Kinetics and Products of the Reactions of Ozone with Toluene
and Its Derivatives in Acetic Anhydride

A. G. Galstyan, S. G. Galstyan, and V. V. Lysak

Institute of Chemical Technologies, East-Ukrainian National University, Rubezhnoe Branch,
Rubezhnoe, Lugansk oblast, Ukraine

e-mail: ozon@megabit.com.ua

Received December 14, 2009

Abstract—The reactions of ozone with toluene and its derivatives in acetic anhydride were studied. It was
found that competing parallel reactions of ozone with the aromatic ring and substituents occurred in the ozone–
arene–acetic anhydride system. The ratio between these reaction paths depended on the arene structure and
reaction conditions. The selectivity of the oxidation of toluene and its derivatives at the methyl group varied
from 0 to 40%. The fraction of aromatic products decreased as the number of methyl groups at the ring was
increased. Tri- and tetramethylbenzenes were oxidized only at the aromatic ring. The stability of an aromatic
system increased upon the introduction of electron-acceptor substituents into the benzene ring. Aminotoluenes
and hydroxytoluenes were oxidized with ozone mainly at the NH₂ and HO groups; however, as in the case of
toluene, the aromatic ring and methyl group became the main directions upon their acylation. The oxidation of
the methyl group in acetic anhydride in the presence of sulfuric acid was finished at the step of the formation
of the acylated derivatives of benzyl alcohols and benzaldehydes, which are resistant to the action of ozone.

DOI: 10.1134/S0023158411040033

Pleiades Publishing home page | journal home page | top

If you have any problems with this server, contact webmaster.