☆ 4.7 Review

Advances of mass spectrometry in characterization of disinfection byproducts in drinking water

TRAC-TRENDS IN ANALYTICAL CHEMISTRY (2023)

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Formation Mechanism of Iodinated Aromatic Disinfection Byproducts: Acid Catalysis with H2OI+

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Summary: This study used computational modeling to investigate the iodination mechanism of aromatic contaminants. It was found that the formation of hydroxylated tyrosylglycine is favored over iodinated tyrosylglycine, but experimental results detected the presence of iodinated tyrosylglycine instead. Further research revealed the thermodynamic role of the reactive iodine species H2OI+ in the formation of aromatic iodinated disinfection byproducts.

ENVIRONMENTAL SCIENCE & TECHNOLOGY (2022)

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Formation and Cytotoxicity of Halophenylacetamides: A New Group of Nitrogenous Aromatic Halogenated Disinfection Byproducts in Drinking Water

Shaoyang Hu et al.

Summary: This study successfully identified a new group of nitrogenous aromatic halogenated disinfection byproducts, halophenylacetamides (HPAcAms), in laboratory experiments and realistic drinking water for the first time. The study investigated the formation mechanism, occurrence frequencies, and concentrations of HPAcAms in authentic drinking water, and developed a quantitative structure-activity relationship (QSAR) model based on cytotoxicity data. The results showed that HPAcAms could form from phenylalanine during chlorination and their yields were influenced by various factors. Multiple HPAcAms were detected in authentic drinking water samples and showed higher cytotoxicity compared to the most abundant aliphatic haloacetamide DBP.

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Identification of unknown disinfection byproducts in drinking water produced from Taihu Lake source water

Jiabao Li et al.

Summary: In this study, unknown disinfection byproducts (DBPs) in drinking water from Taihu Lake source water were identified using LC-QTOF MS. A total of 91 DBPs formulas were discovered, with 81 of them being previously unreported. The results suggest that brominated DBPs formed from industrial pollutants are relevant species in drinking water from Taihu source water, emphasizing the importance of protecting Taihu Lake source water to control DBP risks.

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FT-ICR/MS deciphers formation of unknown macromolecular disinfection byproducts from algal organic matters after plasma oxidation

Ruigang Wang et al.

Summary: This study investigated the diversity of AOM and the formation of macromolecular DBPs in water treatment. The results showed that plasma oxidation effectively removed AOM and reduced the generation of DBPs.

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2,6-Dichloro-1,4-benzoquinone formation from chlorination of substituted aromatic antioxidants and its control by pre-ozonation in drinking water treatment plant

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Summary: Halobenzoquinones, including 2,6-dichloro-1,4-benzoquinone (2,6-DCBQ), are common disinfection by-products in drinking water. This study investigated the formation of 2,6-DCBQ from chlorination of three aromatic antioxidants and found that only one of them produced 2,6-DCBQ. Experimental results showed that pre-ozonation, granular activated carbon, and quartz sand treatments could effectively reduce the formation of 2,6-DCBQ during water treatment.

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Occurrence and transformation of newly discovered 2-bromo-6-chlor-o-1,4-benzoquinone in chlorinated drinking water

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Summary: A new HBQ species, 2-bromo-6-chloro-1,4-benzoquinone (2,6-BCBQ), was detected and identified in drinking water, which has high cytotoxicity. The instability of 2,6-BCBQ during chlorination and its transformation kinetics and mechanisms were studied.

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Closing the gap of known and unknown halogenated nitrogenous disinfection byproducts in water: Advanced mass spectrometry techniques

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Summary: Halogenated nitrogenous disinfection byproducts (X-NDBPs) are unregulated but toxicologically relevant DBPs that can be formed through the substitution of halogens to carbon or nitrogen. Stable X-NDBPs are more toxic than regulated DBPs and play a significant role in the cytotoxicity of disinfected water. Development of simplified sampling techniques, identification of reactive nitrogenous organics in source water, and identification of missing X-NDBPs in disinfected water are necessary for future research.

TRAC-TRENDS IN ANALYTICAL CHEMISTRY (2022)

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Halohydroxybenzonitriles as a new group of halogenated aromatic DBPs in drinking water: Are they of comparable risk to halonitrophenols?

Shaoyang Hu et al.

Summary: A new group of halogenated aromatic disinfection byproducts (DBPs), called halohydroxybenzonitriles (HHBNs), were detected in drinking water samples. These HHBNs exhibited high cytotoxicity and showed transformation during chlorination. Compared to regulated DBPs, HHBNs had similar concentration-cytotoxicity contribution and slightly weaker stability, making them a concern in drinking water.

