Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 3, pp. 394−397.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © E.V. Pyatnitsyna, M.M. El’chaninov, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86, No. 3, pp. 425−428.
AND INDUSTRIAL ORGANIC CHEMISTRY
Liquid-Phase Catalytic Hydrogenation of 2-Butyne-1,4-diol
to 1,4-Butanediol at Atmospheric Pressure
on Suspended Catalysts
E. V. Pyatnitsyna and M. M. El’chaninov
South-Russian State Technical University, Novocherkassk, Russia
Received February 13, 2013
Abstract—The optimum parameters of hydrogenation of 2-butyne-1,4-diol to 1,4-butanediol on the suspended
palladium and Ni-Raney catalysts at atmospheric pressure were found. In selected conditions a yield up to 90%
of 1,4-butanediol was reached.
Butane-1,4-diol (BAD) is increasingly being used as
an intermediate or ﬁ nal product. Researching its selec-
tive synthesis by the hydrogenation of 2-butyne-1,4-diol
(BYD) on ﬁ ne catalysts is of great interest for various
ﬁ elds of engineering and medicine. For example, its
use in the production of easily molded structural mate-
rial polybulylene terephthalate , γ-butyrolactone ,
α-pyrrolidone , tetrahydrofuranm and N- methylpyr-
rolidone is known .
In the study starting data was found for performing
of the selective hydrogenetaion of BYD to BAD on sus-
pended catalysts at atmospheric pressure.
Hydrogenetion of BYD was performed in aqueous
solutions on ﬁ ne catalysts: palladium with 2 wt % of
metal and Ni-Raney:
BYD hydrogenation was carried out in a reactor
(a round-bottomed ﬂ ask) with capacity 100 cm
, ﬁ xed on
a shaking device. The desired temperature in the reactor
and a burette was supported by feeding of thermostated
water to their jackets. The reactor was charged by 1.32 g
of BYD, 20 cm
of water, and a calculated amount of
the ﬁ ne catalyst. On completion of the reaction it was
judged by an amount of hydrogen absorbed, measured
by a gas burette of a volume of 300 cm
. The catalyst
Pd/C-2 (2.0 wt % Pd on carbon OUB) was prepared by
applying palladium(II) chloride from its hydrochloric acid
solution to the carrier, followed by reduction to metal
by formaldehyde . Selective nickel catalyst W-6 was
prepared by leaching of nickel–aluminum Raney alloy
by sodium hydroxide solution (20 wt %) .
The analysis of the hydrogenation catalyzates was
carried out on a chromatograph
a ﬂ ame ionization detector, steel column of 2 m length and
3 mm diameter, ﬁ lled with Khromaton N-super or N-AW-
DMCS of fraction 0.16–0.20 mm with 15% polyethylene