Assembly of Nitrofurazan and Nitrofuroxan Frameworks for High-Performance Energetic Materials

Article abstract of DOI:10.1002/cplu.201700340

The design of novel energetic materials with improved performance, optimized parameters, and environmental compatibility remains a challenging task. In this study, new high-energy materials based on isomeric dinitrobi-1,2,5-oxadiazole structures comprising nitrofurazan and nitrofuroxan subunits were synthesized. Due to planarity and strong noncovalent interactions, these materials display high density values as determined by single-crystal X-ray diffraction. The thermal, impact, and friction sensitivities of both isomers are similar to that of nitroesters. Their high detonation performance along with the combined benefits of high density, high heat of formation, and good oxygen balance make the synthesized compounds promising as explosives and highly-energetic oxidizers.

Full text of DOI:10.1002/cplu.201700340

Accepted Article
Title: Assembly of Nitrofurazan and Nitrofuroxan Frameworks for High-
Performance Energetic Materials
Authors: Leonid Fershtat, Igor Ovchinnikov, Margarita Epishina, Anna
Romanova, David Lempert, Nikita Muravyev, and Nina
Makhova
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ChemPlusChem
10.1002/cplu.201700340
COMMUNICATION
Assembly of Nitrofurazan and Nitrofuroxan Frameworks for High-
Performance Energetic Materials
[
a]
[a]
[a]
[b,c]
Leonid L. Fershtat,* Igor V. Ovchinnikov, Margarita A. Epishina, Anna A. Romanova, David B.
[
d]
[e]
[a]
Lempert, Nikita V. Muravyev, and Nina N. Makhova
Abstract: The design of novel energetic materials with improved
performance, optimized parameters and environmental compatibility
remains a challenging task. In this study, new high energy materials
based on the isomeric dinitrobi-1,2,5-oxadiazole structures
comprising of nitrofurazan and nitrofuroxan subunits were
synthesized. Due to planarity and strong non-covalent interactions,
materials reveal the high density values as determined by single-
crystal X-ray diffraction. Thermal, impact, and friction sensitivity of
both isomers are close to that for nitroesters. High detonation
proposed during the development of the energetic materials,
among them the 1,2,5-oxadiazole (furazan) and its N-oxide
(furoxan) frameworks stand out due to high positive heats of
formation and active oxygen atoms.[1,3a] In last few years these
motifs were successfully incorporated in a number of modern
primary and secondary high-energy materials, mainly by the
efforts of the Shreeve’s team,[ Klapӧtke’s team and some other
research groups.[7] Recently synthesized energetic materials
incorporating a few nitro-1,2,5-oxadiazole moieties are shown in
5]
[6]
performance along with the combination of the benefits of high density, Figure 1. Dinitroazofuroxan (DNAFO) representing two
high heat of formation, and good oxygen balance regard the
synthesized compounds as promising explosives and highly-
energetic oxidizers.
nitrofuroxan fragments linked by an azo bridge has an excellent
energetic performance and zero oxygen balance, however its
synthesis includes multistep reaction sequence with low overall
yield.[8] Bis(nitrofurazanyl)furoxan (BNFF)[9] comprising two
nitrofurazan units, coupled by the C-C bond with a furoxan ring
Common energetic materials from 2,4,6-trinitrotoluene (TNT) to
has
lower
parameters
including
moderate
density.
1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX) synthesized about a
Dinitrobifurazan (DNBF) has seemingly confused high thermal
century ago bring its energy mainly from the carbon backbone
oxidation. Contrary, recently developed explosives comprise the
various heterocycles with high-nitrogen content aiming to
stability (250 °C) along with a moderate density and high
[10]
sensitivity. Only few crystals of dinitrobifuroxan (DNBFO) were
[6a]
isolated and characterized by X-ray diffraction. Despite of its
increase the power mainly due to N
2
formation.[1] These synthetic
high calculated detonation performance, the synthesis of DNBFO
is hardly scalable and no parameters such as mechanical
sensitivity was reported so far. Overall, the analysis of literature
reveals that tradeoff between the synthesis simplicity, high
performance and low sensitivity is still not reached for 1,2,5-
oxadiazole-based explosives, which are of urgent interest as a
platform in the design of novel energetic materials. As a logical
step in the development of the nitro-1,2,5-oxadiazole structures
the alliance of nitrofurazan and nitrofuroxan frameworks linked via
C-C bond (structures 1a,b) is proposed. Hence, here we present
a method for the synthesis of novel high-performance compounds
efforts are driven by a search for a combination of the high
performance, safe handling with a lower environmental impact in
a single compound.[2] More specifically, the promising explosive
should combine the high values of density, heat of formation,
detonation parameters, oxygen balance, thermal stability and,
along with that, possess the low sensitivity toward impact and
friction.[ Unfortunately, in practice the convergence of these
properties remains a challenging task.[4] A variety of moieties were
3]
[
a]
Dr. L. L. Fershtat, Dr. I. V. Ovchinnikov, Dr. M. A. Epishina, Prof. Dr.
