pentanitroaniline

     Pentanitroaniline, or more properly 2,3,4,5,6-pentanitroaniline, is a somewhat sensitive high explosive compound. It was first prepared in 1910 by the team of Flurscheim and Simon by nitrating dinitroaniline. Pentanitroaniline is a powerful explosive with a brisance equal to that of RDX or PETN. It is, however, somewhat sensitive to friction and impact, a characteristic that makes it unsuitable for use in many high explosive applications. It does find use as an initiating explosive and in booster charges. Pentanitroaniline is also used as an intermediate in the preparation of TATB and CL-18.

CHEMICALS	APPARATUS
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     Synthesis 1: Dissolve 1 g of 4-amino-2,6-dinitrotoluene (4-ADNT) in 40 mL of 96% sulfuric acid. Slowly add 3 mL of 90% nitric dropwise to the acid solution while keeping the temperature around 40 C. After adding all of the acid heat the solution to 70 C for 1 hour, and then allow it to cool to room temperature. Place the solution in a separatory funnel and extract the product with several portions of methylene chloride. Combine the extracts in a small Erlenmeyer flask and dry it by adding a few grams of anhydrous magnesium sulfate; allow 10-12 hours for complete drying. Pour the mixture over a filter to remove the magnesium sulfate and heat the filtrate on a steam bath to drive off most of the methylene chloride. Place the remaining solvent solution in a crystallization dish and gently heat in an oven to obtain crystals of pentanitroaniline. Yield is about 62%. Synthesis 2: This method prepares pentanitroaniline in greater yields, but it requires precise control of acid concentrations. Determine the concentration of sulfuric acid via titration with sodium hydroxide. If the acid concentration is precisely 100.0% add exactly 5.28 g of ice to obtain a concentration of 99.5%. It is important to have an acid concentration of precisely 99.5% sulfuric acid. Slowly add 18.3 g of 3,5-dinitroaniline to the acid, with stirring, while maintaining the temperature below 35 C. Prepare a mixture of 50 mL of 90% nitric acid 100 mL of 100.0% sulfuric acid; mix them slowly with cooling as heat will be given off. When the dinitroaniline has dissolved slowly add the mixed acids dropwise, with stirring, while maintaining the temperature below 30 C. Over a period of 75 minutes slowly warm the mixture up to 70 C, and hold at that temperature for 90 minutes while stirring. When finished heating stop stirring and gradually allow the flask to cool to room temperature. Place the solution in a separatory funnel and extract the product with three 1 L portions of dichloroethane. Combine the extracts in an Erlenmeyer flask and dry it by adding 10-20 grams of anhydrous magnesium sulfate; while stirring, allow 10-12 hours for complete drying. Pour the mixture over a filter to remove the magnesium sulfate and distill the filtrate on a steam bath to concentrate the solution to about 400 mL. Cool the solution to -15 C for 10-12 hours to allow for precipitation of the product. Filter to collect the crystals of pentanitroaniline and wash them with 5 mL of cold dichloroethane. A second crop of less pure product can be obtained by concentrating the solution further by heating, placing the solution in a crystallization dish, and gently heating in an oven to dryness. The total yield is around 75%.

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