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Emulsion liquid membranes for chiral separations: Selective extraction of rac ‐phenylalanine enantiomers
Author(s) -
Pickering Paul J.,
Chaudhuri Julian B.
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:3<261::aid-chir10>3.0.co;2-l
Subject(s) - chemistry , membrane , enantiomer , emulsion , enantiomeric excess , chirality (physics) , extraction (chemistry) , chromatography , liquid–liquid extraction , solvent , kinetic resolution , context (archaeology) , enantioselective synthesis , chemical engineering , organic chemistry , combinatorial chemistry , catalysis , biochemistry , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model , paleontology , engineering , biology
We describe the use of emulsion liquid membrane technology to perform chiral separations on low molecular weight species. We have reviewed liquid membrane technology in the context of existing process scale chiral separations. We illustrate the potential of this new technique by presenting our results on the selective extraction of phenylalanine enantiomers, using copper (II) N ‐decyl‐(L)‐hydroxyproline as a chiral selector in an emulsion liquid membrane configuration. This is compared with an analogous batch solvent extraction system. Initial batch enantiomeric excesses of greater than 40% were observed with the emulsion liquid membrane system compared with around 25% for the solvent extraction system. It was also noted that the system is not limited by the equilibrium capacity constraints of the solvent extraction system. We have shown that kinetic chiral liquid membrane technology offers high productivity and flexibility compared with analogous process scale chiral technologies. Recent transfer of highly specific chiral reversed‐phase high‐performance liquid chromatographic chemistries have shown that “one‐stop” enantiomeric excesses of commercial interest (>95%) are achievable using kinetic chiral liquid membrane systems. Solvent and temperature selection strategies also have been outlined as means of increasing the enantioselectivity of existing liquid membrane extraction chemistries. Chirality 9:261–267, 1997. © 1997 Wiley‐Liss, Inc.