Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 9, pp. 1456−1458.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © V.M. Farzaliev, M.R. Bairamov, Z.M. Dzhavadova, I.G. Mamedov, M.A. Dzhavadov, N.Yu. Zeinalov, 2013, published in Zhurnal
Prikladnoi Khimii, 2013, Vol. 86, No. 9, pp. 1490−1492.
Binary Cooligomers of 2-Propenylphenol with 1-Heptene
and 1-Decene as Antimicrobial Additives
for Lubricating Oil I-12A
V. M. Farzaliev
, M. R. Bairamov
, Z. M. Dzhavadova
, I. G. Mamedov
M. A. Dzhavadov
, and N. Yu. Zeinalov
Institute of Chemistry of Additives, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
e-mail: misir.cavadov @mail.ru
Baku State University, Baku, Azerbaijan
Received July 19, 2013
Abstract—Binary cooligomers of C
α-oleﬁ ns with 2-propenylphenol were synthesized in the presence of
a complex catalyst based on aluminum chloride, toluene, and ethyl chloride (1:3.0:0.6 mol). Tests of the cooligo-
mers as antimicrobial additives to I-12A oil showed that, in concentrations of 0.25 and 0.5%, they inhibit fungal
growth, being superior to 8-hydroxyquinoline (reference) in the efﬁ ciency of action.
As known, various microorganisms can modify
the properties of fuels and oils, thereby signiﬁ cantly
affecting their performance characteristics . Also,
microorganisms can cause biocorrosion of oilfield
equipment, which constitutes a serious challenge .
One of the main ways to protect materials against
biocorrosion is via introduction of biocidal additives, for
which purpose various chemical compounds are suitable
Here, we synthesized binary cooligomers of
2-propenylphenol with 1-heptene and 1-decene and
examined their antimicrobial properties in industrial oil
Binary cooligomers of 2-propenylphenol with
1-heptene and 1-decene were synthesized in the
presence of a complex catalyst based on aluminum
chloride, toluene, and ethyl chloride (1:3.0:0.6 mol) at
an equimolar ratio of the monomers, temperature of
90–130°C, and reaction time of 0.5–3 h. The yield was
72–75%. The structures of the compounds synthesized
were determined by
C NMR spectroscopy
(Bruker-300 spectrometer, working frequency 300 and
75 MHz, solvent acetone-d
We present below the NMR spectroscopic data for the
cooligomer of 2-propenylphenol with 1-heptene as an
H NMR spectrum contains the following
signals, δ, ppm: 0.5–1.1 doublet and multiplet (CH
groups), 1.65–2.8 multiplet ((CH
–Ar), 6.65–7.55 multiplet (aromatic ring), 8.1–8.6
singlet (phenol ring, hydroxy group).
C NMR spectrum, δ, ppm: 5–14 (CH
44 (–CH groups), 114–157 (aromatic ring, CH groups).
The spectroscopic examinations suggest that the process
involves mainly oligomerization of 2-propenylphenol and
alkylation by 1-heptene of the side aromatic rings at the
ortho position to the OH group (Scheme 1).
No formation of oligomer of 1-heptene was found
under the actual conditions.
The antimicrobial properties of the compounds
synthesized were examined in accordance with GOST
(State Standard) 9.082–77 and GOST 9.052–88. In our
tests we used mixtures of pure cultures: Pseudomonas
aeruginosa and Mycobacterium lacticolum bacteria and
Aspergillus niger, Penicillium chrysogenum, Penicillium