n-Octanol-water partition coefficients, aqueous solubilities and Henry's law constants of fatty acid esters

Abstract The aqueous solubility and n-octanol-water partition coefficient of fifteen fatty acid esters are determined by the RP-HPLC method. Aqueous solubilities decrease from 5.7 × 10 −5 M for methyl caprate to 5.3 × 10 −12 M for methyl behenate while the log K ow 's increase from 4.4 to 10. Special attention is given to satisfying the statistical assumptions underlying the establishment of the calibration line. Residual plots show that in this case small systematic errors are introduced rapidly even if the selected substances for the calibration line are similar in their physical properties to the fatty acid esters. Combining previously determined vapour pressure data with the estimated solubility values allows for the estimation of Henry's law constants. Although the calculated values are not very accurate, it can be concluded that they are in general lower than those of the halogenated hydrocarbon solvents.

[1]  H. Sobotka,et al.  DETERMINATION OF SOLUBILITY OF SPARINGLY SOLUBLE LIQUIDS IN WATER , 1931 .

[2]  Chris Sutton,et al.  Solubility of alkylbenzenes in distilled water and sea water at 25.0.deg. , 1975 .

[3]  D. H. Freeman,et al.  Determination of the solubility behavior of some polycyclic aromatic hydrocarbons in water , 1978 .

[4]  H. Govers,et al.  Determination of the liquid vapour pressure of low-volatility compounds from the Kovats retention index , 1994 .

[5]  J. Sangster,et al.  Octanol‐Water Partition Coefficients of Simple Organic Compounds , 1989 .

[6]  S. Wasik,et al.  Aqueous solubilities and enthalpies of solution of n-alkylbenzenes , 1986 .

[7]  M. Harnisch,et al.  Relationship between log Pow, shake-flask values and capacity factors derived from reversed-phase high-performance liquid chromatography for n-alkylbenzenes and some oecd reference substances , 1983 .

[8]  C. E. Cowan,et al.  Technical basis for establishing sediment quality criteria for nonionic organic chemicals using equilibrium partitioning , 1991 .

[9]  Mace G. Barron,et al.  Bioconcentration. Will water-borne organic chemicals accumulate in aquatic animals? , 1990 .

[10]  J. A. Rard,et al.  Isopiestic determination of the activity coefficients of some aqueous rare-earth electrolyte solutions at 25.degree.C. 6. Europium trinitrate, yttrium nitrate, yttrium chloride , 1982 .

[11]  K. Ballschmiter,et al.  Reversed phase liquid chromatography of PCBs as a basis for the calculation of water solubility and log Kow for polychlorobiphenyls , 1988 .

[12]  W. Shiu,et al.  Illustrated handbook of physical-chemical properties and environmental fate for organic chemicals. Volume 5: pesticide chemicals. , 1992 .

[13]  Yadu B. Tewari,et al.  Aqueous solubility and octanol/water partition coefficient of organic compounds at 25.0.degree.C , 1982 .

[14]  Michele M. Miller,et al.  Relationships between octanol-water partition coefficient and aqueous solubility. , 1985, Environmental science & technology.

[15]  B. McDuffie,et al.  Estimation of octanol/water partition coefficients for organic pollutants using reverse-phase HPLC , 1981 .

[16]  H. Govers,et al.  Determination of environmentally relevant physical-chemical properties of some fatty acid esters , 1997 .

[17]  Samuel H. Yalkowsky,et al.  Relationships between aqueous solubility and octanol-water partition coefficients , 1980 .

[18]  R. Eganhouse,et al.  Aqueous solubilities, vapor pressures, and 1-octanol-water partition coefficients for C9-C14 linear alkylbenzenes , 1992 .

[19]  O. Hutzinger,et al.  Differences between retentions of various classes of aromatic hydrocarbons in reversed-phase high-performance liquid chromatography. Implications of using retention data for characterizing hydrophobicity. , 1987, Journal of chromatography.

[20]  Joseph J. Pignatello,et al.  Sorption Dynamics of Organic Compounds in Soils and Sediments , 1987 .

[21]  Philip Jonathan,et al.  Statistical thinking and technique for QSAR and related studies. Part I: General theory , 1993 .

[22]  S. Wasik,et al.  Determination of the vapor pressure, aqueous solubility, and octanol/water partition coefficient of hydrophobic substances by coupled generator column/liquid chromatographic methods , 1983 .

[23]  L S McCarty,et al.  Residue-based interpretation of toxicity and bioconcentration QSARs from aquatic bioassays: polar narcotic organics. , 1992, Ecotoxicology and environmental safety.

[24]  S. Eisenreich,et al.  Chromatographic determination of octanol-water partition coefficients (Kow's) for 58 PCB polychlorinated biphenyl congeners. , 1984, Environmental science & technology.

[25]  L. Burkhard,et al.  Evaluation of reverse phase liquid chromatography/mass spectrometry for estimation of n-octanol/water partition coefficients for organic chemicals , 1985 .

[26]  H. Govers,et al.  Retention of neutral and basic heteroaromatic hydrocarbons in RPLC systems and its use in predictive studies. I. Concentration of the organic modifier. , 1991, The Science of the total environment.

[27]  S. Karickhoff,et al.  Organic Pollutant Sorption in Aquatic Systems , 1984 .

[28]  W. Shiu,et al.  Preparation of aqueous solutions of sparingly soluble organic substances: I. Single component systems , 1988 .