Skip to main content
SpringerLink
Log in

Solution Thermodynamics of Ethylhexyl Triazone in Some Ethanol + Ethyl Acetate Mixtures

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Ethylhexyl triazone (EHT) is a sunscreen agent that is widely used in skin care product formulations, whose physicochemical properties have not been previously studied in detail. For this reason, solubility data were measured for EHT in ethanol (EtOH) + ethyl acetate (AcOEt) mixtures at five temperatures. By using the van’t Hoff and Gibbs equations, the thermodynamic functions: Gibbs energy, enthalpy, and entropy of solution, and of mixing, were evaluated from these solubilities. The solubility is greatest in mixtures with 0.10 and 0.20 mass fraction EtOH, but decrease as the EtOH mass fraction increases in the solvent mixtures. By means of an enthalpy-entropy compensation analysis, a nonlinear \(\Delta H_{\mathrm{soln}}^{0}\) versus \(\Delta G_{\mathrm{soln}}^{0}\) compensation plot was obtained having both negative and positive slopes as the solvent composition was varied. Accordingly to these results, it follows that the driving function for solubility of EHT is the entropy for solutions rich in EtOH or AcOEt, whereas in mixtures of medium composition, the driving function is the enthalpy.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Tuchinda, C., Lim, H.W., Osterwalder, U., Rougier, A.: Novel emerging sunscreen technologies. Dermatol. Clin. 24, 105–117 (2006)

    CAS  Google Scholar 

  2. Palm, M.D., O’Donoghue, M.N.: Update on photoprotection. Dermatol. Ther. 20, 360–376 (2007)

    Article  Google Scholar 

  3. Jiménez, F., Martínez, F.: A strategy for systematic selection of cosolvent vehicles in the design of homogeneous liquid pharmaceutical dosage forms. Rev. Colomb. Cienc. Quím. Farm. 24, 19–23 (1995)

    Google Scholar 

  4. Tewes, F., Boury, F., Benoit, J.P.: In: Benita, S. (ed.) Microencapsulation: Methods and Industrial Applications, 2nd edn. Taylor & Francis, New York (2006), pp. 1–53

    Google Scholar 

  5. Bustamante, P., Ochoa, R., Reillo, A., Escalera, J.B.: Chameleonic effect of sulfanilamide and sulfamethazine in solvent mixtures: solubility curves with two maxima. Chem. Pharm. Bull. 42, 1129–1133 (1994)

    CAS  Google Scholar 

  6. Escalera, J.B., Bustamante, P., Martin, A.: Predicting the solubility of drugs in solvent mixtures: multiple solubility maxima and the chameleonic effect. J. Pharm. Pharmacol. 46, 172–176 (1994)

    CAS  Google Scholar 

  7. Bustamante, P., Escalera, B.: Enthalpy and entropy contributions to the solubility of sulfamethoxypyridazine in solvent mixtures showing two solubility maxima. J. Pharm. Pharmacol. 47, 550–555 (1995)

    CAS  Google Scholar 

  8. Romero, S., Reillo, A., Escalera, B., Bustamante, P.: The behaviour of paracetamol in mixtures of aprotic and amphiprotic–aprotic solvents: relationship of solubility curves to specific and nonspecific interactions. Chem. Pharm. Bull. 44, 1061–1066 (1996)

    CAS  Google Scholar 

  9. Romero, S., Escalera, B., Bustamante, P.: Solubility behavior of polymorphs I and II of mefenamic acid in solvent mixtures. Int. J. Pharm. 178, 193–202 (1999)

    Article  CAS  Google Scholar 

  10. Jouyban, A., Romero, S., Chan, H.K., Clark, B.J., Bustamante, P.: A cosolvency model to predict solubility of drugs at several temperatures from a limited number of solubility measurements. Chem. Pharm. Bull. 50, 594–599 (2002)

    Article  CAS  Google Scholar 

  11. Bustamante, P., Navarro, J., Romero, S., Escalera, B.: Thermodynamic origin of the solubility profile of drugs showing one or two maxima against the polarity of aqueous and nonaqueous mixtures: niflumic acid and caffeine. J. Pharm. Sci. 91, 874–883 (2002)

    Article  CAS  Google Scholar 

  12. Peña, M.A., Reillo, A., Escalera, B., Bustamante, P.: Solubility parameter of drugs for predicting the solubility profile type within a wide polarity range in solvent mixtures. Int. J. Pharm. 321, 155–161 (2006)

