Handling Hydrogen Peroxide Oxidations on a Large Scale: Synthesis of 5‑Bromo-2-nitropyridine

5-Bromo-2-nitropyridine was prepared from the corresponding amine via hydrogen peroxide oxidation in large scale production. This transformation initially showed low conversion, high impurity content and lack of reproducibility in lab trials. Parallel to process development, safety studies were cond...

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Bibliographic Details
Published inOrganic process research & development Vol. 21; no. 3; pp. 451 - 459
Main Authors Agosti, Alessandro, Bertolini, Giorgio, Bruno, Giacomo, Lautz, Christian, Glarner, Thomas, Deichtmann, Walter
Format Journal Article
LanguageEnglish
Published American Chemical Society 17.03.2017
Subjects
process safety
ARC
nitro-aromatic
hydrogen peroxide
oxidation
thermal stability
RC1 calorimetry
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Summary:5-Bromo-2-nitropyridine was prepared from the corresponding amine via hydrogen peroxide oxidation in large scale production. This transformation initially showed low conversion, high impurity content and lack of reproducibility in lab trials. Parallel to process development, safety studies were conducted to investigate the stability of oxidant mixture, its composition and the oxidation reaction itself by reaction and adiabatic calorimetry. The resulting robust reaction conditions and appropriate safety boundaries allowed to develop a reproducible, safe protocol for the implementation of this chemistry on large scale, obtaining consistent results throughout the campaign.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.6b00433