Thermal decomposition behavior and thermal stability of DABT·2DMSO

Article abstract of DOI:10.1007/s10973-017-6722-5

The thermal decomposition behavior and thermal stability of 3,3′-diamino-5,5′-bis(1H-1,2,4-triazole) with 2DMSO (DABT·2DMSO) were investigated by thermo gravimetry–derivative thermo gravimetry–differential scanning calorimetry (TG–DTG–DSC), differential thermal analysis (DTA) and accelerating rate calorimeter (ARC). The result of TG–DTG–DSC at a heating rate of 10?°C?min^?1 indicated that an endothermic decomposition and an exothermic decomposition occurred at 388.23 and 468.23?°C, respectively. The apparent activation energy (E_a) and pre-exponential factor (A) of the exothermic decomposition, and the free energy of activation, activation enthalpy and activation entropy at initial decomposition temperature (T_p0) were calculated from the DTA curves recorded at heating rates of 1, 2, 4, 8?°C?min^?1. The critical temperature of thermal explosion (T_bp0) obtained by the Ozawa’s and Kissinger’s methods were calculated as 470.46 and 470.73?°C, respectively. The result of ARC indicated that the self-heating decomposition started at 443.61?°C and ended at 480.91?°C, within the time span of 1397.50?min. The self-heating decomposition parameters, including the onset temperature, final temperature, temperature at max rate, max temperature rate, adiabatic temperature rise and time to maximum rate were obtained, and these parameters were corrected by thermal inertia factor. The E_a and A under adiabatic condition were also calculated. In addition, the self-accelerating decomposition temperature (T_{SADT, 50kg}) was calculated as 429.54?°C.

Full text of DOI:10.1007/s10973-017-6722-5

J Therm Anal Calorim
DOI 10.1007/s10973-017-6722-5
Thermal decomposition behavior and thermal stability
of DABTÁ2DMSO
Fang Bao1 Gongzheng Zhang1 Shaohua Jin2
•
•
Received: 18 June 2017 / Accepted: 18 September 2017
´
´
Ó Akademiai Kiado, Budapest, Hungary 2017
Abstract The thermal decomposition behavior and ther-
mal stability of 3,30-diamino-5,50-bis(1H-1,2,4-triazole)
with 2DMSO (DABTÁ2DMSO) were investigated by
thermo gravimetry–derivative thermo gravimetry–differ-
ential scanning calorimetry (TG–DTG–DSC), differential
thermal analysis (DTA) and accelerating rate calorimeter
(ARC). The result of TG–DTG–DSC at a heating rate of
10 °C min-1 indicated that an endothermic decomposition
and an exothermic decomposition occurred at 388.23 and
468.23 °C, respectively. The apparent activation energy
(Ea) and pre-exponential factor (A) of the exothermic
decomposition, and the free energy of activation, activation
enthalpy and activation entropy at initial decomposition
temperature (Tp0) were calculated from the DTA curves
recorded at heating rates of 1, 2, 4, 8 °C min-1. The crit-
ical temperature of thermal explosion (Tbp0) obtained by
the Ozawa’s and Kissinger’s methods were calculated as
470.46 and 470.73 °C, respectively. The result of ARC
indicated that the self-heating decomposition started at
443.61 °C and ended at 480.91 °C, within the time span of
1397.50 min. The self-heating decomposition parameters,
including the onset temperature, final temperature, tem-
perature at max rate, max temperature rate, adiabatic
temperature rise and time to maximum rate were obtained,
and these parameters were corrected by thermal inertia
factor. The Ea and A under adiabatic condition were also
calculated. In addition, the self-accelerating decomposition
temperature (TSADT, 50kg) was calculated as 429.54 °C.
