title: A hybrid process for chiral separation of compound-forming systems.
abstract: The resolution of chiral compound-forming systems using hybrid processes was discussed recently. The concept is of large relevance as these systems form the majority of chiral substances. In this study, a novel hybrid process is presented, which combines pertraction and subsequent preferential crystallization and is applicable for the resolution of such systems. A supported liquid membrane applied in a pertraction process provides enantiomeric enrichment. This membrane contains a solution of a chiral compound acting as a selective carrier for one of the enantiomers. Screening of a large number of liquid membranes and potential carriers using the conductor-like screening model for realistic solvation method led to the identification of several promising carriers, which were tested experimentally in several pertraction runs aiming to yield enriched (+)-(S)-mandelic acid (MA) solutions from racemic feed solutions. The most promising system consisted of tetrahydronaphthalene as liquid membrane and hydroquinine-4-methyl-2-quinolylether (HMQ) as chiral carrier achieving enantiomeric excesses of 15% in average. The successful production of (+)-(S)-MA with a purity above 96% from enriched solutions by subsequent preferential crystallization proved the applicability of the hybrid process.
authors.affiliation: Max Planck Institute for Dynamics of Complex Technical Systems, Physical and Chemical Foundations of Process Engineering, D-39106 Magdeburg, Germany. gou@mpi-magdeburg.mpg.de
authors.forename: Linzhu
authors.initials: L
authors.lastname: Gou
authors.forename: Simone
authors.initials: S
authors.lastname: Robl
authors.forename: Kai
authors.initials: K
authors.lastname: Leonhard
authors.forename: Heike
authors.initials: H
authors.lastname: Lorenz
authors.forename: Magdalena
authors.initials: M
authors.lastname: Sordo
authors.forename: Annamaria
authors.initials: A
authors.lastname: Butka
authors.forename: Stefan
authors.initials: S
authors.lastname: Kesselheim
authors.forename: Morris
authors.initials: M
authors.lastname: Wolff
authors.forename: Andreas
authors.initials: A
authors.lastname: Seidel-Morgenstern
authors.forename: Karlheinz
authors.initials: K
authors.lastname: Schaber
mesh_terms: D003460:Crystallization; D004987:Ethers / Q000737:chemistry*; D006873:Hydroquinones / Q000737:chemistry*; D008333:Mandelic Acids / Q000737:chemistry* / Q000302:isolation & purification*; D008567:Membranes, Artificial; D008956:Models, Chemical; D011802:Quinidine / Q000737:chemistry; D012995:Solubility; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry
chemical_list: D004987:Ethers; D006873:Hydroquinones; D008333:Mandelic Acids; D008567:Membranes, Artificial; D013764:Tetrahydronaphthalenes; C557460:hydroquinine-4-methyl-2-quinolylether; D011802:Quinidine; C037938:mandelic acid