Measurement and correlation of the solid-liquid equilibrium of 2-(tert-buty)-5-methylphenol and 2-(tert-buty)-4-methylphenol binary system

Abstract

In this work, the enthalpy of fusion and melting points of 2-(tert-butyl)-5-methylphenol (2B5MP) and 2-(tert-butyl)-4-methylphenol (2B4MP) were measured by differential scanning calorimetry (DSC). The binary solid-liquid equilibrium (SLE) of both compounds were predicted by integrated computer aided system (ICAS) and measured by DSC. The corresponding eutectic molar composition is 0.6998 and the eutectic temperature is 281.96 K. The quasi-static heat capacities of 2B5MP and 2B4MP were evaluated by stochastic temperature modulation DSC technique (TOPEM). The SLE experimental data were correlated using the Margules, Wilson, and non-random two liquid (NRTL) equations and a good agreement between measurement and calculation could be obtained.

Keywords

solid-liquid equilibrium (SLE) / eutectic / integrated computer aided system (ICAS) / TOPEM / correlation

References

[1] Attwood B C, Hall C K. Solid-liquid phase behavior of ternary mixtures. AIChE Journal. American Institute of Chemical Engineers, 2008, 54(7): 1886-1894

[2] Takano K, Gani R, Ishikawa T, Kolar P. Conceptual design and analysis methodology for crystallization processes with electrolyte systems. Fluid Phase Equilibria, 2002, 194-197: 783-803

[3] Hammami A, Mehrotra A K. Non-isothermal crystallization kinetics of n-paraffins with chain lengths between thirty and fifty. Thermochimica Acta, 1992, 211: 137-153

[4] Zhu Y G. Research development and application of 6-tert-butyl-m-cresol. Fine and Specialty Chemicals, 2009, 17(19): 18-20 (in Chinese)

[5] Jiang Z H. 6-tert-Butyl-m-cresol applied in pesticide synthesize. Agrochemicals Today, 2010, 11: 34 (in Chinese)

[6] Zhou D G, Xie G C. Plastic aging and anti-aging technology. Beijing: China Light Industry Press, 2000, 111-112 (in Chinese)

[7] Mustaffa A A, Kontogeorgis G M, Gani R. Analysis and application of GC plus models for property prediction of organic chemical systems. Fluid Phase Equilibria, 2011, 302(1): 274-283

[8] Schawea J E K, Hütter T, Heitz C I, Alig D. Stochastic temperature modulation: a new technique in temperature-modulated DSC. Thermochimica Acta, 2006, 446(1): 147-155

[9] Fraga I, Montserrat S, Hutchinson J M. Vitrification during the isothermal cure of thermosets. Part I. An investigation using TOPEM, a new temperature modulated technique. Journal of Thermal Analysis and Calorimetry, 2008, 91(3): 687-695

[10] Carareto N D D, Costa M C, Rolemberg M P, Krähenbühl M A, Meirelles A J A. The solid-liquid phase diagrams of binary mixtures of even saturated fatty alcohols. Fluid Phase Equilibria, 2011, 303(2): 191e1-191e8

[11] Gani R. ICAS manual, 2011, 72-77

[12] Wei D W, Wang L S, Yan F C, Zhang C. Solid-liquid equilibria of acenaphthene with o-, m-, or p-dichlorobenzene. Fluid Phase Equilibria, 2010, 291(1): 66-70

[13] Tulashie S K, Kaemmerer H, Lorenz H, Seidel-Morgenstern A. Solid-liquid equilibria of mandelic acid enantiomers in two chiral solvents: experimental determination and model correlation. Journal of Chemical & Engineering Data, 2010, 55(1): 333-340

[14] Prausnitz J M, Lichtenthaler R N, Azevedo E G A. Molecular Thermodynamics of Fluid-Phase Equilibria. Third ed. Englewood Cliffs: Prentice-Hall, 1999, 254-269

[15] Edalati K, Horita Z. High-pressure torsion of pure metals: Influence of atomic bond parameters and stacking-fault energy on grain size and correlation with hardness. Acta Materialia, 2011, 59(17): 6831-6836

[16] Verevkin S P. Thermochemistry of phenols: quantification of theortho-, para-, and meta-interactions in tert-alkyl substituted phenols. Journal of Chemical Thermodynamics, 1999, 31(5): 559-585

[17] Khimeche K, Dahmani A. Determination by DSC of solid-liquid diagrams for polyaromatic-4,4'diaminodiphenylmethane binary systems—analysis in terms of modified UNIFAC. Journal of Thermal Analysis and Calorimetry, 2006, 84(1): 47-52

Acknowledgments

We are grateful to Prof. Rafiqul Gani for providing the software ICAS. This work is financially supported by the National Natural Science Foundation of China (Grant Nos. 20836005, 21003077 and 21176184) and Open Project of Key Laboratory of Advanced Energy Materials Chemistry (Nankai University) (KLAEMC-OP201201).

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg