SYNTHESIS AND PROPERTIES OF COPOLYMERS
dimethyl-N,N-bis(β-chloroallyl)ammonium chloride
and acrylamide and compared the flocculating ability
of polyelectrolytes (Table 2). As follows from the data
of Table 2, the flocculating ability of the copolymer of
N,N-dimethyl-N,N-bis(β-chloroallyl)ammonium chlo-
ride and acrylamide is practically as good as that of
VPK-402.
1723
Synthesis of N,N-dimethyl-N,N-bis(β-chloroallyl)
ammonium chloride. To 68.2 g (0.5 mol) of 33%
aqueous solution of dimethylamine at 40ºС and
vigorous stirring 55 mL (0.5 mol) of freshly distilled
2,3-dichloropropene-1 and 50 g (0.625 mol) of 50%
aqueous NaOH was added in the course of 20 min. The
obtained mixture was kept for 4–6 h at 60ºС. After
completion of the reaction the organic layer was
separated and stored at room temperature till the
precipitation of the crystals of quaternary salt. Yield
Therefore, a new way of utilization of organo-
chlorine wastes of epichlorohydrin production is found
by converting them into cationic polyelectrolytes and
possible ways of their application are proposed.
–
1
5
1
8.0 g (80%). IR spectrum, ν, cm : 1030, 1230 (C–N),
648, 2975, 3080 (C=C). H NMR spectrum (DMSO-
1
d ), δ, ppm: 6.18 d (4H, =H C, J 96.7 Hz), 4.70 s (4H,
6
2
EXPERIMENTAL
13
2
CH ), 3.41 s (6H, 2CH ). C NMR spectrum
2
3
(
6
DMSO-d ), δ , ppm: 126.12 (=CH ), 125.33 (=CCl),
6.51 (CH ), 47.33 (CH ).
2 3
6 C 2
Acrylamide of “pure” grade was several times
crystallized from benzene and dried in a vacuum at 40°С.
Ammonium persulfate was crystallized from bidistilled
water at the temperature no higher than 30–40°С and
dried in a vacuum dessicator over Р О . Elemental
Homopolymerization of N,N-dimethyl-N,N-bis-
β-chloroallyl)ammonium chloride. Homopolymeriza-
(
2
5
tion was performed in aqueous solution under the
action of ammonium persulfate (0.5 wt %) at 30°С.
Ampules were filled by the gravimetric method. After
polymerization was completed (7 h) the polymer was
purified from the monomer and initiator by dialysis
analysis was performed on gas analyzer Thermo
Finnigan Flash EA 1112 Series. IR spectra were taken
on a Specord 75IR spectrophotometer in KBr. NMR
spectra were registered on a Varian VХR-500S
spectrometer in С D OD with HMDS as an internal
2
5
(
solvent water). After dialysis the solution of polymer
reference.
was precipitated by the mixture acetone–ether. The
formed precipitate of the polymer was filtered, washed
with water, acetone, and dried in a vacuum at 40°С to
a constant mass. Found, %: С, 41.71; H, 6.35; Cl,
4
6
Flocculating ability of polyelectrolytes was
determined as follows: graduated cylinder was charged
with suspension prepared from the mixture of 40 g of
ochre or phosphorous sludges, added 1 L of water was
added and 3 mL of working solution of flocculant.
After active shaking for 5 min the time of full
sedimentation of suspended particles or the time of
reaching of deep cleaning of water was measured.
6.07; N, 5.87. С H NCl . Calculated, %: С, 41.65; H,
8 14 3
.07; Cl, 46.21; N, 6.08.
Copolymerization of N,N-dimethyl-N,N-bis(β-
chloroallyl)ammonium chloride and acrylamide.
Copolymerization was carried out in aqueous solution
by the action of ammonium persulfate (0.5 wt %) at
Isolation of 1,2,3-trichloropropane. Water soluble
admixtures (epichlorohydrin, dichloro-propanol, chloro-
ethers) contained in wastes with 1,2,3-trichloropropane
were removed by washing with water with added 2–
3
0°С. Ampules were filled by the gravimetric method.
After completion (7 h) of the reaction the product was
dissolved in water, the copolymer was precipitated by
the mixture acetone–ether. Copolymers were twice
reprecipitated from aqueous solution by the mixture
acetone–ether and dried in a vacuum to a constant
mass. The composition of the copolymer was cal-
culated from the data of elemental analysis on chlorine
by standard procedure [6].
3
g/L of Na CO or NaOH to maintain pH of 7–8.
2 3
From the residue, 1,2,3-trichloropropane of ≥99%
purity (according to GC) was isolated by azeotropic
distillation and rectification.
Preparation of 2,3-dichloropropene-1. 147.5 g
(
1 mol) of 1,2,3-trichloropropane was treated with
1
4
0% alcoholic NaOH solution at room temperature for
h. The precipitated NaCl was filtered off and from
ACKNOWLEDGMENTS
the filtrate 115 g (80%) of the target product was
isolated by fractional distillation.
This work was financially supported by the
Ministry of Education and Science, project no. 37.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 7 2015