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  Study of system thermodynamics and the feasibility of chiral resolution of the polymorphic system of malic acid enantiomers and its partial solid solutions

Kaemmerer, H., Lorenz, H., Black, S. N., & Seidel-Morgenstern, A. (2009). Study of system thermodynamics and the feasibility of chiral resolution of the polymorphic system of malic acid enantiomers and its partial solid solutions. Crystal Growth & Design, 9(4), 1851-1862. doi:10.1021/cg8010508.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0013-9365-8 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0014-B538-D
Genre: Journal Article

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 Creators:
Kaemmerer, H.1, Author              
Lorenz, H.2, Author              
Black, S. N.3, Author
Seidel-Morgenstern, A.1, 2, Author              
Affiliations:
1Otto-von-Guericke-Universität Magdeburg, External Organizations, ou_1738156              
2Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society, ou_1738150              
3AstraZeneca, Macclesfield, GB, ou_persistent22              

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 Abstract: The appearance of mixed crystals of organic compounds is frequently discussed in recent literature and it can cause difficulties in the downstream process of drug purification. The chiral malic acid system is an example of a system of enantiomers that exhibits partial solid solutions in a large composition range. Measurements and analyses of the binary melting phase diagram and the ternary solution phase diagram were conducted, and the existing phases were characterized by X-ray powder diffraction. Within this study the formations of two phases of mixed crystals were observed and assigned to the underlying polymorphism of the racemic compound. A suggestion for the complex phase diagram of this system is made. Preferential crystallization was performed to assess the feasibility of chiral resolution by crystallization for a system exhibiting high enantiomeric excess at the eutectic point and partial solid solutions. Primary nucleation and seeded crystallization experiments revealed (a) that an initial incorporation of the enantiomer in excess into the crystal lattice of the racemic compound can be altered by the choice of crystallization conditions and (b) why partial solid solutions must be taken into account for the design of separation procedures. Considerations on the crystal structures of malic acid helped to understand the formation of particular partial solid solutions for this compound. Copyright © 2009 American Chemical Society [accessed May 11, 2009]

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Language(s): eng - English
 Dates: 2009
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: -
 Identifiers: eDoc: 378903
Other: 46/09
DOI: 10.1021/cg8010508
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Title: Crystal Growth & Design
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 9 (4) Sequence Number: - Start / End Page: 1851 - 1862 Identifier: ISSN: 1528-7483
CoNE: https://pure.mpg.de/cone/journals/resource/110978984570353