Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 8, pp. 1314−1316.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © A.I. Akhmedov, N.A. Talyshova, A.M. Gasanova, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86, No. 8, pp. 1340−1342.
Cooligomers of 1-Hexene with Dicyclopentadiene as Synthetic
Components to Petroleum Oils
A. I. Akhmedov, N. A. Talyshova, and A. M. Gasanova
Kuliev Institute of Chemistry of Additives, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received April 8, 2013
Abstract—Cooligomers of 1-hexene with dicyclopentadiene were synthesized. Depending on the cooligomerization
conditions, cooligomers with the molecular weight of 1000–4000, containing 10–20% dicyclopentadiene units,
were obtained in a 76–92% yield. Aluminum chloride was used as the cooligomerization catalyst. The cooligomers
synthesized were tested as components to M-6 and I-12A petroleum oils with the view of increasing their viscosity.
The use of 25–40% cooligomer in these oils allows preparation of base oils with the viscosity index of 93–126.
The resultant compounded oil possesses anticorrosive properties due to the presence of the dicyclopentadiene
units in the cooligomer.
Oligomers and cooligomers of higher α-oleﬁ ns are
widely used in various economy sectors, including
petrochemicals, for improving the performance
characteristics of lubricating oils: as viscosity additives,
synthetic components to petroleum oils, feed materials
in development of multifunctional polymeric additives,
and synthetic hydrocarbon oils.
Various polymeric compounds formed from vinyl
monomers are known today as viscosity additives [1–3].
However, when introduced into the composition of
petroleum oils, these additives with their high molecular
weights undergo destruction under operation conditions,
and the viscosity of oil falls below acceptable level,
which is undesirable. For increasing the viscosity index
of petroleum oils, the use of low-molecular-weight
polymers, oligomers and cooligomers of α-oleﬁ ns, more
resistant to the destructive actions, is preferable.
At the same time, functionalization of oligomers of
α-oleﬁ ns requires that their macromolecules contain
a reactive site to facilitate the chemical modiﬁ cation
reactions with a view to develop multifunctional
Here, we synthesized cooligomers of 1-hexene
with dicyclopentadiene and tested them as synthetic
components to petroleum oils.
The choice of 1-hexene as the main monomer was
dictated by its being unique among higher α-oleﬁ ns in
having readily available raw material resources. As to
dicyclopentadiene, it is extensively used in petrochemical
synthesis and in synthesis of additives intended for
Cooligomerization of 1-hexene with dicyclopentadiene
was carried out in the presence of aluminum chloride in a
hexane solution over the temperature range –10…+40°C
(see scheme). The resultant cooligomers with the
molecular weight of 1000–4000, containing 10–20%
dicyclopentadiene units, were obtained in a 76–92% yield.
The composition of the copolymers was determined by
the known technique  from the carbon content.
The constants of copolymerization of 1-hexene with
dicyclopentadiene, estimated by the Fineman-Ross
method for low monomer conversions of up to 10%, were
= 1.3 for 1-hexene and r
=0.0 for dicyclopentadiene.
The zero copolymerization constant for dicyclopenta-
diene means that it is incapable of homopolymerization.
An increase in its content in the initial monomer mixture
leads to decreases in the yield and molecular weight of the
cooligomers and to formation of cooligomers in which the