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Continuous Separation of Racemic 3,5-Dinitrobenzoyl-Amino Acids in a Centrifugal Contact Separator with the Aid of Cinchona-Based Chiral Host Compounds

Hallett, Andrew Jon, Kwant, Gerard J. and de Vries, Johannes G. 2009. Continuous Separation of Racemic 3,5-Dinitrobenzoyl-Amino Acids in a Centrifugal Contact Separator with the Aid of Cinchona-Based Chiral Host Compounds. Chemistry - A European Journal 15 (9) , pp. 2111-2120. 10.1002/chem.200800797

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Abstract

The resolution of racemates is mostly performed by crystallisation of diastereomeric salts. Direct physical separation could be much more efficient,but so far most concepts, with the exception of SMB, have proven to be non-scaleable. Here we report the first scalable process for the resolution of N-protected amino acid derivatives through selective extraction, with the aid of a catalytic amount of a chiral host compound based on Cinchona alkaloids. The method hinges on the use of centrifugal contact separators (CCSs) for fast mixing and separation. Although the highest ee obtained was only 80%, the concept can be extended through the use of a series of CCSs in countercurrent mode to effect full separation.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: amino acids; host–guest systems; liquid-phase separation; membranes; process intensification; transport
ISSN: 1521-3765
Last Modified: 19 Mar 2016 22:15
URI: http://orca-mwe.cf.ac.uk/id/eprint/9694

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