Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 5, pp. 787−789.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © P.G. Asadova, G.Z. Guseinov, M.A. Allakhverdiev, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86, No. 5, pp. 840−843.
AND POLYMERIC MATERIALS
The Reaction of Condensation of Furfural
with Mercaptoacetic Acid Esters
P. G. Asadova, G. Z. Guseinov, and M. A. Allakhverdiev
Baku State University, Baku, Azerbaijan
Received January 14, 2013
Abstract—The condensation reaction of furfural with various mercaptoacetic acid esters was studied. The reaction
products were tested for their corrosion protective properties in M-16 cylinder oil used for marine diesel engines.
It was found that the resulting 2-di(alkoxycarbonylmethylthio)methylfuranes at 2% concentration completely
suppress corrosion of lead plates.
Furfural (furan-2-aldehyde) which is produced com-
mercially from pentosan feedstock is known to be the
most readily available compound in the furan series .
Furfural derivatives are extensively used for preparation
of many technically signiﬁ cant products: plasticizers,
insecticides, fragrances, medicinal substances, furan
resins, etc. [2, 3]. Among furfural derivatives, sulfur-
and nitrogen-containing compounds have a prominent
place. For example, reactions of furoic acid chlorides
with mercaptoaryl- and alkylthiazoles gave sulfur- and
nitrogen-containing derivatives of furfural, which were
suggested as rubber vulcanization accelerators .
It should be noted that there is continuously growing
interest in cyclic compounds containing a furan moiety
and various functional groups. Not only conventional
preparative but also combinatorial chemistry method are
used for synthesis of these compounds [4–6].
Here, we studied the reactions between furfural and
various mercaptoacetic acid esters with a view of syn-
thesizing new sulfur-containing furfural derivatives that
could be used as lubricant additives.
It was expected that a sulﬁ de sulfur, an ester group,
and a furan moiety occurring in these compounds
simultaneously would confer to them useful, in particular
antioxidant and corrosion protective, functional
The new sulfur-containing derivatives of furfural
were synthesized by furfural condensation with various
alkyl esters of mercaptoacetic acid, catalyzed by small
amounts of dilute hydrochloric acid. The condensation
reaction scheme was as follows:
CHO + 2HS
where R = i-C
The reactants, furfural and mercaptoacetic acid,
were freshly distilled prior to use; furfural: bp 161.7°C,
1.159 g cm
; mercaptoacetic acid: bp 124°C/30 mm
1.325 g cm
.The esters used in this study were
obtained by HCl-catalyzed reactions of mercaptoacetic
acid with the corresponding aliphatic alcohols, taken
in a 1 : 1.2 molar ratio. The reaction was carried out in
a three-necked ﬂ ask equipped with a thermometer, a