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'United States Patent [191 ‘United States Patent [191 [11] 4,338,442 ‘Strecker [45] Jul. 6, 1982 [54] PREPARATION OF [56] References Cited RAAZACYCLOOCTANE1,5-METHYLENE-3,7-DINITRO-1,3,5,7-TET- U.S.. PATENT DOCUMENTS ' ' 2,678,927 5/1954 Wright et a1. ..................... .. 544/215 ‘ v 4,069,220 1/ 1978 Orem et a1. .. 544/ 186 [75] Inventor: Richard Strecker, Randolph, NJ. Primary Examingr_He-my R. was ‘ .Assistant Examiner-Robert C; Whittenbaugh [73] Assignee: The United States of America as Attorney, Agent, or Firm-Nathan Edelberg; Robert P. ' represented by the Secretary of the ' GibSOH; A. Victor El'kkila Army, Washington, DC. [57] ABSTRACT ' ‘ 1,5-Methylene-3,7-dinitro-1,3,5,7-tetraazacyclooctane [21] APPL NW 2545567 (DPT) is prepared by reacting nitrourea with formalde ' \ hyde in aqueous solution in the presence of suf?cient - _ ' 7 added water soluble base, such as sodium hydroxide, to [22] F?ed' Apr‘ 15’ 1981 initiate evolution of carbon dioxide gas and formation of ' ‘ an intermediate compound, and reacting the intermedi .[51] Int. Cl.3 ......... ................. ............ .. C07D 251/72 ate compound with aqueous ammonia and formalde [52] U.S. Cl. ............... .' ................... .. 544/215 . hyde to form DPT. ' Field of Search ................... 544/186, 215, 180; [581, ' t _ 260/239 H, 239 M 6 Claims, No ‘Drawings 4,338,442 1 2 manufacturing DPT is impractical in view of its hydro ‘ PREPARATION OF lytic instability and dif?culty and cost of preparation. 1,5-METHYLENE-§,7-DINITRO-1,3,5,7-TET- . I have found a novel and inexpensive process for RAAZACYCLOOCTANE producing DPT by utilizing nitrourea as starting mate rial in place of nitramide. The novel process comprises GOVERNMENT RIGHTS reacting nitrourea with formaldehyde in aqueous me The invention described herein may be manufac dium at a pH of about 2 or higher, preferably between tured, used and licensed by the Government vfor Gov about 2 and 3, to cause evolution of carbon dioxide gas ernment purposes without the payment to me of any and formation of an intermediate compound, and react royalty thereon. > ' - V ‘ . I ' ing the intermediate compound with ammonia and formaldehyde to form DPT. ' BACKGROUND OF THE INVENTION The nitrourea starting material can be obtained in This invention relates‘ to a novel process for prepar high yields from urea nitrate, which in turn can be ing 1,5-methylene-3,7-dinitro-l,3,5,7-tetraazacyclooc readily produced from low cost urea (Organic Synthe .tane, also known as dinitropentamethylenetetramine or ses, vol, 1, page 417). brie?y as DPT, which is an intermediate for producing The process of the present invention can be carried HMX. ' out by mixing the nitrourea with aqueous formaldehyde HMX, tl,3,5,7-tetranitro-l,3,5,7-tetraazacyclooctane, until the nitrourea is completely dissolved. In the ?rst is a very powerful military explosive, but its use has 20 been limited by its high cost and availability. Current stage of the process, the relatively acidic solution thus methods for manufacturing HMX involve the nitrolysis obtained is adjusted to a pH of about 2 or more with a of hexamine. It is known that'HMX can be prepared water soluble base, such as sodium hydroxide, potas from DPT, and indeed DPT has been identi?ed as a key ' sium hydroxide, sodium acetate, and ammonium hy intermediate in the formation of HMX from the nitrol~ 25 droxide to cause a reaction characterized by the evolu ysis of hexamine, which is also known as the Bachmann tion of carbon dioxide gas and the formation of an inter process. (W. J. Chute, D. C. Downing, A. F. McKay, mediate compound. Ammonia is also liberated but in G. S. Myers and G. F. Wright, Can. J. Research, 278, the acid medium is converted to a soluble ammonium 218(1949); W. E. Bachmann, W. J. Horton, E. L. ‘Jen salt. The reaction mixture is stirred preferably with ner, N. wrMacNaughton and L. B. Scott, J. Am. heating until the evolution of carbon dioxide has ceased. Chem. Soc., 73, 2769(1951); ‘and W. E. Bachmann and In the ‘second stage of the process, the intermediate L. Jenner, J. Am. Chem, Soc., 73, 2773(1951). compound is reacted with ammonia and formaldehyde In view of the importance of DPT’in the synthesis of to form DPT. This can be readily accomplished by HMX, a low cost method for producing this intermedi neutralizing the solution with ammonium hydroxide to 35 ate would provide a signi?cant contribution toward about pH 6-7 in the presence of additional formalde- ' reducing the cost of manufacturing HMX. In the past hyde if necessary, whereby the DPT is formed and DPT has been prepared by various methods, viz. precipitates from the solution. (1) nitrolysis of hexamine using acetic anhydride and