ISSN 1070-4272, Russian Journal of Applied Chemistry, 2014, Vol. 87, No. 10, pp. 1446−1449. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © M.K. Mamedov, G.N. Mekhtieva, Kh.G. Gurbanova, 2014, published in Zhurnal Prikladnoi Khimii, 2014, Vol. 87, No. 10, pp. 1445−1448.
ORGANIC SYNTHESIS AND INDUSTRIAL
Synthesis of Bicyclo[2.2.1]heptyl Oxyalkanes
and Acrylates Based on Them
M. K. Mamedov, G. N. Mekhtieva, and Kh. G. Gurbanova
Mammedaliev Institute of Petrochemical Processes, National Academy of Sciences,
pr. Khodzhaly 30, Baku, AZ1025 Azerbaijan
Received October 14, 2014
Abstract—Addition reactions of ethane-1,2-diol, propane-1,3-diol, and butane-1,4-diol to bicyclo[2,2,1]hept-2-
ene in the presence of a catalyst BF
were studied for deriving reactive monomer, therewith bicyclo[2.2.1]
hept-2-oxyalcanols with a yield of 91.2–96.0% were synthesized. In the second stage esteriﬁ cation of the obtained
bicyclo[2.2.1]hept-2-oxyalkanols was conducted with acrylic acid in the presence of a catalyst of KU-2-8 H
grade and acrylates was also derived with a yield of 87.5–93.0%, which are reactive monomers for synthesis of
polymeric glassy products.
It is well known that acrylate monomers are widely
used for various polymeric materials . Previously,
acrylates, which can be used as reactive monomers
for synthesis of polymeric products [2–5] including
functionalized , were produced based on the addition
reaction of acrylic acid to a mono-, bi-, tri-, and tetracyclo-
In this work the reactive monomers were obtained
by adding of ethane-1,2-diol ED, propane-1,3-diol PD,
and butane-1,4-diol BD to bicyclo[2.2.1]hept-2-ene
and by esteriﬁ cation
of simple bicyclo[2.2.1]heptyl-2-
oxyalkanols (BCHOAOL) with acrylic acid AA. The
catalysts used: boron triﬂ uoride BF
, KU-2-8 H
(see the scheme).
For ﬁ nding the optimal reaction conditions for the high
yield synthesis of BCHOAOL an effect of temperature,
amount of catalyst BF
, and the molar ratio of diols
on the experiment time was examined by an example of
The effect of temperature was studied in the range
of 70–110°C. The ﬁ ndings showed that the optimum
temperature for the addition reaction of ED to NB is
100°C, therewith the yield of 2-bicyclo[2.2.1]heptyl-1-
oxyethanol (BCHOEtOL) is 61.4%.
The effect of the amount of catalyst BF
the yield was studied within 0.6–1.4 wt % for ED. The
experimental data showed that the amount of the catalyst
n = 2, 3, 4.