Russian Journal of Applied Chemistry, 2011, Vol. 84, No. 2, pp. 256−260.
Pleiades Publishing, Ltd., 2011.
Original Russian Text © Ch.K. Rasulov, L.B. Zeinalova, R.K. Azimova, Ch.K. Salmanova, S.F. Akhmedbekova, A.P. Mamedov, 2011, published in Zhurnal
Prikladnoi Khimii, 2011, Vol. 84, No. 2, pp. 260−264.
AND INDUSTRIAL ORGANIC CHEMISTRY
Study of the Inhibiting Activity of 4-(4'-Hydroxyphenyl)-
and 4-(2'-Hydroxy-5'-methylphenyl)methyl Cyclohexane
Carboxylic Acid Ethyl Esters in Photooxidation
of Petroleum Phosphors
Ch. K. Rasulov, L. B. Zeinalova, R. K. Azimova, Ch. K. Salmanova,
S. F. Akhmedbekova, and A. P. Mamedov
Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Received April 7, 2010
Abstract—4-(4'-hydroxyphenyl)- and 4-(2'-Hydroxy-5'-methylphenyl)methyl cyclohexane carboxylic acid ethyl
esters were synthesized from phenol and para-cresol. The structure of the esters synthesized was studied, and
their inhibiting activity in photooxidation of a petroleum phosphor produced from the heavy pyrolysis tar fraction
An interesting and promising research area is
photochemical oxidation of petroleum and petroleum
products. In contrast to thermal treatment, light exposure
enables selective delivery of energy to a component
of the reaction mixture, which is important for such
multicomponent systems as oil.
Petroleum phosphors (PPs) are labile oil products and,
when exposed to solar light and atmospheric oxygen,
they are subject to photooxidative processes making
shorter their service life. Therefore, it is necessary to
ﬁ nd inhibitors that stabilize PPs without interfering with
the components responsible for luminescence.
It is known [1, 2] that compounds containing OH,
NH, and SH functional groups, capable of homolytic
dissociation under the action of free radicals, and
aromatic rings are oxidation inhibitors.
There are numerous alkyl phenol compounds [3–
7] serving as additives to oils, fuels, and polymeric
materials, emulsiﬁ ers, inhibitors, and thermal and light
stabilizers [1, 8–10].
In this communication, we present results obtained in
cycloalkylation of phenol and para-cresol with 1-meth-
ylcyclohexenecarboxylic acid ethyl ester (MCHAEE) in
the presence of a KU-23 catalyst in the H-form and in
analysis of synthesized 4-(4'-hydroxyphenyl)- (ester 1)
and 4-(2'-hydroxy-5'-methylphenyl)methyl cyclohex-
ane carboxylic acids ethyl esters (ester 2) as PP photo-
As starting products served phenol [GOST (State
Standard) 6417–74], para-cresol [TU (Technical
Speciﬁ cation) 6-09-244–77] and MCHAEE produced
by reacting isoprene with acrylic acid ethyl ester in
a 1-l autoclave. The reaction was performed in the
atmosphere of argon at a temperature of 200°C in the
course of 2 h at a 1 : 1 isoprene : ester molar ratio. After
the experiment was complete, the reaction products
were subjected to rectiﬁ cation; MCHAEE: bp 211°C,
0.9701, M 168.
We used KU-23 cation exchanger (GOST 20298–
74) as a catalyst. The KU-23 catalyst was prepared by