Although not exactly known, it is believed that in the ' 99+% nitric acid in acetic acid solvent; ?rst stage of the process, the nitrourea reacts with the (2) reaction of hexamine dinitrate and acetic anhy formaldehyde at the nitramide nitrogen to form N (3). reaction of hexamine dinitrate and 90% H2804 methylol nitrourea, which undergoes hydrolysis with and neutralization with ammonia to pH 6.5; scission of the carbamido group and evolution of CO1 and NH3 and reaction with more formaldehyde causing ‘ (4) reaction of hexamine, 99+% nitric acid and am 45 monium nitrate, and neutralization with ammonia the. formation of an intermediate compound believed to to pH 6.5;‘ v t be N-dimethylol nitramide. In the second stage of the (5) reaction of nitramide, formaldehyde and ammo process, the intermediate compound is reacted with nia; and I ammonia and formaldehyde to form DPT. In the ?rst (6) reaction of nitramide, formaldehyde and me reaction stage, two moles of formaldehyde are theoreti thylenediamine sulfate. cally required per mole of nitrourea to form the inter The reactants used in all of these methods are costly mediate compound believed to be N-dimethylol nitra (e.g. acetic anhydride and hexamine), or are dif?cult to mide. In the second reaction stage, two moles of ammo prepare and handle (e. g. nitramide), so that the synthesis nia and one mole of formaldehyde are required to react of HMX from DPT is more costly than the current with two moles of N-dimethylol nitramide (equivalent process for manufacturing HMX by vnitrolysis of hex to two moles of nitrourea starting material) to form t amine. DPT according to the following reactions: An object of this invention is to provide a more eco nomical process for producing DPT by employing re la) actants which are less costly than those used in prior art OZNNHCONHZ + (31120 —%H2NcoNNo2(cH2oH) ( methods. SUMMARY AND DETAILED DESCRIPTION 0 _ THE INVENTION - Previous studies have shown that DPT can be ob 65 tained in high yields by the condensation reaction be ' ' _ (Z) tween nitramide, formaldehyde and ammonia. How 2 ommcmou); + 2NH3 + cnzo 316-19 ever, the use of nitramide on a large scale process for 4,338,442 3 4 -continued and the reaction mixture was stirred until CO2 evolution ceased. The solution was then heated to 65° C. and ‘ H2C—-N—CH2 stirred for about 1 hour, during which further CO2 was OzN-III. (III-i2 III-N02 liberated. The solution was cooled to room temperature and adjusted to a pH of 6-7 by addition of 43% ammo nium hydroxide, whereupon DPT precipitated from The use of larger amounts of ‘formaldehyde and am solution and was separated by ?ltration. The ?ltrate was monia than those theoretically .required is preferred, treated with more ammonium hydroxide, thus produc since it promotes the yield of DPT produced within ing additional precipitate. The process was repeated limits. If desired, the total amount of formaldehyde until no further precipitate was obtained. The collected required in the process may be present in the ?rst reac precipitates of DPT, when dried, weighed 5.8 grams, tion stage and thus be present to react with the 'the corresponding to a 52% of theory yield based on ni intermediate compound to form DPT in the second trourea. Analysis of DPT: Calculated: C, 27.5%; H, reaction stage. ' 15 4.63%; N, 38.5%. Found: C, 27.51%; H, 4.67%; N, In carrying out the ?rst reaction stage of the present 38.38%. ' v process, it is preferred to add suf?cient base, e. g. sodium The foregoing disclosure is merely illustrative of the ‘hydroxide, to bring the solution to about pH 2-3 to principles of this invention and is' not to be interpreted _ initiate and complete the evolution of carbon dioxide in a limiting sense. I wish it to be understood that I do gas, and then neutralize the solution to about pH 6-7 20 not desire to be limited to the exact details described with ammonium hydroxide in the presence of suf?cient because obvious modi?cations will occur to a person formaldehyde to form and precipitate the DPT. Sub skilled inthe art. ' stantially lower yields of DPT are obtained when the I claim: - > I solution is neutralized to pH 6-7 in the ?rst reaction l. A process, for preparing l,5-methylene-3,7-dinitro stage and then mixed with ammonium hydroxide .to 25 l,3,5,7rtetraazacyclooctane (DPT) which comprises form DPT in the second reaction stage. reacting nitrourea and formaldehyde in aqueous me Both stages of the present process can be carried out :at temperatures within the range of about 20° to 100° C. dium at a pH of about 2 to about 6-7 to cause. the evolu ‘The ?rst stage of the process is preferably carried out tion of carbon dioxide gas and formation ofan' interme between about 45° C.
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