Ozonation of Decalin as a Model Saturated Cyclic Molecule: A Spectroscopic Study.

Boris G Ershov,Gennadii L Bykov,Vladimir G Krasovskiy,Alexander L Kustov,Nadezhda M Panich,Leonid M Kustov

doi:10.3390/molecules26185565

Abstract

Ozonolysis is used for oxidation of a model cyclic molecule-decalin, which may be considered as an analog of saturated cyclic molecules present in heavy oil. The conversion of decalin exceeds 50% with the highest yield of formation of acids about 15–17%. Carboxylic acids, ketones/aldehydes, and alcohols are produced as intermediate products. The methods of UV-visible, transmission IR, attenuated total reflection IR-spectroscopy, NMR and mass-spectrometry were used to identify reaction products and unravel a possible reaction mechanism. The key stage of the process is undoubtedly the activation of the first C-H bond and the formation of peroxide radicals.

Highlights

Ozone is known to be an efficient oxidizing agent and is widely used in organic syntheses and in purification of water by the complete oxidation of traces of organic compounds present in water
It was found that the contact of ozone with decalin does not lead to the appearance of a well-resolved characteristic ozone absorption band in an optical spectrum with a maximum at 258 nm, some residual absorption in the region of 260 nm was seen
We conclude that aldehydes, ketones, and carboxylic acids are formed in addition to hydroxydecalin isomers (E- and Z-decalol isomers)

Summary

Introduction

Ozone is known to be an efficient oxidizing agent and is widely used in organic syntheses and in purification of water by the complete oxidation of traces of organic compounds present in water. Ozone is characterized by high reactivity with unsaturated bonds, aromatic structures, and fragments containing electron-donor atoms and groups [1,2,3,4]. Ozonation is an alternative to other known methods of synthesis of oxygenated organic compounds in the oxidation of cycloalkanes. Ozonation of naphthenic molecules has been studied to a much lesser extent than reactions with unsaturated and aromatic substrates. This can be understood considering similarities in the properties of alkanes and cycloalkanes, which are quite inert toward oxidizing agents, except for C3 and

Objectives

Methods

Results

Conclusion