Die Reaktion von Tetramethyltetrazen mit Chloramin

1,1,4,4-Tetramethyl-2-tetrazene (TMTZ) is considered as a prospective replacement for toxic hydrazines used in liquid rocket propulsion. The heat of formation of TMTZ was computed and measured, giving values well above those of the hydrazines commonly used in propulsion. This led to a predicted maximum I of 337 s for TMTZ/N O mixtures, which is a value comparable to that of monomethylhydrazine. We found that TMTZ has a vapor pressure well below that of liquid hydrazines, and it is far less toxic. Finally, an improved synthesis is proposed, which is compatible with existing industrial production facilities after minor changes. TMTZ is thus an attractive liquid propellant candidate, with a performance comparable to hydrazines but a lower vapor pressure and toxicity.

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“…(7)]; iv) TMTZ could be overoxidized to a tetrazenium cation (TAT + ) by monochloramine [Eq. ]

true NH_{2} Cl + Me_{2} NH \to Me_{2} normalN - Cl + NH_{3}

true 2 Me_{2} normalN^{+} = normalN^{-} \to Me_{2} normalN - normalN = CH_{2} (FDMH) + CH_{4} + normalN_{2}

true NH_{2} Cl + OH^{-} \to NH_{2} OH + Cl^{-}

true Me_{2} normalN - normalN = N - NMe_{2} (TMTZ) + 2 NH_{2} Cl \to [Me_{2} N - N = N - NMe = C (NH_{2}) H] Cl (TAT^{+} Cl^{-}) + NH_{4} Cl

…”

Section: Resultsmentioning

confidence: 99%

“…In the presence of NH 2 Cl, [TMTZ] decreases constantly and much faster (−52 % after 30 min, −90 % after 5 h). We attribute this behavior to the formation of a tetrazenium species according to Equation (8) …”

Section: Resultsmentioning

confidence: 99%

(E)‐1,1,4,4‐Tetramethyl‐2‐tetrazene (TMTZ): A Prospective Alternative to Hydrazines in Rocket Propulsion

Dhenain

Darwich

Sabaté

et al. 2017

Chemistry A European J

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N ‐Alkoxydiazenium‐Salze mit substituierten α‐Stellungen

Stöldt

Kreher

1983

Chem. Ber.

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N-Alkoxydiazenium Salts with Substituted a-Positions2,2,6,6-Tetramethyl-N-nitrosopiperidines can be easily alkylated in the usual manner with triethyloxonium tetrafluoroborate. The reaction of the corresponding N-alkoxydiazenium salts, bearing substituents in the a-position, with arene sulfinates seems to be a general route to N,N-disulfonylhydrazines. The condensation with N,N-disubstituted hydrazines providing an elegant route to asymmetric tetrazenes could be effected only in exceptional cases.Nach grundlegenden Untersuchungen von Hunig et al. I s 2 ) gehen N-Alkoxydiazenium-Sake (1) mit Nucleophilen (Hydroxid-, Carboxylat-, Azid-Ionen) mechanistisch interessante und praparativ attraktive Reaktionen ein. Nach der Deprotonierung zur dipolaren Zwischenstufe 2 erfolgt der Angriff des Nucleophils an der a-standigen CH-Gruppe (R = H). Reaktionen der aktivierten Nitrosogruppe mit Nucleophilen gehoren zu den Ausnahmen3s4). Die strukturellen Voraussetzungen fur diesen Reaktionstyp sollten in a,a'-persubstituierten N-Alkoxydiazenium-Salzen (1) mit R = Alkyl gegeben sein. Kondensationsreaktionen mit Hy-

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