ISSN 1070-4272, Russian Journal of Applied Chemistry, 2008, Vol. 81, No. 4, pp. 730 731.
Original Russian Text K.S. Trofimova, V.G. Dronov, N.S. Shaglaeva, R.G. Sultangareev, 2008, published in Zhurnal Prikladnoi Khimii, 2008,
Vol. 81, No. 4, pp. 693 694.
Pleiades Publishing, Ltd., 2008.
BRIEF
COMMUNICATIONS
New Approach to Processing of Chlorine-containing Wastes:
Synthesis of 2,3-Dichloropropene
from 1,2,3-Trichloropropane
K. S. Trofimova, V. G. Dronov, N. S. Shaglaeva, and R. G. Sultangareev
Favorskii Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russia
Irkutsk State Technical University, Irkutsk, Russia
Received August 2, 2007
Abstract Possibilities of utilization of by-products formed in manufacture of epichlorohydrin are considered.
A promising way to utilize wastes from production of epichlorohydrin by synthesis of 2,3-dichloropropene
from 1,2,3-trichloropropane is suggested.
DOI: 10.1134/S1070427208040332
Epichlorohydrin (EPI) is the main component in
synthesis of glycerol, epoxy resins, and a number of
other products, including chlorohydrin caoutchoucs.
At present, more than 1 million tons of epichloro-
hydrin is manufactured by the chlorine method all
over the world.
from a mixture of organochlorine wastes was devel-
oped and the conditions in which 2,3-trichloropropene
(DCP) is produced by dehydrochlorination of the tri-
chloropropane fraction were analyzed.
2,3-Dichloropropene is an important and promising
half-product for synthesis of a large number of poly-
functional highly reactive polymeric compounds. It
has been used to find simple and convenient pathways
[4] to synthesis of tertiary and quaternary polymeric
salts that can be used in oil and textile industries
(see scheme).
Synthesis of EPI is accompanied by a number of
side reactions, which leads to formation of large
amounts of organochlorine wastes: allyl chloride, 2,2-
dichloropropane, 1,2-dichloropropane, 1,3-dichloro-
propene, 1,2,3-trichloropropane, dichloropropanols,
and chloroesters. In the opinion of the authors of [1],
about 400 and 100 kg of the dichloropropane and
1,2,3-trichlopropane fractions, respectively, is pro-
duced per ton of EPI.
EXPERIMENTAL
TCP was isolated from a mixture of organochlorine
wastes as follows. First, all the water-soluble im-
purities (epichlorohydrin, dichloropropanols, chloro-
esters) were extracted with distilled water containing
By now, virtually no economically efficient and
ecologically safe methods have been developed for
utilization of organochlorine wastes. Industrial utiliza-
tion of these wastes encounters severe difficulties.
At the same time, all the above-mentioned kinds of
by-products are promising raw materials for manu-
facture of valuable materials that are in steadily in-
creasing demand.
1
2 3 g l of soda ash (or an alkali for maintaining
the pH of the medium at 7 8). After the water-soluble
impurities were removed (with monitoring by GLC),
the mixture was subjected to azeotropic dehydration,
and then TCP was isolated by rectification ( 99%).
1,2,3-Trichloropropane (1 mol) was treated with
a 10% alcoholic solution of NaOH at room tempera-
ture for 4 h. In the process, a white water-soluble
precipitate (NaCl) is formed. After the precipitate was
filtered off, the liquid phase was distilled and the frac-
tion with bp 94 C was taken.
Commonly, organochlorine wastes are neutralized
by the following methods: regeneration, oxidation,
burning, chemical and plasmochemical processing,
electrocracking, and burial [1 3]. In the present study,
a method for isolation of 1,2,3-trichloropropane (TCP)
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Trofimova