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Molecular transformation of dissolved organic matter and the formation of disinfection byproducts in full-scale surface water treatment processes

Hang He et al.

Summary: This study compared the transformation of DOM and the formation of Cl-DBPs in two different surface water treatment processes and analyzed their reaction pathways. The results showed that coagulation preferentially removed unsaturated and oxidized compounds, and prechlorination produced more Cl-DBPs with specific characteristics. Microorganisms in the filter produced high MW substances that contributed to the formation of Cl-DBPs. CHO molecules and CHON molecules were identified as the main Cl-DBPs precursors in both processes.

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Formation of Larger Molecular Weight Disinfection Byproducts from Acetaminophen in Chlorine Disinfection

Wanxin Li et al.

Summary: A new reaction pathway in the chlorination of acetaminophen, involving oxidative coupling reactions via acetaminophen radicals, was investigated in this study. Over 20 polymeric products, some similar to polychlorinated biphenyls, were detected in chlorinated acetaminophen samples using advanced analytical techniques. Quantum chemical calculations revealed the bonding processes and kinetics of both C-C and C-O bonding products. This study suggests that chlorination may cause both degradation and upgradation of phenolic compounds or contaminants.

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Tracing nitrogenous byproducts during ozonation in the presence of bromide and ammonia using stable isotope labeling and high resolution mass spectrometry

Yao Lu et al.

Summary: The study found that during ozonation in the presence of bromide and ammonia, the formation of nitrogenous byproducts may lead to increased toxicity. Using UPLC-HRMS and an isotope labeling strategy, four newly formed nitrogenous byproducts were detected. This highlights the importance of paying attention to nitrogenous byproducts during ozonation in the presence of bromide and ammonia.

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Characterization of lower Phong river dissolved organic matters and formations of unknown chlorine dioxide and chlorine disinfection by-products by Orbitrap mass spectrometry

Thirawit Prasert et al.

Summary: The characteristics of dissolved organic matter in the lower Phong River in Thailand were found to be influenced by domestic wastewater discharges, anthropogenic activities, and surface runoff, with differences in molecular composition observed between dry season and rainy season. Disinfection by chlorine or chlorine dioxide resulted in the formation of both chlorinated and non-chlorinated disinfection byproducts, with differences in the types and characteristics of DBPs produced by each disinfectant.

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Nontargeted identification and predicted toxicity of new byproducts generated from UV treatment of water containing micropollutant 2-mercaptobenzothiazole

Ping Jiang et al.

Summary: A non-targeted analysis strategy combined with computational toxicity assessment was developed in this study to identify organic transformation products of the micropollutant 2-mercaptobenzothiazole during UV treatment. A total of 22 organic transformation products were successfully identified, with nine new structures being determined for the first time. Computational assessments showed that the estrogenic activity of these new transformation products is higher than the toxic contaminant 2-hydroxybenzothiazole.

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Nontargeted Identification of an N-Heterocyclic Compound in Source Water and Wastewater as a Precursor of Multiple Nitrosamines

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Summary: This study identifies a natural product called MTCCA in source water, which can produce multiple nitrosamines through chloramination. The widespread presence of MTCCA in source water and wastewater, along with its resistance to degradation and removal, suggests that natural N-heterocyclic compounds may be a new source of nitrosamine precursors.

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Non-target screening of dissolved organic matter in raw water, coagulated water, and chlorinated water by Orbitrap mass spectrometry

Warangkana Na Phatthalung et al.

Summary: This study aimed to classify the possible molecular formulas of disinfection by-products (DBPs) in water samples from the U-Tapao Canal, Thailand, and found that CHO and CHON were the main molecular formulas in DOM, and PACl coagulation can reduce the abundance of some lignin, tannin, and condensed aromatic substances.

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Drinking water nitrosamines in a large metropolitan region in Brazil

Beatriz De Caroli Vizioli et al.

Summary: This study developed an analytical method for detecting and quantifying nitrosamines in drinking water, with NDMA being the most frequently detected nitrosamine in the Metropolitan Region of Campinas, São Paulo, Brazil. The levels of nitrosamines found in the drinking water samples are of considerable relevance due to the area's expanded industrial and agricultural activities.

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Aqueous chlorination of herbicide metribuzin: Identification and elucidation of new disinfection by-products, degradation pathway and toxicity evaluation

Andre Luis Correa de Barros et al.

