Synthesis, characterization and thermal properties of energetic compounds derived from 3-amino-4-(tetrazol-5-yl)furazan

Article abstract of DOI:10.1002/cjoc.201190189

Five energetic compounds, 3,3-bis(tetrazol-5-yl)-4,4-azofurazan (DTZAF), 3-nitro-4-(tetrazol-5-yl)furazan (NTZF), hydrazinium 3-amino-4-(tetrazol-5-yl) furazan (HATZF), triaminoguanidinium 3-amino-4-(tetrazol-5-yl)furazan (TAGATZF) and guanylureaium 3-amino-4-(tetrazol-5-yl)furazan (MATZF), were prepared using 3-amino-4-(tetrazol-5-yl)furazan (ATZF) as starting material and their structures were characterized by FT-IR, ¹H NMR, ¹³C NMR and elemental analysis. The properties of NTZF were estimated: density is 1.67 g/cm3, enthalpy of formation +415.41 kJ/mol and detonation velocity 8257.83 m/s. The main thermal properties of four compounds, DTZAF, HATZF, TAGATZF and MATZF, were analyzed by TG and DSC techniques and the results showed that their melting points are 251.9, 159.7, 205.4 and 211.4 °C, respectively, and their first decomposition temperatures are 256.7, 258.6, 231.7 and 268.6 °C, respectively. The fact that their decomposition temperatures were over 230 °C showed that they exhibit better thermal stability.

Full text of DOI:10.1002/cjoc.201190189

FULL PAPER
Synthesis, Characterization and Thermal Properties of
Energetic Compounds Derived from
3
-Amino-4-(tetrazol-5-yl)furazan
,
a
b
a
Wang, Bozhou* (王伯周)
Zhang, Guofang (张国防)
Huo, Huan (霍欢)
a
a
Fan, Yanjie (范艳洁)
Fan, Xuezhong (樊学忠)
a
Xi'an Modern Chemistry Research Institute, Xi'an, Shaanxi 710065, China
b
Key Laboratory of Applied Surface and Colloid Chemistry of MOE, School of Chemistry and Materials Science,
Shaanxi Normal University, Xi'an, Shaanxi 710062, China
Five energetic compounds, 3,3-bis(tetrazol-5-yl)-4,4-azofurazan (DTZAF), 3-nitro-4-(tetrazol-5-yl)furazan
(NTZF), hydrazinium 3-amino-4-(tetrazol-5-yl)furazan (HATZF), triaminoguanidinium 3-amino-4-(tetrazol-
5
-yl)furazan (TAGATZF) and guanylureaium 3-amino-4-(tetrazol-5-yl)furazan (MATZF), were prepared using
1
3-amino-4-(tetrazol-5-yl)furazan (ATZF) as starting material and their structures were characterized by FT-IR, H
13
3
NMR, C NMR and elemental analysis. The properties of NTZF were estimated: density is 1.67 g/cm , enthalpy of
formation ＋415.41 kJ/mol and detonation velocity 8257.83 m/s. The main thermal properties of four compounds,
DTZAF, HATZF, TAGATZF and MATZF, were analyzed by TG and DSC techniques and the results showed that
their melting points are 251.9, 159.7, 205.4 and 211.4 ℃, respectively, and their first decomposition temperatures
are 256.7, 258.6, 231.7 and 268.6 ℃, respectively. The fact that their decomposition temperatures were over 230
℃
showed that they exhibit better thermal stability.
Keywords organic chemistry, 3-amino-4-(tetrazol-5-yl)furazan, energetic derivatives, synthesis, thermal property
Introduction
furazan-functionalized tetrazolate-based salts derived
from 4-amino-3-(5-tetrazolyl)furazn. They demonstra-
ted that these salts exhibit excellent thermal stability and
high positive heats of formation since these salts com-
bine the properties of a furazan fragment and a tetra-
The currently widely used nitro-explosives such as
TNT (trinitrotoluene), RDX (Royal demolition explo-
sive), and HMX (high melting explosive) are the pri-
mary pollutants in the explosives industry and military
testing of explosives. In order to develop environ-
ment-friendly explosives, a number of heterocycle-
based energetic compounds were reported and were ex-
tensively used as high-energy explosives and ingredi-
ents of propellants in recent years. Among them, tetra-
zole and furazan derivatives are interesting high energy
materials due to both tetrazole and furazan units being
typical energetic constitutions with high positive heat of
formation, high nitrogen content, good thermal stability
10
zolate backbone.