N. N. Makhova
–
isomeric 3(4)-nitro-4(3)-(3-nitrofurazan-4-yl)furoxans, their
thermal stability, mechanical sensitivity, and theoretical
detonation and combustion performance.
N. D. Zelinsky Institute of Organic Chemistry
Russian Academy of Sciences
Leninsky Prosp. 47, Moscow 119991 (Russian Federation)
E-mail: fershtat@bk.ru
[
[
[
b]
c]
d]
A. A. Romanova
A. N. Nesmeyanov Institute of Organoelement Compounds
Russian Academy of Sciences
28 Vavilova str., Moscow 119991 (Russian Federation)
A. A. Romanova
Higher Chemical College
Russian Academy of Sciences
9
Miusskaya sq.,, Moscow 125047 (Russian Federation)
Dr. D. B. Lempert
Institute of Problems of Chemical Physics
Russian Academy of Sciences
1
1
Academician Semenov ave., Chernogolovka, Moscow Region
42432 (Russian Federation)
[
e]
Dr. N. V. Muravyev
N. N. Semenov Institute of Chemical Physics
Russian Academy of Sciences
4
Kosygin Str., Moscow 119991 (Russian Federation)
Supporting information for this article is given via a link at the end of
the document.
Figure 1. Several prospective 1,2,5-oxadiazole based high-energy materials.
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COMMUNICATION
Having an experience in the synthesis and reactivity of
furoxans,[11] we decided to develop a synthetic strategy (Scheme
1) to the target 3-nitro-4-(4-nitrofurazan-3-yl)furoxan 1a. It is
based on the readily available furazan precursor – amidoxime 2,
which can be easily obtained by the cascade reactions of
malononitrile.[
12]
Amidoxime 2 was then transformed to the
chloroximinofurazan 3 according to a known procedure.[13] Amino
group in compound 3 was oxidized to the nitro group with a
2 2 2 4
mixture of conc. H O -H SO under mild conditions. The resulted
chloride 4 was involved in one-pot cascade process including
acylation of dinitromethane sodium salt followed by nitrosation of
the formed intermediate 5 and the subsequent regioselective
intramolecular cyclization of the nitrosation product with the
formation of the target compound 1a. To prepare the isomeric 4-
nitro-(4-nitrofurazan-3-yl)furoxan 1b
a possibility of the 3-
nitroisomer 1a to undergo thermal isomerization was studied. The
thermal isomerization of 4-aryl-3-nitrofuroxans into 3-aryl-4-
nitrofuroxans is carried out by refluxing of 3-nitroisomer in toluene
for 3 hours.[ However, these conditions proved to be unsuitable
for the preparation of 4-nitroisomer 1b since 3-nitroisomer 1a
14]
decomposed significantly. Refluxing of compound 1a in CCl
4
for
90 hours was found to be an appropriate approach enabling to
obtain the 4-nitroisomer 1b in high yield (Scheme 1). Importantly,
the developed protocols enable to synthesize the target energetic
materials in gram scale avoiding isolation of very sensitive
intermediates.
Figure 2. 14N NMR spectra of dinitrobi-1,2,5-oxadiazoles 1a and 1b in acetone-
d .
