Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 8, pp. 1252−1255.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © D.B. Tagiev, N.A. Agaeva, M.K. Nazarova, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86, No. 8, pp. 1278−1281.
Catalytic Alkylation of Cresols with Propanol-1
D. B. Tagiev, N. A. Agaeva, and M. K. Nazarova
Sumgait State University, Sumgait, Republic of Azerbaijan
Received July 19, 2013
Abstract—Study of the reaction of alkylation of ortho-, meta-, and para-cresols with propanol-1 in the presence
of ferrite cobalt and manganese catalysts is reported. The effect of the catalyst composition and reaction conditions
on the yield and isomeric composition of the resulting propyl derivatives of cresol was examined and the main
and side conversions occurring in the catalysis were determined.
Propyl derivatives of cresol are valuable half-products
in manufacture of antioxidants, stabilizers, medicinal
preparations, and vitamins [1, 2]. These derivatives
are produced by alkylation of cresols with propene or
propanol in the presence of various catalysts [3, 4];
however, these catalytic systems have low activity and
selectivity in syntheses of propyl derivatives of ortho-,
meta-, and para-cresols.
Our communication presents results of a study of
the reaction of alkylation of of ortho-, meta-, and para-
cresols with propanol-1 in the presence of ferrite cobalt
and manganese catalysts.
Cobalt- and manganese-ferrite catalysts were
synthesized by joint deposition of nitrate salts of
iron(III) and cobalt(II) and(or) manganese onto γ-Al
followed by drying and calcination. The atomic ratio
between a divalent metal and iron, M : Fe, is 1 : (2–2.3).
The preliminarily found optimal content of MFe
in the catalyst is 22 wt %. Improvement of the high-
temperature method for synthesis of ferrite catalyst
makes it possible to obtain chemically homogeneous
and ﬁ nely porous ferrite particles having good catalytic
Experiments were performed on a ﬂ ow-through
laboratory installation in a ﬂ ow of hydrogen. The
volume of the ﬁ xed bed of a ferrite catalyst in the reactor
was 10 cm
. Liquid and gaseous reaction products were
analyzed by gas-liquid chromatography on a Khrom-5
instrument. As the liquid phase was used Apiezon M
deposited in an amount of 12 wt % on Chromaton N.
Isomeric propyl-cresols were also separated by fractional
distillation of the reaction mixture at 0.010 MPa.
We synthesized ﬁ ve mixtures of ferrite catalysts
(x = 0.3, 0.6, 0.9, 1.0) and
studied their catalytic properties in the reaction of
alkylation of ortho-, meta-, and para-cresols with
propanol-1. It can be seen in the ﬁ gure that an increase
in the fraction of cobalt in a mixture with manganese
makes higher the conversion of all the three isomers
of cresol in the alkylation reaction and improves the
formation selectivity of the main propyl isomers of
cresol: 2-propyl-6-methylphenol (1) in the case of
ortho-cresol, 2-propyl-5-methylphenol (2) in alkylation
of meta-cresol, and 2-propyl-4-methylphenol (3) in the
interaction with para-cresol with propanol-1.
As regards the formation selectivity of the above
propyl derivatives of cresol, ortho-cresol surpasses the
other isomers, whereas the highest conversion of cresol
is observed for meta-cresol. Interestingly, the yield and
formation selectivity of the target products of the reaction
of alkylation of ortho-, meta-, and para-cresols with
propanol are at a maximum at x = 0.9. In addition, the
cobalt-ferrite catalyst largely surpasses in activity that of
the manganese-ferrite type in the reaction of propylation
of cresols. For example, the formation selectivities of