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A Study of the pH Dependence of the Two-Step Oximation of Acetone by in situ Fourier Transform Infrared Spectroscopy

✍ Scribed by G. Keglevich; I. Csontos; N. Szilágyi; I. Greiner

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
752 KB
Volume
31
Category
Article
ISSN
0930-7516

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✦ Synopsis

Abstract

In situ Fourier transform IR spectroscopy has been found to be an appropriate tool for the evaluation, monitoring and optimization of the pH dependent and two‐step oximation of acetone in water. When carrying out the reaction at 5 °C, the intermediate formation of the acetone‐hydroxylamine adduct (2) was observed at pH 8.5, while at pH 10, the oxime (3) was formed almost instantly. Identification of the intermediate (2) was promoted by the IR spectrum obtained by B3LYP/6‐31++G(d,p)//PCM calculations. At pH ∼ 2.5, the protonated form of the oxime (3') developed gradually, but the intermediate (2) could not be observed. The pH dependence of the stability of the intermediate (2) and the (3' → 3) and (3 → 3') interconversions were studied in separate experiments. An equilibrium was observed in the latter case.

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