Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 10, pp. 1629−1631.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © A.V. Golounin, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86, No. 10, pp. 1677−1678.
Condensation of Diphenylguanidine
A. V. Golounin
Institute of Chemistry and Chemical Technology, Siberian Branch,
Russian Academy of Sciences, Krasnoyarsk, Russia
Received June 17, 2013
Abstract—Reaction of condensation of diphenylguanidine with hexamethylenediamine was performed. It is
shown that the resulting condensate is a selective ion exchanger.
It is known that long-chain alkylguanidines and
resins containing guanidine functions are anion
exchangers and have high capacity and relative
selectivity for gold [1, 2]. The alkylation of guanidine
and introduction of a guanidine function into the
polymer chain pose a difﬁ cult technological problem.
It has been shown previously how the water-soluble
polymer polyhexamethyleneguanidine can be converted
to a water-insoluble form .
The readily available and inexpensive domestically
manufactured low-basic 1N,3N-diphenylguanidine
10.12) is to be used to obtain water-insoluble ion
exchangers with guanidine functions [4, 5].
Because of the noticeable solubility in water,
diphenylguanidine itself cannot be used as an ion
exchanger. One of ways to render diphenylguanidine
insoluble is to make larger its molecular mass by, e.g.,
performing its condensation with hexamethylenediamine.
It is known that fusion of guanidine with
hexamethylenediamine at temperatures of up to 180°C
yields an oligomer of polyhexamethyleneguanidine
[6, 7]. Because no reaction of this kind with 1N,3N-
diphenylguanidine has been carried out, it seems
advisable to perform the condensation reaction
with hexamethylenediamine. The condensation of
diphenylguanidine is also an issue of current interest
because it has been found that gold can be quantitatively
eluted from low-basic ion exchangers with guanidine
Interaction of 1N,3N-diphenylguanidine with
hexamethylenediamine. To 4.2 g (0.02 mol) of
1N,3N-diphenylguanidine and 2.5 g (0.021 mol) of
hexamethylenediamine were added 10 mL of glycerol
and two drops of phosphoric acid. The mixture was
heated to 160°C, with ammonia bubbles starting to be
evolved, as judged from the staining of litmus paper. The
temperature was gradually raised to 170°C, the mixture
was kept for 1 h and, when the gas evolution ceased, it
was cooled and poured over with an alkali solution. The
precipitated resin was washed with water and dried at
50°C. According to the
H NMR spectrum, a complex
mixure of roducts was thus obtained.
As in the case of polyhexamethyleneguanidine
synthesis [6–9], performing the reaction of 1N,3N-
diphenylguanidine with hexamethylenediamine by
fusion of reagents at temperatures of 180°C and more
is impossible because 1N,3N-diphenylguanidine
decomposes at temperatures higher than 170°C .
The condensation reaction in a dimethyl sulfoxide
solution yielded a pure product. For this purpose, 4.2 g
(0.02 mol) of 1N,3N-diphenylguanidine and 1.2 g