Thermodynamic Modeling of Chiral Compounds Solubility Using Correlative and Predictive Models

Authors

  • Morteza Salimi Seman university
  • Bahman Zarenezhad Seman university
  • Hossein Fakhraian Imam Hossein University
  • Ebrahim Choobdari Shahid Beheshti University

DOI:

https://doi.org/10.6000/1929-5030.2015.04.03.2

Keywords:

Solubility, Chiral compounds, Thermodynamic modeling, NRTL-SAC, UNIFAC, UNIQUAC, NRTL

Abstract

Many intermolecular forces and parameters affect the solubility of a compound in a solvent. Various thermodynamic models are presented to predict these parameters and determine solid liquid equilibrium data. By selecting suitable thermodynamic model for solubility modeling, calculation error is reduced and the results will be closer to the experimental data. Herein, the ability of two predictive and two correlative models in solubility modeling of chiral compounds is investigated. Thus, solubility of pure and racemic forms of chiral Ketamine, Mandelic acid and 3-Chloromandelic acid is evaluated using UNIQUAC and NRTL models. The solubility modeling of pure and racemic forms of Ketamine in Ethanol is also determined by UNIFAC and NRTL-SAC models. There are good agreement between experimental data and results of NRTL and UNIQUAC models. Predictive NRTL-SAC model shows smaller deviation than UNIFAC in solubility determination of pure and racemic form of Ketamine.

