Paper
Synthesis of 1‐amino‐2‐methylindoline by Raschig process: Kinetics of the oxidation of 1‐amino‐2‐methylindoline by chloramine
Published 2002 · M. Elkhatib, C. Duriche, L. Peyrot
International Journal of Chemical Kinetics
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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
The Raschig process for synthesis of 1-amino-2-methylindoline in aqueous solution can be improved by oxidizing 1-amino-2-methylindoline by chloramine, leading to increased yield and improved kinetics.
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