Solubility measurement and thermodynamic properties of sulfamonomethoxine in pure solvents and sulfamonomethoxine hydrate in acetone + water binary solvent at different temperature

doi:10.1016/j.cjche.2020.10.037

Abstract

Abstract: The experimental solubility of sulfamonomethoxine in six different pure solvents (methanol, ethanol, 1-propanol, l-butanol, ethyl acetate and acetone) and sulfamonomethoxine hydrate in acetone + water mixture solvents were measured from 294.55 K to 362.15 K by a laser dynamic method under atmospheric pressure. Experimental results indicated that the solubility data of sulfamonomethoxine increased with temperature increasing in pure solvents and the solubility followed this order: acetone > methanol > ethanol > ethyl acetate > 1-propanol > 1-butanol, but solubility in ethyl acetate was not affected significantly by temperature. In acetone + water mixture solvent, the solubility of sulfamonomethoxine hydrate increased with temperature and the acetone concentration. Thermodynamic equations were applied to correlate solubility data of sulfamonomethoxine and sulfamonomethoxine hydrate including the modified Apelblat equation, λh equation, Wilson equation, NRTL equation, Van’t Hoff-Jouyban Acree equation and modified Apel-Jouyban-Acree equation. Furthermore, thermodynamic properties ΔG_d, ΔH_d and ΔS_d of sulfamonomethoxine and sulfamonomethoxine hydrate in dissolution process were obtained and discussed with the modified Van’t Hoff equation and Gibbs equation.

Key words: Solubility, Sulfamonomethoxine, Sulfamonomethoxine hydrate, Thermodynamic properties

摘要： The experimental solubility of sulfamonomethoxine in six different pure solvents (methanol, ethanol, 1-propanol, l-butanol, ethyl acetate and acetone) and sulfamonomethoxine hydrate in acetone + water mixture solvents were measured from 294.55 K to 362.15 K by a laser dynamic method under atmospheric pressure. Experimental results indicated that the solubility data of sulfamonomethoxine increased with temperature increasing in pure solvents and the solubility followed this order: acetone > methanol > ethanol > ethyl acetate > 1-propanol > 1-butanol, but solubility in ethyl acetate was not affected significantly by temperature. In acetone + water mixture solvent, the solubility of sulfamonomethoxine hydrate increased with temperature and the acetone concentration. Thermodynamic equations were applied to correlate solubility data of sulfamonomethoxine and sulfamonomethoxine hydrate including the modified Apelblat equation, λh equation, Wilson equation, NRTL equation, Van’t Hoff-Jouyban Acree equation and modified Apel-Jouyban-Acree equation. Furthermore, thermodynamic properties ΔG_d, ΔH_d and ΔS_d of sulfamonomethoxine and sulfamonomethoxine hydrate in dissolution process were obtained and discussed with the modified Van’t Hoff equation and Gibbs equation.

关键词: Solubility, Sulfamonomethoxine, Sulfamonomethoxine hydrate, Thermodynamic properties

Yanmin Shen, Wenju Liu, Paifeng Shi, Chao Wang. Solubility measurement and thermodynamic properties of sulfamonomethoxine in pure solvents and sulfamonomethoxine hydrate in acetone + water binary solvent at different temperature[J]. Chinese Journal of Chemical Engineering, 2021, 38(10): 196-204.

