Research on thermal decomposition of trinitrophloroglucinol salts by DSC, TG and DVST

Article abstract of DOI:10.2478/s11532-013-0205-8

The thermal decomposition of the four nitrogen-rich salts of ammonia (NH₄), aminoguanidine (AG), carbohydrazide (CHZ) and 5-aminotetrazo (ATZ) based on trinitrophloroglucinol (H₃TNPG) was investigated using the differential scanning

Full text of DOI:10.2478/s11532-013-0205-8

Cent. Eur. J. Chem. • 11(5) • 2013 • 774-781
DOI: 10.2478/s11532-013-0205-8
Central European Journal of Chemistry
Research on thermal decomposition of
trinitrophloroglucinol salts by DSC, TG and DVST
Research Article
Rui Liu1, Tonglai Zhang1*, Li Yang1,
Zunning Zhou1, Xiaochun Hu2
1State Key Laboratory of Explosion Science and Technology,
Beijing Institute of Technology, Beijing 100081, China
2The 3rd Department, Institute of Chemical Defense,
Beijing 102205, China
Received 28 August 2012; Accepted 4 January 2013
Abstract:
Thethermaldecompositionofthefournitrogen-richsalts of ammonia (NH4), aminoguanidine (AG), carbohydrazide (CHZ) and 5-aminotetrazo
(ATZ) based on trinitrophloroglucinol (H3TNPG) was investigated using the differential scanning calorimetry (DSC), thermogravity (TG), and
dynamic vacuum stability test (DVST). DSC and TG methods research the complete decomposition, while DVST method researches
the very early reaction stage. The peak temperatures of DSC curves are consistent with the temperatures of maximum mass loss
rates of TG curves. The apparent activation energies of these H3TNPG-based salts obtained by DSC and DVST have the same
regularity, i.e., (ATZ)(H2TNPG)•2H2O < (CHZ)(HTNPG)•0.5H2O < NH4(H2TNPG) < (AG)(H2TNPG). The thermal stability order is
(ATZ)(H2TNPG)•2H2O < (CHZ)(HTNPG)•0.5H2O < (AG)(H2TNPG) < NH4(H2TNPG), which was evaluated by DVST according to the
evolved gas amount of thermal decomposition. DVST can monitor the real-time temperature and pressure changes caused by thermal
decomposition, dehydration, phase transition and secondary reaction, and also evaluate the thermal stability and kinetics.
Keywords: Thermal decomposition • H3TNPG-based salts • Kinetic parameters • Thermal stability • DVST
© Versita Sp. z o.o.
reacts with azotic compounds to form the nitrogen-rich
salts which have been widely used as the high-energy
1. Introduction
Trinitrophloroglucinol(2,4,6-trinitro-1,3,5-trihydroxybenzene, and low-sensitivity materials [13–16]. The syntheses,
H3TNPG) is a strong acidic organic nitrocompound which characterizations and properties of many H3TNPG-
has been used as an important ingredient in chemical based salts including the alkali metallic, alkaline earth
industry and as an energetic component in military metallic and organic nitrogen-rich salts have been
and aerospace industry [1,2]. H3TNPG can react with reported [17–29]. Those materials have many potential
metallic, organic and inorganic compounds to form applications as the gas-generating reagents, blowing
salts which have remarkable combustible and explosive agents, solid propellants and other combustible
properties [3–5]. The lead salt of H3TNPG has been ingredients.
extensively studied and recommended as an initiating
Thermal stability, reaction mechanism, and kinetics
explosive [6]. Recently, the hypotoxic, environmentally of thermal decomposition are very important indicators
friendly and high-energy materials have attracted for energetic materials, which help to evaluate their
considerable interest of the researchers all over the practical safety and reliability [30–33]. In this work,
world [7,8]. Heavy metallic salts of H3TNPG are being thermal decomposition of the four nitrogen-rich H3TNPG-
eliminated in the practical applications because of their based salts, ammonia (NH4), aminoguanidine (AG),
ecotoxicity. In recent years, much attention has been carbohydrazide (CHZ), and 5-aminotetrazo (ATZ) were
paid to the study of H3TNPG-based compounds in investigated by differential scanning calorimetry (DSC),
order to develop green energetic materials with better thermogravity (TG), and dynamic vacuum stability test
performance and wider applications [9–12]. H3TNPG (DVST).
