Nitroguanidine nitrate

N-( Hydroxy ethyl), N-nitroguanidine Nitrate (See Hydroxyethylguanidine under "H", and TrinitrophenyInitroguanidine (See Nitrophenyl-guanidine under "N )... 

Nitroguanidine Nitrate, H2N.C NH.NH.N02-HN0g mwl67.09, OB to C02 +4.8% rhomb prisms, mp 147° (dec). May be prepd by dissolving NGu in hot, coned nitric acid and allowing to cool. Loses the nitric acid in contact with air. The salt is an expl detonable by impact, but not by heat... 

Ma.nufa.cture. Nitroguanidine may be made by several methods. In all the processes guanidine nitrate is the iatermediate which is then dehydrated with sulfuric acid. When used ia propellants, the average particle size of nitroguanidine has to be carefully controlled. 

In the commonly used Welland process, calcium cyanamide, made from calcium carbonate, is converted to cyanamide by reaction with carbon dioxide and water. Dicyandiamide is fused with ammonium nitrate to form guanidine nitrate. Dehydration with 96% sulfuric acid gives nitroguanidine which is precipitated by dilution. In the aqueous fusion process, calcium cyanamide is fused with ammonium nitrate ia the presence of some water. The calcium nitrate produced is removed by precipitation with ammonium carbonate or carbon dioxide. The filtrate contains the guanidine nitrate that is recovered by vacuum evaporation and converted to nitroguanidine. Both operations can be mn on a continuous basis (see Cyanamides). In the Marquerol and Loriette process, nitroguanidine is obtained directly ia about 90% yield from dicyandiamide by reaction with sulfuric acid to form guanidine sulfate followed by direct nitration with nitric acid (169—172). 

S. Levmore, PTir Blast Parameters and Other Characteristics of Nitroguanidine and Guanidine Nitrate, TR 4865, PTA, Dover, N.J., 1975. 

Several lesser known nitrating agents, which have been used on a lab scale are metal nitrates in the presence of acetic acid or acetic anhydride, tetranitromethane and hexanitroethane in an alkaline medium, and nitroguanidine in soln in sulfuric acid, used for the nitration of aromatic... 

Ordnance propellants are required to give the minimum of muzzle flash, smoke and barrel erosion. All these objectives are assisted by adding to the propellant a proportion of nitroguanidine (picrite), made by treating guanidine nitrate with sulphuric acid and brought to very fine particle size by recrystallisation and disintegration. 

Marqueyrol and Loriette A process for making nitroguanidine, an explosive. Cyanamide dimer is converted to guanidinium sulfate by heating with sulfuric acid this is then nitrated with nitric acid. See also Welland. 

The main starting compound is the labeled nitroguanidine 257 obtained from guanidine with isotope-labeled potassium nitrate. Reduction of 257 to hydrazine carboximidamide 258 was carried out with zinc and, then, ring closure to 3-amino[l,2,4]triazole 259 was carried out using formic acid. Finally, the ring closure to form the [l,2,4]triazine ring - similar to other procedures presented in Scheme 54 - was perfected by reaction with nitrous acid followed by treatment with ethyl nitroacetate to 260. 

Hydrazine salts have been prepared by the action of hypochlorites on ammonia1 or urea 2 by the hydrolysis of salts of sulfohydrazimethylene disulfonic acid 3 by the hydrolysis of triazoacetic acid 4 by the reduction of diazoacetic ester 5 by the reduction of nitroguanidine followed by hydrolysis 6 by the reduction of the nitroso derivatives of hexamethylene tetramine 7 by the reduction of nitrates or nitrites with zinc in neutral solution 8 by the action of sodium bisulfite on hyponitrous acid... 

Dagley and co-workers reported the synthesis of 2-nitrimino-5-nitrohexahydro-1,3,5-triazine (100) from the Mannich condensation of nitroguanidine (98), formaldehyde and t-butylamine, followed by nitrolysis of the t-butyl group of the resulting product, 2-nitrimino-5-fert-butylhexahydro-l,3,5-triazine (99). The triazine (100) has also been synthesized from the reaction of nitroguanidine and hexamine in aqueous hydrochloric acid, followed by nitration of the resulting product (97) with a solution of nitric acid in acetic anhydride. ... 

To the group 1 belong PETN, RDX, TNT, while to group 2 HN (Hydrazine Nitrate), NGu (Nitroguanidine) and AP (Ammonium Perchlorate) (See Table C)... 

Medard (Ref 8) examined properties of HN mixtures with NH4NO3. Guanidine Nitrate,. Nitroguanidine, and Ethylenediamine Nitrate. 

HCI salt, or by nitrating hydroxyethyl-nitroguanidine to nitroethyInitroguanidine and heating to close the ring. Most recently cyano-genbromide was reacted with... 

Prepd from nitroguanidine and 10% aqueous ethylamine at 60-70°(Ref 2) or by treating the nitrate salt of ethylguanidine with sulfuric acid for 3 hours at 5°(Ref 3)... 

Explosif E. Swiss explosive, received at Picatinny Arsenal from GtBritain and examined by Livingston. Its compn was found to be AN 77, Nitroguanidine 19 St hydrated magnesium nitrate. It could be cast at 111—13°, but was of low brisance Ref S. Livingston, PATR 907 (1938)... 

TrinitrophenyIethylnitramine Bts-(2,4,6-Trinitrophenyl)-ethylenedinitraiiiine (Bitetryl) Cyclotrimethylenetrinitrosamine Ammonium Picrate Nitroguanidine Nitro-urea Urea Nitrate Ethylenediamine Dinitrate and Nitro-iso-butanetriol Trinitrate]... 

This method is commonly applied to the nitration of primary amines (3) and in particular the preparation of nitroguanidine, nitrourea etc., as well as in the nitration of secondary amines (4) ... 

Another method of dehydration of the amine nitrate is based on treatment with concentrated sulphuric acid. This is used commercially in manufacturing such primary amines as nitroguanidine (p. 31). 

Jousselin [26] prepared nitroguanidine by the action of anhydrous nitric acid or sulphuric acid on guanidine nitrate. The preparation of this substance by the action of sulphuric acid has been developed as an industrial method for the production of nitroguanidine. The method described by Marqueyrol and Loriette [27] follows somewhat different principles. It consists in acting with anhydrous nitric acid on guanidine sulphate which, in turn, is obtained on treating dicyandiamide with sulphuric acid. 

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