1
,2
3-Amino-4-(tetrazol-5-yl)furazan (ATZF) is not only
an energetic compound with high nitrogen content but
11
also an important explosive intermediate. Owing to the
reactive amino and tetrazolyl groups in ATZF molecule,
3
,4
a variety of new energetic compounds could be de-
12-14
rived.
3,3-Bis(tetrazol-5-yl)-4,4-azofurazan (DTZAF)
was therefore synthesized by oxidation of ATZF with
potassium permanganate in an acidic medium and
3-nitro-4-(tetrazol-5-yl)furazan (NTZF) was prepared
5
deriving from their aromaticity.
by amino oxidation. In addition, three kinds of nitro-
gen-rich energetic salts with ATZF as their anion were
synthesized in order to decrease the acidity of the aimed
compounds and improve their performances in energetic
compositions including propellants, explosives, gasifiers
Recently, the nitrogen-rich heterocyclic energetic
salts have been paid much more attention owing to their
unique characteristics. They often possess lower vapor
pressures and higher densities on comparison with
3
non-ionic salts. Shreeve et al. have made great contri-
15
and pyrotechnics.
butions to this type of energetic materials. Their groups
have prepared variety of nitrogen-rich energetic salts
including triazolium-, tetazole-, tetrazine- and imida-
3-Amino-4-(tetrazol-5-yl)furazan (ATZF) was syn-
thesized using 3-amino-4-cyanofurazan (CNAF) as a
starting material through addition reaction, diazotization
and cyclization or was prepared, alternatively, by a [3＋
6
-9
zolium-based salts. In this year they reported the
*
E-mail: wbz600@163.com; Tel.: 0086-029-88291050
Received July 29, 2010; revised December 21, 2010; accepted January 28, 2011.
Project supported by the National 973 Project (No. 613740102).
Chin. J. Chem. 2011, 29, 919— 924
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
919

Wang et al.
FULL PAPER
2
] cycloaddition of 3-amino-4-cyanofurazan (CNAF)
Scheme 3 Structures and synthetic routes of three ATZF ener-
getic salts
4
-6
and sodium azide (Scheme 1). The five derived ener-
getic compounds, DTZAF and NTZF and three kinds of
energetic salts of 3-amino-4-(tetrazol-5-yl)furazan
(ATZF) were shown in Scheme 2 and 3, respectively.
The [3＋2] cycloaddition mechanism of 3-amino-4-
cyanofurazan (CNAF) and sodium azide was discussed.
And the properties of 3-nitro-4-(tetrazol-5-yl)furazan
(
NTZF) were estimated. The main thermal properties of
four compounds, 3,3-bis(tetrazol-5-yl)-4,4-azofurazan
DTZAF), hydrazinium 3-amino-4-(tetrazol-5-yl)fura-
(
zan (HATZF), triaminoguanidinium 3-amino-4-(tetra-
zol-5-yl)furazan (TAGATZF) and guanylureaium
3-amino-4-(tetrazol-5-yl)furazan (MATZF), were inves-
tigated by DSC and TG techniques. The fact that nitro-
gen content of the five derived energetic compounds
exceeds 50% and they exhibit better thermal stability
makes them potentially useful as gas generants or ener-
getic materials with low flame temperatures, while si-
multaneously increase impulse of gun or rochet propel-
lants.
NEXUS870-based Fourier infrared spectrometer em-
ploying a KBr matrix. H NMR and C NMR spectra
were recorded with an AV500-type (500 MHz) super-
Scheme 1 The synthetic routes of ATZF
1
13
6
conducting NMR instrument. DMSO-d was the solvent
and tetramethyl silane (TMS) was an internal standard.
Elemental analysis was performed on a Vario EL-Ⅲ
Elemental Analyzer. Differential scanning calorimetry
(DSC) was carried out in a platinum sample container
using a Shimadzu DSC-60. The 1.6—2.0 mg sample
－
1
was heated at a rate of 10 ℃•min . The product purity
was recorded on an LC-2010A ht liquid chromato-
grapher.
