The investigation of thermal pyrolysis of glycerol carbonate derivatives by TG-FTIR

Article abstract of DOI:10.1016/j.tca.2015.12.002

Three new GC derivatives, carbonic acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (CABE), succinic acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (SABE) and terephthalic acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (TABE), were designed and synthesized. We investigated the thermal stability and the thermal pyrolysis of three compounds by TG-FTIR, and the bond dissociation energy was calculated to further demonstrate the decomposition process. The results showed that the three GC derivatives had one, two, three weight loss stages, respectively. Their initial decomposition temperature was as high as 200 °C, which means that the compounds have good thermal stability. 5% weight loss temperature was increased in the order of TABE > SABE > CABE. In thermal pyrolysis process, the C-C, C-O bonds of cyclic carbonate fractured preferentially, and then the C-O bonds nearby cyclic carbonate of SABE and TABE continued to fracture to produce linear ester in the form of fragment.

Full text of DOI:10.1016/j.tca.2015.12.002

Thermochimica Acta 624 (2016) 76–81
Contents lists available at ScienceDirect
Thermochimica Acta
journal homepage: www.elsevier.com/locate/tca
The investigation of thermal pyrolysis of glycerol carbonate
derivatives by TG–FTIR
Rujuan Lia, Jing Liua,∗, Hairong Taob, Donglan Sunc, Dagang Xiaoa, Chunjing Liua
a College of Chemical Engineering and Material Science, Tianjin University of Science & Technology, Tianjin 300457, China
b College of Chemistry, Beijing Normal University, Beijing 100875, China
c College of Science, Tianjin University of Science & Technology, Tianjin 300457, China
a r t i c l e i n f o
a b s t r a c t
Article history:
Three new GC derivatives, carbonic acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (CABE), succinic
acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (SABE) and terephthalic acid bis-(2-oxo-[1,3]dioxolan-
4-ylmethyl) ester (TABE), were designed and synthesized. We investigated the thermal stability and the
thermal pyrolysis of three compounds by TG–FTIR, and the bond dissociation energy was calculated to
further demonstrate the decomposition process. The results showed that the three GC derivatives had
one, two, three weight loss stages, respectively. Their initial decomposition temperature was as high as
200 ◦C, which means that the compounds have good thermal stability. 5% weight loss temperature was
increased in the order of TABE > SABE > CABE. In thermal pyrolysis process, the C C, C O bonds of cyclic
carbonate fractured preferentially, and then the C O bonds nearby cyclic carbonate of SABE and TABE
continued to fracture to produce linear ester in the form of fragment.
Received 21 September 2015
Received in revised form 6 December 2015
Accepted 9 December 2015
Available online 14 December 2015
Keywords:
GC derivatives
Thermal stability
Thermal pyrolysis
TG–FTIR
Bond dissociation energy
© 2015 Elsevier B.V. All rights reserved.
1. Introduction
rather new compound with many unique properties, such as high
boiling point, high flash point, low flammability and low toxicity.
In spite of the successful introduction and increasing distri-
bution of lithium-ion batteries in the world market, large-scale
lithium-ion batteries with higher energy density are not yet
commercially available for their practical application, such as elec-
tric vehicles, cellular phones, digital cameras and notebooks due
to their associated safety problems [1–3]. With the scaling-up
of lithium-ion batteries, the reduction of specific surface areas
reduces the thermal dissipation rate. As heat accumulates in bat-
teries, the thermal risk becomes much more serious than in normal
batteries [4]. Therefore, in order to improve the safety performance
of lithium-ion batteries, many researchers have investigated the
flammability and thermal stability of the electrolyte at high tem-
perature. The cyclic and linear carbonates are widely used for elec-
trolytes of lithium-ion batteries. However, the linear carbonates
have low flashing points and low boiling points, which is disadvan-
tageous in terms of security [5]. By contrast, the cyclic carbonates
have higher flashing points and boiling points, such as ethylene car-
bonate (EC), propylene carbonate (PC). Glycerol carbonate (GC) is a
Recently, it was reported that GC and its derivatives can be used
as electrolytes in lithium-ion batteries instead of EC and PC [6,7].
Therefore, we designed and synthesized three new GC derivatives:
carbonic acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (CABE),
succinic acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (SABE)
and terephthalic acid bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester
(TABE), which combined cyclic carbonate with various linear car-
bonate in order to have a better performance. Chemical structures
of these compounds are shown in Fig. 1.
