title: Physical-Chemical Properties of the Chiral Fungicide Fenamidone and Strategies for Enantioselective Crystallization.
abstract: Thermodynamic and kinetic parameters are of prime importance for designing crystallization processes. In this article, Preferential Crystallization, as a special approach to carry out enantioselective crystallization, is described to resolve the enantiomers of the chiral fungicide fenamidone. In preliminary investigations the melting behavior and solid-liquid equilibria in the presence of solvents were quantified. The analyses revealed a stable solid phase behavior of fenamidone in the applied solvents. Based on the results obtained, a two-step crystallization route was designed and realized capable of providing highly pure enantiomers. An initial Preferential Crystallization of the racemate was performed prior to crystallizing the target enantiomer preferentially out of the enriched mother liquor. Chirality 28:514-520, 2016. © 2016 Wiley Periodicals, Inc.
authors.affiliation: Max Planck Institute for Dynamics of Complex Technical Systems, Magdeburg, Germany.
authors.forename: Anne-Kathleen
authors.initials: AK
authors.lastname: Kort
authors.affiliation: Max Planck Institute for Dynamics of Complex Technical Systems, Magdeburg, Germany.
authors.forename: Heike
authors.initials: H
authors.lastname: Lorenz
authors.affiliation: Max Planck Institute for Dynamics of Complex Technical Systems, Magdeburg, Germany.|Otto von Guericke University Magdeburg, Institute of Process Engineering, Magdeburg, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Seidel-Morgenstern
mesh_terms: D003460:Crystallization / Q000379:methods*; D005659:Fungicides, Industrial / Q000737:chemistry; D012995:Solubility; D013237:Stereoisomerism; D000073739:Strobilurins / Q000737:chemistry*
chemical_list: D005659:Fungicides, Industrial; D000073739:Strobilurins; C540355:fenamidone
keywords: chiral agrochemicals; chiral resolution; fenamidone; phase diagrams; resolution by entrainment; two-step polythermal crystallization