ISSN 1070-4272, Russian Journal of Applied Chemistry, 2008, Vol. 81, No. 1, pp. 74 !77. + Pleiades Publishing, Ltd., 2008.
Original Russian Text + V.M. Farzaliev, A.M. Magerramov, M.R. Bairamov, I.A. Rzaeva, O.N. Dzhavadova, M.A. Allakhverdiev, 2008, published
in Zhurnal Prikladnoi Khimii, 2008, Vol. 81, No. 1, pp. 78!81.
AND INDUSTRIAL ORGANIC CHEMISTRY
Antioxidant Properties of Sulfides Derived from 2-Propylphenol
and of Their Aminomethyl Derivatives
V. M. Farzaliev, A. M. Magerramov, M. R. Bairamov, I. A. Rzaeva,
O. N. Dzhavadova, and M. A. Allakhverdiev
Baku State University, Baku, Azerbaijan
Institute of Chemistry of Additives, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received May 16, 2007
Abstract-Antioxidant properties of sulfides derived from 2-propylphenol and of their aminomethyl deriva-
tives were studied in a model reaction of cumene oxidation. The kinetic parameters of the reactions of these
compounds with cumylperoxy radicals and cumyl hydroperoxide were determined.
In the modern oil-refining technology, there is a
need for the development of advanced processes for
production of petroleum products, including fuel and
lubricating oils of optimal hydrocarbon composition,
to meet the modern engineering and environmental
requirements. At the same time, the use of petroleum
fuels and lubricating oils is impossible without addi-
tives having various functional effects.
Among the most widely used additives to fuels and
lubricating oils are alkylphenols and their various
sulfur-, nitrogen-, and phosphorus-containing deriva-
tives [1, 2].
As antioxidant properties of additives are associ-
ated with the presence of definite functional groups,
it is particularly interesting to prepare organic com-
pounds containing two or more functional groups in
the molecule and to study the mechanism of their anti-
oxidant effect, because such compounds may combine
useful properties of different types of antioxidants.
Studies on the synthesis and mechanism of the
antioxidant effect of compounds containing in their
molecules a sulfide sulfur atom in combination with
phenolic fragment (phenolic sulfides), aromatic amine
(amino sulfides), and phenolic fragment + aromatic
amine (aminophenolic sulfides) showed that these
compounds not only combine the capabilities of sul-
fides to decompose hydroperoxides and of phenols
and amines to terminate oxidation chains in reactions
with peroxy radicals, but also exhibit a new property:
They are capable to catalytically decompose hydro-
peroxides into molecular products .
With the aim to develop a scientific basis for the
purposeful synthesis of an antioxidant of an optimal
structure, exhibiting high performance, we examined
in this study the antioxidant properties of new phenol-
ic sulfides derived from 2-propylphenol and of their
aminomethyl derivatives. The phenolic sulfides were
prepared by homolytic thiylation of 2-propenyl- and
2-allylphenols with amyl and benzyl mercaptans, and
the aminomethyl derivatives were synthesized by the
Mannich condensation of the resulting phenolic sul-
fides with formaldehyde and dimethylamine .
Antioxidant properties of the compounds were
evaluated by the well-known kinetic method based on
inhibition of certain key reaction. As a model hydro-
carbon we chose cumene.
II III IV
Fig. 1. Kinetic curves of cumene autooxidation (0) without
additives and in the presence of compounds I!V. 110oC;
[InH] = 5 0 10
) Oxygen uptake and (t) time; the
same for Fig. 2.