Concentrated sulfuric acid, sodium nitrite, dimethyl
formamide (DMF), anhydrous magnesium sulfate, po-
tassium permanganate and sodium tungstate were all of
AR grade; 50% hydrogen peroxide, 85% hydrazine hy-
drate, azide sodium, sodium hydroxide were all of CP
Scheme 2 The structures and synthetic routes of DTZAF and
NTZF
1
6
grade; triaminoguanidine nitrate, guanylurea hydro-
1
7
18
chloride and 3-amino-4-cyanofurazan (CNAF) were
prepared in our laboratory.
Synthesis of 3-amino-4-aminohydrazolyfurazan
(
AFAD)
3-Amino-4-cyanofurazan (CNAF) (2.00 g, 18.18
mmol) was transferred into a three-necked round bottom
flask fitted with a mechanical stirrer and a dropping
funnel and 25 mL of acetonitrile was then added. 85%
hydrazine hydrate was added dropwise to the reaction
flask at ambient temperature. After hydrazine hydrate
was added completely, it was stirred for another 6 h.
The white precipitate was filtered and 1.80 g white solid
was obtained with a yield of 70.4%. The product (purity
Experimental
9
9.9%) was crystallized from ethanol with a melting
General methods and materials
point of 169—171 ℃ (capillary method).
1
Melting point was determined using an open capil-
lary tube. The IR spectrum was recorded utilizing a
6
H NMR (DMSO-d , 500 MHz) δ: 6.39 (s, 2H,
1
3
2 2 6
NNH ), 5.96 (s, 4H, CNH ); C NMR (DMSO-d , 500
MHz) δ: 154.71, 140.76, 137.68; IR (KBr) v: 3470,
9
20
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© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 919— 924

Synthesis, Characterization and Thermal Properties of Energetic Compounds
－
1
3
415, 3322, 3234 (NH
2
), 1662, 1610, 1500 (C＝N)
DSC (10 ℃•min ): 124.81 ℃ (m.p.), 224.02 ℃
Synthesis of 3,3'-bis(tetrazol-5-yl)-4,4'-azofurazan
(DTZAF)
－
1
cm . Anal. calcd for C
4
3
H
6
N
6
O: C 25.35, N 58.99, H
(T
p
).
.139; found C 25.35, N 59.15, H 4.225.
Synthesis of 3-amino-4-(tetrazol-5-yl) furazan
(ATZF)
ATZF (0.80 g, 5.26 mmol) was transferred into a
three-necked round-bottomed flask fitted with a me-
chanical stirrer and a dropping funnel, 13.5 mL 36%
hydrochloric acid was then added. After the addition of
hydrochloric acid, potassium permanganate (0.83 g,
5.25 mmol) dissolved in 5 mL of distilled water was
added dropwise under stirring at room temperature. The
stirring was continued for another 5 h at 50 ℃. The
reaction mixture was then cooled to 0 ℃. The yellow
precipitate was filtered, washed with ice-water and dried
to obtain 0.75 g solid with a yield of 93.8%. The bright
yellow product was crystallized from ethanol/water
3
-Amino-4-aminohydrazolyfurazan (AFAD) (2.00 g,
12.66 mmol) and 40 mL of 2.0% hydrochloric acid were
added into a three-necked round-bottomed flask fitted
with a mechanical stirrer and a dropping funnel. 10%
NaNO
After complete addition, it was stirred further for 2 h at
1
2
solution (10 mL) was added dropwise at 0 ℃.
5 ℃. The yellow precipitate was filtered and 1.65 g
yellow solid was collected with a yield of 76.7%. The
product (purity 99.7%) was crystallized from water with
1
a melting point of 210—211 ℃. H NMR (DMSO-d
6
,
,
1
3
5
5
3
2
00 MHz) δ: 6.59 (s, 2H, NH ); C NMR (DMSO-d
00 MHz) δ: 155.44, 147.49, 136.20; IR (KBr) v: 3458,
6
1
3
(V∶V＝1∶1). Its melting point is 249—250 ℃.
