1070-4272/05/7804-0584 + 2005 Pleiades Publishing, Inc.
Russian Journal of Applied Chemistry, Vol. 78, No. 4, 2005, pp. 584!587. Translated from Zhurnal Prikladnoi Khimii, Vol. 78, No. 4, 2005,
Original Russian Text Copyright + 2005 by Astaf’eva, Sidoikin, Krichevskii, Kagarlitskii.
AND CORROSION PROTECTION OF METALS
Electrocatalytic Hydrogenation of Nicotine
Z. M. Astaf’eva, P. B. Sidoikin, L. A. Krichevskii, and A. D. Kagarlitskii
Institute of Phytochemistry, Ministry of Education and Science of the Republic of Kazakhstan,
Received November 10, 2004; in final form, January 2005
Abstract-Electrocatalytic reduction of the nicotine alkaloid in the presence of skeletal nickel catalysts was
Natural nicotine, the main alkaloid contained in
tobacco (2310 wt % in a plant), is an (S)-isomer 
and acts as an exceedingly strong poison upon the pe-
ripheral and central nervous systems. For this reason,
it does not find any wide use, even in the form of
a sulfate, as an insecticide for pest control in agricul-
ture and for curing parasitic skin diseases in veterinary
medicine. An attempt to apply this alkaloid in curing
Alzheimer  or Parkinson diseases  proved to be
unsuccessful because of the strong side effects .
The discovery of the bactericide and pesticide ac-
tivity of synthetic analogues of nicotine and products
of its reductive transformations  attracted the at-
tention of researchers to development of methods for
synthesis of compounds of this kind. However, nic-
otine itself was not was used for synthetic purposes.
This was done using not nicotine itself, but a product
of its metabolism in mammal organisms, the cotinine
alkaloid whose skeleton transforms to the structure of
the corresponding nicotine derivative . In this
context, it may be assumed that hydrogenated and
partly hydrogenated nicotine derivatives are of interest
as syntons for obtaining new physiologically active
compounds. As for sources of nicotine, it should be
emphasized that it is important to utilize wastes from
the tobacco industry, whose stock may be as large as
tens of thousands of tons, with this alkaloid and its
analogues contained in an amount of 233wt%.
It is well known that hydrogenation of pyridine
bases requires noble metal catalysts and rather severe
conditions: high temperature and hydrogen pressure
[10, 11]. A fully hydrogenated nicotine, hexahydro-
nicotine, can be obtained either by reduction of nico-
tine with metallic sodium or catalytically, by hydro-
genation in the presence of platinum black ,
Adams catalyst in acetic acid , or skeletal nickel
. The yield of hexahydronicotine under these con-
ditions is as high as 23325%.
Undoubtedly advantageous in reduction of the pyr-
idine ring is the reaction of electrocatalytic hydroge-
nation. It proceeds on a skeletal nickel catalyst under
atmospheric pressure at low temperature [15, 16].
For this reason, the electrocatalytic reduction of
nicotine on a skeletal nickel catalyst under conditions
closely similar to those in reduction of pyridine bases
was studied in order to develop a technique for syn-
thesis of hexahydronicotine.
The skeletal nickel catalyst was obtained by
the Rayney method from a 50 : 50 alloy of nickel and
Experiments on reduction of nicotine were carried
out in a thermostated electrocatalytic diaphragm cell.
As the cathode served a stainless steel disc with a sur-
face area of 0.05 dm
, which was closely adjacent to
the cell bottom. A skeletal nickel catalyst was placed
on the cathode and kept in the reaction zone by the
field of a permanent magnet. A stainless steel plate
was used as the anode. An MA-40 anion-exchange
membrane served as the diaphragm. The anolyte was
a 20% solution of sodium hydroxide; the alkali con-
centration in the catholyte was selected experimental-
ly. The gases evolved were collected into graduated
Nicotine well dissolves in aqueous solutions of
sodium hydroxide in the temperature conditions stud-
ied. Therefore the electrolytic hydrogenation was per-
formed without agitation.
The composition of the reduction products was de-
termined by gas3liquid chromatography with marker