title: Effects of chain length, chlorination degree, and structure on the octanol-water partition coefficients of polychlorinated n-alkanes.
abstract: Log octanol-water partition coefficients (log Kow) of 40 synthesized polychlorinated n-alkanes (PCAs) with different chlorination degrees were determined using reversed-phase high performance liquid chromatography (RP-HPLC). In addition, log Kow values of a technical mixture namely Cereclor 63L as well as 15 individual in house synthesized C10, C11, and C12 chloroalkanes with known chlorine positions were estimated. Based on these results, the effects of chain length, chlorination degree, and structure were explored. The estimated log Kow values ranged from 4.10 (polychlorinated n-decanes with 50.2% chlorine content) to 11.34 (polychlorinated n-octacosanes with 54.8% chlorine content) for PCAs and from 3.82 (1,2,5,6,9,10-hexachlorodecane) to 7.75 (1,1,1,3,9,11,11,11-octachlorododecane) for the individual chloroalkanes studied. The results showed that log Kow value was influenced linearly at a given chlorine content by chain length, while a polynominal effect was observed in dependence on the chlorination degree of an alkane chain. Chlorine substitution pattern influenced markedly the log Kow value of chloroalkanes.
authors.affiliation: Technische Universität München, Research Center Weihenstephan for Brewing and Food Quality, Freising, Germany.
authors.forename: Bettina
authors.initials: B
authors.lastname: Hilger
authors.forename: Hermann
authors.initials: H
authors.lastname: Fromme
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Völkel
authors.forename: Mehmet
authors.initials: M
authors.lastname: Coelhan
mesh_terms: D000473:Alkanes / Q000737:chemistry* / Q000592:standards; D005591:Chemical Fractionation; D002851:Chromatography, High Pressure Liquid; D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry* / Q000592:standards; D008956:Models, Chemical; D015394:Molecular Structure; D000442:Octanols / Q000737:chemistry* / Q000592:standards; D010232:Paraffin / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: D000473:Alkanes; C485044:Cereclor; D006843:Hydrocarbons, Chlorinated; D000442:Octanols; D014867:Water; D010232:Paraffin