ISSN 1070-3632, Russian Journal of General Chemistry, 2011, Vol. 81, No. 3, pp. 620–621. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © R.E. Khoma, A.A. Shestaka, O.V. Shishkin, V.N. Baumer, Yu.E. Brusilovskii, L.V. Koroeva, A.A. Ennan, V.O. Gel’mbol’d, 2011,
published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 3, pp. 525–526.
LETTERS
TO THE EDITOR
Features of Interaction
in the Sulfur(IV) Oxide–Hexamethylenetetramine–Water
System: A First Example of Identification of the Product
with a Sulfur–Carbon Bond
a,b
a
c
c
R. E. Khoma , A. A. Shestaka , O. V. Shishkin , V. N. Baumer ,
d
a
a
a,e
Yu. E. Brusilovskii , L. V. Koroeva , A. A. Ennan , and V. O. Gel’mbol’d
a
Physicochemical Institute of Environmental and Human Protection, Ministry of Education and Science of Ukraine,
National Academy of Sciences of Ukraine, ul. Preobrazhenskaya 3, Odessa, 65082 Ukraine
e-mail: rek@onu.edu.ua, r_khoma@farlep.net
b
Mechnikov Odessa National University, Odessa, Ukraine
c
Institute of Single Crystals, Kharkov, Ukraine
d
Bogatskii Physicochemical Institute, Odessa, Ukraine
e
Odessa State Medical University, Odessa, Ukraine
Received August 9, 2010
DOI: 10.1134/S1070363211030352
Hexamethylenetetramine (HMTA) is a ligand in the
synthesis of coordination compounds and also is used
as a pharmaceutical antiseptic drug and as hexogen
precursor [1]. An attempt is known to use aqueous
solutions of HMTA as an absorbent for extracting
hydrogen fluoride and sulfur dioxide from the flue
gases of aluminum production [2, 3]. In the study on
the interaction in the HMTA–H SO –H O system [4] a
N
O
H O
2
+
SO
2
H N
S
N
2
N
N
OH
O
Aminomethanesulfonic acid. A solution of HMTA
(5.0 g) in 30 ml of water was loaded to a reactor,
cooled, and kept at 0°C for 20 min. Through this mix-
2
3
2
–1
formation was found of compounds 2HMTA·H SO ·
ture gaseous SO
рН < 1.0. The amorphous precipitate formed which
partly dissolved at further SO passage. The solution
with precipitate was kept at room temperature in air to
complete water evaporation (~10 days). Yield 8.2 g
(51.57% by N), white polycrystalline substance. The
product was purified by recrystallization from water.
Found, %: C 10.92; H 4.33; N 12.80; S 27.93.
2
was bubbled at the rate 50 ml min to
2
3
6
H O and HMTA·2H SO ·8H O, the hexamethylene-
2 2 3 2
tetrammonium sulfite and bisulfite, respectively, hyd-
rated forms. On the other hand, in acidic solutions
HMTA is prone to hydrolysis to form ammonia and
formaldehyde that does not exclude further deeper
chemical reactions in the system HMTA–H SO –H O
2
2
3
2
(
HMTA–SO –H O), as indicates indirectly the forma-
2 2
tion of Н NCH SO Na in the reaction of sodium hyd-
CH NO S. Calculated, %: C 10.81; H 4.54; N 12.60; S
5 3
2
2
3
rosulfite with formaldehyde and ammonia [5]. In this
communication we report on the conditions of syn-
thesis and the results of identification of a new com-
pound, H NCH SO H, aminomethanesulfonic acid,
28.86. M 111.1; mp 184°C (decomp.) (184°C [6]). IR
spectrum, ν, cm : 3365, 3220, 3160, 3025 (N–H);
2982, 2908 (C–H); 2673, 2620, 2580, 2488, 2400,
–
1
1971 (N–H in hydrogen bond); 1230, 1207 (SO
1060, 1000 (SO
the range of 3365–1970 cm is characteristic of NH
, as),
2
2
3
2
first isolated as a reaction product in HMTA–SO –H O
2
, s), 579 (S–O). The band ν(N–H) in
2
2
–
1
+
3
system:
-
6
20