Bis -nitramine

This powerful but relatively insensitive explosive decomposes violently at 202° C, and gives lead and silver salts which are highly impact sensitive [1], Though not endothermic (AH°f —103.3 kJ/mol), as a bis-nitramine it has a rather high heat of decomposition (3.91 kJ/g) which it is calculated would attain an adiabatic decomposition temperature over 2250°C, with a 60-fold pressure increase in a closed system [2],... 

Eremenko and co-workers used nitryl fluoride for the deamination of amines at subambient temperatures in acetonitrile. The same reaction occurs with primary nitramines and their alkali metal salts bis-nitramines react to give the corresponding bis-nitrate esters. 

Michael addition reactions are particularly useful when linear aliphatic bis-nitramines are used because the products contain two terminal functional groups like in the diester (182). The terminal functionality of such products can be used, or modified by simple functional group conversion, to provide oligomers for the synthesis of energetic polymers such oligomers often use terminal alcohol, isocyanate or carboxy functionality for this purpose. 

The products obtained from these condensations are predictable for simple mono-functional substrates primary amines usually form compounds where two equivalents of primary nitramine are incorporated into the product (Equation 5.19), whereas simple secondary amines can only combine with one equivalent of nitramine (Equation 5.20). The bis-nitramine (185) is formed from the reaction of methylamine with two mole equivalents each of methyl-nitramine and formaldehyde. 

Eaton and co-workers ° synthesized the cubane-based dinitrourea (42) via iV-nitration of the cyclic urea (41) with nitric acid-acetic anhydride. Cubane-based nitramide (43) is prepared from the IV-nitration of the corresponding bis-amide with acetic anhydride-nitric acid. Bis-nitramine (44) is prepared from the IV-nitration of the corresponding diamine with TFAA-nitric acid. ... 

Wilier synthesized the bis-nitramine (51) via the cyclodehydration of the dioxime (49) with sodium hydroxide in ethylene glycol followed by subsequent nitration of the resulting heterocycle (50). 

Tselinskii and co-workers reported the synthesis of the bis(furazano)piperazine (52) and its nitration to the energetic bis-nitramine (53) (calculated VOD 9700 m/s) with nitrogen... 

The bis-nitramine (155) has been prepared from the reaction of 1,5-diaminotetrazole (152) with glyoxal, followed by reduction of the resulting fused heterocycle (153) with sodium borohydride and subsequent A-nitration of the piperazine nitrogens of (154). ... 

Solomon, of the Illinois Institute of Technology Research Institute (IITR1), has reported the synthesis of HMX from the condensation of straight chained nitramines, bis(hydroxy methyl) methylene dinitramine and methylene dinitramine. However, details of this work were not available as of this writing... 

Die Reduktion lauft auch mit Lithiumalanat in siedendem Tetrahydrofuran nur bis zur Nitramin-Stufe. 

Azidohexyl 6-azidohexanoate, 3551 Bis(2-azidoethoxymethyl)nitramine, 2481 N-Butyl-/V-2-azidoethylnitramine, 2528 1,12-Diazido-3,10-dioxa-5,8-dinitrazadodecane, 3 049 Tris(2-azidoethyl)amine, 2482... 

Hydroxy-4,6-bis(nitroamino)-l,3,5-triazine, 1122 Lead methylenebis(nitramide), 4882 Methylenebis(nitramine), 0483 Methylenebis(3-nitramino-4-methylfurazan), 2805... 

A number of secondary high explosives containing both nitramine and nitrate ester functionality have been reported. Aliphatic examples include A-nitrodiethanolamine dinitrate (DINA) (110), prepared from the nitration of diethanolamine with nitric acid-acetic anhydride in the presence of zinc chloride,and A,A -dinitro-A,A -bis(2-hydroxyethyl)oxamide dinitrate (NENO) (111), prepared from the mixed acid nitration of A,lV -bis(2-hydroxyethyl) oxamide . 

The aromatic nitramine (234) can be prepared by nitratingA, A -diphenylethylenediamine ° or 2,2, 4,4 -tetranitro-A,A -diphenylethylenediamine with mixed acid, the latter synthesized from 2,4-dinitrochlorobenzene. The azoxy-nitramine (235) is prepared by nitrating 4,4 -bis(dimethylamino)azoxybenzene with mixed acid. ... 

Adolph and Cichra synthesized a number of polynitroperhydro-1,5-diazocines and compared their properties with the powerful military explosive HMX. A type of Mannich condensation was used to form the 1,5-diazocine rings the condensation of ammonia and methylamine with formaldehyde and bis(2,2-dinitroethyl)nitramine (46) forming diazocines (47) and (48) respectively. 1,3,3,7,7-Pentanitrooctahydro-1,5-diazocine (47) is A-nitrated to 1,3,3,5,7,7-hexanitrooctahydro-l,5-diazocine (52) in near quantitative yield using mixed acid. 

Displacements with azido anion are tolerant of many pre-existing explosophoric groups but the nitrate ester group readily undergoes displacement as seen for the synthesis of bis(2-azidoethyl)nitramine (13) from Ai-nitrodiethanolamine dinitrate (12) (DINA). " ... 

N 29-15% crysts, mp 148-155°(Ref 3) 154-155°(Ref 2). Prepd from [CH2NHN02]2 in 40% formalin reacted with acet anhyd at 20°, followed by digestion hydrolysis at 65° (Ref 2) N,N-bis(piperidinomethyl)-ethylendi-nitramine refluxed in acetylchloride, then poured into iced water, the pptate is then... 

HOX. Code name for Di- or Bis (2,2,2-Trinitro-ethyl) nitramine (BTNEN) described under Diethylamine and Derivatives in Vol 5 of Encycl, pp D1224-R to D1225-L... 

The nitrolysis of the bond / in substance (XX) results in the formation of products (XXI) l-acetoxymethyl-3,5-dinitro-l,3,5-triazacyclohexane and (XXII) bis(acetoxy-methyl)-nitramine... 

Dinitro-diphenylnitramine Bis (4-nitro-phenyl) -nitramine or N,4,4 -Trinitrodiphenyl amine, 02N.C6H4.N.N02.C6H4.N02 mw... 

Di(2-nitroxy-iso-propyl)-nitramine N,N-Di-(jS-nitroxy-iso-propyl)-nitramine or N,N-Bis-(/3-nitroxy-iso-propyl)-nitramire,... 

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