* E-mail: ztlbit@bit.edu.cn
774

R. Liu et al.
OH
OH
OH
HO3S
HO
SO3H
OH
O2N
HO
NO2
OH
H2SO4
HNO3+H2SO4
HO
OH
SO3H
NO2
(a)
Figure 1. Synthesis scheme of H3TNPG (a).
N
NH
O
C
N
N
NH2
H2N
HN
C
NH2
H2N
HN
NH
NH2
N
H
(b)
(c)
(d)
Figure 2. Chemical structures of AG (b), CHZ (c), and ATZ (d).
NH2
NH2
2. Experimental procedure
NH (H2TNPG)·2H2O
HN
+ 2H O
NH
HN
H3TNPG +
2
2.1. Sample preparation
All raw materials of AR grade are commercially available
~99% pure and were used in this study without further
N
N
N
N
(ATZ)(H2TNPG)·2H2O
purification.H3TNPGwaspreparedfromthesulphonation (the yield of 68%, the purity of 97.8%)
and nitration of 1,3,5-benzenetriol [9] as shown in Fig. 1,
and then recrystallized to obtain the crystal product with
the yield of 83% and the purity of 99.3%.
The crystal structures have been evidenced by
X-ray diffraction analysis [26–28,34], and (CHZ)
H3TNPG (5.22 g, 0.02 mol) was dissolved in (HTNPG)•0.5H2O and (ATZ)(H2TNPG)•2H2O present
50 mL distilled water. The NH4HCO3 (1.70 g, 0.02 mol), co-crystallized water molecules. The basic crystal data
AG•H2CO3 (2.72 g, 0.02 mol), CHZ (1.80 g, 0.02 mol), of the H3TNPG-based salts are listed in Table 1.
and ATZ (1.55 g, 0.02 mol) (the chemical structures
2.2. Apparatus and conditions
of AG, CHZ and ATZ are shown in Fig. 2) were added
The DSC measurement uses Pyris–1 differential
scanning calorimeter (Perkin–Elmer, USA). Sample
of less than 1.0 mg of the compound is weighed and
placed in an uncovered aluminium crucible, and then
heated from 323 K to 673 K at the rates of 5, 10, 15, 20
and 25 K min–1 in pure nitrogen atmosphere.
dropwise into the H3TNPG solution. The mixture solution
was adjusted to pH ≈ 4 and kept under stirring at
338 – 343 K for 40 min, and then cooled to room
temperature. The crystals were formed and collected by
suction filtration. Purities of the products were measured
by DSC according to their melting points. The syntheses
refer to the following schemes:
TG measurement uses Pyris–1 thermogravimetric
analyzer (Perkin–Elmer, USA) with an unsealed
platinum pan. Sample of less than 1.0 mg of the
compund is heated from 323 K to 673 K at the rate
of 10 K min–1. The atmosphere is dry nitrogen with
the flowing rate of 20 mL min–1 under the pressure of
0.2 MPa.
NH4(H2TNPG) + CO2 + H2O
H3TNPG + NH4HCO3
(the yield of 76%, the purity of 98.5%)
NH
NH2
H3TNPG + H2NHNCNH2 · H2CO3
+ CO2 + H2O
(H2NHNCNH2)(H2TNPG)
(AG)(H2TNPG)
DVST can monitor the variables of pressure and
temperature in a constant-volume and vacuum system
directly and dynamically [35]. Sample of about 1.0 g of
the compound is sealed in glass test tube with the initial
pressure below 0.1 kPa. The tube is placed into the
heating block, and then heated from room temperature
(the yield of 63%, the purity of 94.7%)
O
O
H3TNPG +
H2NHNCNHNH2 + 0.5 H2O
(H3NHNCNHNH3)(HTNPG)·0.5H2O
(CHZ)(HTNPG)·0.5H2O
(the yield of 61%, the purity of 94.3%)
775

Research on thermal decomposition
of trinitrophloroglucinol salts by DSC, TG and DVST
to target temperature of 373 K at a constant rate (less
than 3 K min–1), and later kept isothermally for 48 h, at
last cooled to room temperature.