6
Synthesized compounds 1a,b were characterized by spectral
IR, H, 13C, 14N NMR spectroscopy and mass spectrometry) and
1
(
analytical methods. The position of nitro group namely at C(3) or
C(4) carbon atoms of the furoxan ring was defined by 14N NMR
spectra, which may serve as a reliable tool to differ nitrofuroxan
isomers.[14] The chemical shift of the nitro group at the C(3) carbon
of the furoxan ring in compound 1a (-38.9 ppm) is located more
upfield than the corresponding chemical shift of the nitro group at
the furazan one (-37.4 ppm) (Fig. 2, top). In the 14N NMR spectrum
of compound 1b this correlation is inverted and the signal of the
nitro group at the C(4) carbon of the furoxan ring moved downfield
significantly (-36.4 ppm), while the chemical shift of the nitro group
at the furazan ring is rather the same (-37.8 ppm) (Fig. 2, bottom).
Thus, the 14N NMR spectroscopy resolves the isomerization
process of the 3-nitrofuroxan framework.
density of 1a and 1b crystals is high, but slightly different, i.e.,
1.981 and 2.026 g cm-3 for 1а and 1b at 100 K. According to the
structural analysis and DFT calculations (see refs.[15] for more
detailed description of the approach and Supporting information
for the discussion) this difference can be rationalized by the
formation of a quite strong intramolecular contact between the
O(1) atom of the nitroxyl fragment and the nitro group oxygen
atom in 1a (i.e., the O(1)…O(3) distance is 2.707 Å, the interaction
energy is 15.5 kJ mol-1). Namely, the oxygen atoms can be
involved in short intermolecular contacts only if this interaction is
not formed (as in 4-nitroisomer 1b).
The morphology of synthesized energetic dinitrobi-1,2,5-
oxadiazoles 1a,b were additionally characterized by scanning
electron microscopy (SEM). Powder of compound 1a is
comprised with plate-like particles around 10 µm. Contrary,
sample 1b has a coarser elongated particles (ca. 50 µm) (SEM
images are presented in Supporting information).
Finally, the structures of the dinitrobi-1,2,5-oxadiazoles 1a
and 1b were confirmed by a single-crystal X-ray diffraction study
(Figs. 3,4). Analysis of X-ray diffraction data revealed that the
Scheme 1. Synthesis of the dinitrobi-1,2,5-oxadiazoles 1a and 1b.
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COMMUNICATION
Thermal behavior of the isomers 1a and 1b was studied with
differential scanning calorimetry (DSC) and pressure DSC.[16] Bi-
1,2,5-oxadiazole 1a has a lower melting point comparing to 1b
isomer, viz., 96 and 102 °C, however its decomposition onset is
higher – 146°C and 140°C, respectively (Table 1). Based on the
mechanical sensitivity values, both compounds are more
sensitive than nitramines (RDX and HMX) approaching the
nitroesters (PETN: 3.3 J, 70 N for impact and friction sensitivity,
respectively). Kamlet-Jacobs method[ used to calculate the
detonation velocity and the Chapman-Jouguet pressure revealed
the title compounds are superior compared to commonly used
RDX and HMX. Since the dinitrobi-1,2,5-oxadiazoles 1a,b have
higher oxygen content and oxygen balance than DNBF, RDX and
HMX, they can be used as energetic oxidizers. Combustion
performance for model compositions with active and hydrocarbon
binders was obtained using thermodynamic calculations (Section
S6, Supporting information). The optimized metal-free
compositions based on 1a,b reveal the 258-259 s of specific
impulse at chamber pressure 4 MPa. Comparison with the results
for nitramines proves the high potential of the nitrofuroxan-
nitrofurazan based materials, i.e., 1a, 1b and DNBF, DNBFO.
In summary, we present the synthesis of 3-nitro-4-(3-
17]
Figure 3. The general view of the 1a molecule. Atoms are represented by
probability ellipsoids of atomic vibrations (p=0.5). The short intramolecular
contact corresponding to non-covalent interactions is shown by dashed lines.
nitrofurazan-4-yl)furoxan
acylation/nitrosation/cyclization cascade of the 3-(chloroximino)-
-nitrofurazan. 3-Nitrofuroxan motif in the synthesized structure
was isomerized almost quantitatively to the corresponding
through
a
one-pot
Figure 4. The general view of the 1b molecule. Atoms are represented by
probability ellipsoids of atomic vibrations (ρ=50%).
4
Table 1. Functional properties of dinitrobi-1,2,5-oxadiazoles 1a,b compared to DNBF, DNBFO, RDX, and HMX.
