Skip to main content
SpringerLink
Log in

Thermodynamics of Mixtures Containing Organic Carbonates. Part XV. Application of the Kirkwood-Buff Theory to the Study of Interactions in Liquid Mixtures Containing Dialkyl Carbonates and Alkanes, Benzene, CCl4 or 1-Alkanols

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

Abstract

Binary liquid mixtures containing a dialkyl carbonate (dimethyl or diethyl carbonate) and organic solvents such as alkanes, benzene, CCl4, or 1-alkanols were studied within the framework of the Kirkwood-Buff formalism. The Kirkwood-Buff integrals, linear coefficients of preferential solvation and local mole fractions were calculated. Results were interpreted assuming that the mixtures with alkanes or 1-alkanols are not random mixtures, which can be ascribed to the existence of strong dipolar interactions between like molecules. Systems containing benzene or CCl4 are both random and more ordered because of the charge transfer or dipole/induced dipole interactions between the polar group of the solute (O–CO–O) and the polarizable solvent molecules. The effect of increasing temperature was also examined.

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. Parrish, J.P., Salvatore, R.N., Jung, K.W.: Perspectives on alkyl carbonates in organic synthesis. Tetrahedron 56, 8207–8237 (2000)

    Article  CAS  Google Scholar 

  2. Annesini, M.C., De Santis, R., Kikic, I., Marrelli, R.: Excess enthalpy and T-x data of aromatic-propylene carbonate mixtures. J. Chem. Eng. Data 29, 39–41 (1984)

    Article  CAS  Google Scholar 

  3. Naejus, R., Lemordant, D., Coudert, R., Willmann, P.: Excess thermodynamic properties of binary mixtures containing linear or cyclic carbonates as solvents at the temperatures 298.15 K and 315.15 K. J. Chem. Thermodyn. 29, 1503–1515 (1997)

    Article  CAS  Google Scholar 

  4. Tobishima, S., Yamaji, A.: Electrolytic characteristics of mixed solvents electrolytes for lithium secondary batteries. Electrochim. Acta 28, 1067–1072 (1983)

    Article  CAS  Google Scholar 

  5. Rivetti, F.: The role of dimethylcarbonate in the replacement of hazardous chemicals: Comptes Rendus, Acad. Sci. Ser. IIc, Chim. 3, 497–503 (2000)

    CAS  Google Scholar 

  6. Wallington, T.J., Hurley, M.D., Ball, J.C., Straccia, A.M., Platz, J., Christensen, L.N., Sehested, J., Nielsen, O.J.: Atmospheric chemistry of dimethoxymethane (CH3OCH2OCH3): Kinetics and mechanism of its reaction with OH radicals and fate of the alkoxy radicals CH3OCHO•OCH3 and CH3OCH2OCH2O•. J. Phys. Chem. A 101, 5302–5308 (1997)

    Article  CAS  Google Scholar 

  7. Pacheco, M. A., Marshall, C.L.: Review of dimethyl carbonate (DMC) manufacture and its characteristics as a fuel additive. Energy and Fuels 11, 2–29 (1997)

    Article  CAS  Google Scholar 

  8. García, J., Lugo, L., Comuňas, M.J., López, E.R., Fernández, J.: Experimental excess volumes of organic carbonate + alkane systems. Estimation of the parameters of the Nitta-Chao model for this kind of binary mixture. J. Chem. Soc., Faraday Trans. 94, 1707–1712 (1998)

    Article  Google Scholar 

  9. Simeral, L., Amey, R.L.: Dielectric properties of liquid propylene carbonate. J. Phys. Chem. 74, 1443–1446 (1970)

    Article  CAS  Google Scholar 

  10. Payne, R., Theodorou, I.E.: Dielectric properties and relaxation in ethylene carbonate and propylene carbonate. J. Phys. Chem. 76, 2892–2900 (1972)

    Article  CAS  Google Scholar 

  11. Cocero, M.J., García, I., González, J.A., Cobos, J.C.: Thermodynamics of binary mixtures containing organic carbonates. Part VI. Isothermal vapor-liquid equilibria for dimethyl carbonate + normal alkanes. Fluid Phase Equilib. 68, 151–161 (1991)

    Article  CAS  Google Scholar 

  12. Cocero, M.J., González, J.A., García, I., Cobos, J.C., Mato, F.: Liquid-vapor equilibrium, and excess Gibbs energy of diethyl carbonate + normal alkanes (C6, C8, C12). Int. Data Ser., Selected Data Mixtures Ser. A2, 130–138 (1991)

    Google Scholar 

  13. Cocero, M.J., González, J.A., García, I., Cobos, J.C., Mato, F.: Liquid-Vapor equilibrium and excess Gibbs energy of dimethyl or diethyl carbonates + cyclohexane, + benzene or + tetrachloromethane. Int. Data Ser. Selected Data Mixtures Ser. A2, 112–129 (1991)

