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Solubility Determination and Correlation of 1,3,5-Tribromobenzene in Five Kinds of Binary Mixed Solvents

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Abstract

The solubility of 1,3,5-Tribromobenzene (m-TBB) in five kinds of binary solvent mixtures (i.e., N,N-dimethylformamide (DMF) + water, N,N-dimethylacetamide (DMA) + water, 1,4-dioxane + water, DMF + ethanol, and DMA + ethanol) was measured by a gravimetric method. The determination was carried out at temperatures ranging from 288.15 K to 323.15 K under ambient pressure. The solubility data were positively correlated with the molar fraction of good solvent and temperature. The order of solubility is 1,4-dioxane + water > DMA + ethanol > DMF + ethanol > DMA + water > DMF + water. The solubility of m-TBB was negatively correlated with solvent polarity. Four thermodynamic models (including the Jouyban–Acree–Apelblat, the Sun model, the NRTL model, and the Wilson model) were selected to correlate the solubility data of m-TBB. The solubility data are of great significance for solvent selection and yield judgment.

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References

  1. Belaaraj, A., Nguyen ba, C., Haget, Y., Cuevas-Diarte, M.A.: Crystal data for 1,3,5-trichlorobenzene and 1,3,5-tribromobenzene at 293 K. J. Appl. Crystallogr. 17, 211–211 (1984)

    Article  CAS  Google Scholar 

  2. van der Linde, P.R., van Miltenburg, J.C., van den Berg, G.J.K., Oonk, H.A.J.: Low-temperature heat capacities and derived thermodynamic functions of 1,4-dichlorobenzene, 1,4-dibromobenzene, 1,3,5-trichlorobenzene, and 1,3,5-tribromobenzene. J. Chem. Eng. Data 50, 164–172 (2005)

    Article  Google Scholar 

  3. Hu, X., Wang, K.: Synthesis and characterization of 1,3,5-bromobenzene. Chem. Eng. 29, 48–50 (2015)

    Google Scholar 

  4. Yu, S., Wang, Z., Ma, Y., Xue, F.: Effect of natural polymer additives on crystal form and morphology of clozapine anhydrate and monohydrate. J. Mol. Liq. 364, 119985 (2022)

    Article  CAS  Google Scholar 

  5. Yu, S., Yuan, J., Cheng, Y., Du, S., Wang, Y., Xue, F., Xing, W.: Solid–liquid phase equilibrium of clozapine in aqueous binary solvent mixtures. J. Mol. Liq. 329, 115371 (2021)

    Article  CAS  Google Scholar 

  6. Tajmir, F., Roosta, A.: Solubility of cefixime in aqueous mixtures of deep eutectic solvents from experimental study and modeling. J. Mol. Liq. 303, 112636 (2020)

    Article  CAS  Google Scholar 

  7. Lewis, A.E., Seckler, M., Kramer, H.J.M., Rosmalen, G.: Industrial Crystallization: Fundamentals and Applications. Cambridge University Press, Cambridge (2015)

    Book  Google Scholar 

  8. Yu, S., Chen, H., Gao, X., Feng, W., Xing, W., Du, S., Wang, Y., Xue, F., Cheng, Y.: Understanding the reaction crystallization process of glycidyl trimethyl ammonium chloride. Crystals 11, 449 (2021)

    Article  CAS  Google Scholar 

  9. Yu, S., Zhang, Y., Wang, X.Z.: Improved understanding of cefixime trihydrate reactive crystallization and process scale-up with the aid of PAT. Org. Process Res. Dev. 23, 177–188 (2019)

    Article  CAS  Google Scholar 

  10. Noubigh, A., Akremi, A.: Experimental measurements, equilibrium study and model correlation of methyl paraben in ethanol and methanol aqueous solutions from  T = (293.15 to 323.15) K. J. Mol. Liq. 293, 111505 (2019)

    Article  CAS  Google Scholar 

  11. Lee, S.K., Sim, W.Y., Ha, E.S., Park, H., Kim, J.S., Jeong, J.S., Kim, M.S.: Solubility of bisacodyl in fourteen mono solvents and N-methyl-2-pyrrolidone + water mixed solvents at different temperatures, and its application for nanosuspension formation using liquid antisolvent precipitation. J. Mol. Liq. 310, 113264 (2020)

    Article  CAS  Google Scholar 

  12. Alanazi, A., Alshehri, S., Altamimi, M., Shakeel, F.: Solubility determination and three dimensional hansen solubility parameters of gefitinib in different organic solvents: experimental and computational approaches. J. Mol. Liq. 299, 112211 (2020)

    Article  CAS  Google Scholar 

  13. Baluja, S., Alnayab, E.A.M., Hirapara, A.: Solubility and solution thermodynamics of hippuric acid in various solvents from 298.15K to 328.15K. J. Mol. Liq. 238, 84–88 (2017)

