Оxidation of isomeric hydroxytoluenes with ozone in acetic anhydride
DOI:
https://doi.org/10.15587/1729-4061.2014.27703Keywords:
oxidation, acylation, ozonolysis, selectivity, ozone, acetoxytoluene, sulfuric acid, peroxide, acetoxybenzylacetate, acetoxybenzaldiacetateAbstract
The reaction of ozone with isomeric hydroxytoluenes in acetic anhydride medium to obtain corresponding aromatic alcohols and aldehydes was investigated. It was shown that in the research conditions, acetic anhydride acts as both solvent and acylating agent. The main reaction products are aliphatic peroxides (80-90%), corresponding acetoxybenzylacetates (7-14%) and acetoxybenzaldiacetates (3-6%) were identified among the oxidation products by the methyl group of substrates. A scheme for the liquid-phase oxidation of acetoxytoluenes with ozone in acetic anhydride, which explains the obtained experimental data was proposed.
During the studies, the concentration of methylbenzenes and their conversion products in the solution was determined by gas-liquid chromatography at chromatograph with a flame ionization detector. The content of peroxide compounds was determined by iodometric titration. The rate constants of the reaction of ozone with methylbenzenes were calculated using the method, described in the work [3].
The obtained experimental data are the basis for developing environmentally friendly methods of synthesis of hydroxybenzyl alcohols and hydroxybenzaldehydes.
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