TG–FTIR technology is to transmit the escaping gas compo-
sition during the weight loss of sample in thermogravimeter to
the infrared gas detection cell via constant temperature pipeline,
through infrared detection, analysis and judgment the structure
of escaping gas composition, proceeds quantitative and qualitative
analysis, respectively. This method, which can conduct simulta-
neous and continuous real time analysis, is a useful technology for
obtaining mass loss with time and evaluating the functional groups
of the volatiles produced by pyrolysis [8–10]. This technique can
give a deep insight into the evolution of pyrolysis and products
information about the physical–chemical nature of the observed
process. Therefore, it has been widely used in a variety of organic
and inorganic materials in terms of thermal stability and thermal
pyrolysis mechanism, even attracted more attention in the different
research fields for different purposes [11–13].
∗
Corresponding author at: College of Chemical Engineering and Material Science,
Tianjin University of Science & Technology, No. 29, 13th Ave., TEDA, Tianjin 300457,
China.
E-mail address: jingliu@tust.edu.cn (J. Liu).
http://dx.doi.org/10.1016/j.tca.2015.12.002
0040-6031/© 2015 Elsevier B.V. All rights reserved.

R. Li et al. / Thermochimica Acta 624 (2016) 76–81
77
Fig. 1. Chemical structure of compounds.
In present work, three new glycerol carbonate derivatives were
synthesized, and their thermal pyrolysis behaviors were studied by
the TG–FTIR technique. Furthermore, the theoretical calculations
of the bond dissociation energy for these compounds were carried
out for clarifying their thermal behaviors. Our work is focused on
investigation of the relationship between molecular structure and
thermal stability of three GC derivatives (CABE, OABE and TABE)
with TG–FTIR analysis and theoretical calculation. This study may
provide the useful information for molecular design and synthesis
of new carbonates.
atmosphere at 0 ◦C. The mixture was stirred at room temperature
for 12 h. After reaction, the mixture was filtrated and the filtrate
was evaporated under reduced pressure, the residues were puri-
fied by recrystallization from water to give the product (4.95 g,
yield 63.05%) (reaction 2, Scheme 1).
1H NMR (400 MHz, DMSO-d6):
ı
5.12–5.01 (m, 2H),
4.58–4.25(m, 8H) (Fig. S1(a)). FTIR (ꢀmax cm−1): 2925, 1793,
1761, 1176, 1052.
Supplementary Fig. S1 related to this article can be found, in the
online version, at http://dx.doi.org/10.1016/j.tca.2015.12.002.
2.1.3. Synthesis of succinic acid
2. Experimental
bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (SABE)
In a dry 100 mL 3-necked round-bottomed glass flask equipped
with a magnetic stirrer, a funnel with pressure-equalising tube and
a thermometer was placed 2.36 g (0.02 mol) of glycerol carbonate,
1.61 mL (0.02 mol) of pyridine and 30 mL of dry tetrahydrofuran as
solvent. A solution of succinyl chloride (1.11 mL, 0.01 mol) in dry
tetrahydrofuran (5 mL) was added dropwise to the above solution
over 30 min under nitrogen atmosphere at −5 ◦C. The mixture was
stirred for 4 h. After reaction, pyridine hydrochloride was removed
by filtration. The filtrate was evaporated under reduced pressure,
the residue was purified by recrystallization from acetone to give
the product (1.00 g, yield 31.33%) (reaction 4, Scheme 1).
1H NMR (400 MHz, DMSO-d6): ı 5.08–4.99 (m, 2H), 4.57 (t,
J = 8.6 Hz, 2H), 4.35–4.21 (m, 6H), 2.63 (s, 4H) (Fig. S1(b)). FTIR (ꢀmax
cm−1): 2929, 1785, 1736, 1164, 1054.
2.1. Synthesis of compounds
2.1.1. Synthesis of glycerol carbonate (GC)
In a 250 mL 3-necked round-bottomed glass flask equipped with
a magnetic stirrer, a reflux condenser and a thermometer was
placed 36.84 g (0.40 mol) of glycerol, 118 mL (1.40 mol) of dimethyl
carbonate and 1.35 g (0.024 mol) of CaO as a catalyst. The mixture
was stirred at 75 ◦C and kept subsequently under reflux for 5 h. After
reaction, the solid catalyst (CaO) was removed by filtration. Then,
the methanol and the residue of dimethyl carbonate were distilled
off at 45 ◦C under reduced pressure to give colorless liquid glycerol
carbonate (42.13 g, yield 89.19%) (reaction 1, Scheme 1).
