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Enantiomeric 3-Chloromandelic Acid System: Binary Melting Point Phase Diagram, Ternary Solubility Phase Diagrams and Polymorphism

MPS-Authors
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Le Minh,  T.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
International Max Planck Research School (IMPRS);

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von Langermann,  J.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Lorenz,  H.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Seidel-Morgenstern,  A.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Otto-von-Guericke-Universität Magdeburg, External Organizations;

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Citation

Le Minh, T., von Langermann, J., Lorenz, H., & Seidel-Morgenstern, A. (2010). Enantiomeric 3-Chloromandelic Acid System: Binary Melting Point Phase Diagram, Ternary Solubility Phase Diagrams and Polymorphism. Journal of Pharmaceutical Sciences, 99(9), 4084-4095. doi:10.1002/jps.22234.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0013-90C0-1
Abstract
A systematic study of binary melting point and ternary solubility phase diagrams of the enantiomeric 3-chloromandelic acid (3-ClMA) system was performed under consideration of polymorphism. The melting point phase diagram was measured by means of thermal analysis, that is, using heat-flux differential scanning calorimetry (DSC). The results reveal that 3-ClMA belongs to the racemic compound-forming systems. Polymorphism was found for both the enantiomer and the racemate as confirmed by X-ray powder diffraction analysis. The ternary solubility phase diagram of 3-ClMA in water was determined between 5 and 50°C by the classical isothermal technique. The solubilities of the pure enantiomers are extremely temperature-dependent. The solid–liquid equilibria of racemic 3-ClMA are not trivial due to the existence of polymorphism. The eutectic composition in the chiral system changes as a function of temperature. Further, solubility data in the alternative solvent toluene are also presented. copyright 2010 Wiley-Liss, Inc. and the American Pharmacists Association [accessed September 30th 2010]