A hybrid process for chiral separation of compound-forming systems.
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.
Gou
Linzhu
L
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
Robl
Simone
S
Leonhard
Kai
K
Lorenz
Heike
H
Sordo
Magdalena
M
Butka
Annamaria
A
Kesselheim
Stefan
S
Wolff
Morris
M
Seidel-Morgenstern
Andreas
A
Schaber
Karlheinz
K
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
D004987:Ethers; D006873:Hydroquinones; D008333:Mandelic Acids; D008567:Membranes, Artificial; D013764:Tetrahydronaphthalenes; C557460:hydroquinine-4-methyl-2-quinolylether; D011802:Quinidine; C037938:mandelic acid