Synthesis and HPLC Identification of
2/c Anderson, 2/c Miller, 1/c Packer, 2/c Brockway, 2/c Harrison, 2/c Yahle,
and 2/c Zalewski
Department of Science, U.S. Coast Guard Academy, New London, Connecticut
The purpose of this experiment was to use high performance liquid chromatography
coupled with a photodiode array detector to separate, identify, and quantify the
relative amount of each nitrotoluene isomer synthesized.
Synthesis was conducted
using nitric and sulfuric acid in combination with toluene.
Through heating and
mixing, two mixtures, one of nitrotoluene and one of dinitrotoluene, were
synthesized and two HPLC samples were prepared for analysis. The results and
data suggest that HPLC methods for determining isomers and quantifying them are
The calculated relative amounts of each nitrotoluene isomer were
57.1% of 2-nitro, 38.3% of 4-nitro, and 4.56% of 3-nitro for sample 1 and 55.3% of
nitro-2, 40.3% of nitro-4, and 4.38% of nitro-3 for sample 2.
These values are very
close to the book values of 59% for 2-nitro, 37% for 4-nitro, and 4% for 3-nitro.
5.71 grams of 2,4-dinitrotoluene were also produced in sample 2 of this experiment.
The combination of nitric and sulfuric acids with toluene produces an
electrophilic aromatic substitution reaction in which the nitronium ion is substituted for
hydrogens on the aromatic ring.
The reaction results in the production of nitrotoluene.
Nitrotoluene is an organic compound that comes in three isomers.
compounds are ortho-nitrotoluene, para-nitrotoluene, and meta-nitrotoluene.
nitrotoluene synthesis, there is more para and ortho than meta because nitro groups are
Each isomer has varying applications.
Ortho-nitrotoluene is used in
agricultural chemicals, paints, and plastics.
Meta-nitrotoluene is used in dyestuffs and
Likewise para-nitrotoluene is used with dyestuffs, but also
h Corresponding author.
Analytical Methods, Spring 2010