title: Studies on the coupling product between oxidation products derived from pentachlorophenol and cyclodextrins.
abstract: The coupling products (CPs), which were formed via the peroxosulfate catalyzed oxidation of pentachlorophenol (PCP) with iron(III)-tetrakis(sulfonatophenyl)porphyrin (Fe(III)-TPPS) in the presence of hydroxypropyl-beta -cyclodextrin (HP-beta -CD) or HP-gamma -CD, were separated by ultrafiltration from the reaction mixture. When the percentages of chlorine species in the reaction mixture were calculated from the concentrations of organic chlorine in the reaction mixture and CPs, 10-25% of chlorine species in the reaction mixture was organic chlorine that was incorporated into CDs. Analyses of the CPs by pyrolysis-GC/MS (Py-GC/MS) and 13C NMR showed that the PCP-derived products were covalently incorporated into the CDs. To evaluate the acute toxicity of the CPs, a Microtox test was examined. Toxicities of the CPs were reduced slightly, compared to the controls (PCP alone and PCP + reaction blanks). In the reaction blanks, mesaconic acid (MA) moieties were detected as a result of the oxidation of CDs in the absence of PCP. Thus, factors in the toxicities, detected in the CPs, can be attributed to the oxidation products derived from CDs, such as MA, as well as the PCP-derived products incorporated into the CDs.
authors.affiliation: National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan. m-fukushima@aist.go.jp
authors.forename: Masami
authors.initials: M
authors.lastname: Fukushima
authors.forename: Kenji
authors.initials: K
authors.lastname: Tatsumi
mesh_terms: D002384:Catalysis; D017606:Chlorine Compounds / Q000032:analysis / Q000737:chemistry* / Q000633:toxicity; D003505:Cyclodextrins / Q000737:chemistry*; D004785:Environmental Pollutants / Q000032:analysis* / Q000633:toxicity; D005290:Ferric Compounds / Q000737:chemistry*; D005374:Filtration; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010416:Pentachlorophenol / Q000737:chemistry*; D018675:Toxicity Tests
chemical_list: D017606:Chlorine Compounds; D003505:Cyclodextrins; D004785:Environmental Pollutants; D005290:Ferric Compounds; D010416:Pentachlorophenol