13980-04-6Relevant articles and documents
Reactions of amidosulfuric acid salts with formaldehyde
Lyushnina,Bryukhanov,Turkina,Malakhov,Golod
, p. 1030 - 1033 (2007/10/03)
Potassium amidosulfate reacts with formaldehyde at pH 7-12 to afford a mixture of dipotassium 4-hydroxy-1,3-diazabutane-1,3-disulfonate hydrate and tripotassium 6-hydroxy-1,3,5-triazahexane-1,3,5-trisulfonate HO(CH2NSO3K)n·H2O (n = 2, 3). The reaction of the same compounds at pH 1-3 gives diammonium 1,3,5,7-tetraazabicyclo[3.3.1]nonane-3,7-disulfonic acid sulfate dihydrate.
New NO donors with antithrombotic and vasodilating activities, part 22: Nitrosation products of hexamethylenetetramine
Herpel, Martin,Rehse, Klaus
, p. 255 - 257 (2007/10/03)
Two nitrosation products of hexamethylenetetramine, namely 1,3,5- trinitrosohexahydro-1,3,5-triazine (1) and 3,7-dinitroso-1,3,5,7- tetrazabicyclo[3.3.1]nonane (2), were synthesized. It is shown that both compounds in vitro a 37 °C (1 h, pH 7.4) form nitric oxide at a rate of 3.1% (1) or 1.3% (2), respectively. In rats (60 mg/kg p.o.) both compound inhibit thrombus formation in arterioles (1: 20%; 2: 16%) and venules (1. 18%; 2. 9%). Compound 2 does not influence the blood pressure in spontaneously hypertensive rats.
Mechanisms of Nitramine Thermolysis
Oxley, J. C.,Kooh, A. B.,Szekeres, R.,Zheng, W.
, p. 7004 - 7008 (2007/10/02)
The thermal decomposition of a number of nitramines was studied in dilute solution and in the melt.The nitramines included acyclic mononitramines , cyclic mononitramines , cyclic dinitramines , and 1,3,5-trinitro-1,3,5-triazocyclohexane (RDX), octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), hexanitrohexaazaisowurtzitane (HNIW), and 1,3,3-trinitroazetidine (TNAZ).For the acyclic and cyclic mono- and dinitramines, the corresponding nitrosamines were the only or major condensed-phase product.Kinetics and activation parameters were determined for the thermolysis of dilute solutions (0.01-1.0 wtpercent) over the range 200-300 deg C.The thermolyses were found to be first-order with the rate constants unaffected by the use of deuterated solvent.As the nitramines became more complex than dimethylnitramine (DMN), the rate of decomposition increased and the product distribution became more complex.As the length of the aliphatic chain increased (DMN DEN DPN), the rate of thermolysis increased, yet nitrosamine remained the only observed condensed-phase product.When a secondary carbon was attached to the N-nitramine (DIPN) rather than the primary (DPN), the rate of decomposition increased and a new condensed-phase product was observed.Among the cyclic nitramines, the rate of decomposition increased as the number of NNO2 groups increased (NPIP pDNP; NPyr DNI; mDMP RDX).The position of the nitramine groups affected the decomposition: meta NNO2 groups (mDNP) decomposed faster than para (pDNP).Ring strain decreased stability: mDNP DNI; HMX RDX.In complex nitramines, the increase in decomposition rate, the appearance of new products, and the change in the relative importance of nitrosamine and of N2 and N2O are attributed to new decomposition routes available to them.However, since complex nitramines (e.g.RDX) maintain first-order kinetics and since most have activation energies in the range of 40-50 kcal/mol, it is belived that the triggering mechanism remains N-NO2 homolysis.Intramolecular hydrogen transfer is also considered an important mode of nitramine decomposition.
Thermal Decomposition of Energetic Materials. 4. Deuterium Isotope Effects and Isotopic Scrambling (H/D, (13)C/(18)O, (14)N/(15)N) in Condensed-Phase Decomposition of 1,3,5-Trinitrohexahydro-s-triazine
Behrens, Richard,Bulusu, Suryanarayana
, p. 8891 - 8897 (2007/10/02)
The inter- vs intramolecular origin of the products formed in the thermal decomposition of 1,3,5-trinitrohexahydro-s-triazine (RDX) has been traced by isotopic crossover experiments using mixtures of differently labeled analogues of RDX.The isotopic analogues of RDX used in the experiments include (2)H, (13)C, (15)N, and (18)O.The fraction of isotopic scrambling and the extent of the deuterium kinetic isotope effect (DKIE) are reported for all the different decomposition products.Isotopic scrambling is not observed for the N-N bond in N2O and only in small amounts (7percent) in the C-H bonds in CH2O, consistent with a mechanism of their formation through methylene nitramine precursors.A product, oxy-s-triazine (OST, C3H3N3O) does not undergo isotopic scrambling in H/D, (14)N/(15)N, or (13)C/(18)O experiments, and its rate of formation exhibits a DKIE of 1.5.These results are consistent with the formation of OST via unimolecular decomposition of RDX.Another product, 1-nitroso-3,5-dinitrohexahydro-s-triazine (ONDNTA, C3H6N6O5) is found to be formed with complete scrambling of the N-NO bond, suggesting an N-N bond cleavage and a radical recombination process in its formation.One of the hydrogen containing products, H2O, exhibits a DKIE of 1.5 +/- 0.1.In contrast, CH2O and ONDNTA have DKIEs f 1.5 +/- 0.1 and 1.05 +/- 0.2, respectively, indicating that hydrogen transfer is not involved in the rate-limiting step of the reaction pathway leading to the formation of these products.
