ISSN 1070-4272, Russian Journal of Applied Chemistry, 2015, Vol. 88, No. 10, pp. 1733−1735. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © М.K. Mamedov, V.S. Qedirli,
2015, published in Zhurnal Prikladnoi Khimii, 2015, Vol. 88, No. 10, pp. 1511−1515.
Getting New Monomers: Carboxyl Bicyclic Methacrylates
М. K. Mamedov and V. S. Qedirli
Institute of Petrochemical Processes named after Academician Yu.G.Mamedaliyev,
Azerbaijan National Academy of Sciences, pr. Khojali 30, Baku, AZ1025 Azerbaijan Republic
Received April 14, 2015
Currently, the scale of production of methacrylates
are greatly enhanced as they are reactive monomers,
based on them practically valuable products can be
: paints, typographical paint, dentures, covering
pharmaceuticals, and so on [1–3].
acrylic monomers were synthesized,
belong to a mono-, bi-, tri-, and tetratcycloac-
and their practically valuable properties were
In order to expand the range of acrylates reactions of
(CPD) and acrylic (AA) and methacrylic
(MAA) acids were investigated.
It should be noted
that the previously by reacting
with AA and MAA ([4+2]cycloaddition, Diels–Al-
5-carboxybicyclo[2.2.1]hept-2-ene and its
5-methyl substituted derivative were synthesized :
where R = H (I), CH
It was shown that by performing the reaction in a
at elevated temperature and in excess of
two reactions occur: CPD condensation
with acrylic acids and addition of starting acid to derived
I and II with the formation of 5-carboxybi-
cyclo[2.2.1]hept-2-yl acrylate (III) and 5-methyl-5-car-
boxybicyclo[2.2.1]hept-2-yl methacrylate (IV):
where R = H (III), CH
The effect of different factors: temperature (100
to 150°C), the molar ratio of the reactants CPD and
MAA [1 : (1–4)], and also the duration of the reac-
(1 to 4 h) were examined in order to ﬁ nd optimal
the formation of monomers. The ﬁ gure
shows the effect of various parameters on the yield of
As can be seen
from the data, the optimal conditions
producing compound III are: 1 : 4 molar ratio of CPD
to MAA; temperature 140°C; duration 3 h. The yield of
III is more than 90%.
Abstract—5-Carboxybicyclo[2.2.1]hept-2-yl acrylate and 5-carboxy-5-methylbicyclo[2.2.1]hept-2-yl methacry-
late, which can be used for optical lenses and polymeric materials, were synthesized by reaction of cyclopentadiene
and methacrylic acid with a yield of 80.0–90.5%.