1b DNBF DNBFO
1a
RDX
HMX
Formula
C
4
N
6
O
7
C
4
N
6
O
7
C
4
N
6
O
6
C
4
N
6
O
8
C
3
H
6
N
6
O
6
4 8 8 8
C H N O
-1 [a]
FW [g mol ]
244
244
228
260
222
296
-
3
[b]
1.85[n]
85[n]
250[n]
-
1.970[p]
ρ [g cm ]
1.920
96
1.934
102
1.806
204
204
8
1.910
280
280
7
T
m
[oC][c]
-
140 (est.)[p]
-
T
dec [oC][d]
IS [J][e]
146
2.6
140
2.8
FS [N][f]
N [%][g]
67
82
-
-
140
37.84
0
150
37.84
0
34.43
19.67
34.43
19.67
36.84
14.04
32.31
24.62
0
Ω
CO [%][h]
CO2 [%][i]
Ω
–
6.56
–
6.56
–
14.04
413.5[o]
9.22[o]
35.6[o]
257
–
21.61
70.3
8.80
34.9
251
–
21.61
74.8
9.14
39.2
250
ΔH0
D [km s ]
CJ [GPa][l]
SP [s][m]
[kJ mol-1][j]
417.5
9.18
38.8
259
417.5
9.23
39.4
259
448.9[p]
9.53[p]
41.2[p]
263
f
-1 [k]
P
I
-
1
[
a] Molar weight. [b] Density at 298 K. [c] Melting temperature (DSC). [d] Decomposition temperature (pressure DSC, 5 K min ). [e] Impact sensitivity (according
[18]
[19]
to STANAG 4489 ). [f] Friction sensitivity (according to STANAG 4487 ). [g] Nitrogen content. [h] Oxygen balance toward carbon monoxide (ΩCO = nO – xC
yH/2(1600/FW)). [i] Oxygen balance toward carbon dioxide (ΩCO2 = nO – 2xC –yH/2(1600/FW)). [j] Calculated heat of formation via the additive method. [k]
[
20]
–
Calculated detonation velocity. [l] Calculated detonation Chapman-Jouguet pressure. [m] Calculated specific impulse for a model composition (4/0.1 MPa). [n]
[
10]
[5b]
[6a]
Ref. . [o] Ref. . [p] Ref.
.
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COMMUNICATION
4
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type of coupled hydrogen-free high energetic molecules
represents the attractive features as a high energy content and
high density, providing the performance exceeding the nitramines.
Presented synthetic data and detailed characterization appeared
to be an important step toward the development of a nitrofuroxan-
and nitrofurazan-based energetic materials. Described energetic
alliance of nitrofurazan and nitrofuroxan scaffolds resulted in an
excellent combination of easy access, high performance and
acceptable sensitivity. Therefore, these compounds may serve as
well alternative to the known commonly used explosives and, thus,
may be considered to find real-life applications as a new
generation secondary energetic materials.
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This work was supported by the Russian President’s Council for
Grants (Project MK-1302.2017.3) and the Russian Foundation for
Basic Research (Project 16-29-01042). Anna A. Romanova is
grateful to the Russian Science Foundation (Project 14-13-00884)
for the financial support of the X-ray diffraction studies and
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detonation parameters.
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Conflict of interest
The authors declare no conflict of interest.
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Keywords: energetic materials • explosives • nitrogen
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Entry for the Table of Contents
COMMUNICATION
Novel highly energetic heterocyclic
assemblies, incorporating 1,2,5-
oxadiazole motif, were prepared
Leonid L. Fershtat,* Igor V. Ovchinnikov,
Margarita A. Epishina, Anna A.
Romanova, David B. Lempert, Nikita V.
Muravyev, Nina N. Makhova
through a step-economical and gram-
scalable procedure. A unique set of
energetic properties, including high
density, high positive heat of formation
Page No. – Page No.
Assembly of Nitrofurazan and
Nitrofuroxan Frameworks for High-
Performance Energetic Materials
-
1
(
+417.5 kJ mol ), positive oxygen
balance (+19.7%) and moderate
sensitivity provides a high
performance (e.g. detonation velocity
-
1
9
.23 km s ) and an opportunity to
replace commonly used explosives.
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