DSC and TG methods are used to study the
complete thermal decomposition from α=0 to α=1 (where
α depicts the reaction progress), while DVST method
gains better knowledge on the early reaction stage
(α < 0.05) [35] which is very important to predict
the storage life of a material [15]. In these three
thermoanalysis experiments, each sample was tested
at least thrice to ensure uncertainty and accuracy.
3. Results and discussion
3.1. DSC and TG analyses
The DSC and TG curves of the four H3TNPG-based
salts at the heating rate of 10 K min–1 are illustrated in
Fig. 3.
The decomposition characteristics of the four salts
are different, even under the same conditions. The
DSC curve of NH4(H2TNPG) shows only one sharp
exothermic peak starting at 483.2 K and ending at
493.4 K with a peak temperature of 492.4 K. There is also
one corresponding intense mass loss stage in the TG
curve. The (AG)(H2TNPG) exhibits a small endothermic
peak at 471.6 K and a drastic exothermic peak at
481.6 K, which suggests that it melts before
decomposition. The (CHZ)(HTNPG)•0.5H2O presents
one endothermic peak at 419.2 K in the DSC curve
and a corresponding mass loss of 2.88% in the TG
curve; the mass loss just approximates to the crystal
water content of 2.50%. The endothermic peak of DSC
therefore represents the dehydration process. There are
also two consecutive exothermic peaks at 449.2 K and
470.2 K, which suggests that two decomposition
processes overlap in time. The (ATZ)(H2TNPG)•2H2O
shows one endothermic peak at 348.8 K in the DSC
curve and a mass loss of 9.38 % at the same temperature
in the TG curve. This endothermic peak represents the
crystal water removal because its theoretical water
content is 9.43%. An intense exothermic process
occurs with the peak temperature of 476.3 K, and a
small endothermic peak represents melting process
at 451.9 K. All H3TNPG-based salts present similar
decomposition temperatures around 480±10 K, which
suggests the main decomposition involves preferentially
the H3TNPG part of the salts. The previous researches
indicate that the thermal decomposition mechanisms of
the nitrogen-rich salts are controlled by the elimination
of –NO2 and the breakdown of the substituted benzene
ring [36,37]. Because these salts are composed of
the carbon, nitrogen, oxygen and hydrogen atoms,
Figure 3. DSC, TG and DTG curves of NH4(H2TNPG) (a), (AG)
(H2TNPG) (b), (CHZ)(HTNPG)•0.5H2O (c) and (ATZ)
(H2TNPG)•2H2O (d) at the heating rate of 10 K min-1.
776

R. Liu et al.
Table 1. Basic informations of NH4(H2TNPG), (AG)(H2TNPG), (CHZ)(HTNPG)•0.5H2O and (ATZ)(H2TNPG)•2H2O.
Samples
CCDC
No.
Empirical
formula
Molar mass
(g mol-1)
Crystal
system
Space
group
Calculated density
(g cm-3)
NH4(H2TNPG)
670293
683061
679222
668253
C6H6N4O9
C7H9N7O9
278.15
335.21
360.22
764.46
Monoclinic
Triclinic
C2/c
P–1
1.944
1.811
2.008
1.849
(AG)(H2TNPG)
(CHZ)(HTNPG)•0.5H2O
(ATZ)(H2TNPG)•2H2O
C7H10N7O10.5
C14H20N16O22
Triclinic
P–1
Orthorhombic
Pbca
Table 2. Kinetic parameters of the first exothermic process of NH4(H2TNPG), (AG)(H2TNPG), (CHZ)(HTNPG)•0.5H2O and (ATZ)(H2TNPG)•2H2O
tested by DSC.
Sample
Kissinger’s method
ln[AK/(s-1)]
Ozawa-Doyle’s method
[a]
[c]
[b]
[c]
EK (kJ mol-1)
rK
EO (kJ mol-1)
rO
NH4(H2TNPG)
215.9
254.3
132.6
128.2
20.65
25.92
12.59
12.10
-0.9928
-0.9973
-0.9931
-0.9979
213.3
249.5
133.5
129.5
-0.9933
-0.9974
-0.9939
-0.9982
(AG)(H2TNPG)
(CHZ)(HTNPG)•0.5H2O
(ATZ)(H2TNPG)•2H2O
[a] [b]Subscripts K and O denote calculation results by Kissinger method and Ozawa–Doyle method, respectively.