1H NMR (400 MHz, Acetone-d6): ı 4.93–4.82(m, 1H), 4.58(t,
J = 8.4 Hz, 1H), 4.49–4.35(m, 2H), 3.89(d, J = 12.5 Hz, 1H), 3.71(d,
J = 12.4 Hz, 1H). FTIR (ꢀmax cm−1): 3402, 2931, 1784, 1186, 1084.
Supplementary Fig. S1 related to this article can be found, in the
online version, at http://dx.doi.org/10.1016/j.tca.2015.12.002.
2.1.2. Synthesis of carbonic acid
bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (CABE)
2.1.4. Synthesis of terephthalic acid
In a dry 250 mL 3-necked round-bottomed glass flask equipped
with a magnetic stirrer, a funnel with pressure-equalising tube and
a thermometer was placed 8.27 g (0.07 mol) of glycerol carbonate,
8.32 mL (0.06 mol) of triethylamine and 60 mL of anhydrous
dichloromethane as solvent. A solution of bis(trichloromethyl)
carbonate (2.97 g, 0.01 mol) in anhydrous dichloromethane
(40 mL) was added dropwise to the above solution under nitrogen
bis-(2-oxo-[1,3]dioxolan-4-ylmethyl) ester (TABE)
In a dry 100 mL 3-necked round-bottomed glass flask equipped
with a magnetic stirrer, a funnel with pressure-equalising tube and
a thermometer was placed 2.36 g (0.02 mol) of glycerol carbon-
ate, 1.61 mL (0.02 mol) of pyridine and 30 mL dry tetrahydrofuran
as solvent. A solution of terephthaloyl chloride (2.03 g, 0.01 mol)
in dry tetrahydrofuran (15 mL) was added dropwise to the above
Scheme 1. The reaction route.

78
R. Li et al. / Thermochimica Acta 624 (2016) 76–81
solution over 30 min under nitrogen atmosphere at 0 ◦C. The mix-
ture was stirred for 4 h. After reaction, pyridine hydrochloride was
removed by filtration. Then, the filtrate was evaporated under
reduced pressure, and the residue was purified by recrystallization
from dichloromethane to give the product (1.12 g, yield 30.61%)
(reaction 2, Scheme 1).
1H NMR (400 MHz, CDCl3): ı 8.12 (s, 4H), 5.12–5.04 (m, 2H),
4.69–4.61 (m, 4H), 4.58–4.51 (m, 2H), 4.46–4.40 (m, 2H) (Fig. S1(c)).
FTIR (ꢀmax cm−1): 2923, 1786, 1723, 1275, 1052, 729.
Supplementary Fig. S1 related to this article can be found, in the
online version, at http://dx.doi.org/10.1016/j.tca.2015.12.002.
2.2. TG–FTIR measurement
The TG–FTIR system was composed of a TA SDT-600 Instrument
and a Bruker Tensor 27 FTIR spectrometer. For each TG–FTIR mea-
surement, 10–20 mg sample was weighted into an open alumina
crucible. The temperature was set from ambient temperature to
600 ◦C, the heating rate of the TG furnace was 20 ◦C min−1, and high
purity (>99.999%) nitrogen gas with a flow rate of 140 mL min−1
was used as carrier gas, this flow had to be kept high enough to avoid
long residence time in the furnace and thus to prevent secondary
reactions of the volatiles [14]. The transfer line used to connect
TG and FTIR was a 1 m long stainless steel tube with an internal
diameter of 2 mm, in order to reduce the possibility of gases con-
densing along the transfer line, the temperature in the gas cell and
transfer line were set to 200 ◦C. The FTIR spectral region was set as
4000–600 cm−1, with the resolution of 4 cm−1, co-adding 16 scans
per spectrum. The experiment started only when the whole system
was stable. The experimental results of TG and FTIR were recorded
automatically by a computer. Data was processed by the software
OPUS 6.0 (Bruker Company, Germany).
2.3. Bond dissociation energy (BDE) calculation
The quantum chemistry calculations are performed using the
Gaussian 09 program. The molecular structures are optimized at the
M062X/cc-pVTZ level of theory and frequencies and energies of the
molecules are calculated at the same level of theory. All molecular
structures have no imaginary frequencies and are local minima on
the potential energy surface. Formula (1), described by Blanksby
and Ellison [15] is used to calculate the bond dissociation energy
(BDE) for a dissociation process: R − Q → R + Q.
