ORGANIC SYNTHESIS AND INDUSTRIAL
Russian Journal of Applied Chemistry, 2011, Vol. 84, No. 11, pp. 1897−1902.
Pleiades Publishing, Ltd., 2011.
Original Russian Text © S.O. Bondareva, N.G. Afsaletdinova, Yu.I. Murinov, 2011, published in Zhurnal Prikladnoi Khimii, 2011, Vol. 84, No. 11, pp. 1811−1816.
Synthesis and Extracting Properties of Triacylated
S. O. Bondareva, N. G. Afsaletdinova, and Yu. I. Murinov
Institute of Organic Chemistry, Ufa Scientiﬁ c Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia
Received February 25, 2011
Abstract—Series of triacylated ethyleneamines for extraction of metal ions from hydrochloric acid media were
synthesized. The effect of the length of the alkyl radical on the distribution of reagents among the organic and
aqueous phases, stability of the reagents against hydrolysis in acid media, and extracting properties of the reagents
with respect to rhodium(III) chloro complexes were studied.
Bisacylated ethyleneamines, or bisamides, are used
in manufacture of fabric softening and rinsing agents
. As a rule, nontoxic, biodegradable bisamides have
a comparatively high thermal stability, their synthesis
is simple, and starting reagents are produced on the
industrial scale. The extracting properties of bisamides
still remain out of researchers’ sight for not quite
understandable reason. Meanwhile, N-substituted
amides are well known as potential extractive agents of
actinide elements (DIAMEX process) and lanthanides.
Recently, reports devoted to extraction of platinum
metals with N-substituted amides have appeared
[2, 3]. These compounds provide fast extraction
kinetics, are selective, effective, and easily utilizable.
According to some data, the presence of amide groups
in N-substituted amides has a synergistic effect in
extraction of rhodium(III), whose recovery still remains
rather difﬁ cult .
It has been shown that bisamides are also rather
efﬁ cient extractive agents for a number of platinum [5,
6] and nonferrous metals :
R, n = 2
At an aqueous phase acidity pH > 2, bisamides
commonly extract metals by the coordination mechanism.
With increasing acidity of the aqueous phase, nitrogen
atoms in the ethyleneamine moiety of the reagent are
protonated and bisamide salts extract metal acido
complexes by the anion-exchange mechanism. With
increasing number of protonated nitrogen atoms in the
ethyleneamine moiety of bisamide, its solubility in the
aqueous phase grows . At the same time, the greater
the number of nitrogen atoms in the ethyleneamine
moiety of bisamide, the higher its potential extraction
The goal of our study was to synthesize acylated
ethyleneamine for extraction of metals from acid media,
which would have the maximum extraction capacity, by
be hardly soluble in the aqueous phase, and to evaluate
its extracting properties with respect to just rhodium(III)
The solubility of bisamide in the aqueous phase
can be diminished by raising its molecular mass via
introduction of a third acyl group into the molecule of the
reagent. The synthesis was carried out by the following
scheme. In the ﬁ rst stage, bisacylated ethyleneamine
(BA) was obtained:
+ 2 RCOOH