Estimating n-octanol-water partition coefficients for neutral highly hydrophobic chemicals using measured n-butanol-water partition coefficients

Kaila B. Hanson, Dale J. Hoff, Tylor J. Lahren, David R. Mount, Anthony J. Squillace, Lawrence P. Burkhard

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Direct measurement of the n-octanol partition coefficients (KOW) for highly hydrophobic organic chemicals is extremely difficult because of the extremely low concentrations present in the water phase. n-Butanol/water partition coefficients (KBW) are generally much lower than KOW due to the increased solubility of solute in the alcohol saturated aqueous phase, and therefore become easier to measure. We measured the KBW for 25 neutral organic chemicals having measured log KOWs ranging from 2 to 9 and 4 additional highly hydrophobic chemicals, with unmeasured KOWs, having estimated log KOWs ranging from 6 to 18. The measured log KBW and log KOW values were linearly related, r2 = 0.978, and using the regression developed from the data, KOWs were predicted for the 4 highly hydrophobic chemicals with unmeasured KOWs. The resulting predictions were orders of magnitude lower than those predicted by a variety of computational models and suggests the estimates of KOW in the literature for highly hydrophobic chemicals (i.e., log KOW greater than 10) are likely incorrect by several orders of magnitude.

Original languageEnglish (US)
Pages (from-to)616-623
Number of pages8
JournalChemosphere
Volume218
DOIs
StatePublished - Mar 2019
Externally publishedYes

Bibliographical note

Funding Information:
We thank David Tobias for his comments on an earlier draft of this manuscript. The information in this document has been funded wholly by the U.S. Environmental Protection Agency (US-EPA). This manuscript has been reviewed in accordance with the requirements of the US-EPA and approved for publication. Approval does not signify that the contents reflect the views of the Agency, nor does mention of trade names or commercial products constitute endorsement or recommendation for use.

Publisher Copyright:
© 2018

Keywords

  • Collander equation
  • n-Butanol/water partition coefficients
  • n-octanol/water partition coefficients (K)

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