Keywords 3,30-Diamino-5,50-bis(1H-1,2,4-triazole) Á
DABTÁ2DMSO Á Thermal decomposition behavior Á
Thermal stability Á Non-isothermal kinetics
Introduction
3,30-Diamino-5,50-bis(1H-1,2,4-triazole) (DABT) is an
important raw material and widely used in the production
of bistriazoles energetic materials, such as 3,30-dinitro-5,50-
bis(1H-1,2,4-triazole) (DNBT) [1, 2], 3,30-dinitrimino-5,50-
bis(1H-1,2,4-triazole) (DNABT) [1, 3], 3,30-diazide-5,50-
bis(1H-1,2,4-triazole) (DAzBT) [1], 3,30-dinitro-5,50-
bis(1H-1,2,4-triazole)-1,10-diol (DNBTO) [4] and their
derivatives [2–4], carbonic dihydrazidinium bis[3-(5-ni-
troimino-1,2,4-triazolate)] (CBNT) [3], dihydroxylammo-
nium
3,30-dinitro-5,50-bis-1H-1,2,4-triazole-1,10-diolate
(HBNTO) [3], which were reported as two of most
promising ionic salts to possibly replaced 1,3,5-trinitro-
1,3,5-triazacyclohexane (RDX).
We investigated the heat of formation and detonation
properties of DABT by using density functional theory
(DFT-B3LYP) method. Previous studies have shown that
the basis set 6-311 ? G(2df, 2p) is able to predict the
molecular structures and energies of energetic organic
compounds [5–7]. The heat of formation of DABT
(334.77 kJ mol-1) in the gas phase was determined at the
B3LYP/6-311 ? G(2df, 2p) theory level through isodesmic
reaction. The detonation velocity (5.70 km s-1) and deto-
nation pressure (13.79 GPa) were evaluated by Kamlet–
Jacob equations. For the process safety of these bistriazoles
energetic materials synthesized with DABT, the
& Shaohua Jin
jinshaohua@bit.edu.cn
1
School of Chemistry and Chemical Engineering, Beijing
Institute of Technology, Beijing, China
2
School of Materials Science and Engineering, Beijing
Institute of Technology, Beijing, China
123

F. Bao et al.
investigations of thermal decomposition behavior and
thermal stability of DABT were very necessary.
Table 1 X-ray data and parameters of DABTÁ2DMSO
Parameters
Values
Parameters
Values
In order to acquire the thermal decomposition behavior
and thermal stability of DABT under non-isothermal and
adiabatic conditions, the thermo gravimetry–derivative
thermo gravimetry–differential scanning calorimetry (TG–
DTG–DSC), differential thermal analysis (DTA) and
accelerating rate calorimetry (ARC) were carried out. The
thermo-kinetic parameters of the exothermic decomposi-
tion and thermodynamic parameters at the initial decom-
position temperature (Tp0) under non-isothermal condition
were obtained from DTA. The self-heating decomposition
parameters, adiabatic decomposition kinetics parameters,
time to maximum rate (TMR) and self-accelerating
decomposition temperature (TSADT) were obtained from
ARC. To the best of our knowledge, up to now, there are
no report regarding the thermal decomposition behavior
and thermal stability of DABT under non-isothermal and
adiabatic conditions.
Formula
C4H6N8Á2C2H6OS F(000)
340.0
˚
kMo–Ka/A
Formula mass/
g mol-1
322.42
0.71073
Crystal system
Space group
Color, habit
Monoclinic
P21/c
T/K
296
Theta max/° 28.250
Colorless, needle Dataset
h max
12
11
13
˚
a/A
9.6017
8.6632
Dataset
k max
˚
b/A
Dataset
l max
˚
c/A
9.9406
90
Reflections
1564
136
a/°
b/°
c/°
No.
parameters
112.668
R1, wR2
0.0433,
0.1188
90
S
1.052
3
˚
Volume/A
763.00
Device type Oxford
Xcalibur3
CCD
Experimental
Materials
Z
2
Solution
SHELXS-97
SHELXL-97
Calculated
density/
g cm-3
1.403
Refinement
l/mm-1
0.364
Absorption
correction
Multi-scan
DABT was home-made and purified according to the lit-
erature [1, 2]. The synthesis route of DABT was shown in
Scheme 1.
The compound of DABT was additionally characterized
by single-crystal X-ray spectroscopy. The result of single-
crystal X-ray spectroscopy indicated that one molecule of
DABT was associated with two molecules of DMSO.
