Synthesis and Antioxidant Activity
A. T. Guseinova, K. I. Alieva, I. A. Rzaeva, A. M. Magerramov,
I. A. Aliev, V. M. Farzaliev, and M. A. Allakhverdiev
Baku State University, Baku, Azerbaijan
Kuliev Institute of Additive Chemistry, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received February 18, 2008
Abstract—1-Amino-4-phenyl-2-butanethiols were synthesized and characterized and their antioxidant activity
in auto-oxidation of cumene and in their reaction with cumyl peroxide radicals and cumyl hydroperoxide was
ORGANIC SYNTHESIS AND INDUSTRIAL
ISSN 1070-4272, Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 9, pp. 1587–1591. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © A.T. Guseinova, K.I. Alieva, I.A. Rzaeva, A.M. Magerramov, I.A. Aliev, V.M. Farzaliev, M.A. Allakhverdiev, 2009, published in
Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 9, pp. 1488–1492.
A topical task of modern tribochemistry is to
improve the stability of petroleum fuels and oils
against oxidation in prolonged storage and service. The
only way to stabilize fuels and oils is to add antioxi-
dant additives. At present, various alkyl derivatives of
phenols, aromatic amines, aminophenols, various
sulfides, and metal salts of dithio-phosphoric acids are
widely used as antioxidant additives .
Published data on the use of 1,2-aminothiols as
inhibitors of oxidation of fuels and other petroleum
products are scarce. There have been separate reports
that, owing to their antioxidant properties, aminothiols
and amino sulfides can be used to stabilize
polymethacrylic acid under the action of X-rays .
Some aminothiols are used as inhibitors of oxidation
and decomposition of organic peroxides and stabilizers
of fats and fat-containing products .
In this study, we synthesized 1-amino-4-phenyl-2-
propanethiol and examined the relationship between its
structure and antioxidant activity. As the starting
product served 1-chloro-4-phenyl-2-butanol (I) syn-
thesized by reacting benzylmagnesium chloride with
I + KOH
MgCl + CH
The highest yield of 1-chloro-4-phenyl-2-butanol
(I) is obtained at a 1 : 2 ratio between the Grignard
reagent and epichlorohydrin. At a 1 : 1 molar ratio, the
yield of the target product sharply decreases. The
physicochemical constants of 1-chloro-4-phenyl-2-
butanol are consistent with published data .
Finely ground potassium hydroxide in a solution of
anhydrous ether was used to dehydrochlorinate 1,2-
chlorohydrin I and convert it to the corresponding 1,2-
The physicochemical constants of oxirane II we
synthesized are consistent with published data .
1,2-Epithio-4-phenylbutane (III) was synthesized
by anionotropic substitution of the oxygen atom in
oxirane II with a sulfur atom from the thiocarbamide
molecule in the presence of sulfuric acid: