Enantioselective liquid-liquid extraction of (R,S)-phenylglycinol using a bisnaphthyl phosphoric acid derivative as chiral extractant

Boelo Schuur, Bastiaan J.V. Verkuijl, Jeroen Bokhove, Adriaan J. Minnaard, Johannes G. De Vries, Hero J. Heeres, Ben L. Feringa

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32 Citations (Scopus)

Abstract

This study demonstrates that enantioseparation by liquid-liquid extraction can be done in a continuous flow mode on both laboratory and industrial scale and is a promising technique that could become a competitive alternative for crystallization or chromatographic approaches. We studied the enantioselective liquid-liquid extraction of phenylglycinol (Pgl) using a bisnaphthyl phosphoric acid extractant. Batch experiments were performed to estimate extraction model parameters. The system was described using an extraction mechanism with homogeneous organic phase complexation. The complexation constants were very large, in the order of 108-1010 L/mol in the temperature range 279<T<303 K. The developed model was then used to design a multistage countercurrent extraction process with Centrifugal Contactor Separator (CCS) equipment. This study demonstrates that high purity (70% ee) with a reasonable yield (36%) can be obtained for a moderately selective system (α=1.7) with only six extraction stages. The technology is potentially applicable to a wide range of racemates.

Original languageEnglish
Pages (from-to)462-470
Number of pages9
JournalTetrahedron
Volume67
Issue number2
DOIs
Publication statusPublished - 14 Jan 2011
Externally publishedYes

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