AChemLab4 - Synthesis and HPLC Identification of...

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Synthesis and HPLC Identification of Nitrotoluene Explosives 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 06320-8101 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 fairly precise. 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. These three compounds are ortho-nitrotoluene, para-nitrotoluene, and meta-nitrotoluene. In nitrotoluene synthesis, there is more para and ortho than meta because nitro groups are metadirectors. Each isomer has varying applications. Ortho-nitrotoluene is used in agricultural chemicals, paints, and plastics. Meta-nitrotoluene is used in dyestuffs and photographic developers. Likewise para-nitrotoluene is used with dyestuffs, but also h Corresponding author. E-mail: Jessica.P.Anderson@uscga.edu 1 Analytical Methods, Spring 2010
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with plastic foams and paints and pharmaceuticals like ortho-nitrotoluene. 1 As strongly basic compounds, the largest concern associated with them is their prevalence in explosives. Thus, it is important to be able to identify them and determine their concentrations in order to prevent contamination. Though explosives are stable in the environment, rain and other precipitation can drain them into aquifers which could lead to contamination of significant water sources. The compounds also do not degrade. In some instances, trace amounts of dinitrotoluenes will also be present in the reaction. Dinitrotoluene is more polar, thus it comes out before nitrotoluene when using high performance liquid chromatography. Most dinitrotoluene is used in the production of flexible polyurethane foams. 2
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This note was uploaded on 10/01/2010 for the course CHEM 341 taught by Professor Frysinger during the Spring '09 term at Conn College.

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AChemLab4 - Synthesis and HPLC Identification of...

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