N-chloroaldimines. 3. Chlorination of phenylalanine in model solutions and in a wastewater

Conyers, Barbara; Scully, Frank E.

doi:10.1021/es00039a003

Cited by 70 publications

(74 citation statements)

References 12 publications

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“…Previously it was believed that N-chloraldimines were precursors of nitriles (9). Our results suggest, in agreement with Conyers and Scully (18), that the nitrile and the chloraldimine are formed by competitive pathways. Indeed, nitrile was always and only present in water with chloroaldimine but did not increase when chloroaldimine decreased.…”

Section: Resultssupporting

confidence: 91%

“…Samples of phenylalanine (10 -3 mol‚L -1 ) chlorinated at different levels were periodically injected (250 µL) during a week. The results obtained were on the whole in agreement with Conyers and Scully's proposed scheme of pathways (18). The chromatogram of a solution chlorinated to a Cl/N ratio of 1.5 is shown in Figure 2, as an example of the results obtained.…”

Section: Resultssupporting

confidence: 86%

“…Simplified scheme for chlorination of phenylalanine, adaptedfrom Conyers and Scully(18). Principal byproducts formed.…”

mentioning

confidence: 99%

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Odorous Products of the Chlorination of Phenylalanine in Water: Formation, Evolution, and Quantification

Freuze

Brosillon

Herman

et al. 2004

Environ. Sci. Technol.

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To explain some of the possible origins of an odor episode which took place in a drinking water supply in the region of Paris (France), the chlorination reaction in water of phenylalanine was studied. This amino acid was chosen for first experiments because of its physical and chemical particular properties. Changes in the different byproducts formed were followed by high-performance liquid chromatography (HPLC) over a period of time. N-chlorophenylalanine (mono-N-chlorinated amino acid) and then phenylacetaldehyde were the major products formed for the lower chlorine to nitrogen molar ratios. For Cl/N molar ratios of 1 and beyond, phenylacetonitrile and N-chlorophenylacetaldimine appeared and increased with the chlorination level. N-chlorophenylacetaldimine was quantified by using its difference of stability in various organic solvents. Our attention was first directed to the monochlorinated derivative but further examination indicated that it could not be responsible for odor troubles: it dissociated before reaching the consumer's tap and it was produced at consistently low yields under conditions relevant to drinking water treatment. On the contrary, chloroaldimine appeared to be a very odorous and water-stable product: it strongly smells of swimming pool with a floral background. The odor detection threshold is about 3 microg x L(-1) and it can persist for more than one week at 18 degrees C. It is now suspected of being a source of off-flavor concerns among consumers.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 86%

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Odorous Products of the Chlorination of Phenylalanine in Water: Formation, Evolution, and Quantification

Freuze

Brosillon

Herman

et al. 2004

Environ. Sci. Technol.

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“…A Waters Associates liquid chromatography system (HPLC) has been described previously (21,22,24). Separation of chlorination products was carried out on a Whatman 5 µm Partisil ODS-3 RAC column with a dual-solvent system described previously (20).…”

Section: Experimental Methodsmentioning

confidence: 99%

Chloramines VI: Chlorination of Glycylphenylalanine in Model Solutions and in a Wastewater

Keefe

Fox

Conyers

et al. 1997

Environ. Sci. Technol.

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Model solutions of the dipeptide glycylphenylalanine were chlorinated at pH 7.0 to five different chlorine-to-peptide (Cl 2 /peptide) mole ratios and analyzed after 30 min by highperformance liquid chromatography. At Cl 2 /peptide mole ratios e 1, N-chloroglycylphenylalanine (I) appears to be the only product. At mole ratios g 2, N,N-dichloroglycylphenylalanine (II) was the only product. II decomposes in model solutions (t 1/2 ) 6.4 h) at pH 7.0 to form a compound tentatively identified as N-[2-(N′-chloroimino)ethanoyl]phenylalanine (III), an N-chloroaldimine. III, in turn, decomposes (t 1/2 ) 36 h) to IV. From 13 C-and 1 H-NMR, GC/MS, and IR, IV was identified as N-cyanoacylphenylalanine. Glycylp-[ 3 H]-phenylalanine (VI) was synthesized in order to monitor the reaction at low concentrations of the compound in a wastewater. A secondary wastewater (TKN ) 1.29 mg of N/L; [NH 3 ]) 0.074 mg of N/L) was inoculated with VI and chlorinated to nine different chlorine concentrations. The stabilities of the tritiated analogs of II and III in the wastewater were comparable to those determined in model solutions. ES960794A X Abstract published in Advance ACS Abstracts, May 1, 1997.FIGURE 6. Breakpoint curve of a secondary wastewater and the corresponding glycyl-p-[ 3 H]-phenylalanine chlorination products determined 30 min after chlorinating to nine different concentrations of aqueous chlorine (1-9 mg of Cl2/L).

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“…Hrudey et al (1989) identified that aldehydes are associated with a swampy, swimming pool type of odor. Freuze et al (2004) and Conyers and Scully (1993) reported that synthesized chloroaldimine, a nitrogenous chlorination byproduct originating from phenylalanine, possessed a strong swimming pool odor with a floral background. The olfaction properties for synthesized chloroaldimine were determined to have odor threshold concentrations in the low mg/L range by a panel composed of 4 men and 3 women who smelled chlorinated amino acid solutions (Cl/N ratio 2.4).…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of phenylacetonitrile as a nitrogenous disinfection byproduct derived from chlorination of phenylalanine in drinking water

Deng

Feng

et al. 2016

Water Research

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N-chloroaldimines. 3. Chlorination of phenylalanine in model solutions and in a wastewater

Cited by 70 publications

References 12 publications

Odorous Products of the Chlorination of Phenylalanine in Water: Formation, Evolution, and Quantification

Odorous Products of the Chlorination of Phenylalanine in Water: Formation, Evolution, and Quantification

Chloramines VI: Chlorination of Glycylphenylalanine in Model Solutions and in a Wastewater

Identification and characterization of phenylacetonitrile as a nitrogenous disinfection byproduct derived from chlorination of phenylalanine in drinking water

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