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Title: Synthesis of Amino- and Nitro-Substituted Heterocycles as Insensitive Energetic Materials

Abstract

In this paper we will describe the synthesis of several amino- and nitro-substituted heterocycles, examples from a continuing research project targeted at the synthesis of new, insensitive energetic materials that possess at least 80% the power of HMX (28% more power than TATB). Recently we reported the synthesis and scale-up of the insensitive energetic material, 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105). The energy content (81% the power of HMX) and thermal stability of LLM-105 make it a viable candidate material for insensitive boosters and deep oil perforation. We will report on recent synthetic improvements and several performance and safety tests performed on LLM-105, including a 1 in. cylinder shot and plate dent. We will also report on the synthesis and characterization of 4-amino-3,5-dinitropyrazole (LLM-116), an interesting new insensitive energetic material with a measured crystal density of 1.90 g/cc, to our knowledge the highest density yet measured for a five-membered heterocycle containing amino- and nitro-substituents. LLM-116 was synthesized by reacting 3,5-dinitropyrazole with 1,1,1-trimethylhydrazinium iodide (TMHI) in DMSO in the presence of base. The synthesis and characterization of 4-amino-5-nitro-1,2,3-triazole (ANTZ) and 43-dinitro-1,2,3-triazole (DNTZ), first described by Baryshnikov and coworkers, will also be presented along with the synthesis of several new energetic materials derived from ANTZ andmore » DNTZ.« less

Authors:
; ; ;
Publication Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sponsoring Org.:
US Department of Energy (US)
OSTI Identifier:
15005439
Report Number(s):
UCRL-JC-142918
TRN: US200322%%441
DOE Contract Number:  
W-7405-ENG-48
Resource Type:
Conference
Resource Relation:
Conference: 2001 Insensitive Munitions and Energetic Materials Technology Symposium, Bordeaux (FR), 10/08/2001--10/11/2001; Other Information: PBD: 23 Aug 2001
Country of Publication:
United States
Language:
English
Subject:
45 MILITARY TECHNOLOGY, WEAPONRY, AND NATIONAL DEFENSE; IODIDES; MILITARY EQUIPMENT; PERFORMANCE; PLATES; SAFETY; STABILITY; SYNTHESIS; TATB

Citation Formats

Pagoria, P F, Lee, G S, Mitchell, A R, and Schmidt, R D. Synthesis of Amino- and Nitro-Substituted Heterocycles as Insensitive Energetic Materials. United States: N. p., 2001. Web.
Pagoria, P F, Lee, G S, Mitchell, A R, & Schmidt, R D. Synthesis of Amino- and Nitro-Substituted Heterocycles as Insensitive Energetic Materials. United States.
Pagoria, P F, Lee, G S, Mitchell, A R, and Schmidt, R D. 2001. "Synthesis of Amino- and Nitro-Substituted Heterocycles as Insensitive Energetic Materials". United States. https://www.osti.gov/servlets/purl/15005439.
@article{osti_15005439,
title = {Synthesis of Amino- and Nitro-Substituted Heterocycles as Insensitive Energetic Materials},
author = {Pagoria, P F and Lee, G S and Mitchell, A R and Schmidt, R D},
abstractNote = {In this paper we will describe the synthesis of several amino- and nitro-substituted heterocycles, examples from a continuing research project targeted at the synthesis of new, insensitive energetic materials that possess at least 80% the power of HMX (28% more power than TATB). Recently we reported the synthesis and scale-up of the insensitive energetic material, 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105). The energy content (81% the power of HMX) and thermal stability of LLM-105 make it a viable candidate material for insensitive boosters and deep oil perforation. We will report on recent synthetic improvements and several performance and safety tests performed on LLM-105, including a 1 in. cylinder shot and plate dent. We will also report on the synthesis and characterization of 4-amino-3,5-dinitropyrazole (LLM-116), an interesting new insensitive energetic material with a measured crystal density of 1.90 g/cc, to our knowledge the highest density yet measured for a five-membered heterocycle containing amino- and nitro-substituents. LLM-116 was synthesized by reacting 3,5-dinitropyrazole with 1,1,1-trimethylhydrazinium iodide (TMHI) in DMSO in the presence of base. The synthesis and characterization of 4-amino-5-nitro-1,2,3-triazole (ANTZ) and 43-dinitro-1,2,3-triazole (DNTZ), first described by Baryshnikov and coworkers, will also be presented along with the synthesis of several new energetic materials derived from ANTZ and DNTZ.},
doi = {},
url = {https://www.osti.gov/biblio/15005439}, journal = {},
number = ,
volume = ,
place = {United States},
year = {Thu Aug 23 00:00:00 EDT 2001},
month = {Thu Aug 23 00:00:00 EDT 2001}
}

Conference:
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