Solvatación preferencial de 4-hidroxi-2,5-dimetil-3(2H)- furanona (HDMF) en mezclas etanol + agua de acuerdo a los métodos IKBI y QLQC

Jaime Andrés Lasso Pineda; Diego Ivan Caviedes; Daniel Ricardo Delgado

doi:10.25054/22161325.715

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Lasso Pineda, J. A., Caviedes, D. I., & Delgado, D. R. (2015). Preferential solvation of 4-hydroxy-2,5-dimethyl-3(2H)- furanone (DMHF) in ethanol + water mixtures according to IKBI and QLQC methods. Ingeniería Y Región, 13(1), 139–147. https://doi.org/10.25054/22161325.715

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Published: Sep 9, 2015

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https://doi.org/10.25054/22161325.715

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Vol. 13 (2015)

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Esta obra está bajo una Licencia Creative Commons Reconocimiento-NoComercial-CompartirIgual

Jaime Andrés Lasso Pineda

Universidad Cooperativa de Colombia

Diego Ivan Caviedes

Universidad Cooperativa de Colombia

Daniel Ricardo Delgado

Universidad Cooperativa de Colombia Sede Neiva

Abstract

The parameters of preferential solvation of 4-hydroxy-2.5-dimetyl-3 (2H)-furanone (HDMF) in ethanol (EtOH) were derived from its thermodynamic properties of solution by means of inverse Kirkwood-Buff integrals and quasi-lattice-quasi-chemical (QLQC) methods. According to the IKBI method, the preferential solvation parameter δx1,3 of EtOH is negative in water-rich mixtures but positive in ethanol-rich mixtures. It is possible that the hydrophobic hydration around the methyl groups of the HDMF plays a role in the solvation in water-rich mixtures. The greatest EtOH solvation in ethanol-rich mixtures may have been due, mainly, to the effects of polarity and acid-base behavior of the hydroxyl groups in the compound against the most basic solvents in the solution. On the other hand, using the QLQC method, this compound is preferably solvated by the cosolvent in most of the water-ethanol system mixtures.

Keywords

HDMF

ethanol

preferential solvation

inverse Kirkwood-Buff integrals

quasi-lattice-quasichemical

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Author Biographies / See

Jaime Andrés Lasso Pineda, Universidad Cooperativa de Colombia

Estudiante de Ingeniería Industrial. Grupo de investigación en administración de operaciones y producción, Universidad
Cooperativa de Colombia Sede Neiva. Calle 11 No. 1 G-31 B

Diego Ivan Caviedes, Universidad Cooperativa de Colombia

Licenciado en Biología y Química, Esp. Ingeniería Ambiental, M.Sc. en Ecología y Gestion de Ecosistemas Estratégicos
Universidad Surcolombiana, Grupo de investigación en administración de operaciones y producción, Profesor
T.C. Universidad Cooperativa de Colombia Sede Neiva. Calle 11 No. 1 G-31 B.

Daniel Ricardo Delgado, Universidad Cooperativa de Colombia Sede Neiva

Licenciado en Biología y Química Universidad Surcolombiana, M.Sc en Ciencias Químicas, PhD en Ciencias Farmacéuticas, Universidad Nacional de Colombia Sede Bogotá, Grupo de investigación en administración de operaciones y producción, Profesor T.C. Universidad Cooperativa de Colombia Sede Neiva. Calle 11 No. 1 G-31 B.

References

Aulton, M.E., 2002. Pharmaceutics, The Science of Dosage Forms Design, 2nd edn. London: Churchill Livingstone.

Cárdenas, Z.J., Jiménez, D.M., Martínez, F., 2014. Preferential solvation of ketoprofen in some co-solvent binary mixtures. J. Solut. Chem. 43, 1904-1915. Figure 2. IKBI (filled symbols) and QLQC (open symbols) ?x1,3 values of DMHF in ethanol + water mixtures at both temperatures. Circles: 298.2 K; triangles: 313.2 K. 146 Revista Ingeniería y Región. 2015;13(1):139-147 Solvatación preferencial... / Lasso Pineda & Cols.

