Solid−Liquid Phase Equilibria of N-Methylephedrine Enantiomers in Two Chiral 
Solvents

Kaemmerer, H.; Tulashie, S. K.; Lorenz, H.; Seidel-Morgenstern, A.

doi:10.1021/je900572c

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Solid−Liquid Phase Equilibria of N-Methylephedrine Enantiomers in Two Chiral Solvents

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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

Kaemmerer, H., Tulashie, S. K., Lorenz, H., & Seidel-Morgenstern, A. (2010). Solid−Liquid Phase Equilibria of N-Methylephedrine Enantiomers in Two Chiral Solvents. Journal of Chemical and Engineering Data, 55(3), 1131-1136. doi:10.1021/je900572c.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0013-9048-4

Abstract

The ternary solubility phase diagrams of the N-methylephedrine species in two chiral solvents, (S)-ethyl lactate and (2R,3R)-diethyl tartrate, have been studied. Solubility measurements were performed for enantiomeric compositions and temperatures ranging from 1:1 mixtures to the pure enantiomer and from (273 to 313) K. Predicted ideal solubility curves of the N-methylephedrine species in both solvents revealed deviations from experimental data. The nonrandom two-liquid model was applied to quantify and parametrize these nonidealities and nonideal heterochiral interactions among the enantiomers by means of corresponding activity coefficients. The solvent−solute interactions were interpreted as nonchiral specific, since no asymmetry in the chiral systems were found. The selection of an appropriate solvent for a crystallization-based enantioseparation based on the shape of solubility isotherms is discussed. Copyright © 2009 American Chemical Society. [accessed November 26, 2009]