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Vapor–Liquid Equilibrium Measurement and Thermodynamic Correlations of 4-Nonyl Phenol Diethoxylate with sec-Butanol at Elevated Pressures

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Abstract

The isothermal vapor–liquid equilibrium (VLE) data for a binary system of 4-nonyl phenol diethoxylate with sec-butanol at (333.0 to 425.0) K have been measured by using a static-type apparatus. The system pressures at a given feed composition were measured to generate the P–T–x data and are further compared to the pressure values calculated using the Antoine equation. Two thermodynamic models, the UNIQUAC and the NRTL models, were selected to correlate the VLE data at various temperatures. The analysis showed that the experimental data agree well with these activity coefficient models. Finally, the solvent activities were estimated, and the values are consistent with the values calculated from the phase equilibrium data.

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References

  1. Pedrosa, N., Pamies, J.C., Coutinho, J.A.P., Marrucho, I.M., Vega, L.F.: Phase equilibria of ethylene glycol oligomers and their mixtures. Ind. Eng. Chem. Res. 44, 7027–7037 (2005)

    CAS  Google Scholar 

  2. Frensdorff, H.K.: Stability constants of cyclic polyether complexes with univalent cations. J. Am. Chem. Soc. 93, 600–606 (1971)

    CAS  Google Scholar 

  3. Kjellander, R., Florin, E.: Water structure and changes in the thermal stability of the system poly(ethylene oxide). J. Chem. Soc. Faraday Trans. 77, 2053–2077 (1981)

    CAS  Google Scholar 

  4. Powell, G.M.: Polyethylene glycol. In: Davidson, R.L. (ed.) Handbook of Water Soluble Gums and Resins. McGraw-Hill Book Company, New York (1980)

    Google Scholar 

  5. Harris, J.M.: Poly(ethylene glycol) Chemistry, Biothechnical and Biomedical Applications. Plenum Press, New York (1992)

    Google Scholar 

  6. Wyrwas, B., Szymanski, A., Lukaszewski, Z.: Tensammetric determination of non-ionic surfactants combined with the BiAS separation procedure. Part 3. Determination in the presence of hydrocarbons. Talanta 47, 325–333 (1998)

    CAS  PubMed  Google Scholar 

  7. Shelley, J.C., Shelley, M.Y.: Computer simulation of surfactant solutions. Curr. Opin. Colloid Interface Sci. 5, 101–110 (2000)

    CAS  Google Scholar 

  8. Ushakova, A.V., Grivennikova, V.G., Ohnishi, T., Vinogradov, A.D.: Triton X-100 as a specific inhibitor of the mammalian NADH-ubiquinone oxidoreductase (complex I). Biochim. Biophys. Acta 1409, 143–153 (1999)

    CAS  PubMed  Google Scholar 

  9. Preté, P.S.C., Malheiros, S.V.P., Meirelles, N.C., de Paula, E.: Solubilization of human erythrocyte membranes by non-ionic surfactants of the polyoxyethylene alkyl ethers series. Biophys. Chem. 97, 45–54 (2002)

    PubMed  Google Scholar 

  10. Klle, D.E., Chlou, C.T.: Water solubility enhancement of DDT and trichlorobenzene by some surfactants below and above the critical micelle concentration. Environ. Sci. Technol. 23, 832–838 (1989)

    Google Scholar 

  11. Benomar, S.H., Clench, M.R.: The analysis of alkylphenol ethoxysulphonate surfactants by high-performance liquid chromatography, liquid chromatography-electrospray ionisation-mass spectrometry and matrix-assisted laser desorption ionisation-mass spectrometry. Anal. Chim. Acta 445, 255–267 (2001)

    CAS  Google Scholar 

  12. Kamiusuki, T., Monde, T., Nemoto, F., Konakahara, T., Takahashi, Y.: Separation and characterization of octylphenol ethoxylate surfactants used by reversed-phase high-performance liquid chromatography on branched fluorinated silica gel columns. J. Chromatogr. A 852, 475–485 (1999)

    CAS  PubMed  Google Scholar 

  13. Førland, G.M.: Influence of alcohol on the behavior of sodium dodecylsulfate micelles. J. Colloid Interface Sci. 203, 328–334 (1998)

    PubMed  Google Scholar 

  14. Domańska, U., Maciej, Z., Marek, K., Anna, L.: Phase equilibria study of binary and ternary mixtures of {N-octylisoquinolinium bis{(trifluoromethyl)-sulfonyl}imide + hydrocarbon, or an alcohol, or water. Chem. Eng. J. 181, 63–71 (2012)

    Google Scholar 

  15. Wen, H., Elbro, H.S., Alessi, P.: Polymer Solution Data Collection Part 1. DECHEMA Chemistry Data Series. DECHEMA, Frankfurt (1992)

