Advertisement

Experimental determination and thermodynamic modeling of solid–liquid-phase equilibrium for the 3-nitrotoluene and 4-nitrotoluene binary system

  • Yanfei Wang
  • Xiaoyu Liu
  • Xiaoyu ZhaoEmail author
  • Zhao Chen
  • Libin Yang
  • Liang Zhu
Article
  • 14 Downloads

Abstract

Solid–liquid-phase equilibrium is an important part of chemical thermodynamics, and its basic theoretical research plays a vital role in the advancement of the chemical industry. Solid–liquid equilibria for binary mixtures of 3-nitrotoluene and 4-nitrotoluene were measured using differential scanning calorimetry under atmospheric pressure (101.3 kPa). The results showed that the phase diagram of the 3-nitrotoluene + 4-nitrotoluene binary system presented a eutectic behavior, and the eutectic point was x1 = 0.6487, TE = 272.15 K. Furthermore, the experimental results were correlated with Wilson and nonrandom two-liquid (NRTL) activity coefficient models well. The relative standard deviations were 0.496 and 0.236, respectively, and the absolute mean deviations were 0.005 and 0.001, respectively.

Keywords

Eutectic behavior DSC analysis Phase diagram Solid–liquid equilibria 

Notes

Acknowledgements

This work was supported by the Key Technology Support Program of Qinghai Province (No. 215-GX-109A); Natural Science Foundation of Tianjin Municipality (18JCYBJC21200); National Natural Science Foundation of China (U1407204); Yangtze Scholars and Innovative Research Team in Chinese University (IRT-17R81); and the Innovative Research Team of Tianjin Municipal Education Commission (TD12-5004).

Supplementary material

10973_2019_8356_MOESM1_ESM.docx (25 kb)
Supplementary material 1 (DOCX 25 kb)

