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Toward the Rationalization of Facilitated Hydrotropy: Investigation with the Ternary Dimethyl Isosorbide / Benzyl Alcohol / Water System

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Abstract

Solubility enhancement has been achieved by facilitated hydrotropy for the dimethyl isosorbide (DMI) / benzyl alcohol / water system. Facilitated hydrotropy has been studied via three different approaches: the solubilization in water of a hydrophobic dye, the evolution of the surface tension and dynamic light scattering, all as a function of the benzyl alcohol concentration. The facilitated hydrotropy has been rationalized from the solubilization properties of the system according to the ratio between the insoluble hydrotrope (here benzyl alcohol, a preservative used in parenteral injections) and the bio-sourced co-solvant (here the dimethyl isosorbide ether, DMI, a solvent used in pharmaceutical formulation). The presence of self-associated nanostructures has been detected by dynamic light scattering (DLS). It appears that the cosolvent, DMI, has an antagonistic action: DMI increases the facilitated hydrotrope (benzyl alcohol) solubility in the aqueous solution (favoring solute solubilization) but simultaneously decreases the hydrotropic efficiency of benzyl alcohol.

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Acknowledgements

Roquette Frères is gratefully acknowledged for financial support in the research program concerning dimethyl isosorbide, and for providing pure samples of isosorbide and dimethylisosorbide. Dimethyl isosorbide (DMI) is part of the BIOHUB program (http://www.biohub.fr). The French CNRS (Centre National de la Recherche Scientifique) is also acknowledged for promoting German–French cooperation through a PICS (Projet International de Coopération Scientifique) program.

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Authors and Affiliations

  1. Université Lille Nord de France, 59000, Lille, France

    Morgan Durand, Valérie Molinier & Jean-Marie Aubry

  2. USTL, ENSCL, EA Chimie moléculaire et Formulation 4478, 59652, Villeneuve d’Ascq Cedex, France

    Morgan Durand, Valérie Molinier & Jean-Marie Aubry

  3. Institute of Physical and Theoretical Chemistry, University of Regensburg, Universitätstrasse 31, 93053, Regensburg, Germany

    Alexander Stoppa & Didier Touraud

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  1. Morgan Durand
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  2. Alexander Stoppa
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  3. Valérie Molinier
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  4. Didier Touraud
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  5. Jean-Marie Aubry
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Corresponding author

Correspondence to Morgan Durand.

Appendix: Supplementary materials

Appendix: Supplementary materials

Table 1 Phase boundary compositions of the water/BA/DMI ternary diagram. Compositions are expressed in weight fraction
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Table 2 Absorbance (Abs) of Sudan Red III as a function of the DMI/water ratio and the BA weight content (wt%)
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Table 3 Evolution of the hydrodynamic radius (in nm) and the polydispersity index as function of the benzyl alcohol content in a DMI/water solution (40/60 wt%)
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Table 4 Variation of the surface tension (in mN⋅m−1) as a function of benzyl alcohol (in wt%) for a DMI (to water) fraction of 40 wt%
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Durand, M., Stoppa, A., Molinier, V. et al. Toward the Rationalization of Facilitated Hydrotropy: Investigation with the Ternary Dimethyl Isosorbide / Benzyl Alcohol / Water System. J Solution Chem 41, 555–565 (2012). https://doi.org/10.1007/s10953-012-9814-7

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  • DOI: https://doi.org/10.1007/s10953-012-9814-7

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