    Google Scholar 

  16. Wen, H., Elbro, H.S., Alessi, P.: Polymer Solution Data Collection Part 2 + 3. DECHEMA Chemistry Data Series. DECHEMA, Frankfurt (1992)

    Google Scholar 

  17. Danner, R.P., High, M.S.: Handbook of Polymer Solution Thermodynamics. Wiley, New York (1993)

    Google Scholar 

  18. Wohlfarth, C.: Vapour-Liquid Equilibrium Data of Binary Polymer Solutions: Vapour Pressures, Henry-Constants and Segment-Molar Excess Gibbs Free Energies. Elsevier, Amsterdam (1994)

    Google Scholar 

  19. Haynes, C.A., Beynon, R.A., King, R.S., Branch, H.W., Prausnitz, J.M.: Thermodynamic properties of aqueous polymer solutions: poly(ethylene glycol)/dextran. J. Phys. Chem. 93, 5612–5617 (1989)

    CAS  Google Scholar 

  20. Rowley, R.L., Hoffma, G.L.: Vapor–liquid equilibrium measurements on mixtures important to industrial design: triethylene glycol + n-hexane, triethylene glycol + cyclohexane and furfural + isoprene. AIChE Symp. Ser. 86, 6–19 (1990)

    CAS  Google Scholar 

  21. Herraiz, J., Shen, S., Coronas, A.: Vapor liquid equilibria for methanol + poly(ethylene glycol) 250 dimethyl ether. J. Chem. Eng. Data 43, 191–195 (1998)

    CAS  Google Scholar 

  22. Gupta, S.K., Rawat, B.S., Goswami, A.N., Nanoti, S.M., Krishna, R.: Isobaric vapor liquid equilibria of the systems: benzene–triethylene glycol, toluene–triethylene glycol and benzene–n-methylpyrrolidone. Fluid Phase Equilib. 46, 95–102 (1989)

    CAS  Google Scholar 

  23. Breman, B.B., Beenackers, A.A.C.M., Rietjens, E.W.J., Stege, R.J.H.: Gas–liquid solubilities of carbon monoxide, carbon dioxide, hydrogen, water, 1-alcohols (1 < 6), and n-paraffins (2 < 6) in nexadecane, octacosane, 1-hexadecanol, phenanthrene, and tetraethylene glycol at pressures up to 5.5 MPa and temperatures from 293 to 553 K. J. Chem. Eng. Data 39, 647–666 (1994)

    CAS  Google Scholar 

  24. Chaudhari, S.K., Patil, K.R., Allepus, J., Coronas, A.: Measurement of the vapor pressure of 2,2,2-trifluoroethanol and tetraethylene glycol dimethyl ether by static method. Fluid Phase Equilib. 108, 159–165 (1995)

    CAS  Google Scholar 

  25. Jou, F.-Y., Otto, F.D., Mather, A.E.: Solubility of H2S and CO2 in diethylene glycol at elevated pressures. Fluid Phase Equilib. 175, 53–61 (2000)

    CAS  Google Scholar 

  26. Khoiroh, I., Lee, M.-J.: Isothermal (vapour + liquid) equilibrium for binary mixtures of polyethylene glycol mono-4-nonylphenyl ether (PEGNPE) with methanol, ethanol, or 2-propanol. J. Chem. Thermodyn. 43, 1417–1423 (2011)

    CAS  Google Scholar 

  27. Khoiroh, I., Lee, M.-J.: Isothermal vapor–liquid equilibrium for binary mixtures of polyoxyethylene dodecanoate with methanol, ethanol, or propan-2-ol. J. Chem. Eng. Data 57, 545–552 (2012)

    CAS  Google Scholar 

  28. Khoiroh, I., Lee, M.-J.: Vapor–liquid equilibria of binary systems composed of polyoxyethylene 4-octylphenyl ether and alcohols: experimental measurements and correlation. Fluid Phase Equilib. 360, 111–117 (2013)

    CAS  Google Scholar 

  29. Zafarani-Moattar, M.T., Yeganeh, N.: Isopiestic determination of 2-propanol activity in 2-propanol + poly(ethylene glycol) solutions at 25 °C. J. Chem. Eng. Data 47, 72–75 (2002)

    CAS  Google Scholar 

  30. Zafarani-Moattar, M.T., Sarmad, S.: Measurement and correlation of phase equilibria for poly(ethylene glycol) methacrylate + alcohol systems at 298.15 K. J. Chem. Eng. Data 50, 283–287 (2005)

    CAS  Google Scholar 

  31. Esteve, X., Chaudari, S.K., Coronas, A.: Vapor liquid equilibria for methanol + tetraethylene glycol dimethyl ether. J. Chem. Eng. Data 40, 1252–1256 (1995)

