Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 1, pp. 32−36.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © Ch.K. Rasulov, Kh.D. Ibragimov, E.A. Medzhidov, S.Z. Alieva, A.S. Askerova, 2013, published in Zhurnal Prikladnoi Khimii,
2013, Vol. 86, No. 1, pp. 36−41.
Reaction between Phenol and 130–190°C Fraction of Liquid
Pyrolysis Products in the Presence of Catalyst KU-23
in a Continuous Plant
Ch. K. Rasulov, Kh. D. Ibragimov, E. A. Medzhidov, S. Z. Alieva, and A. S. Askerova
Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received June 26, 2012
Abstract—The results of the alkylation of phenol by 130–190°C fraction of the liquid pyrolysis products in the
presence of a catalyst KU-23 of H-form carried out in a continuous plant were reported. Optimal conditions for the
synthesis of p-alkyl phenol were found. It was shown that under the optimal mode a yield of target alkyl phenol
was 69.7% of theory and selectivity, 93.3%. p-Alkyl phenolamine resin tested as an antioxidant engine oil at high
temperatures was synthesized on the basis of p-alkyl phenol and hexamine.
Alkylphenols and its derivatives over the years is the
focus of research primarily due to an unusually wide
range of antioxidant activity of these compounds. They
are the starting material for synthesis of high effective
antioxidants, stabilizers of polyoleﬁ ns, synthetic rubbers,
lubricant additives to oils and fuels [1–5].
Intensive development in the world of low-octane
gasoline pyrolysis has led to production of hydrocar-
bons causing damage to the biosphere. Produced in the
pyrolysis plants liquid products of the gasoline pyrolysis
have not yet found an effective application, so search for
ways of using the liquid product of gasoline pyrolysis in
petrochemical synthesis is relevant, currently.
Alkylation of phenol by various agents is known in the
presence of acidic catalysts [6–11]. Their application is
associated with different engineering difﬁ culties, pollu-
tion of wastewater, formation of by-products and wastes,
and with large catalyst consumption.
The results of an interaction of phenol with 130–190°С
fraction of pyrolysis liquid product (FPLP) are reported.
Fresh sublimated phenol and FPLP (bp 130–190°С,
0.8583, molar weight 120) were used for
synthesis of p-alkyl aryl phenol.
A cation exchanger KU-23 (GOST State Standard
20298-74) in the form of spherical grains with a high
degree of porosity and high average ef
radius of macroporous structure was used as catalyst.
A treatment of the catalyst KU-23 (version 10/60, with
55–70 wt % of water, thermally stable at 150–170°C) for
operation was to remove the water at a temperature less
than 110°C. In the course of the operation KU-23 was
gradually inactivated due to cleavage of sulfo group by
heat and plugging pores by resinous substances. Since
the macroporous structure improves transport properties
of KU-23 its efﬁ ciency is higher comparing to that of
KU-2. Hydrochloric acid (2–4%) was used to regener-
ate the catalyst (4.5–4.0 volumes of acid per 1 volume
of the catalyst).
Alkylation of phenol by FPLP
was carried out in
a laboratory continuously operating setup. Phenol and
FPLP from tanks in a desired ratio were supplied to the
mixer. In the phenol tank temperature was maintained
45°C. Phenol and FPLP after mixing were supplied to the
lower zone of a reactor. The mixture of components pass-
ing through the catalyst bed, after cooling was collected