    Google Scholar 

  14. Sporzynski, A., Szurgocinska, M., Domanska, U., González, J.A.: Thermodynamics of mixtures containing organic carbonates. 14. Excess molar Gibbs energies for 1-hexanol + dimethyl or diethyl carbonate systems at 353.1 K and 363.15 K. Comparison with ERAS results. Ind. Eng. Chem. Res. 42, 4382–4388 (2003)

    Article  CAS  Google Scholar 

  15. González, J.A., García, I., Cobos, J.C., Casanova, C.: Thermodynamics of binary mixtures containing organic carbonates. 4. Liquid-Liquid Equilibria of dimethyl carbonate + selected n-alkanes. J. Chem. Eng. Data 36, 162–164 (1991)

    Google Scholar 

  16. Domanska, U., Szurgocinska, M., González, J.A.: Thermodynamics of binary mixtures containing organic carbonates. Part XI. SLE measurements for systems of diethyl carbonate with Long n-Alkanes: Comparisons with DISQUAC and Modified UNIFAC Predictions. Fluid Phase Equilib. 190, 15–31 (2001)

    Google Scholar 

  17. Domanska, U., Szurgocinska, M., González, J.A.: Thermodynamics of binary mixtures containing organic carbonates. 12. SLE and LLE measurements for systems of dimethyl carbonate with long n-alkanes. Comparisons with DISQUAC and modified UNIFAC predictions. Ind. Eng. Chem. Res. 41, 3523–3259 (2002)

    Article  Google Scholar 

  18. González, J.A., Szurgocinska, M., Domanska, U.: Thermodynamics of mixtures containing organic carbonates. Part XIII. Solid-liquid equilibria of long-chain 1-alkanol + dimethyl or diethyl carbonate systems: DISQUAC and ERAS analysis of the hydroxyl/carbonate interactions. Fluid Phase Equilib. 200, 349–374 (2002)

    Article  Google Scholar 

  19. García de la Fuente, I., González, J.A., Cobos, J.C., Casanova, C.: Excess molar volumes for dimethyl carbonate + heptane, decane, 2,2,4-trimethylpentane, cyclohexane, benzene, toluene, or tetrachloromethane. J. Chem. Eng. Data 37, 535–537 (1992)

    Article  Google Scholar 

  20. García de la Fuente, I., González, J.A., Cobos, J.C., Casanova, C.: Excess molar volumes of diethyl carbonate with hydrocarbons or tetrachloromethane at 25 Ĉ. J. Solution Chem. 24, 827–835 (1995)

    Article  Google Scholar 

  21. García, I., Cobos, J.C., González, J.A., Casanova, C., Cocero, M.J.: Thermodynamics of binary mixtures containing organic carbonates. 1. Excess enthalpies of dimethyl carbonate + hydrocarbons or + tetrachloromethane. J. Chem. Eng. Data 33, 423–426 (1988)

    Article  Google Scholar 

  22. García, I., Cobos, J.C., González, J.A., Casanova, C.: Excess enthalpies of diethyl carbonate + some normal alkanes (C6-C14), + cyclohexane, + methylcyclohexane, + benzene, + toluene, or + tetrachloromethane. Int. Data Ser., Selected Data Mixtures Ser. A3, 164–173 (1987)

    Google Scholar 

  23. Kehiaian, H.V., González, J.A., García, I., Cobos, J.C., Casanova, C., Cocero, M.J.: Prediction of vapour-liquid and liquid-liquid equilibria and of excess enthalpies of mixing in linear carbonates + n-alkane or+ cyclohexane mixtures using DISQUAC. Fluid Phase Equilib. 64, 1–11 (1991)

    Article  CAS  Google Scholar 

  24. Kehiaian, H.V., González, J.A., García, I., Cobos, J.C., Casanova, C., Cocero, M.J.: Steric and inductive in binary mixtures of organic carbonates with aromatic hydrocarbons or tetrachloromethane. Fluid Phase Equilib. 69, 81–89 (1991)

    Article  CAS  Google Scholar 

  25. Kehiaian, H.V.: Thermodynamics of binary liquid organic mixtures. Pure Appl. Chem. 57, 15–30 (1985)

    Article  CAS  Google Scholar 

  26. Guggenheim, E.A.: Mixtures (Oxford University Press, Oxford, 1952)

    Google Scholar 

  27. Heintz, A.: A new theoretical approach for predicting excess properties of alkanol-alkane mixtures. Ber. Bunsenges. Phys. Chem. 89, 172–181 (1985)

    CAS  Google Scholar 

  28. Kirkwood, J. G., Buff, F.P.: The statistical mechanical theory of solutions 1. J. Chem. Phys. 19, 774–777 (1951)

    Article  CAS  Google Scholar 

  29. Ben-Naim, A.: Inversion of the Kirkwood-Buff theory of solutions: Application to the water-ethanol system. J. Chem. Phys. 67, 4884–4890 (1977)

