Abstract
Hydroperoxide atα-position to the aromatic ring is the primary oxidation product formed. In all cases monoalkylbenzenes lead to the formation of benzoic acid. Oxidation in the presence of transition metal salts not only accelerate but also selectively decompose the hydroperoxides. Alkyl naphthalenes mainly produce the corresponding naphthalene carboxylic acids. Hock-rearrangement by the influence of strong acids converts the hydroperoxides to hemiacetals. Peresters formed from the hydroperoxides undergo Criegee rearrangement easily. Alkali metals accelerate the oxidation while CO2as co-oxidant enhances the selectivity. Microwave conditions give improved yields of the oxidation products.
Highlights
The first examination of alkylaromatics with molecular oxygen was published by Ciamician and Silber[1]
Hock and Lang showed that in the oxidation of indane[9] and from simple alkylaromatics like p-xylene[10], ethylbenzene[10] and cumene[11], the corresponding hydroperoxides as primary products could be isolated in which the –OOH group is present at the carbon atom at -position to the aromatic ring
It is obvious to carry out oxidation of alkylaromatics under the conditions where the hydroperoxides formed immediately undergo Hock-rearrangement
Summary
The first examination of alkylaromatics with molecular oxygen was published by Ciamician and Silber[1]. Hock and Lang showed that in the oxidation of indane[9] and from simple alkylaromatics like p-xylene[10], ethylbenzene[10] and cumene[11], the corresponding hydroperoxides as primary products could be isolated in which the –OOH group is present at the carbon atom at -position to the aromatic ring. The radical decomposition of hydroperoxides through alkalies and the catalytic effect of alkali hydroxides and carbonates in cumene oxidation can be supressed when carried out in the presence of small quantities of ethylenediaminetetraacetic acid[35]. Benzoic acid is obtained as expected when the oxidation is carried out in acetic acid as solvent and in the presence of bromide containing catalyst systems from toluene, ethylbenzene and cumene. The further oxidation of the acetophenone formed from ethylbenzene and cumene respectively creates difficulties in the oxidations
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