Proof of concept for continuous enantioselective liquid-liquid extraction in capillary microreactors using 1-octanol as a sustainable solvent

S. Susanti, Tim G. Meinds, Erik B. Pinxterhuis, Boelo Schuur, Johannes G. De Vries, Ben L. Feringa, Jozef G.M. Winkelman, Jun Yue, Hero J. Heeres*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

The use of capillary microreactors for enantioselective liquid-liquid extraction (ELLE) was successfully demonstrated using a model system consisting of a buffered aqueous amino acid derivative (3,5-dinitrobenzoyl-(R,S)-leucine) solution (phosphate buffer, pH 6.58) and a chiral cinchona alkaloid (CA) host in an organic solvent. It was shown that 1-octanol is a suitable replacement for the commonly used chlorinated solvents like 1,2-dichloroethane. Experiments were conducted in a capillary microreactor set-up (0.8 mm internal diameter) operated in the slug flow regime at 294 K (residence times between 12 and 900 s, 1:1 flow ratio of the aqueous to organic phases, 1 mM of host and 1 mM of amino acid derivative). The enantiomeric excess (ee) was shown to be a function of the solvent and residence time and varied between 37% and 49% in 1,2-DCE and 28 and 46% in 1-octanol in the organic phase. The ee values in the organic phase at shorter residence times were higher than the independently determined equilibrium ee values (41% in 1,2-DCE and 31% in 1-octanol at a host concentration of 1 mM). This is an unprecedented observation with large implications for ELLE, as it implies that operation in the kinetic regime may lead to improved enantioseparation performance.

Original languageEnglish
Pages (from-to)4334-4343
Number of pages10
JournalGreen chemistry
Volume19
Issue number18
DOIs
Publication statusPublished - 1 Aug 2017

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