C
－
1
357 (NH
2
), 3050 (N—H), 1641, 1622 (C＝N) cm .
6
NMR (DMSO-d , 500 MHz) δ: 161.83, 146.89 , 140.58;
Anal. calcd for C
found C 23.84, N 64.06, H 1.956.
3
H
3
N
7
O: C 23.53, N 64.05, H 1.961;
IR (KBr) v: 3490 (broad, N—H), 1636 (N＝N), 1058
－
1
6 2 14 2
(furazan) cm . Anal. calcd for C H N O : C 23.84, N
－
1
DSC (10 ℃•min ): 215.79 ℃ (m.p.), 264.43 ℃
64.90, H 0.662; found C 23.99, N 64.76, H 0.826.
(
T
p
).
Synthesis of hydrazinium 3-amino-4-(tetrazol-5-yl)-
furazan (HATZF)
"
One Step" synthesis of 3-amino-4-(tetrazol-5-yl)-
furazan (ATZF)
ATZF (0.20 g, 1.31 mmol) was transferred into a
three-necked round-bottomed flask fitted with a reflux
condenser, and 10 mL of distilled water was added at
room temperature. 85% hydrazine hydrate (0.2 g) was
then added dropwise at 70 ℃. The stirring was contin-
ued for another 3 h at 70 ℃ and then cooled down to 0
℃. The precipitate thus obtained was filtered and
CNAF (3.30 g, 30.00 mmol) and 6 mL DMF were
added in a three-necked round-bottomed flask with a
stirrer. To the reaction mixture, sodium azide (2.40 g,
36.92 mmol) was added and the resulting reaction mix-
ture was poured into 42 mL water and its pH was ad-
justed to 1—2 with 10% hydrochloric acid, then ex-
tracted with ethyl ether (50 mL×4). The combined ex-
washed with ice water and finally dried to obtain 0.22 g
1
tracts were dried on MgSO
4
, evaporated to dryness and
of solid with a yield of 91.7%. H NMR (DMSO-d
6
, 500
＋
13
4.20 g yellow solid was obtained with a yield of 91.3%.
MHz) δ: 6.56 (s, 3H, NH ), 7.15 (s, 4H, 2NH
NMR (DMSO, 500 MHz) δ: 155.59, 150.84, 139.99; IR
(KBr) v: 3452, 3330 (NH
2
);
C
3
The yellow product was crystallized from water with a
＋
melting point of 210—211 ℃ (capillary method).
2
), 3060, 2599, 2508 ( NH ),
3
－
1
1
1
630, 1600 (C＝N) cm . Anal. calcd for C
3
H
7
N
9
O: C
Synthesis of 3-nitro-4-(tetrazol-5-yl)furazan (NTZF)
946, H 8.649, N 68.11; found C 19.32, H 8.652, N
Na
2
WO
4
(6.60 g, 0.011 mol) followed by addition of
67.9.
50% hydrogen peroxide solution (90.00 g, 1.32 mol)
Synthesis of triaminoguanidinium 3-amino-4-
tetrazol-5-yl)furazan (TAGATZF)
were placed in a three-necked round-bottomed flask
with a stirrer and dropping funnel in an ice-salt bath at
(
－
10 ℃, sulfuric acid (88.0 g) was added dropwise to
ATZF (0.20 g, 1.31 mmol) was transferred into a
the reaction flask under stirring at 5 ℃. Then, allow the
three-necked round-bottomed flask fitted with a me-
chanical stirrer and a dropping funnel. 10 mL distilled
water was added. After the addition of water, 0.5 mL
20% sodium hydroxide solution was added dropwise to
the reaction flask under stirring. After 0.5 h, triamino-
guanidine nitrate (0.22 g, 1.32 mmol) was added and the
resulting reaction mixture was stirred for 3 h and then
cooled down to 0 ℃. The precipitate thus obtained was
filtered and washed with ice water and finally dried to
reaction mixture warm to room temperature and CNAF
(1.6 g, 14.55 mmol) was added slowly. After CNAF
was added completely, the reaction mixture was stirred
at room temperature for another 3 h and extracted with
CH
2
Cl
2
(50 mL × 4). The combined extracts were
4
washed with ice-water and dried on MgSO . The yellow
precipitate thus obtained was concentrated on a rotary
evaporator to leave 1.5 g solid with a yield of 83.3 %.