[c] r stands for the linear correlation coefficient.
the gas products are predicted to consist of NH3, CO,
The results calculated by the Kissinger and Ozawa-
CO2, N2, NOx and H2O [38,39]. The total mass loss Doyle methods are similar: the ascending order of Ea and
amounts to 97.46% for NH4(H2TNPG), 76.52% for (AG) A is (ATZ)(H2TNPG)•2H2O < (CHZ)(HTNPG)•0.5H2O
(H2TNPG), 91.21% for (CHZ)(HTNPG) and 83.35% for < NH4(H2TNPG) < (AG)(H2TNPG). The results in this
(ATZ)(H2TNPG)•2H2O. The remaining residues in the work vary from the previous studies [29] because of the
crucibles are almost all the black carbonic residues for differenceofexperimentalatmospheres.Theatmosphere
these four H3TNPG-based salts, and the weights of the of DSC in this work is the pure nitrogen flow, while that in
solid residues are all relatively small. These indicate that [29] is the static air atmosphere. The dynamic nitrogen
they decompose fully and have potential applications in flow can prevent the sample from being oxidized by air
the gas-generating agents [14,40,41].
and remove the gas products continuously, and also
The first exothermic process has a dominant effect maintain the stable and consistent test conditions.
on the thermal decomposition of the H3TNPG-based
salts. The Kissinger and Ozawa-Doyle methods [42] 3.2. DVST analyses
(as Eq. 1 and Eq. 2 show) were applied to calculate the DVST analyses are performed to research thermal
kinetic parameters according to the first decomposition decomposition with the low reaction progress, because
shown by the DSC curves at heating rates of 5, 10, 15, its experimental temperature is relatively low (the
20 and 25 K min–1.
Kissinger method:
Ozawa-Doyle method:
maximum temperature is 200oC) [35]. DVST apparatus
records the real-time temperature and pressure
changes of the whole reaction process and displays the
dynamic curves of the time dependences of the evolved
gas pressure (p–t) and of the pressure-changing rate
(dp/dt–t). The DVST curves of the four H3TNPG-based
salts at the most intense reaction stage (the reaction
time within 0~500 min) are shown in Fig. 4.
The p–t curves show that the evolved gas pressure
of all of the four H3TNPG-based salts increase with time.
The gas is mainly released in the initial decomposition
stage. The thermal decomposition process of (ATZ)
(H2TNPG)•2H2O produces a peak pressure (ppeak) and
the corresponding dp/dt–t curve presents two extreme
values,whilethedecompositionoftheothersaltsproceed
(1)
(2)
where Tp is the peak temperature (K), A is the
pre-exponential factor (s–1), Ea is the apparent
activation energy (J mol–1), R is the gas constant
(8.314 J K–1 mol–1), β is the heating rate (K min–1), and
G(α) is the reaction mechanism function.
The kinetic parameters of Ea and A were derived from
the slope and the intercept of the linear dependence
between Tp and β according to Eq. 1 and Eq. 2. The
results are listed in Table 2.
777

Research on thermal decomposition
of trinitrophloroglucinol salts by DSC, TG and DVST
smoothly at the same conditions. (ATZ)(H2TNPG)•2H2O
dehydrates causing the gas pressure increases sharply,
while the decomposed gas releases slowly due to the
effect of gas diffusion rate. Then a secondary reaction
may occur so that the pressure decreases and the ppeak
emerged. After that the sample decomposes further and
the gas diffuses quickly so the pressure rises again.
The DVST curve of (CHZ)(HTNPG)•0.5H2O does not
display a ppeak. The possible reason for this is that the
p
peak is superimposed with the soaring pressure from the
decomposition of the dehydrated products. The water
content of (CHZ)(HTNPG)•0.5H2O is less than (ATZ)
(H2TNPG)•2H2O, so the total pressure increment of
(CHZ)(HTNPG)•0.5H2O caused by dehydration is lower
than that of (ATZ)(H2TNPG)•2H2O. From the dp/dt–t
curves, the maximum changing rate of pressure
(dp/dt)max representing the most intense reaction
displays at the initial non-isothermal stage, and then
the dp/dt gets smaller gradually. This indicates that the
decomposition of four salts decomposes slowly and
smoothly for a long time in the last stage.
