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Solubility of 1-(3-Bromopropoxy)-4-Chlorobenzene in Aqueous Ethanol Mixtures From (273.15 to 303.15) K

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Abstract

1-(3-Bromopropoxy)-4-chlorobenzene is an important intermediate for the manufacture of omoconazole nitrate. The solubilities of 1-(3-bromopropoxy)-4-chlorobenzene in aqueous ethanol solutions were measured within the temperature range of (273.15–303.15) K using a laser monitoring system. For the temperature range investigated, the solubilities of 1-(3-bromopropoxy)-4-chlorobenzene in the aqueous ethanol mixtures increase with increasing temperature. The solubility data were regressed by the Buchowski–Ksiazaczak λh and the modified Apelblat models. The modified Apelblat equation and the Buchowski–Ksiazaczak λh equation provided accurate mathematical representations of the experimental results. The calculated solubilities showed good agreement with the experimental data. The root-mean-square deviations of the modified Apelblat model were lower than those of the Buchowski–Ksiazaczak λh model. This study provided valuable data for the purification of 1-(3-bromopropoxy)-4-chlorobenzene by crystallization.

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Abbreviations

\( x \) :

Mole fraction solubility

\( x_{i}^{\text{calc}} \) :

Calculated value of the solubility

\( x_{i}^{\exp } \) :

Experimental value of the solubility

\( T \) :

Absolute temperature

\( \omega \) :

Volume fraction of ethanol in the solvent mixture

\( T_{\text{m}} \) :

Melting point

A, B, C:

Empirical constants in Eq. 4

λ, h :

Empirical constants in Eq. 8

\( \gamma_{x} \) :

Activity coefficient on a mole fraction basis

\( \Updelta_{\text{fus}} H \) :

Enthalpy of fusion

\( \Updelta C_{p}^{{}} \) :

Heat capacity difference between the solid and the liquid

\( T_{t} \) :

Triple point temperature

rmsd:

Root-mean-square deviation

R :

Gas constant

C 1, C 2, C 3 :

Molar concentration of ethanol, 1-(3-bromopropoxy)-4-chlorobenzene and water, respectively, in saturated solutions

References

  1. Zirngibl, L., Fischer, J., Jahn, U., Thiele, K.: Structure–activity relationships of 2-(1H-imidazol-1-yl)vinyl ethers. Ann. N. Y. Acad. Sci. 544, 63–73 (1988)

    Article  CAS  Google Scholar 

  2. Itoyama, T., Aoki, Y., Hiratani, T., Uchida, K., Yamaguchi, H.: Various factors influencing in vitro antifungal activities of omoconazole nitrate (OMZ), a new imidazole antimycotic. Jpn. J. Antibiot. 47, 40–49 (1994)

    CAS  Google Scholar 

  3. Itoyama, T., Aoki, Y., Hiratani, T., Uchida, K., Yamaguchi, H.: In vitro antifungal activity of omoconazole nitrate, a new imidazole antimycotic. Jpn. J. Antibiot. 46, 773–780 (1993)

    CAS  Google Scholar 

  4. Itoyama, T., Uchida, K., Yamaguchi, H.: Therapeutic effects of omoconazole nitrate on guinea-pigs experimentally infected with Trichophyton mentagrophytes. J. Antimicrob. Chemother. 39, 825–827 (1997)

    Article  CAS  Google Scholar 

  5. Uchida, K., Itoyama, T., Yamaguchi, H.: In vitro antifungal activity of omoconazole nitrate, a novel imidazone antimycotic drug, against clinical isolates from patients with cutaneous mycosis. Jpn. J. Antibiot. 49, 818–823 (1996)

    CAS  Google Scholar 

  6. Itoyama, T., Uchida, K., Yamaguchi, H., Fujita, S.: Therapeutic effects of omoconazole nitrate on experimental Tinea pedis, an intractable dermatophytosis, in guinea-pigs. J. Antimicrob. Chemother. 40, 441–444 (1997)

    Article  CAS  Google Scholar 

  7. Nishiyama, Y., Itoyama, T., Yamaguchi, H.: Ultrastructural alterations of Candida albicans induced by a new imidazole antimycotic omoconazole nitrate. Microbiol. Immunol. 41, 395–402 (1997)

    CAS  Google Scholar 

  8. Harvey, A.J., Baell, J.B., Wulff, H.: Novel potassium channel blockers and uses thereof. Patent WO2006096911, 2006

  9. Lazewska, D., Kuder, K., Ligneau, X., Schwartz, J.C., Schunack, W., Stark, H., Kiec-Kononowicz, K.: Piperidine variations in search for non-imidazole histamine H(3) receptor ligands. Bioorg. Med. Chem. 16, 8729–8736 (2008)

    Article  CAS  Google Scholar 

  10. Ashwell, M., Tandon, M., Lapierre, J.-M., Ali, S., Vensel, D., Li, C.J.: Novel lapachone compounds and methods of use thereof. Patent WO2007139569, 2007

  11. Cuthbertson, J., Ibanez, M., Rijnbrand, A., Jackson, J., Mittapalli, K., Zhao, F., Flossie, W.-S.: Hepatitis C virus entry inhibitors. Patent WO2008021745, 2008