References

  1. 1.
    Avula SGC, Alexander K, Riga A. Thermal analytical characterization of mixtures of antipsychotic drugs with various excipients for improved drug delivery. J Therm Anal Calorim. 2016;123(3):1981–92.  https://doi.org/10.1007/s10973-015-4763-1.CrossRefGoogle Scholar
  2. 2.
    Boumrah Y, Bouzahia I, Bouanani S, Khimeche K, Dahmani A. Thermodynamic and analytical studies of drugs binary systems of paracetamol mixed with pseudoephedrine HCl, dextropropoxyphene HCl and tramadol HCl. Thermochimica acta. 2016;634:48–56.  https://doi.org/10.1016/j.tca.2016.03.025.CrossRefGoogle Scholar
  3. 3.
    Corvis Y, Menet MC, Espeau P. Incidence of the melting-degradation process of vitamin C on the determination of the phase diagram with acetaminophen enhanced by high performance liquid chromatography tools. New J Chem. 2015;39(3):1938–42.  https://doi.org/10.1039/C4NJ01766H.CrossRefGoogle Scholar
  4. 4.
    Jain H, Khomane KS, Bansal AK. Implication of microstructure on the mechanical behavior of an aspirin–paracetamol eutectic mixture. CrystEngComm. 2014;16:8471–8.  https://doi.org/10.1039/C4CE00878B.CrossRefGoogle Scholar
  5. 5.
    Sifaoui H, Rogalski M. Solid–liquid equilibria of three binary systems of anthracene with 2-phenylimidazole, 4, 5-diphenylimidazole and 2, 4, 5-triphenylimidazole. Thermochim Acta. 2012;543:32–6.  https://doi.org/10.1016/j.tca.2012.04.032.CrossRefGoogle Scholar
  6. 6.
    Maximo GJ, Carareto ND, Costa MC, dos Santos AO, Cardoso LP, Krähenbühl MA, Meirelles AJ. On the solid–liquid equilibrium of binary mixtures of fatty alcohols and fatty acids. Fluid Phase Equilibr. 2014;366:88–98.  https://doi.org/10.1016/j.fluid.2014.01.004.CrossRefGoogle Scholar
  7. 7.
    Salceanu DC, Pincu E, Bruni G, Marini A, Meltzer V. Physico-chemical study of norfloxacin and metronidazole binary mixtures. J Therm Anal Calorim. 2018;132(2):1095–103.  https://doi.org/10.1007/s10973-017-6919-7.CrossRefGoogle Scholar
  8. 8.
    Saganowska P, Wesolowski M. DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers. J Therm Anal Calorim. (1). 2018;133:785–95.  https://doi.org/10.1007/s10973-017-6858-3.CrossRefGoogle Scholar
  9. 9.
    Hillert M. Phase equilibria, phase diagrams and phase transformations: their thermodynamic basis. Cambridge: Cambridge University Press; 2007.CrossRefGoogle Scholar
  10. 10.
    Wei D, Han S, Wang B. “Solid–liquid phase equilibrium study of binary mixtures of n-octadecane with capric, and lauric acid as phase change materials (PCMs). Fluid Phase Equilibr. 2014;373:84–8.  https://doi.org/10.1016/j.fluid.2014.04.020.CrossRefGoogle Scholar
  11. 11.
    Huang CC, Chen YP. Measurements and model prediction of the solid–liquid equilibria of organic binary mixtures. Chem Eng Sci. 2000;55(16):3175–85.  https://doi.org/10.1016/S0009-2509(99)00593-X.CrossRefGoogle Scholar
  12. 12.
    Klimova K, Leitner J. DSC study and phase diagrams calculation of binary systems of paracetamol. Thermochim Acta. 2012;550:59–64.  https://doi.org/10.1016/j.tca.2012.09.024.CrossRefGoogle Scholar
  13. 13.
    Takiyama H, Suzuki H, Uchida H, Matsuoka M. Determination of solid–liquid phase equilibria by using measured DSC curves. Fluid phase equilibr. 2002;194:1107–17.  https://doi.org/10.1016/S0378-3812(01)00656-2.CrossRefGoogle Scholar
  14. 14.
    Meltzer V, Pincu E. A DSC study for binary mixture of 2-chlorobenzoic acid with salicylic acid. Rev Chim-bucharest. 2009;54:333–8.Google Scholar
  15. 15.
    Shirazi L, Hadipour A. Determination of the kinetic parameters and modeling of the reactor for hydrogenation of m-nitroyoluene in a multi phaseslurry reactor. Pet Coal. 2007;49(3):63–70.Google Scholar
  16. 16.
    Priegnitz JW, Landis AM. U.S. Patent No. 4,270,013. Washington, DC: U.S. Patent and Trademark Office. 1981-5-26.Google Scholar
  17. 17.
    Wilson GM. Vapor-liquid equilibrium. XI. A new expression for the excess free energy of mixing. J Am Chem Soc. 1964;86(2):127–30.  https://doi.org/10.1021/acs.jmedchem.5b01416.CrossRefGoogle Scholar
  18. 18.
    Renon H, Prausnitz JM. Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J. 1968;14(1):135–44.  https://doi.org/10.1002/aic.690140124.CrossRefGoogle Scholar
  19. 19.
    Gross PM, Saylor JH. The solubilities of certain slightly soluble organic compounds in water. J Am Chem Soc. 1931;53(5):1744–51.  https://doi.org/10.1021/acs.est.7b03909.CrossRefGoogle Scholar
  20. 20.
    Dessart A. Theory of concentrated solutions: III. Physical constants of mixtures of m-nitrotoluene and m-toluidine with some hydrocarbons. Bull Soc Chim Belg. 1926;35:9.Google Scholar
  21. 21.
    Richardson MJ, Savill NG. Free energy changes by differential scanning calorimetry: application to a low energy but metastable form of p-nitrotoluene. Thermochim Acta. 1979;30:327–37.  https://doi.org/10.1016/0040-6031(79)85068-6.CrossRefGoogle Scholar
  22. 22.
    Marsh KN, Marsh KN, editors. Recommended reference materials for the realization of physicochemical properties. Oxford: Blackwell Scientific Publications; 1987.Google Scholar
  23. 23.
    Cauwood JD, Turner WES. XXXI.—The dielectric constants of some organic solvents at their melting or boiling points. J Chem Soc Trans. 1915;107:276–82.  https://doi.org/10.1039/CT9150700276.CrossRefGoogle Scholar
  24. 24.
    Neubeck F. The molecular volume of aromatic compounds. Z Phys Chem (Leipzig). 1887;1:649–67.Google Scholar
  25. 25.
    Acree WE Jr. Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation. Thermochim Acta. 1991;189:37–56.  https://doi.org/10.1016/0040-6031(91)87098-H.CrossRefGoogle Scholar
  26. 26.
    Singh J, Singh NB. Phase equilibrium, crystallization behavior and thermodynamic studies of (m-dinitrobenzene + vanillin) eutectic system. J Chem Thermodyn. 2015;89:197–204.  https://doi.org/10.1016/j.jct.2015.05.020.CrossRefGoogle Scholar
  27. 27.
    Bi M, Hwang SJ, Morris KR. Mechanism of eutectic formation upon compaction and its effects on tablet properties. Thermochim Acta. 2003;404:213–26.  https://doi.org/10.1016/S0040-6031(03)00185-0.CrossRefGoogle Scholar
  28. 28.
    Boumrah Y, Bouanani S, Khimeche K, Dahmani A. Analysis of synthetic drugs by differential scanning calorimetry. J Therm Anal Calorim. 2015;120:583–90.  https://doi.org/10.1007/s10973-014-4236-y.CrossRefGoogle Scholar
  29. 29.
    Boudouh I, Hafsaoui SL, Mahmoud R, Barkat D. Measurement and prediction of solid–liquid phase equilibria for systems containing biphenyl in binary solution with long-chain n-alkanes. J Therm Anal Calorim. 2016;125:793–801.  https://doi.org/10.1007/s10973-016-5407-9.CrossRefGoogle Scholar
  30. 30.
    Choi PB, Mclaughlin E. Effect of a phase transition on the solubility of a solid. Aiche J. 1983;29:150–3.  https://doi.org/10.1002/aic.690290121.CrossRefGoogle Scholar
  31. 31.
    Weimer RF, Prausnitz JM. Complex formation between carbon tetrachloride and aromatic hydrocarbons. J Chem Phys. 1965;42(10):3643–4.  https://doi.org/10.1063/1.1695773.CrossRefGoogle Scholar
  32. 32.
    Ambrose D, Gundry HA. The vapour pressure of p-nitrotoluene. J Chem Thermodyn. 1980;12(6):559–61.  https://doi.org/10.1016/0021-9614(80)90185-8.CrossRefGoogle Scholar
  33. 33.
    Chernik GG. Phase equilibria in phospholipid-water systems. Adv Colloid Interface. 1995;61:65–129.  https://doi.org/10.1016/0001-8686(95)00262-O.CrossRefGoogle Scholar

Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2019

Authors and Affiliations

  1. 1.Tianjin Key Laboratory of Marin Resources and Chemistry, College of chemical Engineering and Materials ScienceTianjin University of Science and TechnologyTianjinChina

Personalised recommendations