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  Potential of Chiral Solvents for Enantioselective Crystallization. 2. Evaluation of Kinetic Effects

Tulashie, S. K., Lorenz, H., & Seidel-Morgenstern, A. (2009). Potential of Chiral Solvents for Enantioselective Crystallization. 2. Evaluation of Kinetic Effects. Crystal Growth & Design, 9(5), 2387-2392. doi:10.1021/cg801286s.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0013-9369-F Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0014-B588-C
Genre: Journal Article

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Tulashie, S. K.1, 2, Author              
Lorenz, H.1, Author              
Seidel-Morgenstern, A.1, 2, Author              
Affiliations:
1Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society, ou_1738150              
2Otto-von-Guericke-Universität Magdeburg, External Organizations, ou_1738156              

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 Abstract: In part 1 of this work, the potential of chiral solvents in enantioseparation was studied for two pharmaceutical substances with regard to thermodynamics (Cryst. Growth Des. 2008, 8, 3408−3414). Unfortunately, no measurable chiral recognition in terms of the solubility equilibria was observed between the chiral solvents and the chiral systems investigated. In this part 2, studies are directed toward the potential of chiral solvents in enantioseparation based on differences in crystallization kinetics. For the case study performed, mandelic acid as a racemic compound forming system has been chosen. The crystallization kinetics (metastable zone width data with regard to primary nucleation) determined for mandelic acid in the chiral solvents (S)-ethyl lactate and (2R,3R)-diethyl tartrate are shown and discussed. On that basis successful preferential nucleation/crystallization experiments allowed for racemate resolution. To explain the observed results solvation enthalpy data obtained from dissolution enthalpy measurements are considered. Copyright © 2009 American Chemical Society [accessed March 17, 2009]

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Language(s): eng - English
 Dates: 2009
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: eDoc: 412634
Other: 42/09
DOI: 10.1021/cg801286s
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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 (5) Sequence Number: - Start / End Page: 2387 - 2392 Identifier: ISSN: 1528-7483
CoNE: https://pure.mpg.de/cone/journals/resource/110978984570353