Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 11, pp. 1986−1990.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
M.A. Mirzoeva, V.S. Gasanov, V.A. Abbasova, M.A. Allakhverdiev, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82,
No. 11, pp. 1838−1842.
AND INDUSTRIAL ORGANIC CHEMISTRY
as Additives to Lubricating Oils
M. A. Mirzoeva, V. S. Gasanov, V. A. Abbasova, and M. A. Allakhverdiev
Baku State University, Baku, Republic of Azerbaijan
Azerbaijani State Pedagogical University, Baku, Republic of Azerbaijan
Received November 11, 2008
Abstract—Possibility to obtain 1-heptylthio-3-(2'-chlorophenoxy)-2-propanol by reacting 1-heptylthio-3-chloro-
2-propanol with o-chlorophenol in an alkaline medium and synthesize its carbamates, thiocarbamates, and
acetyl, alkoxymethyl, and amino methyl derivatives was studied. The compounds synthesized were examined as
anticorrosion and antimicrobial additives to lubricating oils
It is known that various nitrogen- and sulfur-containing
phenol derivatives are widely used as antioxidant and
anticorrosion additives. Joint presence of these elements
improves these anticorrosion properties, compared
with compounds containing only nitrogen and sulfur
. Proceeding with studies in the ﬁ eld of synthesis
of various classes of nitrogen- and sulfur-containing
compounds and analysis of their functional properties
[2–5], we synthesized and examined 1-heptylthio-3-(2'-
chlorophenoxy)-2-propanol and its various derivatives.
was synthesized in 71% yield by reacting 1-heptylthio-
3-chloro-2-propanol with 2-chlorophenol in an alkaline
medium (Scheme 1).
1-Heptylthio-3-(2'-chlorophenoxy)-2-propanol (I) is
a transparent ﬂ uid with a characteristic odor and purity
of 99.5% (determined by GLC). Its IR spectra contain
broad absorption bands at 3430–3450 cm
of hydroxy groups.
was reacted with aromatic isocyanates, isothiocyanates,
α-chloroesters, chloranhydrides, and secondary amines in
the presence of formaldehyde to give the corresponding
derivatives by Scheme 2.
Carbamates II–VII are colorless crystals well soluble
in acetone and chloroform. Thiocarbamates VIII–IX are
yellowish crystals soluble in various organic solvents
Alkoxymethyl, acetyl, and alkylaminomethyl
derivatives X–XVI are transparent liquids with
a characteristic odor, soluble in various organic solvents
The IR spectra of compounds II–IX contain no
absorption bands at 2250–2390, 1990–2140, and 3430–
, which are characteristic of the isocyanate,
isothiocyanate, and hydroxy groups, but show absorption
at 1715–1725, 1480–1510, and 3300–3330 cm
indicates the presence of carbamate, thiocarbamate, and
NH groups, respectively .
In the 1H NMR spectrum of 1-heptylthio-3-(2'-
chlorophenoxy)-2-propanol (I), protons of the terminal