    Article  CAS  Google Scholar 

  14. Agredo-Collazos, J.J., Ortiz, C.P., Cerquera, N.E., Cardenas-Torres, R.E., Delgado, D.R., Peña, M.Á., Martínez, F.: Equilibrium solubility of Triclocarban in (cyclohexane + 1,4-dioxane) mixtures: determination, correlation, thermodynamics and preferential solvation. J. Solution Chem. 51, 1603–1625 (2022)

    Article  CAS  Google Scholar 

  15. Boudouh, I., Coto, B., González, J.A., Wazeer, I., Salleh, M.Z.M., Djemai, I., Robustillo, M.D., Hadj-Kali, M.K.: Experimental data and modeling of solid–liquid equilibria of binary systems containing dibenzofuran and long chain n-alkanes. J. Solution Chem. 52, 1083–1106 (2023)

    Article  CAS  Google Scholar 

  16. Moradi, M., Rahimpour, E., Jafari, P., Jouyban, A.: Solubility measurement and mathematical modeling for bosentan in mixtures of ethylene glycol and water at 293.15–313.15 K. J. Solution Chem. 52, 218–227 (2023)

    Article  CAS  Google Scholar 

  17. Sha, J., Ma, T., Huang, Z., Hu, X., Zhang, R., Cao, Z., Wan, Y., Sun, R., He, H., Jiang, G., Li, Y., Li, T., Ren, B.: Solubility determination, model evaluation, Hansen solubility parameter and thermodynamic properties of benorilate in six pure solvents and two binary solvent mixtures. J. Chem. Thermodyn. 153, 106301 (2021)

    Article  CAS  Google Scholar 

  18. Alqarni, M.H., Haq, N., Alam, P., Abdel-Kader, M.S., Foudah, A.I., Shakeel, F.: Solubility data, Hansen solubility parameters and thermodynamic behavior of pterostilbene in some pure solvents and different (PEG-400 + water) cosolvent compositions. J. Mol. Liq. 331, 115700 (2021)

    Article  CAS  Google Scholar 

  19. Li, H., Zhang, H., Li, Y., Zhang, H., Liu, X.: Investigation of the solubility and phase diagrams of sodium 4-tolylsulfinate in different solvents and ternary sodium 4-tolylsulfinate + sodium chloride/sodium sulfate + water systems. J. Solution Chem. 52, 790–804 (2023)

    Article  CAS  Google Scholar 

  20. Liu, L., Jia, L., Yang, W., Xiao, Y., Dai, J., Cui, P., Zhou, L., Yin, Q.: Measurement and correlation of solubility of L-tryptophan in aqueous solutions with a wide range of pH and different monovalent counterions from 283.15 to 323.15 K. J. Solution Chem. 52, 228–250 (2023)

    Article  CAS  Google Scholar 

  21. Apelblat, A., Manzurola, E.: Solubilities of o-acetylsalicylic, 4-aminosalicylic, 3,5-dinitrosalicylic, and p-toluic acid and magnesium-DL-aspartate in water from T = (278 to 348) K. J. Chem. Thermodyn. 31, 85–91 (1999)

    Article  CAS  Google Scholar 

  22. Li, Z., Jia, S., Gao, Y., Wang, M., Hong, W., Gao, Z., Gong, J.: Solid–liquid equilibrium behavior and thermodynamic analysis of p-aminobenzoic acid using experimental measurement and molecular dynamic simulation. J. Mol. Liq. 323, 114964 (2021)

    Article  CAS  Google Scholar 

  23. Ouyang, J., Liu, L., Zhou, L., Liu, Z., Li, Y., Zhang, C.: Solubility, dissolution thermodynamics, Hansen solubility parameter and molecular simulation of 4-chlorobenzophenone with different solvents. J. Mol. Liq. 360, 119438 (2022)

    Article  CAS  Google Scholar 

  24. Gao, X., Yu, S., Zhang, G., Cheng, Y., Wang, S., Xue, F.: Solid–liquid equilibrium, thermodynamic modelling and the solvent effect of glimepiride in mono-solvents and binary mixed solvents. J. Mol. Liq. 360, 119402 (2022)

    Article  CAS  Google Scholar 

  25. Carlson, H.C., Colburn, A.P.: Vapor–liquid equilibria of nonideal solutions. Ind. Eng. Chem. Res. 34, 581–589 (1942)

    Article  CAS  Google Scholar 

  26. Yu, S., Xing, W., Xue, F., Cheng, Y., Liu, Y., Chen, H., Hao, C., Sun, Y.: Measurement and correlation of solubility and thermodynamic properties of fluoxetine hydrochloride in 15 pure solvents and a methanol + water binary solvent system. J. Chem. Eng. Data 65, 4656–4668 (2020)

    Article  CAS  Google Scholar 

  27. Zhan, N., Zhang, Y., Wang, X.Z.: Solubility of N-tert-butylbenzothiazole-2-sulfenamide in several pure and binary solvents. J. Chem. Eng. Data 64, 1051–1062 (2019)