The kinetic parameters and the reaction mechanism
of the thermal decomposition were determined by the
integral and differential methods [42], respectively, as
Eq. 3 and Eq. 4 show.
Integral method:
(3)
Differential method:
(4)
where G(α) and f(α) denote the reaction mechanism
function in integral and differential form, T0 is the initial
temperature (K), T is the test temperature (K), Ea is the
activation energy (J mol–1), A is the pre-exponential
factor (s–1), β is the heating rate (K min–1), R is the gas
constant (8.314 J K–1 mol–1), α is the reaction progress
(or conversion ratio).
(5)
where p is the evolved gas pressure at certain time (kPa),
pt is the total final gas pressure (kPa). The dependence
of pressure-temperature (p–T) is converted into the α–T
by Eq. 5, and then into dα/dT–T by differentiation.
The linear dependence of the reaction mechanism
function on temperature are established according
to Eq. 3 and Eq. 4. The reaction mechanism function
is selected from the 41 types of mechanism models
p-t and dp/dt-t curves of NH (H TNPG) (a), (AG)(H TNPG)
Figure 4.
(b), (CHZ)(HTNPG)•0.5H2O4(c)2and(ATZ)(H2TNPG2)•2H2O including the multi-dimensional diffusion, chemical
(d) at 373 K by DVST.
reaction, nucleation and growth, autocatalytic reactions
778

R. Liu et al.
Table 3. Kinetic parameters of NH4(H2TNPG), (AG)(H2TNPG), (CHZ)(HTNPG)•0.5H2O and (ATZ)(H2TNPG)•2H2O tested by DVST.
Sample
Reaction model
Integral method
Differential method
EI[a]/(kJ mol-1) ln[AI(s-1)]
rI
ED[b]/(kJ mol-1) ln[AD(s-1)]
rD
Avrami-Erofeev
equation[c]
NH4(H2TNPG)
207.9
235.2
150.9
139.7
27.49
30.11
18.13
17.17
-0.9971
-0.9958
-0.9979
-0.9984
214.4
245.2
148.9
141.7
29.09
32.25
18.29
18.06
-0.9912
-0.9933
-0.9928
-0.9954
Avrami-Erofeev
equation
(AG)(H2TNPG)
Z-L-T
(CHZ)(HTNPG)•0.5H2O
(ATZ)(H2TNPG)•2H2O
equation[d]
Z-L-T e
quation
[a] [b] Subscript I and D denote calculation results by integral method and differential method, respectively.
[c] The equation indicates the mechanism of random nucleation and subsequent growth model.
[d]It is the abbreviation of Zhuralev-Lesokin-Tempelman equation which describes the mechanism of three-dimensional diffusion.
Table 4. Evolved gas amount of NH4(H2TNPG), (AG)(H2TNPG), (CHZ)(HTNPG)•0.5H2O and (ATZ)(H2TNPG)•2H2O tested by DVST and VST.
Sample
T0(K)
V (mL g-1)
DVST method
VST method
NH4(H2TNPG)
483.2
465.5
413.6
334.8
1.73
4.58
1.05
2.14
2.25
2.80
(AG)(H2TNPG)
(CHZ)(HTNPG)•0.5H2O
(ATZ)(H2TNPG)•2H2O
10.14
13.27
and so on [42]. The Ea and A are derived from the slope same reaction mechanisms and larger values of Ea than
and the intercept of the fitted line according to the least the other two.
squares method. The most optimal linear regression
Ea denotes the energy barrier of the reaction
equation is selected from 41 results. The derived kinetics and reflects whether a reaction is slower or faster,
parameters of the four H3TNPG-based salts are shown however, it doesn’t imply the stability of the material.
in Table 3.
