Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 5, pp. 918−920.
Pleiades Publishing, Ltd., 2010.
Original Russian Text
N.F. Akhmedov, S.E. Mamedov, R.A. Akhmedova, 2010, published in Zhurnal Prikladnoi Khimii, 2010, Vol. 83, No. 5, pp. 865−867.
Cycloalkyldecalins as Components of Jet Fuels
N. F. Akhmedov, S. E. Mamedov, and R. A. Akhmedova
Baku State University, Baku, Azerbaijan
Received July 22, 2009
Abstract—The possibility of obtaining cycloalkyldecalins by the alkylation of 1- and 2-methylnaphthalenes
by cyclooleﬁ ns with subsequent hydrogenation of methylcycloalkylnaphthalenes was studied. Physicochemical
parameters of reaction products were determined, and their structure was deﬁ ned on the basis of IR and NMR
As ﬂ ight velocities in aviation increase the require-
ments to the quality of applied jet fuels raise. They should
have a high density, a maximal heat of combustion, and
a low solidiﬁ cation temperature. The most suitable com-
ponents of jet fuels are cycloalkylnaphtene hydrocarbons
possessing optimal properties for such fuels. However the
content of such hydrocarbons in commercial-grade fuel,
as a rule, is not sufﬁ ciently high, therefore the attempts
to ﬁ nd synthetic methods for obtaining fuels with high
contents of naphthene hydrocarbons are undertaken [1,
2]. From this point of view the hydrogenation of cyclo-
alkylnaphthalene hydrocarbons with the aim of obtaining
cycloalkyldecalins and their applications as components
of jet fuels seems promising.
In the pyrolysis of low-octane petrol and gas oils with
the purpose of obtaining low-molecular oleﬁ ns a pyrolysis
resin is formed as a side product containing signiﬁ cant
amounts of naphthalene (~27%), methylnaphthalenes
(~20%), and other aromatic hydrocarbons, which do
not ﬁ nd a qualiﬁ ed application as yet, but can be a good
source for obtaining naphthene hydrocarbons. It is known
 that the fraction 200–350°С obtained in the pyrolysis of
oil hydrocarbons during their hydrogenation on Raney
nickel gives a product meeting the requirements for jet
fuels by its quality. It was also offered  to hydroge-
nate the fraction 150–320°С of liquid pyrolysis products
or on a tungsten-nickel sulﬁ de catalyst at
temperatures of 150–350°С and pressures of 5–25 MPa
with the formation of naphthenes.
The aim of the present work was to obtain cycloal-
kyldecalins promising as highly heat-producing stable
components of jet fuel.
To synthesize cycloalkyldecalins, we used naphtha-
lene and 1- and 2-methylnaphthalenes as initial feed
stock, which were isolated by the fractionation and
crystallization methods from the fraction 200–250°С of
heavy pyrolysis resins (HPR). Cycloalkyldecalins were
synthesized in two stages.
(1) The alkylation of naphthalene and 1- and 2-meth-
ylnaphthalenes by cycloolefins (С
) was carried out on Y-form zeolite catalysts in
a ﬂ owing system at 250°С. Physicochemical parameters
of the cycloalkylnaphthalenes are presented in Table 1.
It was found on the basis of IR and NMR spectra that
1- and 1,2-substituted naphthalenes are the main reac-
(2) Resulting cycloalkylnaphthalenes were subjected
to hydrogenation on a nickel-chromic catalyst. The
hydrogenation was carried out in a rotating (50 rpm)
stainless-steel autoclave of volume 1 l in the presence of
a nickel-chromic catalyst. Cycloalkylnaphthalene, 310 g,
and the catalyst, 10% the cycloalkylnaphthalene weight,
were loaded into the autoclave. After blowing through by
hydrogen, the autoclave was ﬁ lled with hydrogen up to
the pressure of 9 MPa. At 170–190°С hydrogen absorption