    Article  CAS  Google Scholar 

  30. Matteoli, E., Lepori, L.: Solute-solute interactions in water. II. An analysis through the Kirkwood-Buff integrals for 14 organic solutes. J. Chem. Phys. 80, 2856–2863 (1984)

    Article  CAS  Google Scholar 

  31. Marcus, Y.: Preferential solvation in mixed solvents. X. Completely miscible aqueous co-solvent binary mixtures at 298.15 K. Monatsh. Chem. 132, 1387–1411 (2001)

    CAS  Google Scholar 

  32. Zielkiewicz, J.: Solvation of DMF in the N,N-dimethylformamide + alcohol + water mixtures investigated by means of the Kirkwood-Buff integrals. J. Phys. Chem. 99, 4787–4793 (1995)

    Article  CAS  Google Scholar 

  33. Zielkiewicz, J.: Solvation of amide group by water and alcohols investigated using the Kirkwood-Buff theory of solutions. J. Chem. Soc. Faraday Trans. 94, 1713–1719 (1998)

    Article  CAS  Google Scholar 

  34. Allen, G., Chai, Z., Chong, C.L., Higgins, J.S., Tripathi, J.: Thermodynamics of oligomeric binary mixtures of polyethylene glycol and polypropylene glycol methylethers. Polymer 25, 239–244 (1984)

    Article  CAS  Google Scholar 

  35. Pardo, J.M., Tovar, C.A., Cerdeiriňa, C.A., Carballo, E., Romaní, L.: Excess molar volumes and excess molar heat capacities of dimethyl carbonate, or diethyl carbonate + n-heptane at several temperatures. J. Chem. Thermodyn. 31, 787–796 (1999)

    Article  CAS  Google Scholar 

  36. Pardo, J.M., Tovar, C.A., Cerdeirińa, C.A., Carballo, E., Romaní, L.: Excess quantities of dialkyl carbonate+ cyclohexane mixtures at a variable temperature. Fluid Phase Equilib. 179, 151–163 (2001)

    Article  CAS  Google Scholar 

  37. Zielkiewicz, J.: Preferential solvation of N-methylformamide, N,N-dimethylformamide and N-methylacetamide by water and alcohols in the binary and ternary mixtures. Phys. Chem. Chem. Phys. 2, 2925–2932 (2000)

    Article  CAS  Google Scholar 

  38. Orye, R. V., Prausnitz, J.M.: Thermodynamic properties of some binary solutions containing hydrocarbons and polar organic solvents. Trans Faraday Soc. 61, 1338–1346 (1965)

    Article  CAS  Google Scholar 

  39. Negadi, L., Blondel, A., Mokbel, I., Ait-Kaci, A., Jose, J.: Liquid-vapor equilibria, excess Gibbs energies, and excess volumes of dimethyl carbonate + heptane, + 1-hexene, + cyclohexane, or + benzene. Int. Data Ser., Sel. Data Mixtures Ser. A 21, 169–194 (1993)

    Google Scholar 

  40. Rodríguez, A., Canosa, J., Tojo, J.: Physical properties of binary mixtures (dimethyl carbonate + alcohols) at several temperatures. J. Chem. Eng. Data 46, 1476–1486 (2001)

    Article  Google Scholar 

  41. Comelli, F., Francesconi, R.: Isothermal vapor-liquid equilibria measurements, excess molar enthalpies and excess molar volumes of dimethyl carbonate + methanol, + ethanol, and + propan-1-ol at 313.15 K. J. Chem. Eng. Data 42, 705–709 (1997)

    Article  CAS  Google Scholar 

  42. Riddick, J.A., Bunger, W.B., Sakano, T.K.: Organic solvents, in techniques of chemistry, Vol. II A. Weissberger, Ed. (Wiley, New York, 1986)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. G.E.T.E.F. Dpto Termodinámica y Física Aplicada, Facultad de Ciencias, Universidad de Valladolid, Valladolid, 47071, Spain

    Juan Antonio González, Ismael Mozo, S. Villa, Nicolás Riesco, Isaías García de la Fuente & José Carlos Cobos

Authors
  1. Juan Antonio González
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ismael Mozo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Villa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nicolás Riesco
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Isaías García de la Fuente
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. José Carlos Cobos
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Juan Antonio González.

Rights and permissions

Reprints and permissions

About this article

Cite this article

González, J.A., Mozo, I., Villa, S. et al. Thermodynamics of Mixtures Containing Organic Carbonates. Part XV. Application of the Kirkwood-Buff Theory to the Study of Interactions in Liquid Mixtures Containing Dialkyl Carbonates and Alkanes, Benzene, CCl4 or 1-Alkanols. J Solution Chem 35, 787–801 (2006). https://doi.org/10.1007/s10953-006-9030-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-006-9030-4

Keywords

Search

Navigation