The crude compound was crystallized from ethyl acetate
obtain 0.32 g of the desired compound with a yield of
1
3
1
with a melting point of 123—124 ℃ . C NMR
94.1%. H NMR (DMSO-d
), 6.56 (s, 2H, NH), 8.60 (s, 3H, NH
(DMSO, 500 MHz) δ: 159.08, 155.46, 150.59, 139.92;
6
, 500 MHz) δ: 4.51 (s, 6H,
＋
13
(
(
(
DMSO-d
6
, 500 MHz) δ: 159.62, 146.96, 140.93; IR
3NH
2
3
); C NMR
KBr) v: 3250 (broad, N—H), 1566, 1345 (NO
2
), 1622
－
1
C＝N) cm . Anal. calcd for C
3
HN
7
O
3
: C 19.67, N
IR (KBr) v: 3425, 3333, 3213 (NH
2
), 1683, 1632, 1632
H N13O: C18.68, H
－
1
5
3.55, H 0.55; found C 19.63, N 54.01, H 0.58.
(C＝N) cm . Anal. calcd for C
4 11
Chin. J. Chem. 2011, 29, 919— 924
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
921

Wang et al.
FULL PAPER
6
.226, N 70.82; found C 18.64, H 6.231, N 70.56.
Thermal studies
Thermal studies of DTZAF The DSC and TG
analyses revealed that DTZAF was thermally stable up
to 256.7 ℃. The DSC curve (Figure 1) of DTZAF ex-
Synthesis of guanylureaium 3-amino-4-(tetrazol-5-
yl)furazan (MATZF)
ATZF (0.20 g, 1.31 mmol) was transferred into a
three-necked round-bottomed flask fitted with a me-
chanical stirrer and a dropping funnel, then 10 mL dis-
tilled water was added at constant temperature. After the
addition of water, 0.5 mL 20% sodium hydroxide solu-
tion was added dropwise to the reaction flask under stir-
ring at 70 ℃. The stirring was continued for another
hibited a melting point, T , at 251.9 ℃ and two
max
thermal decomposition peaks at 256.7 and 300.8 ℃,
respectively. In the TG curve (Figure 2), DTZAF
showed two stages of decomposition. The first stage
amounts to 32.70% in the range of 250.2—264.7 ℃,
and the second stage occurs with a weight loss of
5
8.73% in the range of 264.7—300.7 ℃.
0
.5 h at 70 ℃. Guanylurea hydrochloride (0.18 g, 1.29
mmol) was added and the resulting reaction mixture
stirred for 3 h and subsequently cooled down to ice
temperature. The precipitate thus obtained was filtered
and washed with ice water and finally dried to obtain
1
0
.3 g product with a yield of 90.9%. H NMR
(
DMSO-d
6
, 500 MHz) δ: 6.56 (s, 3H, NH
2
linked with
＋
furazan), 7.01 (s, 2H, NH ), 8.07 (s, 4H, 2NH ), 9.70
2
2
1
3
(s, 1H, NH); C NMR (DMSO, 500 MHz) δ: 206.69,
155.53, 154.52, 150.73, 139.93; IR (KBr) v: 3441, 3387,
3
338 (NH ), 1741 (C＝O), 1631, 1653, 1603 (C＝N)
2
－
1
cm . Anal. calcd for C H N O : C 25.10, H 6.695, N
6
5
9
11
2
4.44; found C 25.03, H 6.671, N 64.95.
Results and discussion
Reaction mechanism of tetrazole cyclization
Figure 1 DSC curve of DTZAF.
Because sodium azide might be dissolved in di-
methyl formamide (DMF), in DMF medium sodium
3-amino-4-(tetrazol-5-yl) furazan was produced by the
[
3＋2] cycloaddition of sodium azide and cyano group
in 3-amino-4-cyanofurazan (CNAF), followed by acidi-
fication by hydrochloric acid. The assumed reaction
mechanism is as follows:
1
9
Scheme 4 Mechanism of tetrazole cyclization
Figure 2 TGA curve of DTZAF.
