Prediction of the n-hexane/water and 1-octanol/water partition coefficients for environmentally relevant compounds using molecular simulation

Authors

  • Nuno M. Garrido,

    1. LSRE Laboratory of Separation and Reaction Engineering, Departamento de Engenharia Química, Faculdade de Engenharia, Universidade do Porto, Rua do Dr. Roberto Frias, 4200 - 465 Porto, Portugal
    2. The Petroleum Institute, Dept. of Chemical Engineering, PO Box 2533, Abu Dhabi, United Arab Emirates
    Search for more papers by this author
  • Ioannis G. Economou,

    Corresponding author
    1. The Petroleum Institute, Dept. of Chemical Engineering, PO Box 2533, Abu Dhabi, United Arab Emirates
    • The Petroleum Institute, Dept. of Chemical Engineering, PO Box 2533, Abu Dhabi, United Arab Emirates

    Search for more papers by this author
  • António J. Queimada,

    1. LSRE Laboratory of Separation and Reaction Engineering, Departamento de Engenharia Química, Faculdade de Engenharia, Universidade do Porto, Rua do Dr. Roberto Frias, 4200 - 465 Porto, Portugal
    Search for more papers by this author
  • Miguel Jorge,

    1. LSRE Laboratory of Separation and Reaction Engineering, Departamento de Engenharia Química, Faculdade de Engenharia, Universidade do Porto, Rua do Dr. Roberto Frias, 4200 - 465 Porto, Portugal
    Search for more papers by this author
  • Eugénia A. Macedo

    1. LSRE Laboratory of Separation and Reaction Engineering, Departamento de Engenharia Química, Faculdade de Engenharia, Universidade do Porto, Rua do Dr. Roberto Frias, 4200 - 465 Porto, Portugal
    Search for more papers by this author

Abstract

In recent years molecular simulation has emerged as a useful tool to predict physical properties of complex chemical systems. A methodology to estimate the n-hexane/water and 1-octanol/water partition coefficients of environmentally relevant solutes, namely substituted alkyl-aromatic molecules, chlorobenzenes, polychlorinated biphenyls (PCBs) and polychlorinated diphenyl ethers (PCDEs) using molecular simulation is elucidated here. The partition coefficients are calculated based on the absolute solvation Gibbs energies in each phase which are estimated from molecular dynamics simulations employing the thermodynamic integration approach. Very encouraging results, with average absolute deviations of 0.4 log P units are presented. Consequently, this molecular-based approach with a strong physical background can provide reliable prediction of the partition coefficients in different solvent pairs without the a priori knowledge of experimental data. © 2011 American Institute of Chemical Engineers AIChE J, 58: 1929–1938, 2012

Ancillary