    CAS  Google Scholar 

  32. Zheng, D.-Q., Ma, W.-D., Wei, R., Guo, T.-M.: Solubility study of methane, carbon dioxide and nitrogen in ethylene glycol at elevated temperatures and pressures. Fluid Phase Equilib. 155, 277–286 (1999)

    CAS  Google Scholar 

  33. Yu, Y.-X., Liu, J.-G., Gao, G.-H.: Isobaric vapor–liquid equilibria of three aromatic hydrocarbon–tetraethylene glycol binary systems. Fluid Phase Equilib. 157, 299–307 (1999)

    CAS  Google Scholar 

  34. Renon, H., Prausnitz, J.M.: Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J. 14, 135–144 (1968)

    CAS  Google Scholar 

  35. Abrams, D.S., Prausnitz, J.M.: Statistical thermodynamics of liquid mixtures: a new expression for the excess Gibbs energy of partly or completely miscible systems. AIChE J. 21, 116–128 (1975)

    CAS  Google Scholar 

  36. Khoiroh, I., Shu, S.S., Lee, M.-J.: Vapor–liquid equilibrium of polyethylene glycol monooleyl ether with 2-butanol, tert-butanol, or 1-pentanol. Fluid Phase Equilib. 404, 81–88 (2015)

    CAS  Google Scholar 

  37. Ambrose, D., Sprake, C.H.S.: Thermodynamic properties of organic oxygen compounds XXV. Vapor pressure and normal boiling temperatures of aliphatic alcohols. J. Chem. Thermodyn. 2, 631–645 (1970)

    CAS  Google Scholar 

  38. Haynes, C.A., Beynon, R.A., King, R.S., Blanch, H.W., Prausnitz, J.M.: Thermodynamic properties of aqueous polymer solutions. J. Phys. Chem. 93, 5612–5617 (1989)

    CAS  Google Scholar 

  39. Tsuji, T., Hasegawa, K., Hiaki, T., Hongo, M.: Isothermal vapor−liquid equilibria for the propan-2-ol + water system containing poly(ethylene glycol) at 298.15 K. J. Chem. Eng. Data 41, 956–960 (1996)

    CAS  Google Scholar 

  40. Pfohl, O., Riebesell, C., Dohrn, R.: Measurement and calculation of phase equilibria in the system n-pentane + polydimethylsiloxane at 308.15–423.15 K. Fluid Phase Equilib. 202, 289–306 (2002)

    CAS  Google Scholar 

  41. Press, W.H., Flannery, P.B., Teukolsky, S.A., Vetterling, W.T.: Numerical Recipes, 2nd edn. Cambridge University Press, Cambridge (1992)

    Google Scholar 

  42. Chen, C.C., Mathias, P.M.: Applied thermodynamics for process modelling. AIChE J. 48, 194–200 (2002)

    CAS  Google Scholar 

  43. Bondi, A.: van der Waals volumes and radii. J. Phys. Chem. 68, 441–451 (1964)

    CAS  Google Scholar 

  44. Barker, J.A.: Determinations of the activity coefficients from total pressure measurements. Aust. J. Chem. 6, 207–210 (1953)

    CAS  Google Scholar 

  45. Abbott, M.M., Van Ness, H.C.: An extension of Barker's method for reduction of VLE data. Fluid Phase Equilib. 1, 3–11 (1977)

    Google Scholar 

  46. Britt, H.I., Luecke, R.H.: The estimation of parameters in nonlinear, implicit models. Technometrics 15, 233–247 (1973)

    Google Scholar 

  47. Poling, B.E., Prausnitz, J.M., O’Connell, J.: The Properties of Gases and Liquids. McGraw-Hill, New York (2000)

    Google Scholar 

  48. Lee, M.-J., Chen, J.-T.: An improved model of second virial coefficients for polar fluids and fluid mixtures. J. Chem. Eng. Jpn. 31, 518–526 (1998)

    CAS  Google Scholar 

  49. Tsonopoulos, C.: An empirical correlation of second virial coefficients. AIChE J. 20, 263–272 (1974)

    CAS  Google Scholar 

  50. Wilding, W.V., Johnson, J.K., Rowley, R.L.: Thermodynamic properties and vapor pressures of polar fluids from a four-parameter corresponding-states method. Int. J. Thermophys. 8, 717–735 (1987)

    CAS  Google Scholar 

  51. Harlacher, E.A., Braun, W.G.: A four-parameter extension of the theorem of corresponding states. Ind. Eng. Chem. Process Des. Dev. 9, 479–483 (1970)

    CAS  Google Scholar 

  52. Gonzalez, J.A., De La Fuente, I.G., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviation from Raoult's law: part 1. Application of the DISQUAC model to mixtures of alkan-1-ols and propanal or linear alkanones and trichloromethane. J. Chem. Soc. Faraday Trans. 93, 3773–3780 (1997)

