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Water solubility and partitioning behavior of brominated phenols
Author(s) -
Kuramochi Hidetoshi,
Maeda Kouji,
Kawamoto Katsuya
Publication year - 2004
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1897/03-279
Subject(s) - chemistry , solubility , enthalpy , partition coefficient , bromine , phenols , enthalpy of fusion , aqueous solution , differential scanning calorimetry , analytical chemistry (journal) , melting point , chromatography , thermodynamics , organic chemistry , physics
The water solubility ( S w ) in the temperature range from 283 to 308 K and 1‐octanol/water partition coefficient ( K ow ) for the nonionic form of brominated phenols (BPhs) of varying bromine content (4‐bromophenol, 2,4‐dibromophenol, 2,4,6‐tribromophenol, and pentabromophenol) were measured by the generator‐column or shake‐flask method and by the high‐performance liquid chromatography method, respectively. The temperature dependence of S w , namely enthalpy of solution (Δ H solution ), was calculated using the van't Hoff Equation. To determine the activity coefficients in water (γ w ) of BPhs from the S w data, enthalpy of fusion (Δ H fusion ) and melting point ( T m ) were measured by a differential scanning calorimetry method. The γ w was used for evaluating data consistency as well as for predicting other physico‐chemical properties, such as the Henry's law constant ( H w ). The present work systematically reports, to our knowledge for the first time, the experimental values of S w , K ow , Δ H solution , Δ H fusion , T m , and γ w for BPhs with one to five bromines, and it discusses the effects of bromine content on these physico‐chemical properties. Finally, the overall physico‐chemical characteristics of BPhs are compared with those of polychlorinated phenols, polycyclic aromatic hydrocarbons, and brominated benzenes with the same solubility level as BPhs.