1070-4272/05/7806-0950 + 2005 Pleiades Publishing, Inc.
Russian Journal of Applied Chemistry, Vol. 78, No. 6, 2005, pp. 950!954. Translated from Zhurnal Prikladnoi Khimii, Vol. 78, No. 6, 2005,
Original Russian Text Copyright + 2005 by Glazko, Gur’yanova, Levanova, Kozlova, Neiman.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis of Esters of Dioxane Alcohols and Their Performance
as Plasticizers for Polyvinyl Chloride Compounds
I. L. Glazko, O. P. Gur’yanova, S. V. Levanova, S. A. Kozlova, and N. S. Neiman
Samara State Technical University, Samara, Russia
Polimerstroimaterialy Combine, Joint-Stock Company, Samara, Russia
Received December 7, 2004; in final form, March 2005
Abstract-A procedure was developed for preparing a plasticizer for polyvinyl chloride compounds from
the fraction of dioxane alcohols. The main physicochemical properties of the new plasticizer were determined.
Items prepared from formulations containing the new plasticizer were fabricated and tested in laboratory.
Since the discovery of the dioxane method for pre-
paring isoprene, the utilization or reprocessing of
dioxane alcohols has been topical problem.
The world’s annual production of isoprene reaches
now 100031100 thousand tons, of which 250 thou-
sand tons (23325% of the total amount) is produced
by the dioxane method. In Russia, the annual produc-
tion of isoprene is 7003800 thousand tons, of which
190 thousand tons (24327% of the total amount) is
produced by the dioxane method. In this method, the
amount of dioxane alcohols (by-products) reaches
1003110 kg per ton of isoprene. Thus, formation of
large amounts of dioxane alcohols is inevitable .
The fraction of dioxane alcohols from the produc-
tion of isoprene rubber is a colorless or light yellow
mobile liquid containing 50370 wt % dioxane alco-
hols; the boiling onset temperature is no less than
225oC, and the flash point, no less than 120oC. The
fraction belongs to hazard class 3, recommended value
of MPC (with respect to dioxane alcohol) 10 mg m
for mice 2700 mg kg
The fraction of dioxane alcohols contains three
The major component (60370% of the sum of
the isomers) is 4-methyl-4-(2-hydroxyethyl)-1,3-di-
A number of possible applications of dioxane alco-
hols have been outlined in the literature: as an ef-
ficient solvent for nitrocellulose, nitrocellulose lac-
quers, rosin, lac, for bakelite, epoxy, and polyvinyl
chloride resins, and for insulating lacquer; as a com-
ponent of epoxy hardener . One of promising
ways of processing of the fraction of dioxane alcohols
is preparation of plasticizers for polyvinyl chloride
resins and rubbers .
However, proper utilization of this large-tonnage
waste remains a matter of current interest.
We believe that the presence of hydroxy and acetal
groups in molecules of dioxane alcohols, their low
toxicity, absence of odor and color, and high boiling
and flash points make these compounds interesting
both as objects for theoretical studies (reactivity) and
as potential raw materials for chemical industry.
Our goal was to examine the possibility of prepar-
ing esters from dioxane alcohols and carboxylic acids,
as potential plasticizers.