3 - nitramino - 4 - nitrofurazan can be depicted by the following formula : ## str1 ## the compound has a density of about 1 . 93 g / ml . the energetic salts of 3 - nitramino - 4 - nitrofurazan comprise useful ingredients for use in energetic compositions . these salts are exemplified by the formula mx n wherein m is a cation , x is the anion of 3 - nitramino - 4 - nitrofurazan , and n is an integer corresponding to the valence of the cation x . the value of n depends on the valence of m , and can be , for instance , 1 , 2 , 3 , 4 , or higher . when m is a metal cation , the metal thereof can be selected from the group consisting of metals from groups ia , iia , iiia , iva , va , via , ib , iib , iiib , ivb , vb , viib , viiib , and the lanthanide elements ( 51 - 71 ) of the periodic table . advantageously , m is selected from the group consisting of li , na , k , rb , cs , ca , ba , sr , mg , cu , ag , au , zn , cd , hg , al , sc , y , ga , b , in , lanthanide elements ( 57 - 71 ), ti , zr , hf , ge , sn , v , nb , ta , cr , mo , w , mn , tc , re , fe , co , ni , ru , rh , pd , os , ir , pt , and mixtures thereof . the cation of an energetic salt of 3 - nitramino - 4 - nitrofurazan can be non - metallic . non - metallic cations can be nitrogen and / or carbon containing . the class of non - metallic cations includes nitrogen - containing and carbon - containing cations such as , for example , ammonium , hydroxyl ammonium , dinitroazetidium , hydrazinium , guanidinium and ( c ( ch 2 nh 3 ) 4 ) + 4 , among others . salts according to the present invention can have increased electron densities on the nitramino functionality and exhibit an attendant desired but unexpected enhanced thermal stability . typifying this unexpected combination of properties are , for instance , the ammonium salt which has a decomposition temperature of about 121 ° c ., the hydroxylammonium salt which has a decomposition temperature of about 163 ° c . and a hydrazinium salt which has a decomposition temperature of about 184 ° c . by way of comparison , a methylene - bis compound described in j . heterocyclic chem . 29 : 1835 ( 1992 ) possesses insufficient thermal stability and decomposes at less than 100 ° c . metal salts according to the present invention are also sufficiently thermally stable to be useful in energetic applications . for instance , illustrative of the mono - valent metal salts are the potassium salt which is thermally stable to about 206 ° c ., and the sodium salt which is relatively stable even above 100 ° c . the present salts of 3 - nitramino - 4 - nitrofurazan are also generally relatively dense materials . the hydroxylammonium salt has a density of about 1 . 875 g / ml . certain energetic compositions containing at least one salt according to the present invention are superior to comparably formulated energetic compositions containing cl - 20 . the 3 - amino - 4 - nitrofurazan starting material can be obtained , for instance , by treating 3 , 4 - diaminofurazan with peroxytrifluoroacetic acid to obtain a blue - green solution . that solution is heated under reflux until light yellow . further heating will reduce the yield . the light yellow solution is , in turn , treated with na 2 co 3 ( aqueous ) and the desired 3 - amino - 4 - nitrofurazan is extracted from the treated solution . the extrated 3 - amino - 4 - nitrofurazan can be further purified by recrystallization . a synthesis starting from 3 , 4 - diaminofurazan is described in , for example , j . heterocyclic chem ., 5 : 83 ( 1968 ), the disclosure of which is incorporated herein by reference . various strong nitrating reagents can , in principle , be used and include nitric acid -- acetic anhydride or dinitrogen pentoxide ( n 2 o 5 ) in methylene chloride . the latter reagent is preferred , and can be prepared according to inorganic synthesis , ix : 83 - 88 ( 1967 ), the disclosure of which is incorporated herein by reference . the concentration of the nitrating reagent does not appear to be critical . the actual concentration will be suitably selected as a function of various pragmatic objectives such as minimization of solvents . the nitration is generally conducted in the presence of a non - reactive solvent . illustrative of the various suitable solvents are methylene chloride , chloroform , carbon tetrachloride , and dichloroethane . the solvent for the nitration can also serve as the solvent for the nitrating reagent . the nitration can be conducted across a wide temperature range . the temperature is not particularly critical . an exemplary temperature range is , for instance , from sub - ambient , such as - 30 ° c ., to above 0 ° c . such as 15 ° c . sub - ambient temperatures can be obtained according to various means known to those skilled in the art such as an ice bath , brine chiller or , for instance , nitromethane / co 2 . the reactions are , as a matter of course , conducted anhydrous and also , preferably , in an inert atmosphere such as nitrogen . metal salts of 3 - nitramino - 4 - nitrofurazan are readily obtainable according to procedures known to those skilled in the art . metal salts can be obtained , for instance , by allowing a metal hydroxide or oxide in a solvent , such as methanol , to react with 3 - nitramino - 4 - nitrofurazan . the reactants can be combined at a rate which permits control over the exothermic reaction . non - metallic salts of 3 - nitramino - 4 - nitrofurzan can be facilely produced in an analogous manner . other energetically useful compounds can be derived or synthesized from 3 - nitramino - 4 - nitrofurazan . an exemplary liquid gun propellant composition can comprise an energetically effective amount of a salt of 3 - nitramino - 4 - nitrofurazan and water . such a mono - propellant can exhibit unexpectedly enhanced impetus values compared to a comparable formulation based on hydroxylammonium nitrate (&# 34 ; han &# 34 ;) and triethanol amine (&# 34 ; tean &# 34 ;). for instance , a liquid gun propellant containing an energetic salt of 3 - nitramino - 4 - nitrofurazan , such as the hydroxylammonium salt ( 60 wt . %), can have approximately the same impetus value obtainable from a liquid gun propellant containing han ( 60 wt . %) and tean ( 20 wt . %). conventional han / tean - based liquid gun propellants can be moderately energetically tailored by including an energetically enhancing amount of at least one salt of 3 - nitramino - 4 - nitrofurazan as a supplement to the energetic components ( han and tean ). 1 h - nmr spectra reported herein were recorded ( varian em - 360a nmr spectrometer ) and referenced the tms . ir spectra reported herein were also recorded ( nicolet 5dxb ftir spectrometer ) as either films ( liquids ) or kbr pellets ( solid ). the melting points , decomposition points , were measured using a dupont 910 dsc coupled to a ta 2200 thermal analyzer at 10 ° c ./ min . elemental analyses were also conducted as reported herein . to a dry 50 ml r . b . flask cooled to - 30 ° c . was added 3 . 015 g of a 1m n 2 o 5 in methylene chloride solution . 3 - amino - 4 - nitrofurazan (&# 34 ; anf &# 34 ;; 0 . 10 g , 0 . 77 mole ) was then added in small portions over 15 minutes . the temperature was raised to 0 ° c . and the solution was stirred for one hour . the methylene chloride , excess n 2 o 5 , and nitric acid were removed in vacuo . ammonium hydroxide ( 1 g ) was added and the excess ammonia and water removed in vacuo . the product was titrated with a mixture of ether / ethylacetate to yield a crystalline product ( 0 . 120 g , 63 mmoles , 82 % yield ). dsc analysis showed a sharp exotherm at 133 ° c . the product was recrystallized from ethyl acetate to yield off white crystals which were subjected to x - ray structure analysis . ft - ir analysis ( kbr ) showed absorptions at 3207 ( b ) , 1584 ( s ) , 1467 ( m ) , 1418 ( s ), 1346 ( m ), 1292 ( s ), 1045 ( w ), 1009 ( w ), 934 ( w ), 830 ( w ), 800 ( m ), 780 ( 2 ), cm - 1 . a clean , dry , 300 ml 3 neck round bottom flask was equipped with a vacuum adapter ( for n 2 ), rubber septa , magnetic stirring bar and thermocouple . the flask was charged with 99 . 94 g ( 0 . 09m ) 10 % n 2 o 5 in anhydrous ch 2 cl 2 via syringe . it was immediately set in a nitromethane / co 2 bath and cooled to - 20 ° c ., as the septa was exchanged for a glass stopper . aminonitrofurazan (&# 34 ; anf &# 34 ;; 9 . 75 grams ; 0 . 75m ) was preweighed into a glass vial . the anf was added over an 8 minute period not exceeding - 17 ° c . all residue was rinsed down with 2 mls anhydrous ch 2 cl 2 . the bath was exchanged for an ice / water bath and the mixture was stirred for 3 . 