ISSN 1070-4272, Russian Journal of Applied Chemistry, 2014, Vol. 87, No. 2, pp. 214−216. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © A.G. Gasanov, A.G. Azizov, S.R. Khalilova, I.G. Ayubov, M.M. Gurbanova, S.T. Alieva, 2014, published in Zhurnal Prikladnoi Khimii,
2014, Vol. 87, No. 2, pp. 234−236.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis of 8-Heptadecene by Decarboxylation of Oleic Acid
in Various Catalyst Systems
A. G. Gasanov, A. G. Azizov, S. R. Khalilova, I. G. Ayubov,
M. M. Gurbanova, and S. T. Alieva
Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan,
pr. Khodzhaly 30, Baku, AZ1025 Azerbaijan
Received February 18, 2014
Abstract—Decarboxylation of oleic acid in the presence of various catalysts synthesized in a ﬂ ow system was
performed to produce 8-heptadecene, which is an important product of the petrochemical and other industries.
An effect of reaction temperature on the product yield was demonstrated.
It is known that higher linear internal oleﬁ ns are
widely used in various ﬁ elds of industry and agricul-
ture. They are part of extracts of plant oils, are natural
repellents and lures for catching insects, markers in ra-
diolytic reactions, and are also precursors in metathesis
reactions for the synthesis of surfactants [1–4].
In this respect C
internal oleﬁ ns (8-heptadecene,
heptadecadienes, heptadecatrienes, etc.) should be not-
ed, which have a number of speciﬁ c properties [5–8],
and, therefore, the synthesis of hydrocarbons by afford-
able and environmentally appropriate methods is of
theoretical and practical interest.
Oleic acid (OA) isolated from biorenewable sources
(vegetable oil) was used as a raw material. Synthetic and
natural aluminosilicates as well as nano-sized titanium
and magnesium oxides were used as the catalysts. Oleic
acid was of the following physicochemical parameters:
bp 223°C (100 mmHg), the density of 0.9 g mL
1.4582, acid number (AN) 179 mg KOH per g, an io-
dine number (IN) 70.7 g I
per 100 g.
The experimental technique was as follows. Through
a stationary reactor heated to a certain temperature and
ﬁ lled with a catalyst an estimated amount of OA fed
with a preset volume velocity using a dispenser. After
cooling the resultant condensate was collected in a re-
ceiver, and its acid number was determined. A conver-
sion and yield of the main product, 8-heptadecene, was
calculated based on the acid number
Natural aluminosilicate is a technical mixture of
kaolin and alumina used in industrial production of
(briquettes as a “dump” and “siftings”). The
catalyst composition (%) was: 55.0–65.0 of SiO
35.0 of Al
, 1.1–1.3 of CaO, 0.2–0.3 of K
0.4 of MgO.
Industrial catalyst Zeokar-5 was used as synthetic
aluminosilicate catalyst. The catalyst composition
(wt %) was: 83–85 of SiO
, 9–11 of Al
, 0.3 of Na
Activity index was 49%, stability index, 50%,, average
particle diameter, 3–4 mm.
The experimental results are listed in Table 1.
Table 1 shows that decarboxylation of OA over the
natural aluminosilicate at temperatures 350–400°C, the
conversion reaches 81.56%, while the initial acid num-
ber decreases to 7.31 mg KOH per g In the presence of
a synthetic aluminosilicate in the range of 350–400°C
the conversion reaches 85.46%, acid number is reduced
to 25 mg KOH per g.
These results show that changing the catalyst type is
not so greatly inﬂ uenced by the yield and acid number.
Therefore, it was decided to devise more efﬁ cient cata-