References

[1] P. Sukul, M. Spiteller, Sulfonamides in the Environment as Veterinary Drugs, Reviews of Environmental Contamination and Toxicology, Springer, New York (2006)
[2] S.S. Weng, K.L. Ku, H.T. Lai, The implication of mediators for enhancement of laccase oxidation of sulfonamide antibiotics, Bioresour. Technol. 113 (2012) 259-264
[3] A.Y.C. Lin, T.H. Yu, C.F. Lin, Pharmaceutical contamination in residential, industrial, and agricultural waste streams: Risk to aqueous environments in Taiwan, Chemosphere 74 (2008) 131-141
[4] J.S. Lin, H.Y. Pan, S.M. Liu, H.-T. Lai, Effects of light and microbial activity on the degradation of two fluoroquinolone antibiotics in pond water and sediment, J. Environ. Sci. Health Part B 45 (2010) 456-465
[5] C.L. Zhang, F.A. Wang, Y. Wang, Solubilities of sulfadiazine, sulfamethazine, sulfadimethoxine, sulfamethoxydiazine, sulfamonomethoxine, sulfamethoxazole, and sulfachloropyrazine in water from (298.15 to 333.15) K, J. Chem. Eng. Data 52 (2007) 1563-1566
[6] C.L. Zhang, S.Y. Li, Y. Wang, Solubilities of sulfamethazine, sulfadimethoxine, sulfamethoxydiazine, sulfamonomethoxine, sulfamethoxazole, and sulfaquinoxaline in 1-octanol from (298.15 to 333.15) K, J. Chem. Eng. Data. 54 (2009) 1131-1134
[7] G.T. Hefter, R.P.T. Tomkins, John Wiley & Sons Ltd, Chichester, UK (2004) 259-311
[8] Y.L. Shi, C. Qian, X.Z. Chen, Solubility measurement and correlation of (+)-biotin intermediate lactone in different organic solvents from 287.15 to 323.75 K, J. Chem. Eng. Data. 61 (2016) 1509-1516
[9] M. Charles, Hansen, Hansen Solubility Parameters - A User’s Handbook, CRC Press, New York (1998)
[10] C.M. Hansen, A.L. Smith, Using Hansen solubility parameters to correlate solubility of C60 fullerene in organic solvents and in polymers, Carbon 42 (2004) 1591-1597
[11] Y.M. Wan, H.X. He, P.S. Zhang, Z.B. Huang, R. Zhao, J. Sha, T. Li, B.Z. Ren, Solid-liquid equilibrium solubility and thermodynamic properties of cis-5-norbornene-endo-2,3-dicarboxylic anhydride in fourteen pure solvents and three binary solvents at various temperatures, J. Mol. Liq. 297 (2020) 111396
[12] A. Apelblat, E. Manzurola, Solubility of oxalic, malonic, succinic, adipic, maleic, malic, citric, and tartaric acids in water from 278.15 to 338.15 K, J. Chem. Thermodyn. 19 (1987) 317-320
[13] D. Xu, X. Xiong, L. Yang, Z. Zhang, X. Wang, Determination of the solubility of ammonium dihydrogen phosphate in water-ethanol system at different temperatures from 283.2 to 343.2 K, J. Chem. Eng. Data 61 (2016) 78-82
[14] N. Tang, W. Shi, W. Yan, Modified method for measuring the solubility of pharmaceutical compounds in organic solvents by visual camera, J. Chem. Eng. Data 61 (2016) 35-40
[15] H. Buchowski, A. Khiat, Solubility of solids in liquids: one-parameter solubility equation, Fluid Phase Equilibria 25 (1986) 273-278
[16] K. Zhao, L. Lin, C. Li, S. Du, C. Huang, Y. Qin, P. Yang, K. Li, J. Gong, Measurement and correlation of solubility of γ-aminobutyric acid in different binary solvents, J. Chem. Eng. Data 61 (2016) 1210-1220
[17] S.M. Walas, 8 - Liquid-Solid Equilibrium, Phase Equilibria in Chemical Engineering, Butterworth-Heinemann, Boston, USA (1985) 395-432
[18] H. Shi, Y. Xie, C. Du, Y. Cong, J. Wang, H. Zhao, Thermodynamic study of the solubility of 2,4'-dihydroxydiphenyl sulfone in nine organic solvents from T=(278.15 to 313.15)K and thermodynamic properties of dissolution, J. Chem. Thermodyn. 102 (2016) 79-88
[19] G.M. Wilson, Vapor-Liquid Equilibrium. XI. A new expression for the excess free energy of mixing, J. Am. Chem. Soc. 86 (1964) 127-130
[20] Front Matter A2 - Smallwood, Ian M, Handbook of Organic Solvent Properties, Butterworth-Heinemann, Oxford, 1996.
[21] H. Renon, J.M. Prausnitz, Estimation of parameters for the NRTL equation for excess Gibbs energies of strongly nonideal liquid mixtures, Ind. Eng. Chem. Process Des. Dev. 8 (1969) 413-419
[22] M. Valavi, M. Svard, A.C. Rasmuson, Prediction of the solubility of medium-sized pharmaceutical compounds using a temperature-dependent NRTL-SAC model, Ind. Eng. Chem. Res. 55 (2016) 11150-11159
[23] A. Jouyban, Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures, J. Pharm. Pharm. Sci. 11 (2008) 32
[24] A. Jouyban, M. Fakhree, W.E. Acree Jr., Correct derivation of cosolvency models and some comments on “Solubility of fenofibrate in different binary solvents: Experimental data and results of thermodynamic modelling”, J. Chem. Eng. Data 62 (2017) 1153–1156.
[25] H. Rezaei, E. Rahimpour, T. Ghafourian, F. Martinez, M. Barzegar-Jalali, A. Jouyban, Solubility of caffeine in N-methyl-2-pyrrolidone + ethanol mixture at different temperatures, J. Mol. Liq. 300 (2020) 112354
[26] Y.M. Shen, W.J. Liu, Z.H. Bao, Solubility measurement and thermodynamic modeling of DoxycyclineHyclate two binary solvent systems at 276.95-323.75 K, J. Mol. Liq. 289 (2019) 111138
[27] O. Ferreira, S.P. Pinho, Solubility of flavonoids in pure solvents, Ind. & Eng. Chem. Res. 51 (2012) 6586-6590
[28] W. Liu, Y. Guo, J. Chen, X. Yu, Measurement and correlation of the solubility of telmisartan (Form A) in nine different solvents from 277.85 to 338.35 K, J. Solu. Chem. 45 (2016) 932-946
[29] G.T. Hefter, R.P.T. Tomkins, John Wiley & Sons, Ltd, Chichester, UK (2004)
[30] B. Liu, H. Sun, J. Wang, Q. Yin, Thermodynamic analysis and correlation of solubility of disodium 5-guanylate heptahydrate in aqueous ethanol mixtures, Fluid Phase Equilib. 370 (2014) 58-64