Crystallographic data and parameters as well as the mor-
phology have been compiled in Table 1. The crystal
structure of DABT was shown in Fig. 1.
a
b
C4’
c
S1’
C3’
N2H
N2
N1
O1’
C
H
S
N4HA
N4
N4HB
C2
N3’
N1’
C1
N4HB’
N4’
N4HA’
Instruments
C1’
N3
C2’
The TG–DTG–DSC measurement was performed with a
PerkinElmer STA6000 simultaneous thermal analyzer at a
heating rate of 10 °C min-1 under a nitrogen flow of
50 mL min-1. The non-isothermal DTA measurements
were performed with a Shimadzu DTG-60H simultaneous
O1
N2’
N2H’
C3
O
N
S1
C4
Fig. 1 Crystal structure of DABTÁ2DMSO. Thermal ellipsoids are
0
˚
set to 50% probability. Selected bond lengths/A: C1–C1 1.461(2),
C1–N1 1.318(15), C1-N3 1.367(15), C2-N2 1.339(16), C2–N3
1.337(2), C2–N4 1.347(17), N1–N2 1.374(15), N4HBÁÁÁO1
2.058(91). Selected bond angles/°: C10–C1–N1 121.61(13), C1–N1–
N2 102.09(10), C1–N3–C2 102.52(10), N4–C2–N2 122.59(12), N4–
C2–N3 127.31(12). Selected torsion angles/°: C2–N3–C1–C10
178.19(120), N2–N1–C1–C10 - 178.08(116), C1–N3–C2–N4
- 177.36(142), N3–C2–N4–N4HB - 0.028(254), N3–C2–N4–
N4HB - 179.97(144), C2–N4–N4HBÁÁÁO1 167.12(924)
NH
HO
O
1)
HC1
2) NaOH
CH3COOH
NH H2CO3
H2N
N
H
3)
O
N
OH
H2N
HN
N
N
NH
N
NH2
Scheme 1 The synthesis route of DABT
123

Thermal decomposition behavior and thermal stability of DABTÁ2DMSO
thermal analyzer at heating rates of 1, 2, 4, 8 °C min-1
under a nitrogen flow of 50 mL min-1. All samples were
2.0 mg and placed in open alumina crucibles, and they
were heated from 50 to 650 °C.
The ARC measurement was performed with a Thermal
Hazard Technology accelerating rate calorimeter in the
Heat-Wait-Search mode. The experiment conditions were
listed in Table 2.
2
120
100
80
60
40
20
0
4
495.23 °C
TG
0
DTG
DSC
0
535.73 °C
468.23 °C
–4
–2
–4
–8
–12
–16
449.23
°C
100
200
300
400
500
600
Temperature/°C
Fig. 2 TG–DTG–DSC curve of DABT at
10 °C min-1
a
heating rate of
Results and discussion
Thermal decomposition processes
30
494.09 °
C
1 °C min–1
2 °C min–1
The TG–DTG–DSC curve at a heating rate of 10 °C min-1
was given in Fig. 2. From the TG and DTG curves, two
stages were obviously seen. The first stage was started at
388.23 °C and ended at 462.73 °C, and the mass loss was
49.00%. This was a process of lost DMSO, and the theo-
retically calculated value of the process was in exact
accordance with the experimental value. The second stage
was started at 468.23 °C and ended at 535.73 °C, and the
mass loss was 21.20%. From the DSC curve, the first stage
was an endothermic decomposition, and the peak temper-
ature was determined as 449.23 °C, and the second stage
was an exothermic decomposition, and the peak tempera-
ture was determined as 495.23 °C.
20
10
479.09 °
466.74 °
C
C
4 °C min–1
8 °C min–1
447.59 °
C
0
–10
–20
100
200
300
400
500
600
Temperature/°C
Fig. 3 DTA curves of DABT at heating rates of 1, 2, 4, 8 °C min-1
8 °C min-1, respectively. When the heating rate was high,
the onset temperature of the exothermic decomposition was
delayed, and the corresponding peak temperature shifted to
a higher temperature.
