Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 10, pp. 1622−1626.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © T.I. Gorbunova, M.G. Pervova, E.B. Trushina, S.V. Pavlyshko, A.Ya. Zapevalov, V.I. Saloutin, 2012, published in Zhurnal Prikladnoi
Khimii, 2012, Vol. 85, No. 10, pp. 1693−1698.
AND POLYMERIC MATERIALS
A New Application of Derivatives of Polychlorobiphenyls
and Polyethylene Glycols
T. I. Gorbunova
, M. G. Pervova
, E. B. Trushina
, S. V. Pavlyshko
A. Ya. Zapevalov
, and V. I. Saloutin
Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, Yekaterinburg, Russia
Institute of Engineering Science, Ural Branch, Russian Academy of Sciences, Yekaterinburg, Russia
Received July 26, 2012
Abstract—The reaction of congeners of Sovol technical mixture of polychlorobiphenyls with polyethylene glycols
was studied. Mixtures of hydroxy and mono(polyethylene glycol)oxy derivatives were obtained. The mixtures syn-
thesized, which are of low hazard, were used as additives to industrial oil to improve its tribological characteristics.
n + m = 3
x = 9
+ KCl + H
The reaction of chlorinated aromatic compounds with
polyethylene glycols (PEGs) is one of nondestructive
methods for chemical processing of polychlorinated bi-
phenyls (PCBs), which are artiﬁ cial pollutants. Published
data show that this method can be useful for cleaning
up PCB-containing equipment and oils to remove PCB
residues, for converting toxic PCBs into solid products
convenient for disposal, or for preparing useful materials
with the permissible level of toxicity.
Previously the procedures for reactions of PCBs with
PEGs were implemented as applied to cleaning up trans-
formers to remove traces of PCBs . They consist in
treatment of residues of technical PCBs in transformers
with a mixture of KOH and higher PEGs at 100°С for
2 h. The reaction results in nucleophilic replacement of
aromatically bound Cl atoms in PCBs by poly(ethylene
glycol)oxy groups. The subsequent removal of solid waxy
compounds from transformer walls involves no problems.
Because the resulting mixtures are readily soluble in
water, their trace amounts can be removed with water.
In removal of traces of technical PCBs 1 from dielec-
tric oils under the action of KOH and PEG-400 at 110°С
for 5 h, the highly chlorinated congeners containing 5–7
chlorine atoms are more reactive than the tri- and tetra-
chlorinated PCB congeners . In the process, 99.8%
conversion of PCBs 1 is attained, and it was concluded
from the chromatograms that the reaction involved re-
placement of one chlorine atom by the poly(ethylene
glycol)oxy group with the formation of products 2
(Scheme 1). The process kinetics was studied in .
Replacement of two chlorine atoms in PCB congeners
1 by PEG residues, conﬁ rmed by elemental analysis,
was reported in [4, 5] (Scheme 2). Derivatives 3a–3d
were obtained. Experiments were performed with Sovol