Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 10, pp. 1577−1580.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © Yu.G. Khabarov, D.E. Lakhmanov, D.S. Kosyakov, N.V. Ul’yanovskii, 2012, published in Zhurnal Prikladnoi Khimii, 2012, Vol. 85,
No. 10, pp. 1644−1647.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis of 2,4-Dinitrophenol
Yu. G. Khabarov, D. E. Lakhmanov, D. S. Kosyakov, and N. V. Ul’yanovskii
Lomonosov Northern (Arctic) Federal University, Arkhangelsk, Russia
Received May 10, 2012
Abstract—New highly selective method is suggested for synthesis of 2,4-dinitrophenol by nitration of phenol
with nitric acid in an aqueous-alcoholic medium at the boiling point of the reaction mixture. The yield of 2,4-di-
nitrophenol is as high as 80%.
2,4-Dinitrophenol is an important product of organic
synthesis used as means of corrosion protection of metals
, styrene polymerization inhibitor , antiseptic for
wood impregnation , and raw material for synthesis
of aromatic amino and nitro derivatives [4–6], dyes ,
and chemicals for agriculture [8, 9].
The main method for obtaining 2,4-dinitrophenol is
by nitration of benzene, phenol, or mononitrophenol;
it is also synthesized by alkaline hydrolysis of
2,4-Dinitrophenol is produced from benzene via
oxidative nitration with nitric acid in the presence of
mercury(II) hydroxide and a minor addition of sodium
nitrite. The yield of the product is 56.8% .
Another method for oxidative nitration of benzene
consists in bubbling of air or nitrose gases through
a nitric acid solution of mercury(II) nitrate, heated to
above 40°C. 2,4-Dinitrophenol with a melting point of
about 105°C has been produced by this technique .
A synthesis of 2,4-dinitrophenol has been described
in which nitrosophenol is produced from phenol and
then is subjected to oxidative nitration with nitric
acid at 90°C in the course of 1.5 h . The yield of
2,4-dinitrophenol is 79%.
2,4-Dinitrophenol is produced from 2,4-dinitrochloro-
benzene by the reaction of nucleophilic substitution
. The reaction is performed in an alkaline medium at
a temperature of 95–97°C in the course of 3.5 h.
By the nitration reaction, 2,4-dinitrophenol can
be synthesized using the classical nitrating mixture
. The reaction product is dark red oil. After the
reaction product is puriﬁ ed with bone coal, the yield of
2,4-dinitrophenol is 65%.
A method has been suggested for synthesis of mono-
and dinitrophenol, in which sodium nitrite, oxalic
acid, and wet silicon dioxide are used. The reaction is
performed in methylene chloride .
Nitration of phenol with liquid N
2,4-dinitrophenol . The expenditure of N
is 4–6 mL g
phenol. It is recommended to purify
2,4-dinitrophenol by heating its alcoholic solution with
bone coal. The yield of 2,4-dinitrophenol is 76%.
2,4-Dinitrophenol is formed from sodium
nitromalonic aldehyde monohydrate and 1-nitro-2-
propanone via cyclodehydration in an alkaline medium
at room temperature in the course of 18 h. A puriﬁ cation
by column chromatography (SiO
440 mg of pale yellow 2,4-dinitrophenol from 2 g of
sodium nitromalonic aldehyde monohydrate and 1.18 g
of 1-nitro-2-propanone .
Thus, a large number of multistage labor-
consuming methods have been developed for synthesis
of 2,4-dinitrophenol. The goal of our study was to
develop a new high-selectivity method for synthesis
of 2,4-dinitrophenol, based on the reaction of phenol