189 https://www.mdpi.com/1420-3049/27/9/2988 1 af6dc45e-cf8c-11ec-8aca-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=156188 Zdravstvena fakulteta 0 0 0