Strictly speaking, the evolved gas amount of thermal
The ascending order of Ea is (ATZ)(H2TNPG)•2H2O decomposition (V, mL g–1) is an important indicator for
< (CHZ)(HTNPG)•0.5H2O < NH4(H2TNPG) < (AG) the thermal stability of a material [43]. The V values of
(H2TNPG), which is consistent with the order obtained the four H3TNPG-based salts are calculated by DVST
by DSC. The reaction mechanisms of NH4(H2TNPG) and traditional vacuum stability test (VST) methods, and
and (AG)(H2TNPG) are the Avrami-Erofeev equation the results are listed in Table 3.
with n equaling to 4 which is described as the random
nucleation and subsequent growth process. The by DVST is NH4(H2TNPG) > (AG)(H2TNPG) > (CHZ)
mechanisms of (ATZ)(H2TNPG)•2H2O and (CHZ) (HTNPG)•0.5H2O (ATZ)(H2TNPG)•2H2O, which
Thermal stability order from high to low judged
>
(HTNPG)•0.5H2O conform to the Z-L-T function which agrees with the stability judged by the onset temperature
is the three-dimensional diffusion process. The results (T0) of DSC (see Table 4). The evolved gas amounts
show an obvious regularity that the crystal water has of DVST are much larger than those of VST. Actually,
a great influence on the reaction mechanisms. For VST records the difference of the gas amount between
(ATZ)(H2TNPG)•2H2O and (CHZ)(HTNPG)•0.5H2O, the beginning and end of the reaction both at the room
their initial reactions are dominated by the dehydration temperature. The reaction system should be cooled at
process, which are proved by the endothermic dehydration the end, and the gas-liquid phase transition occurs that
process in the DSC curves. Because the binding energy is the gaseous water condenses to the liquid, which lead
of water is weaker than the covalent bond energy, the to the decrease of the total gas amount. DVST derives
water molecules absorb a small amount of energy to the gas amount directly by the ideal gas equation of
overcome the diffusion resistance,hencethe dehydration state without the interference of the phase transition.
process takes place easily. For NH4(H2TNPG) and Thus, (CHZ)(HTNPG)•0.5H2O is more thermally stable
(AG)(H2TNPG) they absorb more energy in order to than (ATZ)(H2TNPG)•2H2O, and these two salts are
break some covalent bonds and form the new ones. less thermally stable than NH4(H2TNPG) and (AG)
NH4(H2TNPG) and (AG)(H2TNPG) therefore have the (H2TNPG). H3TNPG is a strong acid and the alkalinity
779

Research on thermal decomposition
of trinitrophloroglucinol salts by DSC, TG and DVST
of NH3•H2O is stronger than AG, so NH3•H2O reacts with the apparent activation energy is (ATZ)(H2TNPG)•2H2O
H3TNPG to form more stable salt. The DVST results < (CHZ)(HTNPG)•0.5H2O < NH4(H2TNPG) < (AG)
suggest that the crystal water content and the acid-base (H2TNPG). The thermal stability judged by the evolved
bonding strength are the key factors for the thermal gas amount of DVST is NH4(H2TNPG) > (AG)(H2TNPG)
stability evaluation of the H3TNPG-based salts. DVST > (CHZ)(HTNPG)•0.5H2O > (ATZ)(H2TNPG)•2H2O. The
can trace and exhibit the real-time changes of evolved stability depends on the interplay of three factors: the
gas amount and temperature caused by the thermal stability of the molecular configuration, the content of
decomposition, dehydration, phase transition, and crystal water, and the bonding strength of the acid-base
secondary reaction dynamically and directly, and can pairs. The different thermal analysis methods can fully
also evaluate the thermal stability and decomposition investigate the thermal decomposition of the H3TNPG-
kinetics. Therefore, DVST is a more sensitive and more based salts, which are important to explore their further
accurate method to quantify the evolved gas amount applications.
and to evaluate the thermal properties of materials than
VST.
Acknowledgement
4. Conclusions
This work was financially supported by the
Science and Technology Fund on Applied Physical
The thermal decomposition of the four H3TNPG-based Chemistry Laboratory (Nos. 9140C3703051105 and
salts was investigated under the complete reaction by 9140C370303120C37142), and the Key Support
DSC and TG, as well as under the low-extent reaction by Foundation of State Key Laboratory of Explosion
DVST. The kinetic parameters from different analysis Science and Technology (Nos. QNKT12-02 and YBKT
methods show a similar trend: the ascending order of 10-05).
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