Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 8, pp. 1201−1203.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © Yu.V. Popov, Ya.L. Uskach, S.M. Ledenev, N.Yu. Tokmacheva, O.N. Dontsova, 2012, published in Zhurnal Prikladnoi Khimii, 2012,
Vol. 85, No. 8, pp. 1262−1264.
OF SYSTEMS AND PROCESSES
Synthesis of an Antiscuff Additive to Gear Oils
from the Amylene Fraction
Yu. V. Popov, Ya. L. Uskach, S. M. Ledenev,
N. Yu. Tokmacheva, and O. N. Dontsova
Volgograd State Technical University, Volgograd, Russia
Received June 26, 2012
Abstract—Interaction of the amylene fraction with sulfur monochloride was studied and the optimal conditions
were determined for synthesis of a sulfur- and chlorine-containing additive to GL-4 gear oils of quality class TM-
4-12, SAE 80W-85, API.
Among the main criteria for assessment of
service properties of lubricants are their tribological
characteristics. Antiwear and antiscuff additives are
used to improve service properties of oils. To the most
efﬁ cient antiscuff and antiwear additives belong organic
compounds containing sulfur and chlorine, which can
be produced by reactions of α-oleﬁ ns of varied structure
with sulfur monochloride .
We studied the synthesis of an amylene-fraction-
based antiscuff additive to gear oils. As a raw material
for synthesizing the additive served the amylene
fraction having the form of a colorless transparent ﬂ uid
(density 0.640 g cm
, bp 38–41°C, 97.3% unsaturated
hydrocarbons) and sulfur monochloride.
The reaction of the amylene fraction with sulfur
monochloride is exothermic and fast, and, therefore,
when performing this reaction, we gradually added
sulfur monochloride to the amylene fraction under
vigorous agitation and cooling.
The reaction of α-oleﬁ ns of varied structure with
sulfur monochloride has been extensively described
in the literature. However, published data on the
mechanism of the chlorosulfation reaction are rather
contradictory because, depending on the structure
of a starting oleﬁ n, this reaction may occur both in
conformity with, and contrary to, the Markovnikov
rule [2, 3]. Because of the lack of evidence about the
interaction mechanism of the amylene fraction with
sulfur monochloride, we performed the reaction of
chlorosulfation of pentene-1 under similar conditions.
The structure of the thus synthesized compound was
conﬁ rmed by IR and
H NMR spectroscopies. The
IR spectrum of the compound contains absorption
bands characteristic of disulfochloride. Stretching
vibrations of the S–S and C–S bonds are represented
by the bands at 550 and 600 cm
, and those of the C–
Cl bond appear as a broad absorption band peaked at
H NMR spectrum of the disulfochloride
we synthesized is characterized by the presence of
signals from protons of methyl and methylene groups
of the alkyl moiety of the molecule. At the same time,
the fact that the spectrum contains resonance peaks
from protons of the –S–CH
–C– group (3.807 ppm)
as a multiplet and from the tertiary carbon bonded to
the chlorine atom (4.5 ppm) conﬁ rms the structure of
di(β-chloropentyl) disulﬁ de. The spectral characteristics
and physicochemical properties of the compound
are presented in Experimental. Thus, the reaction of
chlorosulfation of pentene-1 with sulfur monochloride
yields only di-(β-chloropentyl) disulﬁ de, i.e., it occurs
exclusively in conformity with the Markovnikov rule.
To examine the possibility of using the sulfur- and
chlorine-containing additive (SCCA) synthesized from