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Preparative separation of isomeric and stereoisomeric dicarboxylic acids by pH-zone-refining counter-current chromatography.

Weisz A, Idina A, Ben-Ari J, Karni M, Mandelbaum A, Ito Y

Office of Cosmetics and Colors, Center for Food Safety and Applied Nutrition, US Food and Drug Administration, College Park, MD 20740, USA. adrianweisz@fda.hhs.gov

This work involves the preparative separation of some isomeric dicarboxylic acids using pH-zone-refining counter-current chromatography (CCC), a relatively new preparative technique for the separation of ionizable compounds. The paper concentrates especially on the separation of a synthetic mixture of closely related cis and trans pairs of 1-methyl- and 1,3-dimethyl-1,3-cyclohexanedicarboxylic acids. The elution sequence of the isomers is discussed in terms of their relative acidities (pK(a) values) in solution and gas phase, hydrophobicities, and steric configuration. Two possible explanations are suggested for the mechanism of separation. They both involve the amount of retainer acid used, as it affects the separation and plays a role in the chemohydrodynamic equilibrium of the dicarboxylic acids in the column.

Published 9 May 2007 in J Chromatogr A, 1151(1): 82-90.
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