ISSN 1070-4272, Russian Journal of Applied Chemistry, 2008, Vol. 81, No. 10, pp. 1808–1812. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © O.V. Platonova, Yu.G. Akhmetshin, A.A. Kossoi, M.Z. Vdovets, B.M. Laskin, A.S. Malin, A.T. Sitdikov, 2008, published in Zhurnal
Prikladnoi Khimii, 2008, Vol. 81, No. 10, pp. 1684–1689.
Kinetic Model of Acylation of Diacetylethylenediamine
O. V. Platonova, Yu. G. Akhmetshin, A. A. Kossoi, M. Z. Vdovets, B. M. Laskin,
A. S. Malin, and A. T. Sitdikov
Applied Chemistry, Russian Scientific Center, Federal State Enterprise, St. Petersburg, Russia
New Chemical Technologies, Limited Liability Company, St. Petersburg, Russia
Received May 16, 2008
Abstract—Descriptive kinetics of synthesis of tetraacetylethylenediamine by acylation of diacetyl-
ethylenediamine with acetic acid anhydride was examined. The apparent rate constants of the process were
obtained, and a mathematical model adequately describing the process was constructed.
In recent years, the developmental efforts in deter-
gent chemistry have been mainly focused on a search
for, and preparation of new composite systems and
additives to provide a highly efficient bleaching and
removal of contaminations from fabrics at as low
temperatures as possible. Among such additives is
tetraacetylethylenediamine (TAED), a low-temperature
peroxide bleaching activator [1, 2].
Tetraacetylethylenediamine is a typical represen-
tative of the class of polyacylated aliphatic diamines,
which is produced by acylation of diacetylethylenedia-
mine (DAED) with acetic acid anhydride (AАA).
The procedures for preparation of TAED were de-
scribed in detail in patents [3–5], the mechanism and
kinetics of the process were disregarded. At the same
time, it is known that acylation of DAED into TAED
involves formation of an intermediate, triacetylethyl-
enediamine (TrAED) :
Hence, for simulating the commercial process of
DAED acylation, we examined the macrokinetic rela-
tionships. To this end, we carried out a series of kinetic
experiments with varied DAED : AAA molar ratio
(1 : 6.5; 1 : 8.5; 1 : 17) and temperature (120 and 140°С).
AND INDUSTRIAL ORGANIC CHEMISTRY
To study the formal-kinetic aspects of DAED
acylation and TAED deacylation, we used a three-
necked temperature-controlled flask equipped with a me-
chanical stirrer, thermometer, and reflux condenser.
The structure of the reaction mass was analyzed by
gas–liquid chromatography on a Kristall 2000 chro-
matograph with a flame-ionization detector and a 30 m ×
0.53 mm CPS sil-5CB capillary column in the column-
temperature-programming mode (initial temperature