Non-isothermal decomposition kinetics
The DTA curves at heating rates of 1, 2, 4, 8 °C min-1
were given in Fig. 3. Both an endothermic decomposition
of lost DMSO and an exothermic decomposition were
observed. Different onset temperatures (429.62, 446.91,
454.33, 465.45 °C) and peak temperatures (447.59, 466.74,
479.09, 494.09 °C) of the exothermic decomposition pro-
cesses were observed at heating rates of 1, 2, 4,
To determine the non-isothermal decomposition kinetics
parameters of energetic materials, Ozawa’s method [8] and
Kissinger’s method [9] were employed. The Ozawa Eq. (1)
and Kissinger Eq. (2) were given below:
ꢀ
ꢁ
0:4567Ea
1
log b ¼ À
þ C
ð1Þ
ð2Þ
R
Tp
"
#
ꢀ
ꢁ
ꢀ
ꢁ
Table 2 Experimental conditions of DABT by ARC
b
Tp2
Ea
1
RA
ln
¼ À
þ ln
Parameters
Values
Parameters
Values
R Tp
Ea
Sample mass/g
0.1008
Start temperature/°C
End temperature/°C
50
where b is the heating rate, Ea is the apparent activation
energy, R is the gas constant, Tp is the peak temperature, C
is an arbitrary constant and A is the pre-exponential factor.
The logb against 1/Tp and ln(b/T2p) against 1/Tp were two
straight lines. According to Eqs. (1) and (2), the slops of
two lines were used to calculate the activation energies.
According to Eq. (3), the obtained activation energies were
used to calculate the logarithm of pre-exponential factor
(logA/s-1).
Sample heat capacity/ 2.00a
kJ kg-1 K-1
500
Test cell type
Hastelloy Temperature step/°C
15
Test cell mass/g
14.1784
Temperature rate
sensitivity/°C min-1
Wait time/min
0.02
Test cell heat
capacity/
kJ kg-1 K-1
0.42
15
aHeat capacity of organic sample default 2.00, the value is taken from
Refs. [17, 18]
123

F. Bao et al.
Table 3 Non-isothermal kinetics and thermodynamics parameters of DABT obtained by Ozawa’s and Kissinger’s methods
Method
Ea/kJ mol-1
logA/s-1
r
Tp0/°C
DG=/kJ mol-1
DH=/kJ mol-1
DS=/J mol-1 K-1
Tbp0/°C
Ozawa
197.54
195.41
12.94
12.79
0.9843
0.9824
447.19
447.19
200.77
200.78
191.55
189.42
-12.80
-15.77
470.46
470.73
Kissinger
Table 4 Self-heating decomposition parameters of DABT by ARC
Parameters
Values
Corr.
Parameters
Values
Corr.
Onset temperature/°C
443.61
0.02
403.72
0.55
Adiabatic temperature rise/°C
Time to maximum rate/min
Max pressure/bar
37.30
686.30
7.84
1139.06
Onset temperature rate/°C min-1
Temperature at max rate/°C
Max self-heating rate/°C min-1
Final temperature/°C
22.47
463.00
0.04
996.00
1.34
–
–
Thermal inertia factor
30.54
480.91
1542.78
ꢂ
ꢃ
pffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffiffi
Ea À Ea2 À 4EaRTP0
Ea
RTp2
Ea
A ¼ b
exp
ð3Þ
Tbp0
¼
ð8Þ
RTp
2R
The Ea, logA/s-1 and corresponding regression coeffi-
cient (r) which were obtained by Ozawa’s and Kissinger’s
methods were listed in Table 3.
Self-heating decomposition parameters
Under experiment conditions of ARC, heat from the
exothermic reaction of the sample induced the temperature
rise of both the sample and the reaction cell, The rela-
tionship between the real adiabatic and near adiabatic
conditions was described as follows [14–16]. The corrected
and measured self-heating decomposition parameters of
DABT were given in Table 4.
Thermodynamics at initial decomposition
temperature (Tp0)
The value of initial decomposition temperature (Tp0) in the
exothermic decomposition process corresponding to b ? 0
was calculated by Eq. (4) [10, 11]
Tpi ¼ Tp0 þ abi þ bb2i i ¼ 1; 2; 3; 4
ð4Þ
MbCv;b
/ ¼ 1 þ
ð9Þ
MsCv;s
where Tpi is the peak temperature of a heating rate of bi,
a and b are the coefficients.