5 hrs , not exceeding + 10 ° c . the reaction mixture was then transferred to a one neck tarred round bottom flask , and the solvent was removed in vacuo at ambient and crystals were obtained . the crystals were then placed under high vacuum for 1 / 2 hour to remove trace ( hno 3 ), yield 95 - 100 % of theoretical . the product was recrystallized using 16 . 2 ml of dry chloroform per gram of crude product . a slurry in chloroform was formed and was stirred at 41 ° c . until all crystals dissolved , then set into a refrigerator - freezer at - 20 ° c . for 16 hrs . the crystals were collected ( 84 % theoretical yield ) on a paper filter using glass spatulas for transfer . a discoloration was noted when stainless steel was used in a high humidity situation . dsc analysis : melt at 57 ° c . decomposition temperature 101 ° c . crystals which were recrystallized twice were more needle like with dsc melt at 60 ° c ., decomposition 101 . 5 ° c . the crystals had a density ( gas picnometer ) of 1 . 93 g / cc . ftir analysis ( kbr ) 3278 ( s ); 1631 , 1606 ( d ); 1549 , 1503 ( d ); 1383 , 1337 ( d ). δh c 1567 / g , δh f + 60 kcal / mole . a dry clean 250 ml 3 neck round bottom flask equipped with a nitrogen port , magnetic stirring bar , thermocouple was set into an ice bath . 3 - nitroamino - 4 - nitrofurazan ( 5 . 0 grams 0 . 0285m ) was added with 40 ml distilled water . hydroxyl amine ( ha ) ( 11 . 5 % wt in water ) was preweighed into a vial , ( 8 . 20 grams 0 . 94 grams ha ; 0 . 0285m ). ha was added over three minutes with a pipet at a temperature not exceeding 3 ° c . the vial was rinsed with 2 mls h 2 o for quantitative transfer of its contents . following ten minutes the reaction mixture was stirred cold , then the ice bath was withdrawn and stirred at ambient for 11 / 2 - 2 hrs . after transfer to a tarred one neck flask , the water was removed in vacuo at 40 ° c . to obtain crystals . crystals were then placed under high vacuum for at least 8 hrs ., giving 101 % theoretical yield . the product was recrystallized using 9 . 87 ml of nitromethane per gram of crude product nitromethane . a slurry was formed and was stirred at 63 ° c ., then a few drops of methanol was added and all crystals went into solution . the solution was then set into a refrigerator - freezer at - 20 ° c . for 16 hrs . sparkly pearlescent flaky crystals were collected on paper and dried to give 84 % theoretical yield . dsc : melt 132 ° c ., exothermic decomposition 162 . 9 ° c . ftir , 3200 - 2700 ( m ), 1582 ( s ), 1510 ( s ), 1336 , 1303 ( d ). empirical formula , c 2 h 4 n 6 o 6 , density , ( x - ray analysis ) 1 . 875 g / cc . δh c 1648 cal / g , δh f + 18 kcal / mole . into a clean 250 ml 3 neck round bottom flask equipped with a nitrogen port , magnetic stirring bar , and thermocouple was placed 3 - nitroamino - 4 - nitrofurazan (&# 34 ; anf &# 34 ;; 4 . 44 grams 0 . 025m ). thirty - five mls of distilled water was then added and the flask set into an ice bath . fuming hydrazine ( 95 %; 0 . 942 g ; 0 . 028m ) was preweighed into a vial , then added over three minutes while not letting the reaction temperature exceed + 8 ° c . the reaction mixture was kept cold for 10 minutes , then the ice bath was withdrawn and the reaction mixture was stirred 2 . 5 hrs . after transfer to a tarred one neck flask , the water was removed in vacuo at 40 ° c . to obtain crystals ( 94 % yield ). the crystals were dissolved in approximately 200 ml thf at 40 ° c . then the amount of solvent present was reduced and thereafter the solution was refrigerated at - 20 ° c . for 16 hrs . the resulting yellow green crystals were collected and placed over high vacuum ( 68 . 5 % theoretical yield ). dsc : decomposition at 184 ° c . ftir 3500 - 3000 ( m ), 1583 ( s ), 1467 , 1422 , 1395 , 1348 , 1296 ( m ). the density of the hydrate ( x - ray analysis ) was 1 , 704 g / ml . a clean 3 neck round bottom flask was equipped with magnetic stirring bar , thermocouple and set into an ice bath . 3 - nitroamino - 4 - nitrofurazane ( 0 . 5 g ; 0 . 0029m ) was added with 4 ml distilled h 2 o . ammonium hydroxide , ( 29 %; 0 . 20 g ; 0 . 