Preparative separation of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione monosulfonic acids of the color additive D&C Yellow No. 10 (quinoline yellow) by pH-zone-refining counter-current chromatography.
The main components of the color additive D&C Yellow No. 10 (Quinoline Yellow, Color Index No. 47005), 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-6'-sulfonic acid (6SA) and 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-8'-sulfonic acid (8SA), were isolated from the dye mixture by pH-zone-refining counter-current chromatography (CCC) in the ion-exchange mode. These positional isomers were separated from a portion of dye using sulfuric acid as the retainer acid and dodecylamine as the ligand (ion exchanger). The added ligand enhanced the partitioning of the hydrophilic components in the organic stationary phase of the two-phase solvent system that consisted of isoamyl alcohol-methyl tert.-butyl ether-acetonitrile-water (3:1:1:5). Thus, separation of 1.8 g of D&C Yellow No. 10 using the above method resulted in 0.6 g of 6SA and 0.18 g of 8SA of over 99% purity. The isolated compounds were characterized by mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments. The study exemplifies a new field of applications for pH-zone-refining CCC, to the separation of positional isomers of strongly hydrophylic compounds containing sulfonic acid groups.
Weisz
A
A
Office of Cosmetics and Colors, Food and Drug Administration, Washington, DC 20204, USA. aweisz@cfsan.fda.gov
Mazzola
E P
EP
Matusik
J E
JE
Ito
Y
Y
D002851:Chromatography, High Pressure Liquid; D002852:Chromatography, Ion Exchange / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D011804:Quinolines / Q000737:chemistry* / Q000302:isolation & purification*; D013451:Sulfonic Acids / Q000302:isolation & purification*
D011804:Quinolines; D013451:Sulfonic Acids; C019303:quinoline yellow; C445091:2-(2-quinolinyl)-1H--indene-1,3(2H)-dione-8'-sulfonic acid; C445090:2-(2-quinolinyl)-1H-indene--1,3(2H)-dione-6'-sulfonic acid