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Nitro compounds for use in explosive charges

thesis
posted on 2024-09-02, 21:44 authored by Stefan Ek

This first part of this thesis describes synthesis of and characterisation of energetic plasticisers. The general concepts and requirements of energetic plasticisers are introduced. The remainder of this part further describes the work published in three publications. The first paper included here outlines the work on derivatives of 2,2-dinitropropane-1,3-diol. The second paper contains information on synthesis attempts of other gem-dinitrodiols and the successful synthesis and characterisation of derivatives of 4,4-dinitroheptane-1,7-diol, e.g. 1,7-diazido-4,4-dinitroheptane. The third paper focuses on a new class of energetic plasticisers, namely derivatives of 3(5),4-dinitropyrazole. Two of the obtained compounds had satisfactory thermal properties to enable their use as energetic plasticisers. These two are the aforementioned 1,7-diazido-4,4-dinitroheptane and 1-allyl-3(5),4-dinitropyrazole.

This second part of this thesis describes synthesis of potentially low-sensitive explosives, i.e. 4-amino-3,5-dinitropyrazole in the fourth IV and 1,1-diamino-2,2-dinitroethene in the fifth paper. Both products are known. The work was directed towards process development to facilitate large scale synthesis. Four syntheses of the former were evaluated. Out of these, one was suitable for scale-up and 200 g per batch could be produced. For the latter, a new synthesis procedure without hazardous intermediated or by-products is suggested.

List of scientific papers

I. Ek, S., Eldsäter, C., Goede, P., Holmgren, E., Tryman, R., and Latypov, N. C Eur J Energ Mater. Synthesis and Characterisation of 2,2-Dinitro-1,3-propanediol-based Plasticisers. 2005, 2(4), 33-45.

II. Ek, S., Latypov, N., Goede, P., Lee, Y., and Yang, G. J Energ Mater. Energetic Plasticizers Based on gem-Dinitrodiols. 2012, 30:4, 324-334.
https://doi.org/10.1080/07370652.2011.578960

III. Ek, S., Wahlström, L., and Latypov, N. J Chem Chem Eng. Derivatives of 3(5),4-Dinitropyrazole as Potential Energetic Plasticisers, 2011, 5, 929-935.

IV. Ek, S., and Latypov, N., J. Heterocycl. Chem., Four syntheses of 4-amino-3,5-dinitropyrazole. [Accepted]
https://doi.org/10.1002/jhet.1725

V. Jalový, Z., Ek, S., Ottis, J., Dudek, K., Růžicka, A., Lyčka, A., and Latypov, N. J Energ Mater. Scalable Synthesis of 1,1-Diamino-2,2-dinitroethene Without Hazardous Intermediates or by-Products. 2013, 31:2, 87-99.
https://doi.org/10.1080/07370652.2011.633964

History

Defence date

2012-11-23

Department

  • Department of Medicine, Huddinge

Publisher/Institution

Karolinska Institutet

Main supervisor

Latypov, Nikolaj

Publication year

2012

Thesis type

  • Doctoral thesis

ISBN

978-91-7457-918-5

Number of supporting papers

5

Language

  • eng

Original publication date

2012-10-25

Author name in thesis

Ek, Stefan

Original department name

Department of Biosciences and Nutrition

Place of publication

Stockholm

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