Cristancho, D.M., Delgado, D.R., Martínez, F., 2013. Preferential Solvation of Ethylhexyl Triazone in Ethyl Acetate + EtOH Mixtures According to the Inverse Kirkwood-Buff Integrals Method. Lat. Am. J. Pharm. 32 (10) 1538-1545.

Delgado, D.R., Holguín, A.R., Almanza, O.A., Martínez, F., Marcus, Y., 2011. Solubility and preferential solvation of meloxicam in ethanol + water mixtures. Fluid Phase Equilib. 305, 88-95

Delgado, D.R., Martínez, F., 2015. Preferential solvation of some structurally related sulfonamides in 1-propanol + water co-solvent mixtures. Phys. Chem. Liq. 53(3), 293-306.

Delgado, D.R., Martínez F., 2014. Preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in ethanol + water solvent mixtures according to the IKBI method. J. Mol. Liq. 193, 152-159.

Delgado, D.R., Martínez, F., 2014. Solubility and preferential solvation of sulfadiazine in methanol + water mixtures at several temperatures. Fluid Phase Equilib. 379, 128-138.

Delgado, D.R., Peña, M.A., Martínez, F., 2014. Preferential solvation of some sulfonamides in 1,4-dioxane + water co-solvent mixtures at 298.15 K according to the inverse Kirkwood-Buff integrals method. Rev. Acad. Colomb. Cienc. 38(146), 104-114.

Delgado, D.R., Peña, M.A., Martínez, F., 2014. Preferential Solvation of Some Sulfonamides in Propylene Glycol + Water Solvent Mixtures According to the IKBI and QLQC Methods. J. Solution Chem. 43, 360-374.

Delgado, D.R., Peña, M.A., Martínez, F., 2013. Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse Kirkwood-Buff integrals method. Rev. Colomb. Cienc. Quím. Farm. 42(2), 298-314.

Delgado, D.R., Vargas, E., Martínez, F., 2013. Preferential solvation of xylitol in ethanol + water co-solvent mixtures according to the IKBI and QLQC methods. Rev. Colomb. Quim. 42(1), 59-66.

Fedors, R. F., 1974. A method for estimating both the solubility parameters and molar volumes of liquids. Polym. Eng. Sci. 14,147-154.

Honkanen, E., Pyysalo, T., Hirvi, T., 1980. The aroma of Finnish wild raspberries, Rirbus idaeirs L. Z. Lebensm. Unters. Forsch. 171, 180-182.

Jiménez, J., Manrique, J., Martínez, F., 2004. Effect of temperature on some volumetric properties for ethanol + water mixtures. Rev. Colomb. Cienc. Quim. Farm. 33, 145-155.

Jiménez, J., Martínez, F., 2005. Study of some volumetric properties of 1,2-propanediol + water mixtures at several temperatures. Rev. Colomb. Cienc. Quim. Farm. 34, 46-57.

Jiménez, D.M., Cárdenas, Z.J., Delgado, D.R., Martínez, F., Jouyban, A., 2014. Preferential solvation of methocarbamol in aqueous binary cosolvent mixtures at 298.15 K. Phys. Chem. Liq. 52, 726-737.

Jiménez, D.M., Cárdenas, Z.J., Delgado, D.R., Peña, M.A., Martínez, F., 2015. Solubility temperature dependence and preferential solvation of sulfadiazine in 1,4-dioxane + water co-solvent mixtures. Fluid Phase Equilib. 397, 26-36.

Jouyban, A., 2010. Handbook of Solubility Data for Pharmaceuticals. CRC Press, Boca Raton (FL).

Kallio, H., 1976. Identification of vacuum steam distilled aroma components in the press juice of arctic bramble, Rubus arcticus, L. J. Food. Sci. 41, 555-562.

Kamlet, M.J., Taft, R. W., 1976. The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J. Am. Chem. Soc. 98, 377-383.

Marcus, Y., 1998. The Properties of Solvents. John Wiley & Sons, Chichester.

