Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 1, pp. 102−107.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © T.I. Gorbunova, A.Ya. Zapevalov, D.N. Bazhin, L.G. Korshunov, V.S. Gaviko, V.I. Saloutin, 2012, published in Zhurnal Prikladnoi
Khimii, 2012, Vol. 85, No. 1, pp. 107−112.
AND INDUSTRIAL ORGANIC CHEMISTRY
Antifriction Properties of New Fluorine-containing Derivatives
of Natural Graphite
T. I. Gorbunova
, A. Ya. Zapevalov
, D. N. Bazhin
, L. G. Korshunov
V. S. Gaviko
, and V. I. Saloutin
Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, Yekaterinburg, Russia
Institute of Metal Physics, Ural Branch, Russian Academy of Sciences, Yekaterinburg, Russia
Received September 6, 2011
Abstract—Interaction of natural graphite with potassium salts of perﬂ uoro(ω-chloroperﬂ uoro)carboxylic acids in
the presence of potassium persulfate was studied. The derivatives obtained were used as independent lubricants
for a chromium-containing-steel friction pair.
Natural graphite has a layered structure and is widely
used as a lubricant [1, 2]. However, the antifriction
properties of graphite are markedly deteriorated under
high loads and wide pressure ﬂ uctuations. Therefore,
graphite is used as an ingredient in multicomponent
lubricants whose application areas are widely diverse:
for cold pressure processing of metals , as rail friction
modiﬁ er , for improving the sealing properties
of plastic lubricants , and for enhancing the wear
resistance of friction units at high loads and temperatures
To improve the antifriction properties of graphite
itself, it is modiﬁ ed by various methods [7–12]. Because
the most promising among organic lubricants are
ﬂ uorine-containing compounds, a possibly preferable
method for chemical modiﬁ cation of graphite is by
introduction of ﬂ uorine atoms of various ﬂ uorine-
containing groups into its structure.
The best known among ﬂ uorine-containing
derivatives of graphite is ﬂ uorinated graphite
(ﬂ uorographite) produced by the reaction of graphite
with elementary ﬂ uorine to give new C–F bonds:
nC + nF
nC + nF
Introduction of ﬂ uorine atoms in the structure of
graphite enhances its antifriction properties both in
lubricating formulations and in the case of its use
as an independent lubricant . Fluorographite has
high hydrophobicity, but poor adhesion to various,
including metallic, surfaces. In contrast to the
conventional lubricants exhibiting high adhesion to
metals, ﬂ uorographite provides friction by the cohesion
mechanism, which restricts its application areas.
A possible solution to the problem of changing the
friction mechanism from cohesion to adhesion, with
ﬂ uorine-containing graphite derivatives, is to use ﬂ uoro
derivatives of graphite, with new covalent C–C bonds.
The goal of our study was to synthesize derivatives
of natural graphite with perﬂ uoroalkyl substituents and
to examine their antifriction characteristics.
Graphite is an inert material and its chemical
modiﬁ cation is only possible under severe conditions
or under action of highly reactive species, e.g.,
radicals. The interaction between graphite of Cabot
Vulcan XC72R brand with radical ﬂ uorine-containing
species formed in situ from peroxide compounds