The free energy of activation (DG=), activation
enthalpy (DH=) and activation entropy (DS=) were cal-
culated by Eqs. (5), (6) and (7) [11]:
ꢀ
ꢁÀ1
1
R
To;corr
¼
þ
ln /
ð10Þ
To Ea
Tf;corr ¼ /DTad þ To;corr
DTad;corr ¼ /DTad
mo;corr ¼ /mo
ð11Þ
ð12Þ
ð13Þ
ð14Þ
ð15Þ
ꢀ
ꢁ
Ah
¼
DG ¼ Ea À RTP0 ln
ð5Þ
ð6Þ
ð7Þ
kBTP0
¼
mm;corr ¼ /mm
DH ¼ Ea À RTp0
Tm;corr ¼ To;corr þ /ðTm À ToÞ
TMR
¼
¼
DH À DG
¼
DS ¼
Tp0
TMRcorr
¼
ð16Þ
/
where Ea is the apparent activation energy, h is the Planck
constant, kB is the Boltzmann constant. The Tp0, DG=,
DH= and DS= were listed in Table 3.
where u is the thermal inertia factor, Mb is the test cell
mass, Cv,b is the test cell heat capacity, Ms is the sample
mass, Cv,s is the sample heat capacity. To,corr and To are the
corrected and measured onset decomposition temperature,
respectively; Tf,corr and Tf are the corrected and measured
final decomposition temperature, respectively; DTad,corr and
DTad are the corrected and measured adiabatic temperature
rise, respectively; mo,corr and mo are the corrected and
Critical temperature of thermal explosion (Tbp0
)
The value of critical temperature of thermal explosion
(Tbp0) was calculated by Eq. (8) [12, 13]:
123

Thermal decomposition behavior and thermal stability of DABTÁ2DMSO
measured onset temperature rate, respectively; mm,corr and
mm are the corrected and measured max self-heating rate,
respectively; Tm,corr and Tm are the corrected and measured
temperature at max rate, respectively; TMRcorr and TMR
are the corrected and measured time to maximum rate,
respectively.
Rearranging Eq. (17), we had [14, 16]:
mT
i
kà ¼ kC0nÀ1
¼
ð18Þ
h
nDTad
TfÀT
DTad
where k* is a pseudo zero-order rate constant at the tem-
perature T. According to the Arrhenius equation, one could
The ARC curves of DABT were given in Fig. 4. As seen
from Fig. 4a, an endothermic decomposition and an
exothermic decomposition were observed. The endother-
mic decomposition of lost DMSO started at 395.10 °C and
ended at 441.09 °C, and the pressure of the period
increased 5.80 bar (Fig. 4b). The exothermic decomposi-
tion started at 443.61 °C and ended at 480.91 °C, within
the time span of 1397.50 min (Fig. 4c). The max self-
heating rate was 0.04 °C min-1 at 463.00 °C (Fig. 4d).
From Fig. 4, it could be concluded that when the ambient
temperature below 395.10 °C, DABT was not
decomposition.
obtain [14, 16].
ꢀ ꢁ
Ea
R
1
ln kà ¼ ln C0nÀ1A À
ð19Þ
T
The curves of lnk* versus T -1 for the self-heating
decomposition of DABT were illustrated in Fig. 5. The Ea
and A could be calculated from the plot, and they were
listed in Table 5.
Time to maximum rate (TMR)
According to the literature, the TMR and T have the fol-
lowing relationship [16–18].
ꢀ ꢁ
Adiabatic decomposition kinetics
Ea
1
RT2
h
i
ln TMR ¼
À ln A þ ln
ð20Þ
Tf ÀT
R T
C0nÀ1
nDTadEa
For an nth-order single step reaction with a single reaction,
the self-heating rate could be expressed as following
[14, 16]:
DTad
From Table 5, n = 2, Ea was 345.76 kJ mol-1, logA/s-1
was19.66.Then,theplotofTMRversusTwasgiveninFig. 6.
ꢀ
ꢁ
n
dT
dt
Tf À T
DTad
mT ¼
¼ k
DTadC0nÀ1
ð17Þ
Self-accelerating decomposition temperature
(TSADT
where mT is the temperature rate at the temperature T, k is
the rate constant of the reaction at temperature T, T is the
temperature at time t, C0 is the initial concentration of the
reactant.
