Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 1, pp. 85−88.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © A.N. Agaev, S.M. Velieva, N.N. Zeinalova, I.D. Kulaliev, 2012, published in Zhurnal Prikladnoi Khimii, 2012, Vol. 85, No. 1, pp. 89−92.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis of Oil-Soluble Multipurpose Sulfonate Additives
Based on Low-Molecular-Weight Alkylphenols
A. N. Agaev, S. M. Velieva, N. N. Zeinalova, and I. D. Kulaliev
Kuliev Institute of Chemistry of Additives, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received April 5, 2011
Abstract—New multipurpose sulfonate additives improving the detergent, dispersant, anticorrosive, and
antioxygenic properties of lubricant oils were developed on the basis of sulfomethylated alkyl(С
formaldehyde condensation product.
Additives providing different functionalities, in partic-
ular detergent-dispersant additives of the sulfonate type,
are widely used in development of high-performance
motor oils complaint with tightened current and future
technology regulations . The most promising additives
include neutral and high-basicity alkylphenol sulfonates
of alkaline earth metals which, when in low concentra-
tions, improve simultaneously several properties (de-
tergent, dispersant, anticorrosive, and antioxygenic) of
lubricant oils and thereby are suitable as multipurpose
additives for compositions . As shown previously ,
the best stock material for preparation of these additives
with high performance characteristics can be found in
ethylene oligomers of the С
high-temperature ethylene oligomerization catalyzed by
triethylaluminum, yields, along with this fraction, ca.
fraction oleﬁ ns unsuitable for synthesis of
sulfonate additives because their salts are insufﬁ ciently
soluble in lubricant oils and are ineffective.
To prepare additives with improved solubility in oil and
efﬁ ciency, the initial alkyl(С
by alkylation of phenol with ethylene oligomers of the
fraction was condensed with formaldehyde in an
acidic medium. The resulting methylenebis(alkylphenol)
was sulfomethylated with sodium hydroxymethane
sulfonate into the sodium salt of the corresponding
methylenebis(alkylphenol sulfonic) acid, which reacted
with calcium hydroxide to give a neutral sulfonate.
Treatment of the latter with carbon dioxide in the pres-
ence of excess calcium hydroxide yielded medium- and
high-basicity additives. The additives were synthesized
by the scheme.
The composition and structure of the sulfonates were
conﬁ rmed by elemental analysis and IR spectroscopic
The IR spectra of the sulfonates contain absorption
bands at 1050–1070 and 1160–1250 cm
with symmetric and antisymmetric stretching vibrations
of the S=О bonds in the SО
group, as well as bands at
due to the stretching vibrations of the
OH group. Bands at 840–880 cm
are associated with
bending vibrations of the 1,2,4,6-substituted benzene
ring, and those at 1420–1440 cm
are characteristic of
bending vibrations of the CH
The characteristics of the synthesized neutral (NSK
and alkaline (SS-150
) sulfonate additives
against those of the known Hitec 6060M additive are
listed in Table 1.
Table 1 shows that the new modiﬁ cations of alkylphe-
nol sulfonate additives synthesized are completely soluble
in oil and possess high physicochemical and functional
properties. These multipurpose additives signiﬁ cantly
improve the detergent, dispersant, anticorrosive, and
antioxygenic properties of M-11 oil and are superior in
efﬁ ciency to the foreign analog, Hitec 6060M additive.
For example, the corrosion on lead plates for M-11oil
with 5% SS-150
additives was estimated