Abstract
The solubility of (1R,2R)-(+)-1,2-diaminocyclohexane L-tartrate (DHT) in methanol + water, ethanol + water, and 2-propanol + water mixed solvents were measured using a synthetic method with alcohols mass fractions varying from 0.1 to 0.5 over 278.15 to 318.15 K under atmospheric pressure (P = 0.1 MPa). It was proved that the solubility of DHT in the three binary solvents increased with increasing temperature, while decreased with the mass fraction of alcohols rising. The experimental solubility data were correlated by the modified Apelblat equation and Sun model. The modified Apelblat model showed better agreement with the experimental data than the other model. Furthermore, the thermodynamic parameters including \(\Delta G_{{{\text{sol}}}}^{^\circ }\), \(\Delta H_{{{\text{sol}}}}^{^\circ }\), and \(\Delta S_{{{\text{sol}}}}^{^\circ }\) for DHT in the dissolution process were obtained from Van’t Hoff plots.
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REFERENCES
R. Kowalczyk, Ł. Sidorowicz, and J. Skarżewski, Tetrahedron Asymmetry 40, 2310 (2009).
R. G. Kostyanovsky, F. A. Lakhvich, P. M. Philipchenko, et al., Mendeleev Commun. 12, 147 (2002).
H. J. Schanz, M. A. Linseis, and D. G. Gilheany, Tetrahedron: Asymmetry 14, 2763 (2003).
A. Galland, V. Dupray, A. Lafontaine, et al., Tetrahedron: Asymmetry 21, 2212 (2010).
T. Tashiro, Y. Kawada, Y. Sakurai, et al., Biomed. Pharmacother. 43, 260 (1989).
E. Raymond, S. Faivre, J. M. Woynarowski, et al., Seminars Oncol. 25 (2 Suppl 5), 4 (1998).
D. Y. K. Chen, R. H. Pouwer, and J. A. Richard, Chem. Soc. Rev. 41, 4642 (2012).
Z. X. Miao, M. X. Li, M. Shao, et al., Inorg. Chem. Commun. 10, 1120 (2007).
J. W. Mullin, Crystallization (Butterworth-Heinemann, London, 2001).
Q. Yu, S. Black, and H. Wei, J. Chem. Eng. Data 54, 2125 (2009).
H. Li, Y. Dou, J. Zhang, et al., J. Mol. Liq. 243, 394 (2017).
J. Zhang, S. Yang, H. Li, et al., J. Mol. Liq. 238, 315 (2017).
F. Zhang, Y. Tang, L. Wang, et al., J. Chem. Eng. Data 60, 2509 (2015).
K. D. Bhesaniya, K. Nandha, and S. Baluja, J. Chem. Thermodyn. 74, 38 (2014).
L. C. Wang and F. A. Wang, J. Chem. Eng. Data 49, 155 (2004).
H. Ma, Y. Qu, Z. Zhou, et al., J. Chem. Eng. Data 57, 2121 (2012).
Y. Wu, Y. Qin, L. Bai, et al., J. Chem. Thermodyn. 103, 284 (2016).
H. Guo, X. Dang, F. Yang, et al., J. Mol. Liq. 247, 327 (2017).
Y. Zhang, F. Guo, Q. Cui, et al., J. Chem. Eng. Data 61, 420 (2015).
R. R. Krug, W. G. Hunter, and R. A. Grieger, J. Phys. Chem. 80, 2335 (1976).
D. R. Delgado and F. Martínez, Fluid Phase Equilib. 360, 96 (2013).
W. E. Acree and A. I. Zvaigzne, Thermochim. Acta 178, 167 (1991).
J. Li, Z. Wang, Y. Bao, et al., Ind. Eng. Chem. Res. 52, 3019 (2013).
J. Su, C. Qian, N. Luo, et al., J. Chem. Eng. Data 59, 3894 (2014).
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Huanxin Li, Zhang, H., Dou, Y. et al. Solubility and Thermodynamic Properties of (1R,2R)-(+)-1,2-Diaminocyclohexane L-Tartrate in Methanol (Ethanol or 2-Propanol) + Water Binary Solvents at Various Temperatures. Russ. J. Phys. Chem. 93, 696–702 (2019). https://doi.org/10.1134/S0036024419040149
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DOI: https://doi.org/10.1134/S0036024419040149