)
The TSADT is defined as the lowest ambient air temperature
at which self-accelerating decomposition may occur within
Fig. 4 ARC curves of DABT.
a Temperature and pressure
versus time, b loss of DMSO
temperature and pressure versus
time, c decomposition
temperature and pressure versus
time, d decomposition
temperature and temperature
rate versus time
10
700
600
500
400
300
200
100
0
460
Temperature
Pressure
Temperature
Pressure
(a)
(b)
8
6
4
2
0
8
6
4
2
0
440
420
400
380
0
500 1000 1500 2000 2500 3000
Time/min
800
850
900
950
1000
Time/min
0.08
500
480
460
440
420
8.0
7.8
7.6
7.4
7.2
Temperature
(c)
(d)
Temperature rate
Pressure
0.06
0.04
0.02
0.00
800
1200
1600
2000
2400
430 440 450 460 470 480 490
Temperature/°C
Time/min
123

F. Bao et al.
–3
–4
–5
–6
–7
Table 6 Onset temperatures of DABT and DNABT
n = 1
Compounds
Onset temperature
by DSCa
Onset temperature
by ARCb
n = 2
n = 3
n = 4
DABT
468.23
210.86
443.61
200.22
DNABT
aOnset temperatures by DSC at 10 °C min-1, the value of DNABT is
taken from our previous work
bOnset temperatures by ARC, the value of DNABT is taken from our
previous work
–8
0.00134
0.00136
0.00138
0.00140
where U is the heat transfer coefficient, a is the contact area
of the system and environment. Assuming 50 kg DABT is
loaded in the cylinder with the height of 60 cm and the
diameter of 30 cm, so the contact area of the system and
environment was 0.5652 m2. In this study, the heat transfer
coefficient U = 5 J m-2 K-1 s-1 had been chosen for
prediction of the TSADT. The TSADT of DABT was calcu-
lated as 429.54 °C.
/K–1
T–1
Fig. 5 Lnk* versus T-1 of DABT
Table 5 Adiabatic decomposition kinetic parameters of DABT by
ARC
n
Ea/kJ mol-1
logA/s-1
r
1
2
3
4
183.57
345.76
507.95
667.68
8.49
19.66
30.82
41.82
0.9689
0.9801
0.9827
0.9834
Comparison of onset temperatures of DABT
with DNABT
The values of onset temperatures of DABT and its
derivative DNABT were listed in Table 6.
From Table 6, it could be concluded that the onset tem-
peratures of DABT were determined in the DSC and ARC
experiments were found to be higher than that of DNABT.
DABT was a stable compound compared with DNABT
700
600
500
400
300
Conclusions
The thermal decomposition behavior of DABT were
studied by TG–DTG–DSC, DTA and ARC techniques. The
results from TG–DTG–DSC, DTA and ARC all suggested
that DABT had an endothermic decomposition of lost
DMSO and an exothermic decomposition. The TG–DTG–
DSC measurement showed that the endothermic decom-
position of lost DMSO started at 388.23 °C and ended at
462.73 °C, and the exothermic decomposition started at
468.23 °C and ended at 535.73 °C. The values of non-
isothermal decomposition kinetics and thermodynamics
parameters that were obtained by the Ozawa’s and Kis-
singer’s methods for DABT showed good correlation. The
critical temperature of thermal explosion (Tbp0) obtained by
the Ozawa’s and Kissinger’s methods were calculated as
470.46 and 470.73 °C, respectively. The self-heating
decomposition parameters, including the T0, Tf, Tm, mm,
DTad and TMR, were obtained and corrected by u. The
440
45
0
4
60
470
Temperature/°C
Fig. 6 TMR versus T of DABT
a substance in the packaging as used in transport and
storage. The adiabatic decomposition kinetics parameters
were used for the estimation of the TSADT for DABT in a
50 kg package. Firstly, Eq. (21) was used to get the time
constant (s), then, the temperature of no return (TNR) would
be obtained from the curve of TMR versus T. Lastly, the
TSADT was calculated based on Eq. (22) [19, 20].
MsCv;s
s ¼
ð21Þ
ð22Þ
Ua
self-accelerating decomposition temperature (TSADT, 50kg
)
RTN2R
was calculated as 429.54 °C. DABT was a stable com-
pound compared with DNABT.
TSADT ¼ TNR
À
Ea
123

Thermal decomposition behavior and thermal stability of DABTÁ2DMSO
11. Hu RZ, Gao SL, Zhao FQ. Thermal analysis kinetics. 2nd ed.
Beijing: Science Press; 2008.
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