Fig. 2. The curves of TG, DTG, Gram–Schmidt, the FTIR absorbance intensity of CO2
and H2O during the thermal pyrolysis of compounds: (a) CABE, (b) SABE and (c)
TABE.
D0(R − Q) = E0(R) + E0(Q) − E0(R − Q)
(1)
where D0(R − Q), E0(R), E0(Q) and E0(R − Q) denote to be calculated
BDE, computed electronic energies at 0 K with zero-point energy
(ZPE) corrections for R, Q and R − Q, respectively.
The weight loss of 99% of CABE took place in the temperature
range of 210–385 ◦C. The first stage of SABE with weight loss of
60% happened in the temperature range of 210–361 ◦C, which was
followed by the second weight losing stage in 361–500 ◦C, the over-
all weight loss of SABE was 97%. The first two slow weight losing
stages of TABE took place in the temperature range of 230–309 ◦C
and 309–380 ◦C, which was followed by a sharp weight loss of 52%
in 380–500 ◦C, the overall weight loss of TABE measured at 600 ◦C
was 91%. The Gram–Schmidt evolution peaks matched with the
DTG peaks very well, and the temperature of the IR absorbance
peaks coincided with that of the DTG peaks. There was a slight dis-
placement between the peaks of the DTG and the Gram–Schmidt
curves, because of the delay between the gas generation and its
detection in the FTIR equipment [16].
3. Results and discussion
Fig. 2 presents the weight loss (TG), the corresponding derivative
thermogram (DTG), Gram–Schmidt, the FTIR absorbance intensity
of CO2 and H2O curves of CABE, SABE and TABE as a function of
temperature at a heating rate of 20 ◦C min−1. The TG curves showed
the compounds weight loss during the thermal pyrolysis, and the
Gram–Schmidt curves that based on vector analysis reconstructed
the acquired interferograms, allowing the plots of the total evolved
gases detected by the spectrometer to be obtained [16]. As can be
seen in Fig. 2, the TG/DTG curves showed CABE had one weight
loss stage, and SABE had two weight loss stages, while TABE had
three weight loss stages. In other words, the major thermal pyroly-
sis reaction of CABE was finished in one step, SABE’s major thermal
pyrolysis reactions were finished in two steps, while the thermal
pyrolysis processes of TABE were mainly divided into three steps.
We used 5% weight loss temperature as a measure to study
the decomposition behavior [12]. The results of thermogravimetric
analysis of three compounds were summarized in Table 1. Accord-
ing to the data in Table 1, we can see 5% weight loss temperature
is high in the order of TABE > SABE > CABE, this result showed that

R. Li et al. / Thermochimica Acta 624 (2016) 76–81
79
Table 1
vibrational modes of the different chemical bonds and functional
groups versus the wavenumber and versus the time, and provides
a clear qualitative picture of the overall information for the evo-
lution of the FTIR spectra. Fig. 3 showed that the 3D diagrams of
these three compounds were quite different from each other. It
may mean that the thermal pyrolysis process of them should obey
different pyrolysis pathway.
Data of thermogravimetric analysis of CABE, SABE and TABE.
Compound
t5%/◦C
tmax1/◦C
tmax2/◦C
tmax3/◦C
Carbon residue rate/%
CABE
SABE
TABE
254
262
284
322
319
289
–
405
339
–
–
426
1
3
9
In order to study the volatile components released in the pyrol-
ysis process, the FTIR spectra obtained at the maxima of the
Gram–Schmidt curves (such as 322 ◦C of CABE, 321 ◦C and 424 ◦C
of SABE, 307 ◦C, 371 ◦C and 427 ◦C of TABE) had been selected.
The characteristic FTIR spectra of the gaseous products obtained
at different temperatures were shown in Fig. 4. According to
chemistry principles and some previous studies, some typical
small molecular gaseous species can be easily identified by their
the thermal decomposition temperature of CABE, SABE and TABE
gradually increased. In other words, their thermal stability was
improved. This also means a benzene ring can make a better ther-
mal stability for GC derivatives than a linear saturated hydrocarbon
or carbonate block. According to the above mentioned, CABE, SABE
and TABE behave differently during the thermal pyrolysis because
of their different chemical structures.
