Separation using high-speed counter-current chromatography and identification of 1,3-bis(4-phenylazophenyl)triazene, an impurity in the color additive D&C Red No. 17 (Sudan III)
2019
Weisz, Adrian | Ridge, Clark D. | Perez-Gonzalez, Marianita | Ito, Yoichiro
The present work describes the application of high-speed counter-current chromatography to the preparative separation of a previously unreported impurity in the color additive D&C Red No. 17 (R17, Colour Index No. 26100, Sudan III). Due to the hydrophobic nature of the impurity, a hydrophobic two-phase solvent system (hexane-ethanol-water, 5:4:1) was used for its separation. The separated impurity was chemically characterized by spectroscopic methods as a disazo triazene, 1,3-bis(4-phenylazophenyl)triazene (PAPT). This impurity was synthesized and used as a reference material to quantify it in 15 batches of the color additive produced by various domestic and foreign manufacturers and certified by the U.S. Food and Drug Administration (FDA). Analysis of test portions by high-performance liquid chromatography showed a range of PAPT levels, from “not detected” (<0.006%) to 0.70%, across batches. The variability suggests that contamination by PAPT can be decreased or eliminated through manufacturing modifications. A chemical pathway for PAPT formation and an associated adjustment to minimize it during the process of manufacturing R17 are proposed.
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