    CAS  Google Scholar 

  53. González, J.A., De La Fuente, I.G., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviations from Raoult's law: part 2. Application of the DISQUAC model to mixtures of CHCl3 or CH2Cl2 with oxaalkanes. Comparison with Dortmund UNIFAC results. Phys. Chem. Chem. Phys. 1, 275–283 (1999)

    Google Scholar 

  54. Gonzalez, J.A., De la Fuente, I.G., Cobos, J.C.: (2000) Thermodynamics of mixtures with strongly negative deviations from Raoult's law: part 3. Application of the DISQUAC model to mixtures of triethylamine with alkanols. Comparison with Dortmund UNIFAC and ERAS results. Can. J. Chem. 78, 1272–1284 (2000)

    CAS  Google Scholar 

  55. González, J.A., De la Fuente, I.G., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviations from Raoult's law: part 4. Application of the DISQUAC model to mixtures of 1-alkanols with primary or secondary linear amines. Comparison with Dortmund UNIFAC and ERAS results. Fluid Phase Equilib. 168, 31–58 (2000)

    Google Scholar 

  56. Villa, S., Riesco, N., de la Fuente, I.G., González, J.A., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviations from Raoult's law Part 5. Excess molar volumes at 298.15 K for 1-alkanols + dipropylamine systems: characterization in terms of the ERAS model. Fluid Phase Equilib. 190, 113–125 (2001)

    CAS  Google Scholar 

  57. Villa, S., Riesco, N., de la Fuente, I.G., González, J.A., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviations from Raoult's law Part 6. Excess molar volumes at 298.15 K for 1-alkanols + dibutylamine systems. Characterization in terms of the ERAS model. Fluid Phase Equilib. 198, 313–329 (2002)

    CAS  Google Scholar 

  58. Villa, S., Riesco, N., De La Fuente, I.G., González, J.A., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviations from Raoult's law. VII. Excess molar volumes at 25 °C for 1-alkanol + N-methylbutylamine systems—characterization in terms of the ERAS model. J. Solution Chem. 32, 179–194 (2003)

    CAS  Google Scholar 

  59. Villa, S., Riesco, N., De La Fuente, I.G., González, J.A., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviations from Raoult's law. Part 8. Excess molar volumes at 298.15 K for 1-alkanol + isomeric amine (C6H15N) systems: characterization in terms of the ERAS model. Fluid Phase Equilib. 216, 123–133 (2004)

    CAS  Google Scholar 

  60. Villa, S., Garriga, R., Pérez, P., Gracia, M., González, J.A., de la Fuente, I.G., Cobos, J.C.: Thermodynamics of mixtures with strongly negative deviations from Raoult's law: part 9. Vapor–liquid equilibria for the system 1-propanol + di-n-propylamine at six temperatures between 293.15 and 318.15 K. Fluid Phase Equilib. 231, 211–220 (2005)

    CAS  Google Scholar 

  61. Kwak, K., Rosenfeld, D.E., Chung, J.K., Fayer, M.D.: Solute−solvent complex switching dynamics of chloroform between acetone and dimethylsulfoxide—two-dimensional IR chemical exchange spectroscopy. J. Phys. Chem. B 112, 13906 (2008)

    CAS  PubMed  PubMed Central  Google Scholar 

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Acknowledgements

This work was supported by the Ministry of Higher Education of Malaysia under Fundamental Research Grant Scheme (FRGS) through Grant No. FRGS/1/2019/STG07/UNIM/02/3.

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Authors and Affiliations

  1. Department of Chemical and Environmental Engineering, Faculty of Science and Engineering, University of Nottingham Malaysia, Jalan Broga, 43500, Semenyih, Selangor Darul Ehsan, Malaysia

    Ianatul Khoiroh

  2. Department of Chemical Engineering, National Taiwan University of Science and Technology, 43 Keelung Road, Section 4, Taipei, 106-07, Taiwan

    Ming-Jer Lee

  3. Department of Chemical Engineering, Faculty of Engineering, Universitas Negeri Semarang, Kampus Sekaran, Gunungpati, Semarang, 50229, Indonesia

    Dhoni Hartanto

  4. Department of Chemical Engineering, Politeknik Negeri Malang, Jl. Soekarno Hatta No. 9, Malang, 65141, Indonesia

    Asalil Mustain

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  1. Ianatul Khoiroh
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Khoiroh, I., Lee, MJ., Hartanto, D. et al. Vapor–Liquid Equilibrium Measurement and Thermodynamic Correlations of 4-Nonyl Phenol Diethoxylate with sec-Butanol at Elevated Pressures. J Solution Chem 49, 1052–1067 (2020). https://doi.org/10.1007/s10953-020-01014-x

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