Water solubility and partitioning behavior of brominated phenols

Abstract

The water solubility (Sw) in the temperature range from 283 to 308 K and 1-octanol/water partition coefficient (Kow) 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 Sw, namely enthalpy of solution (deltaHsolution), was calculated using the van't Hoff Equation. To determine the activity coefficients in water (gammaw) of BPhs from the Sw data, enthalpy of fusion (deltaHfusion) and melting point (Tm) were measured by a differential scanning calorimetry method. The gammaw was used for evaluating data consistency as well as for predicting other physico-chemical properties, such as the Henry's law constant (Hw). The present work systematically reports, to our knowledge for the first time, the experimental values of Sw, Kow, deltaHsolution, deltaHfusion, Tm, and gammaw 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.

Reprint of: Crystalline and liquid vapour pressures of the four p-monohalophenols: A thermodynamic study of their phase transitions

“…For p-bromophenol, the temperature of the triple point is 1.4 K lower than the temperature of fusion obtained from DSC measurements and ca. 0.7 K lower than the mean value of the temperatures of fusion reported in literature [28,29]. The enthalpy of fusion obtained indirectly from the vaporisation and sublimation enthalpies is in excellent agreement with the mean of the values published in literature [28,29] and only 0.9 kJ Á mol À1 higher than the DSC results.…”

“…0.7 K lower than the mean value of the temperatures of fusion reported in literature [28,29]. The enthalpy of fusion obtained indirectly from the vaporisation and sublimation enthalpies is in excellent agreement with the mean of the values published in literature [28,29] and only 0.9 kJ Á mol À1 higher than the DSC results. The proximity between the results derived indirectly (from vapour pressure measurements) and the calorimetric values provides additional reliability to the measured vapour pressures.…”

Natural transformation of chlordecone into 5b-hydrochlordecone in French West Indies soils: statistical evidence for investigating long-term persistence of organic pollutants

“…In the same way, if 5b-hydroCLD is more water soluble that CLD, then it also has necessarily a lower Kow (octanol water partition coefficient) since Kow and solubility are inversely correlated (Kow is a measure of the hydrophobicity of a compound). Remembering that 5b-hydroCLD has one Cl less than CLD, the previous deduction is fully supported by the literature where it is now established that the Kow of haloorganic compounds decreases concurrently with the decrease of the number of halogen atoms bound to the carbon skeleton (Kuramochi et al 2004a;van Noort 2009;Gewurtz et al 2009;Bettina et al 2011). The propensity of a non-ionic organic compound to partition between an aqueous solution and soil is commonly described by the soil water distribution coefficient normalized to the soil organic content, Koc.…”

Estimating the physicochemical properties of polyhalogenated aromatic and aliphatic compounds using UPPER: Part 2. Aqueous solubility, octanol solubility and octanol–water partition coefficient

“…The distribution and environmental fate of these compounds is largely determined by their aqueous solubilities, S w , octanol solubilities, S o , and octanol-water partition coefficients, K ow (Katritzky et al, 1998;Makino, 1998;Xiao et al, 2004;Kuramochi et al, 2007;Xu et al, 2008;Zeng et al, 2012). The latter gives insight into the hydrophobicity of a compound and is often used as a surrogate for biological membranes and to predict their biological activity, bioconcentration factor and soil/water partition coefficients (Kuramochi et al, 2004;Lu et al, 2007;Zeng et al, 2012).…”