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Preparative separation of di- and trisulfonated components of Quinoline Yellow using affinity-ligand pH-zone-refining counter-current chromatography

Weisz, Adrian, Mazzola, Eugene P., Ito, Yoichiro
Journal of chromatography 2009 v.1216 no.19 pp. 4161-4168
color, countercurrent chromatography, hydrochloric acid, ion exchange, mass spectrometry, nuclear magnetic resonance spectroscopy, quinoline, solvents, sulfuric acid
Four positionally isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dionedisulfonic acids (SA) and one triSA, components of the color additive Quinoline Yellow (QY, Color Index No. 47005), were isolated from the dye mixture by affinity-ligand pH-zone-refining counter-current chromatography (CCC) through complementary use of ion-exchange and ion-pair reagents as the ligand. The added ligands facilitated the partitioning of the very polar polysulfonated components into the organic stationary phase of the two-phase solvent systems that consisted of isoamyl alcohol-methyl tert-butyl ether-acetonitrile-water (3:5:1:7), (3:4:1:7) or (3:1:1:5). Thus, separation of a 5-g portion of QY using sulfuric acid as the retainer and dodecylamine as the ligand (an ion-exchange reagent, 20% in the stationary phase), resulted in 1.21g of 6',5-diSA and 1.69g of 6',8',5-triSA, both of over 99% purity. A minor component, 8',4-diSA, not previously reported was also obtained (4.8mg of over 94% purity) through a similar separation of a different batch of QY using hydrochloric acid as the retainer and 10% dodecylamine as the ligand in the stationary phase. Two components that co-eluted (0.55g) in the 5g separation were separated when trifluoroacetic acid was used as the retainer and tetrabutylammonium hydroxide (an ion-pair reagent) as the ligand. The separation resulted in 20.7mg of 6',4-diSA, not previously reported, and 111.8mg of 8',5-diSA, both of over 98% purity. The isolated compounds were characterized by high-resolution mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments.