Hydrolysis of haloacetonitriles: LINEAR FREE ENERGY RELATIONSHIP, kinetics and products

Glezer, Victor; Harris, Batsheva; Tal, Nelly; Iosefzon, Berta; Lev, Ovadia

doi:10.1016/s0043-1354(98)00361-3

Cited by 178 publications

(96 citation statements)

References 23 publications

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“…Recent studies have shown that HANs, except for Iodo-THMs and HNMs, are chemically unstable, and their stability decreases with increasing pH [25]. Ascorbic acid does not significantly affect the stability of HANs [26], while sodium sulfite and sodium thiosulfate have been found to degrade HANs [27].…”

Section: Investigation Of the Stability Of Target Compoundsmentioning

confidence: 94%

Simultaneous and high-throughput analysis of iodo-trihalomethanes, haloacetonitriles, and halonitromethanes in drinking water using solid-phase microextraction/gas chromatography-mass spectrometry: an optimization of sample preparation

Luo

Chen

et al. 2014

Journal of Chromatography A

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Section: Investigation Of the Stability Of Target Compoundsmentioning

confidence: 94%

Simultaneous and high-throughput analysis of iodo-trihalomethanes, haloacetonitriles, and halonitromethanes in drinking water using solid-phase microextraction/gas chromatography-mass spectrometry: an optimization of sample preparation

Luo

Chen

et al. 2014

Journal of Chromatography A

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“…DCAN can hydrolyze to form DCAcAm (e.g., from 1 to 6 h), and DCAcAm can 212 further hydrolyze to produce DCAA (e.g., after 6 h) (Table S3, Eq. S2) (Glezer et al, 1999; The yields of C-and N-DBPs upon 24-h chlorination of Tyr at different pH levels are 233 summarized in Figures 2A and B, respectively. As shown, CF and DCAA yields kept 234 growing with increasing pH from 5 to 9.…”

Section: Analytical Methods 171mentioning

confidence: 99%

Formation of halogenated C-, N-DBPs from chlor(am)ination and UV irradiation of tyrosine in drinking water

Chu

Gao

Krasner³

et al. 2012

Environmental Pollution

151

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39The formation of regulated and emerging halogenated carbonaceous (C-) and 40 nitrogenous disinfection by-products (N-DBPs) from the chlor(am)ination, UV irradiation of 41 tyrosine (Tyr) was investigated. Increased chlorine contact time and/or Cl 2 /Tyr ratio 42 increased the formation of most C-DBPs. In contrast, 4-chlorophenol, dichloroacetonitrile, 43 and dichloroacetamide had their greatest yields at particular conditions. Chloroform and 44 dichloroacetic acid increased with increasing pH, dichloroacetonitrile first increased and 45 then decreased, and other DBPs had maximum yields at pH 7 or 8. The addition of 46 ammonia significantly reduced most C-DBPs formation but increased 4-chlorophenol, 47 dichloroacetonitrile, dichloroacetamide, and trichloroacetonitrile yields for short 48 pre-chlorination contact times before dosing ammonia. When UV irradiation and 49 chlorination were performed simultaneously, the relatively stable C-DBPs increased, and 50 dichloroacetonitrile, dichloroacetamide, and 4-chlorophenol decreased with increasing UV 51 dose. This information was used to develop a mechanistic model for the formation of 52 intermediate DBPs and endproducts from the interaction of disinfectants with tyrosine. 53 54 Capsule abstract 55Exploring the integrated formation mechanism of regulated and emerging highly toxic 56 DBPs, which is expected to preferably reduce their occurrence in drinking water. 57

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“…The concentration of NOM is the most significant parameter affecting DBP formation (Liang and Singer, 2003;Ates et al, 2007). The temperature and pH also affect the reaction rates of chlorine depletion in water, and aqueous stability of DBPs (Villanova et al, 1997;Glezer et al, 1998;Kim et al, 2002). In addition, increase in the bromide ion concentration shifts the type of DBPs from chlorinated compounds to brominated ones (Heller and Grossman, 1999;Kampioti and Stephanou, 2002).…”

Section: Introductionmentioning

confidence: 99%

Seasonal variation in drinking water concentrations of disinfection by-products in IZMIR and associated human health risks

Baytak

Sofuoğlu

İnal

et al. 2008

Science of The Total Environment

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Seasonal variation in concentrations of two different disinfection by-product groups, trihalomethanes (THMs) and haloacetonitriles (HANs), was investigated in tap water samples collected from five sampling points (one groundwater and four surface water sources) in İzmir, Turkey. Estimates of previously published carcinogenic and noncarcinogenic risks through oral exposure to THMs were re-evaluated using a probabilistic approach that took the seasonal concentration variation into account. Chloroform, bromoform, dibromochloromethane and dichloroacetonitrile were the most frequently detected compounds. Among these, chloroform was detected with the highest concentrations ranging from 0.03 to 98.4 µg/L. In tap water, at the groundwater supplied sampling point, brominated species, bromoform and dibromoacetonitrile, were detected at the highest levels most probably due to bromide ion intrusion from seawater. The highest total THM and total HAN concentrations were detected in spring while the lowest in summer and fall. The annual average total THM concentration measured at one of the surface water supplied sampling points exceeded the USEPA's limit of 80 µg/L. While all non-carcinogenic risks due to exposure to THMs in İzmir drinking water were negligible, carcinogenic risk levels associated with bromodichloromethane and dibromochloromethane were higher than one in million. IntroductionChlorination of drinking water leads to formation of disinfection by-products (DBPs) which may create adverse health effects on human beings. The DBPs are formed as a result of reactions between the precursor materials (natural organic matter and bromide ion) and aqueous forms of the disinfectants. The major groups of DBPs are trihalomethanes (THMs), haloacetic acids (HAAs), haloacetonitriles (HANs), and halogenated ketones (HKs). THMs include four species; chloroform (CF), bromodichloromethane (BDCM), dibromochloromethane (DBCM) and bromoform (BF). Epidemiological studies have suggested that exposure to DBPs increases the risk of bladder, colon-rectum, leukemia, stomach and rectal cancers as well as abortion, low birth weight, and birth defects (IARC, 1991;Calderon, 2000;Villanueva et al., 2004). The formation of DBPs is affected by several factors including water temperature and pH, nature and concentration of the

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Hydrolysis of haloacetonitriles: LINEAR FREE ENERGY RELATIONSHIP, kinetics and products

Cited by 178 publications

References 23 publications

Simultaneous and high-throughput analysis of iodo-trihalomethanes, haloacetonitriles, and halonitromethanes in drinking water using solid-phase microextraction/gas chromatography-mass spectrometry: an optimization of sample preparation

Simultaneous and high-throughput analysis of iodo-trihalomethanes, haloacetonitriles, and halonitromethanes in drinking water using solid-phase microextraction/gas chromatography-mass spectrometry: an optimization of sample preparation

Formation of halogenated C-, N-DBPs from chlor(am)ination and UV irradiation of tyrosine in drinking water

Seasonal variation in drinking water concentrations of disinfection by-products in IZMIR and associated human health risks

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