Analysis and occurrence of odorous disinfection by-products from chlorination of amino acids in three different drinking water treatment plants and corresponding distribution networks

Brosillon, Stéphan; Lemasle, M.; Renault, Emilie; Tozza, Dominique; Heim, Véronique; Laplanche, A.

doi:10.1016/j.chemosphere.2009.09.031

Cited by 58 publications

(31 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Dependence of the rate constant in the decomposition process of N ‐chloramines with pH at 25 °C. (▲) N ‐chloro‐2‐amino‐1‐butanol, (○) N ‐chloro‐2‐amino‐2‐methyl‐1‐propanol, (●) N ‐chloro‐sec‐butylamine, (□) N ‐chlorobenzylamine, (∇) N ‐chlorobenzylamine (15 °C), (▼) N ‐chlorobenzylamine (this work), (∆) N ‐chlorobenzylamine (this work)…”

Section: Discussionmentioning

confidence: 91%

“…Also, they allow us to establish structure–reactivity relationships, comparing the results obtained in this work with bibliographic results. On the other hand, we have at our disposal information regarding the kinetic studies of these amines with other chlorinating agents (HOCl, N ‐chloro‐ N ‐methyl‐ p ‐toluenesulfonamide), so it is also interesting to compare the effectiveness of the different N ‐chlorinating agents because of the great importance of these N ‐chlorination reactions in environmental and biochemical processes …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Kinetic study of the formation of N‐chloro compounds using N‐chlorosuccinimide

Pastoriza

Antelo

Crugeiras

et al. 2014

J of Physical Organic Chem

View full text Add to dashboard Cite

b Second-order rate constants were determined for the chlorination reaction of 2,2,2-trifluoethylamine and benzylamine with N-chlorosuccinimide at 25°C and an ionic strength of 0.5 M. These reactions were found to be of first order in both reagents. According to the experimental results, a mechanism reaction was proposed in which a chlorine atom is transferred between both nitrogenous compounds. Kinetics studies demonstrate that the hydrolysis process of the chlorinating agent does not interfere in the chlorination process, under the experimental conditions used in the present work. Free-energy relationships were established using the results obtained in the present work and others available in the literature for chlorination reactions with N-chlorosuccinimide, being the pK a range included between 5.7 and 11.22.

show abstract

Section: Discussionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Kinetic study of the formation of N‐chloro compounds using N‐chlorosuccinimide

Pastoriza

Antelo

Crugeiras

et al. 2014

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

“…Reactions of chlorinating agents (e.g., HOCl, Cl 2 , or ClO 2 ) with amines can result in different chloramine products,1, 2 some of them with carcinogenic and/or mutagenic properties 3, 4. These N ‐chlorination reactions are of importance in environmental chemistry and biochemistry, playing a key role in the formation of disinfection byproducts in recreational waters,5, 6 in wastewater treatment plants,7, 8 in chemical fate of pharmaceuticals,9, 10 or in oxidation processes in biological systems,11, 12 to name a few areas of research.…”

Section: Introductionmentioning

confidence: 99%

Disparities in survival among women with invasive cervical cancer

Brookfield

Cheung

Lucci

et al. 2008

Cancer

View full text Add to dashboard Cite

N‐Chlorination reactions of alkyl‐, cycloalkyl‐, heterocyclic, and aromatic amines by HOCl have been investigated in the gas and aqueous phase. Density functional (B3LYP), double hybrid (B2PLYPD), and composite theoretical model (G3B3) have been used to assess steric, electronic, and solvent effects on the reactivity of different families of amines toward HOCl. When solvent effects are included by using CPCM/UAHF model, all computational methods predict the same order of reactivity within each group of amines. In agreement with experimental data, heterocyclic amines have the highest reactivity, with energy barriers calculated between 160 and 225 kJ mol−1 (B2PLYPD/AUG‐cc‐pVTZ//B3LYP/6‐31G(d) level). The substituted anilines are the least reactive species, with energy barriers calculated as high as 300 kJ mol−1. Two different reaction mechanisms of N‐chlorination have been considered in the gas phase: the one which includes the transition state TSa with cyclic arrangement of four atoms (N, Cl, O, and H) involved in an intramolecular rearrangement, and the second in which the hydrogen‐bridged structure TSb is characterized with the linear NClO moiety. The former is energetically more feasible (ca. 120 kJ mol−1) for alkyl‐, cycloalkyl‐, and heterocyclic amines, whereas the latter is operative in the case of aromatic amines. If two water molecules are explicitly included in the calculations, the rate‐determining transition state TSw has been located for N‐chlorination of all amines under study. It is characterized by eight‐membered ring geometry in which water molecules assist the simultaneous transfer of the three hydrogen atoms coupled with the NCl bond formation. To reproduce the experimentally observed trends in reactivity of amines, the inclusion of bulk and specific solvent effects is mandatory. Steric effects have been found to govern the reactivity of alkylamines, that is, more bulkier amines react slower with HOCl. It has been found that electronic structure parameters (HOMO–LUMO gap, natural bond orbital occupancy, and NPA charge on N atom) can be successfully used as descriptors for the reactivity of heterocyclic and aromatic amines. These results indicate the predictive power of our computational approach, which can be applied to calculate nucleophilic reactivities of more complex structures of environmentally or biologically relevant amines. © 2012 Wiley Periodicals, Inc.

show abstract

“…Since GC analysis of (chloro-)aldimines is difficult due to their thermal instability and low half-life times in water (Brosillon et al 2009), there is hardly any data on this group of DBPs with suspected low odor thresholds. LC-MS techniques may be an alternative; however, chromatographic separation by HPLC is yet incomplete and requires long retention times (Grübel et al 2011).…”

Section: Disinfection By-productsmentioning

confidence: 99%

New developments in the trace analysis of organic water pollutants

Fischer

Fries

Körner

et al. 2012

Appl Microbiol Biotechnol

View full text Add to dashboard Cite

Challenging tasks, increasing demands, and new generations of powerful analytical instruments initiated considerable progress in aquatic environmental analysis and led to a considerable improvement of analytical performance during the last few years. The ever growing number of emerging pollutants is tackled by specific and highly sensitive analytical methods with detection limits of a few nanogram per liter and even lower. Wide-scope monitoring techniques and multiclass and multiresidue analysis allow for the simultaneous determination of hundreds of compounds. The high mass resolution capability and mass accuracy of advanced mass spectrometric instruments, i.e., time-of-flight (TOF) MS or Fourier transform (FT)-Orbitrap MS, enable combined target and non-target analysis, including the identification of metabolites and abiotic degradation products. This minireview highlights some of the most recent developments in the trace analysis of important organic water pollutants and focuses on some specific groups of emerging contaminants, i.e., pharmaceuticals, flame retardants, disinfection by-products, surfactants, per- and polyfluorinated compounds, benzotriazoles, and benzothiazoles, as well as on the identification of transformation products and on non-target analysis. References were selected according to their exemplary and innovative character and to their practical relevance.

show abstract

Analysis and occurrence of odorous disinfection by-products from chlorination of amino acids in three different drinking water treatment plants and corresponding distribution networks

Cited by 58 publications

References 24 publications

Kinetic study of the formation of N‐chloro compounds using N‐chlorosuccinimide

Kinetic study of the formation of N‐chloro compounds using N‐chlorosuccinimide

Disparities in survival among women with invasive cervical cancer

New developments in the trace analysis of organic water pollutants

Contact Info

Product

Resources

About