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Introducing Tetrazole Salts as Energetic Ingredients for Rocket Propulsion

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Chemical Rocket Propulsion

Part of the book series: Springer Aerospace Technology ((SAT))

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Abstract

Two tetrazole salts, hydroxylammonium 2-dinitromethyl-5-nitrotetrazolate (HADNMNT) and dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (HATO), were synthesized and characterized. HADNMNT is a new compound, whose structure was determined by 15N NMR experimentally and GIAO calculation, the thermal decomposition temperature, the explosion probabilities of impact sensitivity, and friction sensitivity of which were tested to be 141.9 °C, 96 %, and 100 %, respectively. The detonation parameters of HADNMNT were predicted to be equal to those of 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX). It was found theoretically that HADNMNT is a potential oxidizer for composite propellants to replace ammonium perchlorate (AP), 1,3,5-trinitro-1,3,5-triazinane (RDX), HMX, and 2,4,6,8,10,12-hexanitro-,2,4,6,8,10,12-hexazaisowurtzitane (CL-20). Safety tests for HATO were performed, and results showed that HATO exhibits excellent thermal stability (the decomposition temperature is 230.3 °C, and the volume of the released gas is 0.30 mL·g−1 at 100 °C for 48 h) and low mechanical sensitivities (the explosion probabilities of impact sensitivity and friction sensitivity are 16 % and 24 %, respectively). The compatibilities of HATO with hydroxyl-terminated polybutadiene (HTPB), AP, RDX, and aluminum powder (Al) were reexamined to be good, using the vacuum stability test. Results from comparative study of HATO and RDX as ingredient for composite propellant showed that the composite propellant composed HATO offer the advantages of high burning rate and low mechanical sensitivities.

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Abbreviations

ADNMNT:

Ammonium 2-dinitromethyl-5-nitrotetrazolate

Al:

Aluminum powder

ANT:

2-acetonyl-5-nitrotetrazole

AP:

Ammonium perchlorate

AT:

5-aminotetrazole

CEA:

Chemical equilibrium with applications

CL-20:

2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane

DSC:

Differential scanning calorimetry

GAP:

Glycidyl azide polymer

GIAO:

Gauge Independent Atomic Orbitals

HADNMNT:

Hydroxylammonium 2-dinitromethyl-5-nitrotetrazolate

HATO:

Dihydroxylammonium 5,5’-bistetrazole-1,1’-diolate

HATO-HTPB:

Composite propellant formulation containing HATO

HDNMNT:

2-dinitromethyl-5-nitrotetrazole

HEDMs:

High-energy density materials

HMX:

1,3,5,7-Tetranitro-1,3,5,7-tetrazocane

HNE:

Hexanitroethane

HTPB:

Hydroxyl-terminated polybutadiene

HyDNMNT:

Hydrazinium 2-dinitromethyl-5-nitrotetrazolate

KBr:

Potassium bromide

K-J:

Kamlet-Jacobs

NASA:

National Aeronautics and Space Administration

NMR:

Nuclear magnetic resonance

RDX:

Cyclotrimethylenetrinitramine

RDX-HTPB:

Composite propellant formulation containing RDX

TNT:

2,4,6-Trinitrotoluene

D :

Detonation velocity

H 50 :

50% Probability of explosion

I s :

Specific impulse

M c :

Molecular mass of combustion products

N :

Nitrogen content

n :

Pressure exponent

OB :

Oxygen balance

P :

Detonation pressure

P F :

Explosion probability of fraction sensitivity

P I :

Explosion probability of impact sensitivity

Q V :

Heat of explosion

T c :

Adiabatic flame temperature

T d :

Thermal decomposition temperature

u :

Burning rate

ΔHf :

Heat of formation

ρ :

Density

Φ :

Oxygen coefficient

References

  1. Joo Y, Shreeve JM (2009) Energetic mono-, di-, and trisubstituted nitroiminotetrazoles. Angew Chem Int Ed 48:564–567

    Article  Google Scholar 

  2. Stierstorfer J, Tarantik KR, Klapötke TM (2009) New energetic materials: functionalized 1-ehyl-5-aminotetrazoles and 1-ethyl-5-nitriminotetrazoles. Chem Eur J 5:5775–5792

    Article  Google Scholar 

  3. Klapötke TM, Sproll SM (2009) Alkyl-bridged Bis-5-azidotetrazoles: a safer way of preparation. Eur J Org Chem 74:4284–4289

    Article  Google Scholar 

  4. Tao G, Guo Y, Parrish DA et al (2010) Energetic 1,5-diamino-4H-tetrazolium nitro-substituted azolates. J Mater Chem 20:2999–3005

    Article  Google Scholar 

  5. Joo Y, Shreeve JM (2010) High-density energetic mono- or Bis(oxy)-5-nitroiminotetrazoles. Angew Chem Int Ed 49:7320–7323

    Article  Google Scholar 

  6. Fischer N, Hüll K, Klapötke TM, Stierstorfer J, Laus G, Hummel M, Froschauer C, Wurstb K, Schottenbergerb H (2012) 5,5′-azoxytetrazolates- a new nitrogen-rich dianion and its comparison to 5,5′-azotetrazolate. Dalton Trans 41:11201–11211

    Article  Google Scholar 

  7. Tao GH, Parrish DA, Shreeve JM (2012) Nitrogen-rich 5-(1-methylhydrazinyl)tetrazole and its copper and silver complexes. Inorg Chem 51:5305–5312

    Article  Google Scholar 

  8. Bonegerg F, Kirchner A, Klapötke TM, Piercey DG, Poller MJ, Stierstorfer J (2013) A study of cyanotetrazole oxides and derivatives thereof. Chem Asian J 8:148

