ISSN 1070-4272, Russian Journal of Applied Chemistry, 2014, Vol. 87, No. 9, pp. 1364−1366. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © A.I. Akhmedov, D.Sh. Gamidova, E.I. Isakova, E.I. Gasanova, 2014, published in Zhurnal Prikladnoi Khimii, 2014, Vol. 87, No. 9,
Alkyl Phenolate Lubricant Additive
Based on Oligohexenyl-substituted Phenol
A. I. Akhmedov, D. Sh. Gamidova, E. I. Isakova,
and E. I. Gasanova
Kuliyev Institute of Chemistry of Additives, Azerbaijan National Academy of Sciences,
ul. Istiglaliyyat., Baku, Az1001 Azerbaijan Republic
Received September 5, 2014
Abstract—The possibility of synthesis of a multifunctional phenolate additive based on the oligohexenyl phenol
was examined. For this oligohexenyl phenol was condensed with formaldehyde with further neutralizing of the
condensate with calcium hydroxide and treating the resulting product with carbon dioxide. The resulting additive
was used to improve the performance parameters of petroleum oils.
It is known that for the preparation of polymeric
additives possessing a multifunctional action different
groups or elements are introduced into the α-olefin
oligomers, i.e., functionalization occurs. Given the fact
that the majority of lubricant additives are produced on
the basis of alkylphenols [1, 2], it was of particular interest
to obtain similar additive of polymeric type, i.e., to use
oligohexenyl phenol in the synthesis of the additives
instead of alkylphenol.
For synthesis of the oligoalkylphenol 1-hexene was
subjected to oligomerization in the medium containing
The resulting oligohexenyl phenol was used in the
synthesis of alkyl phenolate additives. The advantage of
using the compounds synthesized as an original material
in the preparation of alkyl phenolate additives is that
unlike known additives new compounds together with
other operational characteristics increase also viscosity
index of petroleum oil. Preparation alkylphenol is
performed in one step, and by a known method at ﬁ rst
α-oleﬁ n oligomer is synthesized, and then it used in the
alkylation of phenol.
For the synthesis of the phenolate additive oligoalkyl-
phenol was subjected to condensation with formaldehyde.
This reaction has been well studied. The process was
carried out in benzene solution at 80–85°C, the ratio of
oligoalkylphenol : formaldehyde = 2 : 1 (mol) with a
catalytic amount of NaOH (2% of the reaction mass). A
released water was distilled azeotropically with benzene.
The process was continued until the stabilization of the
refractive index of the reaction products (n
On completion of the reaction the condensate was cooled
to room temperature and to it a 15–20% solution of
was added, and it was neutralized at 95–110°C.
The reaction mass was carbonized at 115–120°C, and as
a result the drying of the product occurred.
The scheme process was shown above.
Table 1. An effect of concentration of calcium oligo hexyl
phenolate on the viscosity-temperature parameters of M-6 oil
Kinematic viscosity mm
at a temperature, °C
0 6.5 – 89
6.8 46.20 92
1 7.0 47.30 93
3 7.5 51.70 96
5 8.0 57.30 106
7 8.7 64.20 106