title: Occurrence and production of chloramines in the chlorination of creatinine in aqueous solution.
abstract: Occurrence and production of stable chloramines in the chlorination of creatinine, a constituent of perspiration and urine, in aqueous media were studied. Creatinine (5 x 10(-5)M) was treated with free chlorine in aqueous solutions at molar ratios of 0.5-8 (chlorine/creatinine) at pH 7.0 at room temperature for several days. At lower ratios of chlorine, two stable N-chlorocreatinine derivatives, which were determined as dichloramine fractions by the DPD method, were isolated by HPLC and identified by EI-MS and (1)H-NMR. One was 2-chloroamino-1-methylimidazolin-4-one (creatinine chloramine) and the other was 2-chloroamino-5-hydroxy-1-methylimidazolin-4-one (hydroxycreatinine chloramine). In addition, the formation of methylamine was identified by GC-MS analyses of its imine derivative formed with pentafluorobenzaldehyde. Methylamine forms stable chloramines, which might be determined as mono- and/or di-chloramine fractions together with free chlorine by the DPD method in the reaction mixtures at higher molar ratios of chlorine. In practice, small amounts of methylamine (ca. 19 microg/L) were detected in water samples collected from several swimming pools. Hence, methylamine may be an origin of elusive organic chloramine formed in the chlorination of swimming pools. A probable mechanism of the occurrence and processing of chlorination products of creatinine is suggested.
authors.affiliation: College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi 274-8555, Japan. tachikaw@pha.nihon-u.ac.jp
authors.forename: Mariko
authors.initials: M
authors.lastname: Tachikawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Aburada
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Tezuka
authors.forename: Ryoji
authors.initials: R
authors.lastname: Sawamura
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D002700:Chloramines / Q000032:analysis / Q000138:chemical synthesis*; D002713:Chlorine / Q000737:chemistry* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003404:Creatinine / Q000737:chemistry*; D004202:Disinfectants / Q000737:chemistry* / Q000494:pharmacology; D013058:Mass Spectrometry; D008744:Methylamines / Q000032:analysis / Q000737:chemistry; D012996:Solutions; D014867:Water / Q000737:chemistry*; D018508:Water Purification / Q000379:methods; D005464:Fluorobenzenes; D005466:Fluorocarbons
chemical_list: D001547:Benzaldehydes; D002700:Chloramines; D002713:Chlorine; D003404:Creatinine; D004202:Disinfectants; D008744:Methylamines; D012996:Solutions; D014867:Water; C027451:methylamine; C413389:pentafluorobenzaldehyde; D005464:Fluorobenzenes; D005466:Fluorocarbons