DINA

     DINA, and acronym for dinitroxydiethylnitramine, is an insensitive high explosive nitrate ester. Other names for DINA include 1,5-dinitrato-3-nitrazapentane; 2,2'-(nitroimino)bis-ethanol dinitrate ester; 2,2'-(nitroimino)di-ethanol dinitrate; 1,5-dinitroxy-3-nitro-3-azapentane; 2,2'-(nitroimino)diethanol dinitrate; 2,2'-(nitroimino)ethanol dinitrate; 2,2'-dinitroxydiethylnitamine; 2,2'-dinitroxydiethylnitramine; 2,2'-nitroiminobis(ethyl nitrate); diethanol-N-nitramine dinitrate; diethanolnitramine dinitrate; N-nitrodiethanolamine dinitrate; nitrodiethanolamine dinitrate; and sym-dinitroxydiethylnitramine. DINA is used in a variety of high explosive formulations and as an ingredient in the preparation of some energetic plasticizers.

CHEMICALS	APPARATUS
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     Prepare a mixture of 850 g of acetic anhydride and 10 g of 37% hydrochloric acid cooled in an ice bath to 5 C. Add 42.4 g of concentrated nitric acid, and then add 400 mL of methylene chloride. Simultaneously add 210 g of diethanolamine and 424.4 g of concentrated nitric acid to the mixture via dropwise addition with two separate addition funnels. The rate of nitric acid addition should be slightly faster than the rat of diethanolamine addition. The addition should take 45 minutes and the temperature should be kept between 20-25 C. When the addition is complete warm the mixture at 40 C for 10 minutes. Allow the mixture to cool to room temperature and carefully add 650 mL of cold water. Allow the layers to separate and transfer the aqueous layer to a separatory funnel. Extract the aqueous layer twice with 100 mL of methylene chloride. Combine the methylene chloride extract and wash it with water, sodium carbonate solution, and with water again until the pH of the wash is neutral. Dilute the washed solvent with 1000 mL of methylene chloride and pass it through a chromatographic column of silica gel. The column should be 10” long and 2” wide. Of the material that emerges from the colume the solvent is removed and pure DINA remains. Yield is about 80%. Synthesis 2: Into a 1-L round-bottomed flask equipped with a stirrer, thermometer and addition funnel place 315 g of 98% nitric acid. Immerse the flask in an ice bath and cool the acid to 2 C. The flask is flushed with inert nitrogen gas and closed off from the atmosphere by a drying tube filled with Drierite. Slowly add 159 g of diethanolamine beneath the surface of the acid while vigorously stirring. It will take about 4.2 hours to add all of the acid. The reaction mixture is stirred at 11-16 C for 1 hour, and the temperature is allowed to rise to 25 C for another 30 minutes with stirring. After standing for 12 hours, the amine/nitric acid mixture should be a clear pale-yellow solution, which is transferred to an addition funnel for the next step of the reaction. A solution of 3.34 g of acetyl chloride in 536 g of acetic anhydride is charged to the 1-L flask, and the temperature is adjusted to 31 C. The amine/nitric acid solution is added dropwise over a period of 2.3 hours while vigorously stirring. The clear pale-yellow reaction mixture is stirred at 35-37 C for another 1.7 hours and poured onto 3600 g of distilled water/ice to precipitate small white crystals of crude DINA. The white solid DINA is filtered to collect it and washed with three 350 mL portions of water. The solid DINA is partially air dried, and then dissolved in 1200 mL of acetone. The resulting clear pale-yellow solution is neutralized with 50 mL of 0.5-molar aqueous potassium carbonate. The acetone solution initially turned orange-red, then slowly to yellow with a pH of 8. The neutralized solution is filtered to remove impurities and added dropwise to 3200 g of distilled water/ice over 1.6 hours while vigorously stirring. White flocculent crystals of DINA will form immediately and continue to form throughout the addition. After stirring for another 1.5 hours, the mixture is refrigerated for 12 hours at 0-5 C. The DINA crystals are filtered to collect them and washed with four 400 mL portions of water. Final yield is 277 g or 76%. The DINA is stored water wet.

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