    Article  Google Scholar 

  13. Jouyban, A., Acree, Jr. W.E.: Prediction of drug solubility in ethanol–ethyl acetate mixtures at various temperatures using the Jouyban–Acree model. J. Drug Del. Sci. Technol. 17, 159–160 (2007)

    CAS  Google Scholar 

  14. Ruidiaz, M.A., Martínez, F.: Extended Hildebrand solubility approach in the estimation of indomethacin solubility in ethyl acetate + ethanol mixtures. Rev. Colomb. Quím. 38, 235–247 (2009)

    CAS  Google Scholar 

  15. Ruidiaz, M.A., Vargas, E.F., Martínez, F.: Study of some volumetric properties of the pharmaceutical model solvent system ethanol + ethyl acetate at several temperatures. Lat. Am. J. Pharm. 29, 306–312 (2010)

    CAS  Google Scholar 

  16. Resa, J.M., González, C., Goenaga, J.M., Iglesias, M.: Temperature dependence of excess molar volumes of ethanol + water + ethyl acetate. J. Solution Chem. 33, 169–198 (2004)

    Article  CAS  Google Scholar 

  17. Belda, R., Herraez, J.V., Diez, O.: Rheological study and thermodynamic analysis of the binary system (water/ethanol): influence of concentration. Phys. Chem. Liq. 42, 467–476 (2004)

    Article  CAS  Google Scholar 

  18. Jiménez, J.A., Martínez, F.: Temperature dependence of solubility of acetaminophen in propylene glycol + ethanol mixtures. J. Solution Chem. 35, 335–352 (2006)

    Article  Google Scholar 

  19. Kristl, A., Vesnaver, G.: Thermodynamic investigation of the effect of octanol–water mutual miscibility on the partitioning and solubility of some guanine derivatives. J. Chem. Soc. Faraday Trans. 91, 995–998 (1995)

    Article  CAS  Google Scholar 

  20. Barton, A.: Handbook of Solubility Parameters and Other Cohesion Parameters, 2nd edn. CRC Press, New York (1991), pp. 157–193

    Google Scholar 

  21. Krug, R.R., Hunter, W.G., Grieger, R.A.: Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effects. J. Phys. Chem. 80, 2341–2351 (1976)

    Article  CAS  Google Scholar 

  22. Bustamante, P., Romero, S., Peña, A., Escalera, B., Reillo, A.: Nonlinear enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide and nalidixic acid in dioxane–water. J. Pharm. Sci. 87, 1590–1596 (1998)

    Article  CAS  Google Scholar 

  23. Bevington, P.R.: Data Reduction and Error Analysis for the Physical Sciences. McGraw-Hill, New York (1969)

    Google Scholar 

  24. Perlovich, G.L., Kurkov, S.V., Kinchin, A.N., Bauer-Brandl, A.: Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs. Eur. J. Pharm. Biopharm. 57, 411–420 (2004)

    Article  CAS  Google Scholar 

  25. Bustamante, P., Romero, S., Reillo, A.: Thermodynamics of paracetamol in amphiprotic and amphiprotic-aprotic solvent mixtures. Pharm. Sci. 1, 505–507 (1995)

    CAS  Google Scholar 

  26. Leffler, J.E., Grunwald, E.: Rates and Equilibria of Organic Reactions. Wiley, New York (1963)

    Google Scholar 

  27. Tomlinson, E.: Enthalpy-entropy compensation analysis of pharmaceutical, biochemical and biological systems. Int. J. Pharm. 13, 115–144 (1983)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Grupo de Investigaciones Farmacéutico-Fisicoquímicas, Departamento de Farmacia, Facultad de Ciencias, Universidad Nacional de Colombia, A. A. 14490, Bogota, D.C., Colombia

    Sylvia J. Rodríguez, Diana M. Cristancho, Paula C. Neita & Fleming Martínez

  2. Laboratorio de Termodinámica de Soluciones, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Bogota, D.C., Colombia

    Edgar F. Vargas

Authors
  1. Sylvia J. Rodríguez
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Diana M. Cristancho
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Paula C. Neita
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Edgar F. Vargas
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fleming Martínez
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Fleming Martínez.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rodríguez, S.J., Cristancho, D.M., Neita, P.C. et al. Solution Thermodynamics of Ethylhexyl Triazone in Some Ethanol + Ethyl Acetate Mixtures. J Solution Chem 39, 1122–1133 (2010). https://doi.org/10.1007/s10953-010-9575-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-010-9575-0

Keywords

Search

Navigation