Marcus, Y., 2002. Solvent Mixtures: Properties and Selective Solvation. Marcel Dekker, Inc., New York.

Marcus, Y., 2008. On the preferential solvation of drugs and PAHs in binary solvent mixtures. J. Mol. Liq. 140, 61-67.

Marcus, Y., 2009. Preferential solvation of ibuprofen and naproxen in aqueous 1,2-propanediol. Acta Chimica Slovenica, 56, 40-44. 147 Solvatación preferencial... / Lasso Pineda & Cols. Revista Ingeniería y Región. 2015;13(1):139-147

Marcus, Y., 2013. Preferential solvation in mixed solvents. In: Smith, P. E., Matteoli, E., O’Connell, J. P. (Eds.). Fluctuation Theory of Solutions: Applications in Chemistry, Chemical Engineering, and Biophysics. CRC Press, Taylor & Francis Group, Boca Raton.

Muñoz, M., Delgado, D.R., Peña, M.A., Jouyban, A., Martínez, F., 2015. Solubility and preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in propylene glycol + water mixtures at 298.15 K. J. Mol. Liq. 204, 132-136.

Ohloff, G., 1969. Chemie der Geruchs-und Geschniacksstoffe. Fortschr. Chem. Forsch. 12, 185-259.

Peña, M.A., Delgado, D.R., Martínez, F., 2014. Preferential Solvation of Acetaminophen in Propylene Glycol + Water Co-Solvent Mixtures. J Appl Sol Chem Model. 3, 65-73.

Rapp. A., Knipser, W., Engel, L., Ullemeyer, H., Heimann, W., 1980. Fremdkomponenten im Aroma von Trauben und Weinen interspezifischer Rebsorten: I. Die Erd be ernote. Vitis. 19, 13-23.

Rodin, J.O., Himel, C.M., Silverstein, R.M., Leeper, R.W., Gortner, W.A., 1965. Volatile flavor and aroma components of pineapple. I. Isolation and tentative identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone. J. Food. Sci. 30, 280-285.

Rubino, J.T., 1988. Cosolvents and cosolvency. In: Swarbrick, J., Boylan, J.C. (Eds.). Encyclopedia of Pharmaceutical Technology. Marcel Dekker, Inc.,Vol 3, New York.

Ruidiaz, M.A., Delgado, D.R., Martínez, F., Marcus, Y., 2010. Solubility and preferential solvation of indomethacin in 1,4-dioxane + water solvent mixtures. Fluid Phase Equilib. 299, 259-265.

Sheldon, R.M., Lindsay, R.C., Libbey, L.M., 1972. Identification of volatile flavor compounds from roasted filberts. J. Food. Sci. 3, 13-316.

Smolinske, S.C., 1992. Handbook of Drug, Food and Cosmetic Excipients. CRC Press LLC, Boca Raton.

Tatum, J.H., Nagy, S., Berry, R.E., 1975. Degradation products formed in canned single-strength orange juice during storage. J. Food. Sci. 40, 707-709.

Tonsbeek, C.H.T., Plancken, A.J., Weerdhof, T.v.d., 1978. Components contributing to beef flavor. Isolation of 4-hydroxy-5-methyl-3(2H) furanone and its 2,5-dimethyl homolog from beef broth. J. Agric. Food Chem. 16, 101-1021.

Tressl, R., Bahri, D., Koppler, H., Jensen, A., 1978. Diphenole und Caramelkomponenten in Rostkaffees verschiedener Sorten. Z. Lebensm. Unters. Forsch. 16, 111-114.

Wang, L-Y., Lia, X-C., Zhua, L., Shaa, Z-L., Wang, Y-F., Yang, L-B., 2015. Experimental determination and correlation of the solubility of 4-hydroxy-2,5- dimethyl-3(2H)-furanone (DMHF) in binary (ethanol + water) solvent mixtures. J. Mol. Liq. 208, 211-218.

Yalkowsky, S.H., 1999. Solubility and Solubilization in Aqueous Media. American Chemical Society and Oxford University Press, New York.