006m ) was preweighed , then added via syringe over two minutes while the temperature did not exceed 7 ° c . the mixture was stirred cold for 10 minutes , then stirred an additional hour at ambient . the mixture transferred to a tarred one neck flask , and the water was removed in vacuo at 38 ° c . upon completion of high vacuum , the yield of crystals was calculated as 105 % of theoretical . the crystals were dissolved in a ethylacetate and precipitated by an equal amount of hexanes at - 20 c . the resulting crystals were collected ( 65 % yield ). dsc : decomposition 121 ° c . ftir : 3300 - 3000 ( m ), 1579 ( s ), 1464 , 1423 , 1390 ( t ), 1347 ( s ), 1281 , 1250 ( d ). a clean 3 neck round bottom flask was equipped with magnetic stirring , thermocouple , and set into an ice bath . 3 - nitroamino - 4 - nitrofurazane ( 0 . 5 g ; 0 . 0029m ) was added with 4 ml distilled h 2 o . potassium hydroxide ( 0 . 1957 g ; 0 . 003m ) was preweighed in a vial then dissolved in 2 ml distilled h 2 o . this was then added slowly over three minutes not exceeding 10 ° c . the mixture was stirred cold for 10 minutes , then stirred an additional hour at ambient . after transfer to a tarred 1 neck flask , the water was removed in vacuo at 38 ° c ., upon completion of high vacuum treatment , the yield of crystals was 102 % of theoretical . dsc : exothermic peaks at 206 ° c ., 210 ° c ., and 437 ° c . ftir : 3500 ( broad ), 1577 ( s ), 1458 , 1425 , 1393 , 1345 , 1289 ( m ). a 3 neck round bottom flask was equipped with magnetic stirring bar , thermocouple , and set in an ice bath . 3 - nitramino - 4 - nitrofurazan ( 0 . 5 g ; 0 . 002m ) was added with 4 ml distilled h 2 o . sodium hydroxide ( 0 . 1263 g ; 0 . 003m ) was preweighed into a vial and dissolved in 2 ml distilled h 2 o . the sodium hydroxide solution was slowly added to the 3 - nitramino - 4 - nitrofurazan over four minutes while the temperature did not to exceed 10 ° c . the mixture was initially stirred 10 minutes cold , and was then stirred another one hour at ambient . upon transfer a one neck flask , the water was removed in vacuo . after a period of high vacuum , circular crystals were noted with a yield of 105 % theoretical dsc : melt 103 ° c ., strong exothermic decomposition peak at 129 . 5 ° c ., several weaker ones at 136 ° c ., 147 ° c ., 162 ° c ., and 208 ° c . ftir : 3578 , 3513 ( d ), 1645 , 1582 , 1537 ( t ), 1471 , 1442 ( d ), 1351 , 1299 , 1267 ( t ). a clean 3 neck round bottom flask was equipped with magnetic stirring , thermocouple , and nitrogen and placed into an ice bath . 3 - nitroamino - 4 - nitrofurazan ( 1 . 75 grams ; 0 . 01m ) is added to 5 mls dry methanol . dinitroazetidinium ( 1 . 47 grams ; 0 . 01 mol ) is added slowly over 10 minutes not exceeding 10 ° c . the resulting mixture is stirred cold for 10 minutes , then the mixture is stirred for an additional hour at room temperature . after transfer to a tarred one neck flask , the solvent is removed in vacuo at 35 ° c . recrystallization followed . a clean dry 3 neck round bottom flask was equipped with magnetic stirring bar , thermocouple , and nitrogen inlet is placed in an ice bath . 3 - nitroamino - 4 - nitrofurazan ( 1 . 75 grams ; 0 . 1 mol ) was added with 5 mls dry methanol . guanidine ( 0 . 59 grams ; 0 . 01 mol ) was preweighed into a vial and dissolved in 5 ml dry methanol . the guanidine - containing mixture was added over 5 minutes while the temperature did not exceed 10 ° c . the resulting mixture was stirred cold for 10 min , and then stirred for an additional hour at ambient . after transfer to a tarred one neck flask , the solvent was removed in vacuo at 35 ° c . after a period of high vacuum , the yield of crystals was 100 % of theoretical . dsc : exothermic peak at 90 . 96 ° c . ftir : 3517 , 3413 , 3270 , 3212 ( m ), 1660 ( d ), 1576 ( s ), 1386 , 1344 , 1311 ( t ). a three neck round bottom flask was equipped with a magnetic stirring bar and thermocouple and then set in an ice bath . 3 - nitramino - 4 - nitrofurazan ( 0 . 546 g , 0 . 00312m ) was added with 4 . 3 ml distilled water . zinc oxide ( 0 . 1396 g ; 0 . 0017m ) was slowly added over two minutes , at a temperature not exceeding 7 ° c . the mixture was stirred cold for 10 minutes , then stirred an additional hour at ambient . upon transfer to a one neck flask , the water was reduced in vacuo , after which high vacuum followed yielding 107 % theoretical of a paste . dsc : exothermic peak at 111 ° c ., 250 ° c . and 314 ° c . ftir : 3563 ( broad ), 1583 ( s ), 1467 , 1423 , 1348 , 1297 ( m ).