ISSN 1070-4272, Russian Journal of Applied Chemistry, 2006, Vol. 79, No. 10, pp. 1593!1599. + Pleiades Publishing, Inc., 2006.
Original Russian Text + G.R. Anpilogova, A.I. Vorob’eva, S.A. Onina, R.A. Khisamutdinov, Yu.I. Murinov, Yu.B. Monakov, 2006, published in Zhurnal
Prikladnoi Khimii, 2006, Vol. 79, No. 10, pp. 1613!1620.
AND ION-EXCHANGE PROCESSES
Vinyl 2-Hydroxyethyl Sulfide Polymers and Their Sorption
Properties with Respect to Transition Metals
G. R. Anpilogova, A. I. Vorob’eva, S. A. Onina, R. A. Khisamutdinov,
Yu. I. Murinov, and Yu. B. Monakov
Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences,
Ufa, Bashkortostan, Russia
Received May 30, 2006
Abstract-Vinyl 2-hydroxyethyl sulfide (VHES) homopolymer and the homopolymer and vinyl 2-hydroxy-
ethyl sulfide-acryl amide copolymer cross-linked by bisacrylamide were prepared by radical polymerization.
The sorption of Au(III), Ag(I), Pd(II), Pt(IV), Hg(II), Pb(II), Fe(III), Ni(II), Cu(II) on these polymers under
the static conditions was studied in relation to the solution pH. The polymers are highly selective and efficient
sorbents for Au(III), Ag(I) and Hg(II).
Vinyl 2-hydroxyethyl sulfide (VHES), as well as
alklyl vinyl sulfides , is a promising monomer for
directed synthesis of functionalized polymers [23 4].
This monomer can be selectively prepared in high
yield by the procedure described in [5, 6]. Radical
copolymerization of VHES with acrylic monomers
, N, N-dimethyl-N, N-diallylammonium chloride ,
and N-vinylpyrrolidone  in the presence of azo-
bis(isobutyronitrile) (AIBN) has been studied. Simple
procedures for preparing these copolymers have been
developed. The copolymers consist of randomly dis-
tributed monomeric units and are soluble in water or
acid aqueous solution.
It is known  that complexing sorbents con-
taining dialkyl sulfide and alkyl 2-hydroxyethyl sul-
fide functional groups selectively sorb Au(III), Pd(II),
and Pt(IV) from hydrochloric acid solutions Ag(I) and
Pd(II) from nitric acid solutions and Hg(II) from nitric
and hydrochloric acid solutions at room temperature.
Hydrophilic sorbents with primary amide groups ef-
fectively and selectively sorb Hg(II) from hydrochlo-
ric and acetic acid solutions [123 14]. Therefore, pre-
paration of VHES polymers insoluble in water and
study of their sorption properties with respect to
d metals are of interest.
The aim of this study was to prepare water-insolu-
ble VHES homopolymer, VHES homopolymer cross-
linked by N, N-methylenebisacrylamide, and VHES3
acrylamide (AA) copolymer cross-linked by N, N-
methylenebisacrylamide and to examine their sorption
properties with respect to nonferrous, heavy, and
Vinyl 2-hydroxyethyl sulfide was prepared by vi-
nylation of 2-mercaptoethanol with acetylene by the
procedure described in ; bp 74375oC (9 mm Hg),
1.0612. The purity of the monomer
was determined by GLC, and by IR and NMR spec-
troscopy . The properties of all the monomers,
AIBN, and solvents purified by the conventional
procedures were consistent with published data.
Our preliminary experiments showed that VHES
readily polymerizes in the presence of AIBN both
in the bulk and in a DMSO solution, with the poly-
merization being fast (up to 20% per hour) and pro-
ceeding to deep (about 70%) conversion.
VHES homopolymer (Table 1, polymer no. 1),
VHES homopolymer cross-linked by N, N-methylene-
bisacrylamide (bis-AA) (no. 2), and VHES3acryl-
amide (AA) copolymer cross-linked by bis-AA (no. 3)
were prepared by radical polymerization in the bulk
(no. 1) or in solution (nos. 2, 3) under a reduced
pressure in the presence of AIBN as an initiator.
The total monomer concentration in the initial solu-