    Article  Google Scholar 

  9. Tang Y, Yang H, Wu B, Ju X, Lu C, Cheng G (2013) Synthesis and characterization of a stable, catenated N11 energetic salt. Angew Chem Int Ed 52:4875–4877

    Article  Google Scholar 

  10. Klapötke TM, Sabaté CM, Stierstorfer J (2009) Neutral 5-nitrotetrazoles: easy initiation with low pollution. New J Chem 33:136–147

    Article  Google Scholar 

  11. Klapötke TM, Mayer P, Sabaté CM (2008) Simply, nitrogen-rich, energetic salts of 5-nitrotetrazole. Inorg Chem 47:6014–6027

    Article  Google Scholar 

  12. Li Y, Liu W, Pang S (2012) Synthesis and characterization of 5-nitro-2-nitratomethyl-1,2,3,4-tetrazole: a high nitrogen energetic compound with good oxygen balance. Molecules 17:5040–5049

    Article  Google Scholar 

  13. Gao HX, Shreeve JM (2011) Azole-based energetic salts. Chem Rev 111:7377–7436

    Article  Google Scholar 

  14. Fischer N, Klapötke T M, Stierstorfer J (2011) The hydroxylammonium cation in tetrazole based energetic materials. In: Proceedings of the 14th seminar on, new trends in research of energetic materials 1, Czech Republic, 13–15 April, pp 128–156

    Google Scholar 

  15. Semenov VV, Kanischev MI, Shevelev SA, Kiselyov AS (2009) Thermal ring-opening reaction of N-polynitromethyl tetrazoles: facile generation of nitrilimines and their reactivity. Tetrahedron 65:3441–3445

    Article  Google Scholar 

  16. Zhang M, Ge Z, BI F, Xu C, Liu Q, Wang B (2013) Study on the synthesis, thermal performance and quantum chemistry of 2-dinitromethyl-5-nitrotetrazole. Chin J Explos Propellants 36(3):14–19

    Google Scholar 

  17. Semenov VV, Ugrak BI, Shevelev SA, Kanishchev MI, Baryshnikov AT, Fainzil’berg AA (1990) Investigation of the alkylation of nitroazoles with α-haloketones by 13C,15N, and 14N NMR. Russ Chem Bull 39:1658–1666

    Article  Google Scholar 

  18. Aridoss G, Zhao C, Borosky GL, Laali KK (2012) Experimental and GIAO 15N NMR study of substituent effects in 1H-tetrazoles. J Org Chem 77:4152–4155

    Article  Google Scholar 

  19. Kamlet MJ, Jacobs SJ (1968) Chemistry of detonation I. A simple method for calculating detonation properties of CHNO explosives. J Chem Phys 48(1):23–35

    Article  Google Scholar 

  20. Gordon S, McBride BJ (1996) Computer program for calculation of complex chemical equilibrium compositions and applications. NASA Reference Publication 1311

    Google Scholar 

  21. Fischer N, Fischer D, Klapötke TM, Pierceya DG, Stierstorfera J (2012) Pushing the limits of energetic materials-the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate. J Mater Chem 22:20418

    Article  Google Scholar 

  22. Fischer N, Klapötke TM, Matecic Musanic S, Stierstorfera J, Suceska M (2013) TKX-50. In: 16th new trends in research of energetic materials, Pardubice, pp 574–585

    Google Scholar 

  23. Golubev V, Klapötke TM (2014) Comparative analysis of shock wave action of TKX-50 and HMX blasting performance in one-, two- and three-dimensional geometry. In: 17th new trends in research of energetic materials, Pardubice, p 66

    Google Scholar 

  24. Golubev V, Klapötke TM (2014) Comparative analysis of shock wave action of TKX-50 and other explosives on various barriers. In: 17th new trends in research of energetic materials, Pardubice, p 67

    Google Scholar 

  25. Bi F, Xiao C, Xu C, Ge Z, Wang B, Fan X, Wang W (2014) Synthesis and properties of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate. Chin J Energ Mater 22(2):272–273

    Google Scholar 

  26. Huang H, Shi Y, Yang J, Li B (2015) Compatibility study of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50) with some energetic materials and inert materials. J Energ Mater 33(1):66–72

    Article  Google Scholar 

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Authors and Affiliations

  1. Xi’an Modern Chemistry Research Institute, Xi’an 710065, Shaanxi, China

    Xuezhong Fan, Fuqiang Bi, Min Zhang, Jizhen Li, Weiqiang Pang, Bozhou Wang & Zhongxue Ge

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  1. Xuezhong Fan
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  2. Fuqiang Bi
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  3. Min Zhang
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  4. Jizhen Li
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  6. Bozhou Wang
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  7. Zhongxue Ge
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Correspondence to Xuezhong Fan .

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Editors and Affiliations

  1. Space Propulsion Laboratory (SPLab) Department of Aerospace Science and Technology, Politecnico di Milano, Milan, Italy

    Luigi T. De Luca

  2. Institute of Space and Astronautical Science (ISAS), Japan Aerospace Exploration Agency (JAXA), Sagamihara, Japan

    Toru Shimada

  3. Department of Chemical Engineering, Mendeleev University of Chemical Technology, Moscow, Russia

    Valery P. Sinditskii

  4. The Inner Arch, Poissy, France

    Max Calabro

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Fan, X. et al. (2017). Introducing Tetrazole Salts as Energetic Ingredients for Rocket Propulsion. In: De Luca, L., Shimada, T., Sinditskii, V., Calabro, M. (eds) Chemical Rocket Propulsion. Springer Aerospace Technology. Springer, Cham. https://doi.org/10.1007/978-3-319-27748-6_6

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  • DOI: https://doi.org/10.1007/978-3-319-27748-6_6

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  • Print ISBN: 978-3-319-27746-2

  • Online ISBN: 978-3-319-27748-6

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