  12. Yi, Y., Hatziavramidis, D., Myerson, A.S., Waldo, M., Beylin, V.G., Mustakis, J.: Development of a small-scale automated solubility measurement apparatus. Ind. Eng. Chem. Res. 44, 5427–5433 (2005)

    Article  CAS  Google Scholar 

  13. Mullin, J.-W.: Crystallization, 3rd edn. Butterworth–Heinemann, Oxford, UK (1997)

    Google Scholar 

  14. Yang, W.-G., Yao, J.-F., Zhao, X.-L., Hu, Y.-H.: 1-(3-Bromopropoxy)-4-chlorobenzene. Acta Crystallogr. E64, o2422 (2008)

    CAS  Google Scholar 

  15. Hu, Y.-H., Chen, X., Yang, W.-G., Guan, J.: Measurement and correlation of the solubility of urea l-tartaric acid in aqueous ethanol solution. Thermochim. Acta 484, 38–40 (2009)

    Article  CAS  Google Scholar 

  16. Chen, Z.-G., Yang, W.-G., Hu, Y.-H., Lei, Z.-Y., Wang, Y.-H., Wan, W.-Q.: Measurement and correlation for the solubility of dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate in different dolvents at temperatures from (278.15 to 323.15) K. J. Chem. Eng. Data 56, 2726–2729 (2011)

    Article  CAS  Google Scholar 

  17. Ullah, I., Baloch, M.-K., Durrani, G.-F.: Solubility of nonsteroidal anti-inflammatory drugs (NSAIDs) in aqueous solutions of non-ionic surfactants. J. Solution Chem. 40, 1341–1348 (2011)

    Article  CAS  Google Scholar 

  18. Zhang, J., Hu, J.-W., Wang, J.-L., Chen, L.-Z.: Solubility of 1,3,3-trinitroazetidine in ethanol + water systems from (293.15 K to 323.15 K). J. Solution Chem. 40, 703–708 (2011)

    Article  CAS  Google Scholar 

  19. Li, D.-Q., Liu, D.-Z., Wang, F.-A.: Solubility of 4-methylbenzoic acid between 288 and 370 K. J. Chem. Eng. Data 46, 234–236 (2001)

    Article  CAS  Google Scholar 

  20. Zi, J.-Q., Peng, B., Yan, W.-D.: Solubilities of rutin in eight solvents at T = 283.15, 298.15, 313.15, 323.15, and 333.15 K. Fluid Phase Equilib. 261, 111–114 (2007)

    Article  CAS  Google Scholar 

  21. Prausnitz, J.-M., Lichtenthaler, R.-N., Azevedo, E.-G.: Molecular Thermodynamics of Fluid-Phase Equilibria, 3rd edn. Prentice Hall PTR, Upper Saddle River (1998)

    Google Scholar 

  22. Dong, H., Fu, R–.R., Yan, W.-D., Zhu, M.: Solubility and density of the disodium salt hemiheptahydrate of ceftriaxone in (acetone + water) at T = (298.15, 308.15, and 318.15) K. J. Chem. Thermodyn. 36, 155–159 (2004)

    Article  CAS  Google Scholar 

  23. Apelblat, A., Manzurola, E.: Solubilities of l-aspartic, dl-aspartic, dl-glutamic, p-hydroxybenzoic, o-anisic, p-anisic, and itaconic acids in water from T = 278 K to T = 345 K. J. Chem. Thermodyn. 29, 1527–1533 (1997)

    Article  CAS  Google Scholar 

  24. 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 = (278–348) K. J. Chem. Thermodyn. 31, 85–91 (1999)

    Article  CAS  Google Scholar 

  25. Manzurola, E., Apelblat, A.: Solubilities of l-glutamic acid, 3-nitrobenzoic acid, p-toluic acid, calcium-l-lactate, calcium gluconate, magnesium dl-aspartate, and magnesium-l-lactate in water. J. Chem. Thermodyn. 34, 1127–1136 (2002)

    Article  CAS  Google Scholar 

  26. Buchowski, H., Ksiazczak, A., Pietrzyk, S.: Solvent activity along a saturation line and solubility of hydrogen-bonding solids. J. Phys. Chem. 84, 975–979 (1980)

    Article  CAS  Google Scholar 

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Acknowledgments

This research work was financially supported by the Fundamental University Science Project of Jiangsu Province in China (No. 12KJA180002). This Research work was also supported by the Grant from the Natural Science Foundation of China (NSFC) (No. 31171644). We thank the editors and the anonymous reviewers.

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Authors and Affiliations

  1. College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, No. 200, North Zhongshan Road, Nanjing, 210009, China

    Xin-Min Jiang, Yong-Hong Hu, Wen-Ge Yang, Zi-Yu Lei & Rong-Rong Tang

  2. Jiangsu Engineering Technology Research Center of Polypeptide Pharmaceutical, Nanjing, 210038, China

    Yong-Hong Hu, Rong-Rong Tang & Fei Shen

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  1. Xin-Min Jiang
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Correspondence to Wen-Ge Yang.

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Jiang, XM., Hu, YH., Yang, WG. et al. Solubility of 1-(3-Bromopropoxy)-4-Chlorobenzene in Aqueous Ethanol Mixtures From (273.15 to 303.15) K. J Solution Chem 42, 272–281 (2013). https://doi.org/10.1007/s10953-013-9962-4

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