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Investigation of the physicochemical basis of enantiomeric enrichment: The example of α‐phenylethylamine with achiral dicarboxylic acids
Author(s) -
Kozma Dávid,
Simon Helén,
Kassai Csaba,
Madarász Zoltán,
Fogassy Elemér
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/1520-636x(2001)13:1<29::aid-chir6>3.0.co;2-p
Subject(s) - chemistry , enantiomer , crystallization , organic chemistry , salt (chemistry) , solubility , enantiomeric excess , eutectic system , chromatography , distillation , enantioselective synthesis , catalysis , alloy
We investigated the enantiomeric enrichment of enantiomeric mixtures of α‐phenylethylamine by achiral dicarboxylic acids. As achiral agents oxalic, malonic, fumaric, and phthalic acids were used. The results of the enantiomeric enrichment via partial salt formation followed by distillation were compared with enantiomer separation via crystallization of the neutral salt. Without the presence of a solid phase, enantiomeric separation is impossible. Our results show that the properties of the solid phase determine the separation. It is also confirmed by our observation that the eutectic points, which are observed on the 3‐phase solubility diagrams of the solid neutral salts, can be found at the same initial enantiomeric composition as the point of intersection of distillate and residue of the distillation curves and the point of intersection of precipitated salt and mother liquor of the crystallization curves. Chirality 13:29–33, 2001. © 2000 Wiley‐Liss, Inc.