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Synthesis of 1-amino-2-methylindoline by Raschig process: Kinetics of the oxidation of 1-amino-2-methylindoline by chloramine

✍ Scribed by M. Elkhatib; C. Duriche; L. Peyrot; R. Metz; H. Delalu

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
220 KB
Volume
34
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The synthesis of 1‐amino‐2‐methylindoline by the Raschig process was undertaken in aqueous solution. The principal side reaction that occurs in the medium is the oxidation of 1‐amino‐2‐methylindoline formed by chloramine. To increase the yield of 1‐amino‐2‐methylindoline, its oxidation by chloramine was studied by GC and HPLC at various concentrations of reactants and for a pH interval ranging between 9.9 and 13.5. The reaction is bimolecular and exhibits a specific acid catalysis. In alkaline medium, 1‐amino‐2‐methylindole is the principal product. The enthalpy and entropy of activation were determined at pH 12.89. In unbuffered solution, the interaction was autocatalyzed by the ammonium ions formed, which indicates a competitive oxidation of neutral and ionic forms of 1‐amino‐2‐methylindoline by chloramine. A mathematical treatment based on one implicit equation allows a quantitative interpretation of all the phenomena observed over the above pH interval. It takes both acid–base dissociation equilibrium and alkaline hydrolysis of chloramine into account. © 2002 Wiley Periodicals, Inc. Int J Chem Kinet 34: 515–523, 2002

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