Continuous Chiral Separation of Amino Acid Derivatives by Enantioselective Liquid−Liquid Extraction in Centrifugal Contactor Separators

Boelo Schuur, Joelle Floure, Andrew J. Hallett, Jozef G.M. Winkelman, Johannes G. DeVries, Hero J. Heeres

Research output: Contribution to journalArticleAcademicpeer-review

71 Citations (Scopus)

Abstract

The continuous enantioselective liquid-liquid extraction of aqueous 3,5-dinitrobenzoyl-D,L-leucine (DNB-d,l-leu) by a cinchona alkaloid extractant (CA) in 1,2-dichloroethane using a centrifugal contact separator (CCS) was studied at 294 K. Typical concentrations were in the order of 1 mM for both DNB-d,l-leu and CA. The best results were found at a pH of 6, with 61% yield for DNB-l-leu and an enantiomeric excess of 34%. Back-extraction studies at different pH values showed that the host can be recovered efficiently in a single CCS, provided that pH > 9. Experimental studies indicate that the CCS behaves as an equilibrium extraction stage, even at total throughputs exceeding 50% of the equipment capacity (1.9 L min-1). A previously developed equilibrium stage extraction model was successfully applied to describe the data for both the extraction and the back-extraction experiments.

Original languageEnglish
Pages (from-to)950-955
Number of pages6
JournalOrganic Process Research and Development
Volume12
Issue number5
DOIs
Publication statusPublished - 19 Sep 2008
Externally publishedYes

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