Aqueous Chlorination of D-Limonene

Lebedev, Albert T. (avtor), Detenchuk, Elena Andreevna (avtor), Latkin, Tomas B. (avtor), Bavcon Kralj, Mojca (avtor), Trebše, Polonca (avtor)

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.

• Jezik: Angleški jezik
• Ključne besede: limonene, aqueous chlorination, GC-HRMS, haloforms, electrophilic addition, disinfection by-products
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: ZF - Zdravstvena fakulteta
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Datum objave: 06.05.2022
• Leto izida: 2022
• Št. strani: 14 str.
• Številčenje: Vol. 27, iss. 9, art. 2988
• PID: 20.500.12556/RUL-136502
• UDK: 543.422.3
• ISSN pri članku: 1420-3049
• DOI: 10.3390/molecules27092988
• COBISS.SI-ID: 107060739
• Datum objave v RUL: 09.05.2022

Gradivo je del revije

• Naslov: Molecules
• Skrajšan naslov: Molecules
• Založnik: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.
• Začetek licenciranja: 06.05.2022

Sekundarni jezik

• Jezik: Ni določen
• Ključne besede: limonen, vodno kloriranje, GC-HRMS, haloforme, elektrofilni dodatek, stranski proizvodi dezinfekcije

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P3-0388
• Naslov: Mehanizmi varovanja zdravja

• Financer: Drugi - Drug financer ali več financerjev
• Program financ.: RFBR
• Številka projekta: 19-33-90042