101. Preparative separation of 1,3,6-pyrenetrisulfonic acid trisodium salt from the color additive D&C Green No. 8 (pyranine) by pH-zone-refining counter-current chromatography
- Author
-
Yoichiro Ito, Eugene P. Mazzola, and Adrian Weisz
- Subjects
Salt (chemistry) ,Mass spectrometry ,Biochemistry ,Mass Spectrometry ,Article ,Analytical Chemistry ,Pyranine ,chemistry.chemical_compound ,Countercurrent chromatography ,Amines ,Arylsulfonates ,Countercurrent Distribution ,Nuclear Magnetic Resonance, Biomolecular ,Chromatography, High Pressure Liquid ,chemistry.chemical_classification ,Pyrenes ,Chromatography ,Organic Chemistry ,Sulfuric acid ,General Medicine ,Hydrogen-Ion Concentration ,Reference Standards ,chemistry ,Sodium hydroxide ,Proton NMR ,Spectrophotometry, Ultraviolet ,Sulfonic Acids ,Counterion - Abstract
In developing analytical methods for batch certification of the color additive D&C Green No. 8 (G8), the U.S. Food and Drug Administration needed the trisodium salt of 1,3,6-pyrenetrisulfonic acid (P3S) for use as a reference material. Since P3S was not commercially available, preparative quantities of it were separated from portions of a sample of G8 that contained ∼3.5% P3S. The separations were performed by pH-zone-refining counter-current chromatography using dodecylamine (DA) as the hydrophobic counterion. The added DA enabled partitioning of the polysulfonated components into the organic stationary phase of the two-phase solvent system used, 1-butanol–water (1:1). Thus, a typical separation that involved 20.3 g of G8, using sulfuric acid as the retainer acid and 20% DA in the stationary phase and 0.1 M sodium hydroxide as the mobile phase, resulted in ∼0.58 g of P3S of greater than 99% purity. The identification and characterization of the separated P3S were performed by elemental analyses, proton nuclear magnetic resonance, high-resolution mass spectrometry, ultra-violet spectra, and high-performance liquid chromatography.
- Published
- 2011