Thermal studies of HATZF The DSC and TG
analyses revealed that HATZF is thermally stable up to
Performance evaluation of 3-nitro-4-(tetrazol-5-yl)-
furazan (NTZF)
2
30.3 ℃. The DSC curve (Figure 3) of HATZF exhib-
ited a melting point, Tmax, at 159.7 ℃ and four thermal
The structure of NTZF was optimized by Gaussian
decomposition peaks at 258.6, 272.3, 308.8 and 330.1
98 in order to obtain its stable geometric configuration,
℃
, respectively. In the TG curve (Figure 4), HATZF
and its density and enthalpy of formation were then
computed. The explosive parameters were obtained by
VLW equation using density and enthalpy of formation
showed the mass loss of 67.77% before 248.1 ℃, and
only 6.75% residue at 289.5 ℃.
Thermal studies of TAGATZF The DSC and TG
analyses revealed that TAGATZF is thermally stable up
to about 206 ℃. The DSC curve (Figure 5) of TAGATZF
2
0
as basic data. The predicted performance data of
3
NTZF were: density 1.67 g/cm , detonation velocity
8257.83 m/s, C-J pressure 27.78 GPa and enthalpy of
exhibited a melting point, T , at 205.4 ℃ and three
max
formation ＋415.41 kJ/mol.
thermal decomposition peaks at 231.7, 281.6 and 327.4
9
22
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© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 919— 924

Synthesis, Characterization and Thermal Properties of Energetic Compounds
Figure 3 DSC curve of HATZF.
Figure 6 TGA curve of TAGATZF.
Figure 7 DSC curve of MATZF.
Figure 8 TGA curve of MATZF.
Figure 4 TGA curve of HATZF.
Figure 5 DSC curve of TAGATZF.
℃
, respectively. In the TG curve (Figure 6), TAGATZF
50.68% before 299.6 ℃, and 12.48% residue at 594.9
℃.
showed the mass loss of 81.48% before 322.5 ℃, and
1
4.50% residue at 494.1 ℃.
The above-mentioned DSC and TGA results showed
that their melting points were 251.9, 159.7, 205.4 and
211.4 ℃ and their first decomposition temperatures
were 256.7, 258.6, 231.7 and 268.6 ℃, respectively.
The fact that their decomposition temperatures were
over 230 ℃ showed that they exhibited excellent
thermal stability and they might be potentially useful as
Thermal studies of MATZF The DSC and TGA
revealed that MATZF is thermally stable up to 160.7 ℃.
The DSC curve (Figure 7) of MATZF exhibited a melt-
ing point, Tmax, at 211.4 ℃ and two thermal decompo-
sition peaks at 268.6 and 3225.1 ℃, respectively. In the
TG curve (Figure 8), MATZF showed the mass loss of
Chin. J. Chem. 2011, 29, 919— 924
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
923

Wang et al.
FULL PAPER
gas generants or rochet propellants.
thesis and Applications, Chemical Industry Press, Beijing,
2
005, p. 158 (in Chinese).
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6
7
8
9
0
Conclusions
2
3-Amino-4-(tetrazol-5-yl)furazan (ATZF) was syn-
thesized with a total yield of 54.0% using 3-amino-4-
cyanofurazan (CNAF) as a starting material and with a
yield of 91.3% by [3 ＋ 2] cycloaddition of
3-amino-4-cyanofurazan (CNAF) and sodium azide.
Five new energetic compounds derived from ATZF
were synthesized and characterized. The properties of
1
Wang, R.; Guo, Y.; Zeng, Z.; Twamley, B.; Shreeve, J. M.
Chem. Eur. J. 2009, 15, 2625.
3-nitro-4-(tetrazol-5-yl)-furazan (NTZF) were estimated:
3
density is 1.67 g/cm , enthalpy of formation ＋415.41
kJ/mol and detonation velocity 8257.83 m/s. The main
thermal properties of four new compounds, DTZAF,
HATZF, TAGATZF and MATZF, were investigated by
DSC and TG techniques and the results showed that
their melting points were 251.9, 159.7, 205.4 and 211.4
1
1
1
2
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Chin. J. Chem. 2011, 29, 919— 924