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Issue 13, 2001
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FTIR spectroscopic study of the OH-induced oxidation of two linear acetates: ethyl and n-propyl acetates

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Abstract

OH-induced oxidation mechanisms of ethyl and n-propyl acetates have been investigated at room temperature (298 ± 5 K) and atmospheric pressure by photolysing CH3ONO/acetate/NO mixtures with FTIR spectroscopy as analytical device. The main oxidation products and their yields were as follows: from ethyl acetate, acetic acid (0.75 ± 0.13), acetoxyacetaldehyde (0.15 ± 0.05), acetic anhydride (0.02 ± 0.01), formic acetic anhydride (0.02 ± 0.01) and peroxyacetyl nitrate (PAN); from n-propyl acetate, acetoxyacetaldehyde (0.22 ± 0.06), formic acetic anhydride (0.28 ± 0.03), acetic acid (0.15 ± 0.02), acetaldehyde (0.35 ± 0.10), peroxypropionyl nitrate (PPN) and probably acetoxypropionaldehyde (0.30 ± 0.10). From these data, oxidation schemes of these two acetates were elucidated. This study reveals in particular the specific reactivity of acetates by confirming the novel α-ester rearrangement proposed recently by Tuazon et al. (J. Phys. Chem. A, 1998, 102, 2316) and then by showing that oxygenated alkoxyl radicals may not follow the same rules of reactivity as other alkoxyl radicals. This last observation shows the necessity for further experiments to understand the influence of the oxygenated function on alkoxyl reactivity.

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Article information


Submitted
22 Feb 2001
Accepted
26 Apr 2001
First published
05 Jun 2001

Phys. Chem. Chem. Phys., 2001,3, 2595-2606
Article type
Paper

FTIR spectroscopic study of the OH-induced oxidation of two linear acetates: ethyl and n-propyl acetates

B. Picquet-Varrault, J. Doussin, R. Durand-Jolibois and P. Carlier, Phys. Chem. Chem. Phys., 2001, 3, 2595
DOI: 10.1039/B101704G

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