Summary: This study evaluated the degradation, mineralization, and DBPs formation of the widely used herbicide metribuzin during aqueous chlorination. The results showed that DBPs formed during chlorination were more toxic than the precursor metribuzin, with increased toxicity effects on Anemia salina nauplii. Additionally, chlorinated solutions exhibited high estrogenicity to human receptors and mutagenic and developmental toxicant effects in BLYES and Q(SAR) tests.

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Characterization of Dissolved Organic Matter from Wildfire-induced Microcystis aeruginosa Blooms controlled by Copper Sulfate as Disinfection Byproduct Precursors Using APPI(-) and ESI(-) FT-ICR MS

Huan Chen et al.

Summary: Copper-based algaecides are used to control algae blooms after wildfires, leading to higher reactivity of dissolved organic matter in forming disinfectant byproducts. The disappeared DOM during disinfection had higher average molecular weight and double-bond equivalent, indicating larger MW and more double bonds/rings as preferable DBP precursors. The treatments with Cu2+ addition showed higher reactivity in forming N-nitrosodimethylamine, while the control group without Cu2+ had lower DOM chlorine reactivity in forming carbonaceous and oxygenated DBPs.

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Accelerated oxidation of the emerging brominated flame retardant tetrabromobisphenol S by unactivated peroxymonosulfate: The role of bromine catalysis and formation of disinfection byproducts

Haiyan Xu et al.

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Formation of nitrogenous disinfection byproducts in MP UV-based water treatments of natural organic matters: The role of nitrate

Xiao Liu et al.

Summary: The presence of nitrate was found to impact the degradation of NOMs during UV water treatment processes. Nitrate accelerated NOM degradation in MP UV treatment but inhibited it in MP UV/H2O2 treatment. Furthermore, the presence of nitrate led to the formation of nitrate-derived N-DBPs, which induced genotoxicity during the treatments.

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A New Group of Heterocyclic Nitrogenous Disinfection Byproducts (DBPs) in Drinking Water: Role of Extraction pH in Unknown DBP Exploration

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Molecular characterization of transformation and halogenation of natural organic matter during the UV/chlorine AOP using FT-ICR mass spectrometry

Xiaoxue Ruan et al.

Summary: UV/chlorine process is effective in removing micro-pollutants but may lead to NOM transformation and DBPs formation, with ClO, Cl, and HO promoting NOM transformation and causing increased formation of Cl-DBPs. UV/chlorine AOP generated more CHON-containing compounds and higher CHOCl compounds compared to dark chlorination, with different chlorine substitution (SR) and addition reactions (AR) occurring based on precursor properties.

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Novel four-dimensional approach for the structural characterization of neutral nitrogen compounds in vacuum gas oils using UHPLC-IM-QqToF analysis

Julie Guillemant et al.

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ANALYTICA CHIMICA ACTA (2021)

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Identification of chloramination disinfection by-products from phenylalanine in tap drinking water

Peilu Zhai et al.

Summary: Phenylalanine (Phe) is a precursor of disinfection by products (DBPs) in natural water, and new chloramination DBPs were identified using UHPLC and MS/MS, with three DBPs found to be exceptionally stable in chlorinated tap water and able to form under wide conditions.

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Nontargeted identification of chlorinated disinfection byproducts formed from natural organic matter using Orbitrap mass spectrometry and a halogen extraction code

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Species and formation characteristics of halogenated DBPs in chloramination of tannic acid after biodegradation

Qiuhong Liang et al.

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Xueke Liu et al.

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Yuanxiang Mao et al.

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High-Resolution Mass Spectrometry Identification of Novel Surfactant-Derived Sulfur-Containing Disinfection Byproducts from Gas Extraction Wastewater

Hannah K. Liberatore et al.

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Identification of N-Nitrosamines and Nitrogenous Heterocyclic Byproducts during Chloramination of Aromatic Secondary Amine Precursors

Xueke Liu et al.

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Characterization of organic matter by HRMS in surface waters: Effects of chlorination on molecular fingerprints and correlation with DBP formation potential

Josep Sanchis et al.

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Detection, transformation, and toxicity of indole-derivative nonsteroidal anti-inflammatory drugs during chlorine disinfection

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Influence of the UV/H2O2 Advanced Oxidation Process on Dissolved Organic Matter and the Connection between Elemental Composition and Disinfection Byproduct Formation

Yingying Xiang et al.

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To regulate or not to regulate? What to do with more toxic disinfection by-products?

Susan D. Richardson et al.

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Guang Huang et al.

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Identification of a mutagenic chlorination by-product produced from (E)-1, 3-dichloropropene (a component of nematocide DD) by using high resolution LC/MS and multivariate analysis

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Fast selective detection of polar brominated disinfection byproducts in drinking water using precursor ion scans

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