Author Biographies

Morteza Salimi, Seman university

Faculty of Chemical, Gas and Petroleum Engineering

Bahman Zarenezhad, Seman university

Faculty of Chemical, Gas and Petroleum Engineering

Hossein Fakhraian, Imam Hossein University

Department of Chemistry

Ebrahim Choobdari, Shahid Beheshti University

Department of Chemistry

References


[1] Bruice PY. Organic Chemistry. 6th ed. Pearson International Edition: USA 2011
[2] Fox MA. Whitesell JK. Organic Chemistry. Jones & Bartlett Publishers: Boston 1994.
[3] Drayer DE. Pharmacodynamic and Pharmacokinetic Differences between Drug Enantiomers in Humans: An Overview. Clin Pharmacol Ther 1986; 40: 125-133. http://dx.doi.org/10.1038/clpt.1986.150
[4] Polenske D, Lorenz H, Seidel-Morgenstern A. The Binary Phase Diagram of Propranolol Hydrochloride and Crystallization-Based Enantioseparation. J Pharm Sci 2010; 99: 1762-1773. http://dx.doi.org/10.1002/jps.21943
[5] Collet A. Separation and Purification of Enantiomers by Crystallization Methods. Enantiomer 1999; 4: 157-172.
[6] Lorenz H, Seidel-Morgenstern A. Binary and Ternary Phase Diagram of Two Enantiomers in Solvent Systems. Thermochimica Acta 2002; 382: 129-142. http://dx.doi.org/10.1016/S0040-6031(01)00746-8
[7] Wilson GM. Vapor-Liquid Equilibrium. XI. A New Expression for the Excess Free Energy of Mixing. J Am Chem Soc 1964; 86: 127-130. http://dx.doi.org/10.1021/ja01056a002
[8] Renon H. Prausnitz JM. Local Compositions in Thermodynamic Excess Functions for Liquid Mixtures AIChE 1968; 14: 135-144. http://dx.doi.org/10.1002/aic.690140124
[9] Abrams DS, Prausnitz JM. Statistical Thermodynamics of Liquid Mixtures: A New Expression for the Excess Gibbs Energy of Partly or Completely Miscible Systems. AIChE 1975; 21: 116-128. http://dx.doi.org/10.1002/aic.690210115
[10] Hansen CM. Hansen Solubility Parameters: A User’s Handbook; CRC Press: Boca Raton, FL 2000.
[11] Fredenslund A, Jones RL, Prausnitz JM. Group Contribution Estimation of Activity Coefficient in non Ideal Liquid Mixtures. AIChE J 1975; 21: 1086-1099. http://dx.doi.org/10.1002/aic.690210607
[12] Chen C-C, Song Y. Solubility Modeling with a Non-Random Two- Liquid Segment Activity Coefficient Model. Ind Eng Chem Res 2004; 43: 8354-8362. http://dx.doi.org/10.1021/ie049463u
[13] Mirmehrabi M, Rohani S, Murthy KSK, Radatus B. Solubility, Dissolution Rate and Phase Transition Studies of Ranitidine Hydrochloride Tautomeric Forms. Int J Pharmaceut 2004; 282: 73-85. http://dx.doi.org/10.1016/j.ijpharm.2004.05.031
[14] Mirmehrabi M, Rohani S, Perry L. Thermodynamic Modeling of Activity Coefficient and Prediction of Solubility: Part 2. Semipredictive or Semiempirical Models. J Pharmaceut Sci 2006; 95(4): 798-809. http://dx.doi.org/10.1002/jps.20576
[15] Doman ska U, Pelczarska A, Pobudkowska A. Solubility and pKa Determination of Six Structurally Related Phenothiazines. Int J Pharmaceut 2011; 421: 135-144. http://dx.doi.org/10.1016/j.ijpharm.2011.09.040
[16] Sheikhzadeh M, Rohani S, Taffish M, Murad S. Solubility Analysis of Buspirone Hydrochloride Polymorphs Measurements and Prediction. Int J Pharmaceut 2007; 338: 55-63. http://dx.doi.org/10.1016/j.ijpharm.2007.01.022
[17] Manifar T, Rohani S. Measurement and Prediction of Solubility of Four Arylamine Molecules in Benzene, Hexane, and Methanol. J Chem Eng Data 2005; 50: 1794-1800. http://dx.doi.org/10.1021/je0495785
[18] Sheikholeslamzadeh E, Rohani S. Vapour–Liquid and Vapour–Liquid–Liquid Equilibrium Modeling for Binary, Ternary, and Quaternary Systems of Solvents. Fluid Phase Equilibria 2012; 333: 97-105. http://dx.doi.org/10.1016/j.fluid.2012.07.016
[19] Prausnitz JM, Lichtenthaler RN, Azevedo EG. Molecular Thermodynamics of Fluid-Phase Equilibria. 2nd ed. PTR Prentice-Hall, Inc. Englewood Cliffs NJ, USA 1986. http://dx.doi.org/10.1002/cjce.5450780222
[20] Tamagawa RE, Miranda EA, Santana CC, Giulietti M. Determination of the Binary and Ternary Phase Diagrams of R(+)-/S(-)-Ketamine Using Differential Scanning Calorimetry. J Chem Eng Data 2009; 54: 16-21. http://dx.doi.org/10.1021/je8002207
[21] Zhang Y, Ray A, Rohani S. Measurement and Prediction of Phase Diagrams of the Enantiomeric 3-Chloromandelic Acid System. Chem Eng Sci 2009 64: 192-197. http://dx.doi.org/10.1016/j.ces.2008.10.010
[22] Lorenze H, Sapoundjiev D, Seidel-Morgenstern A. Enantiomeric Mandelic acid system-melting point phase diagram and solubility in water. J Chem Eng Data 2002; 47: 1280. http://dx.doi.org/10.1021/je0200620
[23] Atashpaz-Gargari E, Lucas C. Imperialist Competitive Algorithm: An Algorithm for Optimization Inspired by Imperialistic Competition, Evolutionary Computation. 2007. CEC 2007; IEEE Congress on, 4661-4667. http://dx.doi.org/10.1109/CEC.2007.4425083
[24] Hansen HK, Rasmussen P, Fredenslund A, Schiller M, Gmehling J. Vapor–Liquid Equilibria by UNIFAC Group Contribution. 5. Revision and Extension. I & EC Res 1991; 30: 2352-2355. http://dx.doi.org/10.1021/ie00058a017

Downloads

Published

2015-09-08

How to Cite

Salimi, M., Zarenezhad, B., Fakhraian, H., & Choobdari, E. (2015). Thermodynamic Modeling of Chiral Compounds Solubility Using Correlative and Predictive Models. Journal of Applied Solution Chemistry and Modeling, 4(3), 143–151. https://doi.org/10.6000/1929-5030.2015.04.03.2

Issue

Section

General Articles