HAVANA Electrochemical Hofmann degradation of carboxylic acid amides

The HAVANA consortium aims to make one of the most important substance classes in the pharmaceutical industry - amines - electrochemically accessible. An attractive approach to these is the electrochemical Hofmann degradation of carboxamides.
Carboxylic acids represent a very broad and readily available substrate class that can be easily converted into carboxamides. Treatment with halogens, such as bromine or chlorine, in an alkaline environment induces a rearrangement on nitrogen. This produces the corresponding carbamates, which can then be easily converted into the corresponding amines.

However, the halogens used are highly corrosive and toxic, which is why their use poses a high safety risk. The anodic oxidation of easy-to-handle bromides is an efficient and mild process to avoid the use of hazardous bromine.

The HAVANA consortium will therefore electrify this important transformation and make it suitable for process engineering applications. The pharmaceutical-related requirements, as well as product quality, compatibility with complex structures and robustness of the scaled process, play a central role. To achieve these goals, the electrosynthetic, electrolyzer and process expertise of Johannes Gutenberg-University, Fraunhofer Institute for Mikrotechnology und Mikrosystems (IMM) and Boehringer Ingelheim are bundled and thus represent a cross-disciplinary cooperation.

Coordinator:
Siegfried R. Waldvogel (MPI CEC) siegfried.waldvogel@cec.mpg.de

Further project participants:
Bernd Werner (Boehringer Ingelheim) bernd.werner@boehringer-ingelheim.com
Patrick Löb (Fraunhofer-Institut für Mikrotechnik und Mikrosysteme (IMM))
Athanassios Ziogas (Fraunhofer-Institut für Mikrotechnik und Mikrosysteme (IMM))