Abstract
Hydroxyacetophenones, especially the para-isomer, are important compounds in the pharmaceutical industry. They can be obtained through acylation of phenol but no data about the thermodynamic properties of this reaction are available. The estimation of the properties of this reaction, using the Benson method, shows that the formation of hydroxyacetophenones is favorable at temperatures between 300 K and 800 K. Higher temperatures favor the formation of phenyl acetate. In this temperature range, meta-hydroxyacetophenone is more stable than the other isomers.
Highlights
Acylation reactions are largely employed in the fine chemical industry, producing a variety of synthetic fragrances and pharmaceuticals
This work presents the necessary steps for the calculation of thermodynamic properties of hydroxyacetophenones, an important group of compounds employed in the pharmaceutical industry
The Benson method, employed to estimate thermodynamic properties of the compounds involved in the reaction, was considered adequate for this system, since it gave an isomer distribution resembling other similar aromatic compounds
Summary
Acylation reactions are largely employed in the fine chemical industry, producing a variety of synthetic fragrances and pharmaceuticals. Hydroxyacetophenones, especially the ortho and paraisomers, which are required in the fabrication of pharmaceutical products[4,5] stand out among the aromatic products. These compounds can be obtained by direct C-acylation of phenol with acetic acid or rearrangement of phenyl acetate (Fries Reaction, Eq 2, Fig. 1). Several authors have studied this route in liquid phase[3] or gas phase[4,5,6]. In both case the primary product is the phenyl acetate and the hydroxyacetophenones are secondary products. To the best of our knowledge, no thermodynamic study of this reaction has been carried out, aiming to evaluate the appropriate conditions for the optimal formation of the desired isomers
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