    Article  CAS  Google Scholar 

  28. Liu, J., Li, Z., Wang, M., Wan, X., Jia, S., Cao, Y., Gao, Z.: Solid–liquid phase equilibrium of N,N’-diphenyl thiourea (DPTU) in twelve pure solvents: Solubility determination, correlation, molecular simulation and thermodynamic analysis. J. Chem. Thermodyn. 163, 106605 (2021)

    Article  CAS  Google Scholar 

  29. Ha, E., Park, H., Lee, S., Sim, W., Jeong, J., Kim, M.: Equilibrium solubility and modeling of trans-resveratrol in dichloromethane and primary alcohol solvent mixtures at different temperatures. J. Mol. Liq. 311, 113363 (2020)

    Article  CAS  Google Scholar 

  30. Smallwood, I.M.: Nitropropane - Handbook of Organic Solvent Properties, vol. 11, pp. 285–287. Butterworth-Heinemann, Oxford (1996)

    Book  Google Scholar 

  31. Grønvold, F.: Enthalpy of fusion and temperature of fusion of indium, and redetermination of the enthalpy of fusion of tin. J. Chem. Thermodyn. 25, 1133–1144 (1993)

    Article  Google Scholar 

  32. Yu, S., Cheng, Y., Du, S., Wang, Y., Xue, F., Xing, W.: Thermodynamic analysis of the solubility of clozapine in organic solvents. J. Chem. Thermodyn. 158, 106451 (2021)

    Article  CAS  Google Scholar 

  33. Yu, S., Xing, W., Xue, F., Cheng, Y., Li, B.: Solubility and thermodynamic properties of nimodipine in pure and binary solvents at a series of temperatures. J. Chem. Thermodyn. 152, 106259 (2021)

    Article  CAS  Google Scholar 

  34. Yu, S., Cheng, Y., Feng, W., Xing, W., Li, H., Xue, F.: Solid–liquid equilibrium solubility measurement, model evaluation and Hansen solubility parameter of 2,4,5-trimethoxybenzaldehyde in four aqueous binary solvent mixtures. J. Mol. Liq. 339, 116750 (2021)

    Article  CAS  Google Scholar 

  35. Yu, S., Cheng, Y., Xing, W., Xue, F.: Solubility determination and thermodynamic modelling of gliclazide in five binary solvent mixtures. J. Mol. Liq. 311, 113528 (2020)

    Article  Google Scholar 

  36. Yu, S., Xu, X., Xing, W., Xue, F., Cheng, Y.: Solubility, thermodynamic parameters, and dissolution properties of gliclazide in seventeen pure solvents at temperatures from 278.15 to 318.15 K. J. Mol. Liq. 312, 113425 (2020)

    Article  CAS  Google Scholar 

  37. Moghimi, M., Roosta, A., Hekayati, J., Rezaei, N.: Estimating VLE behavior from SLE data in aqueous mixtures of choline chloride–sorbitol deep eutectic solvents: experimental investigation and thermodynamic modeling using the e-NRTL model. J. Mol. Liq. 371, 121126 (2023)

    Article  CAS  Google Scholar 

  38. van der Veen, A.M.H., Linsinger, T.P.J., Schimmel, H., Lamberty, A.: Uncertainty calculations in the certification of reference materials. Accredit. Qual. Assur. (2001). https://doi.org/10.1007/PL00010459

    Article  Google Scholar 

  39. Huinink, J., Van Miltenburg, J.C., Oonk, H.A.J., Schuijff, A.: ChemInform abstract: vapor-pressure measurements and thermodynamic properties: 1,3,5-tribromobenzene. ChemInform 107(3), 273–277 (1988)

    CAS  Google Scholar 

  40. Barton, A.F.M.: Handbook of Solubility Parameters and Other Cohesion Parameters. CRCPress, Boca Raton (1991)

    Google Scholar 

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Acknowledgements

This investigation work received support from the National Natural Science Foundation of China (Grant reference: 82204288), Shandong Provincial Natural Science Foundation (Grant reference: ZR2023MB036), Central Guidance on Local Science and Technology Development Fund of Shandong Province (Grant reference: YDZX2022098), Science, Education and Industry Integration Technology Innovation Project (2022PT117). Talent Research Project of Qilu University of Technology (Grant reference: 2023RCKY088).

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Xian Sun contributed toward conceptualization, methodology, formal analysis, software, investigation, and writing - original draft. Xingzhu Wang contributed toward conceptualization, and methodology. Min Wan contributed toward investigation and methodology. Degan Lu contributed toward investigation and methodology. Wenguo Xing contributed toward investigation and methodology. Shuai Yu contributed toward conceptualization, methodology, formal analysis, software, investigation, writing - original draft, visualization, supervision, and funding acquisition. Fumin Xue contributed toward resources, and project administration.

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Correspondence to Shuai Yu or Fumin Xue.

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Sun, X., Wang, X., Wan, M. et al. Solubility Determination and Correlation of 1,3,5-Tribromobenzene in Five Kinds of Binary Mixed Solvents. J Solution Chem (2024). https://doi.org/10.1007/s10953-024-01370-y

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