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Limitations during the Resolution of (±)‐Epinephrine by Using Tartaric Acid
Author(s) -
Couvrat Nicolas,
Mahieux Julien,
Sanselme Morgane,
Coquerel Gérard
Publication year - 2018
Publication title -
chemical engineering and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.403
H-Index - 81
eISSN - 1521-4125
pISSN - 0930-7516
DOI - 10.1002/ceat.201700557
Subject(s) - tartaric acid , epinephrine , resolution (logic) , chromatography , chemistry , process engineering , computer science , organic chemistry , artificial intelligence , engineering , medicine , anesthesia , citric acid
Attempts to perform Pasteurian resolution on epinephrine (or adrenaline) hydrogeno‐tartrate always lead to limited enrichments in (–)‐epinephrine. Structural and thermal investigations are performed on the diastereomeric system to understand this behavior. The analyses revealed the existence of a (metastable) total solid solution between the two anhydrous diastereomeric salts. This solid solution is partially inhibited by the crystallization of a stable hydrate; nevertheless, its extension still prevents high enrichment by single‐step crystallization. Phase diagrams are proposed to illustrate this non‐favored and non‐predictable behavior.