In this work, TG–FTIR was used to explore the dynamic decom-
position and analyze the gaseous products during the thermal
pyrolysis of compounds. The 3D diagrams corresponding to gases
evolved in the thermal pyrolysis of CABE, SABE and TABE were
shown in Fig. 3. It showed the absorbance corresponding to the
Fig. 3. The 3D diagrams corresponding to gases evolved in the thermal pyrolysis of
Fig. 4. The FTIR spectra of evolved gases from the thermal pyrolysis of compounds
compounds: (a) CABE, (b) SABE and (c) TABE.
corresponding to the Gram–Schmidt peaks: (a) CABE, (b) SABE and (c) TABE.

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R. Li et al. / Thermochimica Acta 624 (2016) 76–81
cyclic carbonate in the first stage. After that, it stepped into the sec-
ond pyrolysis stage. Compared with the former, CABE, we can see
clearly the C O (linear) at 1732 cm−1 in the FTIR spectra at 424 ◦C.
It is mainly attributed to the BDE of linear C O bond of compound
is 390.01 kJ/mol, higher than cyclic C C bond (332.03 kJ/mol). And
linear ester group existed in the form of fragment.
For the molecular structure of SABE and TABE, the middle sec-
tion of SABE’s molecular structure is 1,2-ethylidene ( CH2 CH2 ),
while the middle section of TABE’s molecular structure is
1,4-phenylene. Different molecular structure leads to different
pyrolysis process. The first two stages’ weight loss of TABE was
small, and their main gaseous product still was CO2. This is also
mainly because the C C, C O bonds cracking of cyclic carbon-
ate. When it went into the third pyrolysis stage, decomposition
rate significantly increased. From the peak position of the FTIR
spectra at 427 ◦C in Fig. 4(c), we can infer the existence of C
(linear) and phenylene, which suggests that BDE of linear C
O
O
bond of compound is 393.23 kJ/mol, higher than cyclic C C bond
(328.81 kJ/mol). And linear ester group existed in the form of frag-
ment.
4. Conclusions
The thermal pyrolysis of CABE, SABE and TABE was investigated
by TG–FTIR technology in the ambient temperature to 600 ◦C. The
results indicated that these three compounds had one, two, three
weight loss stages, respectively. They had better thermal stabil-
ity and their initial decomposition temperature was as high as
200 ◦C, which can satisfy the using demand of the electrolyte in
lithium-ion batteries. The thermogravimetric analysis showed that
5% weight loss temperature was increased in the following order:
TABE > SABE > CABE, it means the thermal stability of TABE is better.
And benzene ring was introduced to improve the thermal stability
of the GC derivatives greater than saturated hydrocarbon block. And
the TG–FTIR test also demonstrated the three GC derivatives behave
quite differently during the thermal decomposition. According to
the FTIR spectra at the maxima of the Gram–Schmidt curves and the
theoretical calculation of bond dissociation energy (BDE), the C C,
Fig. 5. The bond dissociation energy (BDE) of CABE, SABE and TABE (energy unit is
kJ/mol).
characteristic absorbance: CO2 at 2359 cm−1 and 669 cm−1; H2O
at 3400–4000 cm−1 and 1300–1900 cm−1; CO at 2175 cm−1 and
2111 cm−1. In order to further demonstrate the decomposition pro-
cess of compounds, we calculated the bond dissociation energy
(BDE) of CABE, SABE and TABE, and these data were shown in Fig. 5.
BDE value can reflect the degree of difficulty of a bond fracture. The
smaller the value is, the easier the bond cracks.
C
O bonds of cyclic carbonate fracture prior to others to generate
CO2 and other products. For CABE, part of the compound escaped
in the form of molecule in the pyrolysis process because of its’ low
boiling point. For SABE and TABE, they continued to crack, the C
O
As Fig. 4(a) showed, when CABE was heated up to 322 ◦C, there
were several small molecular gaseous products released, such as
CO2 and H2O, which meant that some bond of compound cracked.
For instance, the release of CO2 is mainly because of the cracking
of ester group, which exhibits the most intense absorbance peak
in the pyrolysis process. From the BDE data of CABE in Fig. 5, the
BDE value of cyclic carbonate is very low, therefore the correspond-
ing bonds (C C, C O) should fracture prior to others to generate
CO2 and other substances. However, we found the C O (cyclic) at
1869 cm−1 in the FTIR spectra. This may be related to a low molec-
ular weight of CABE. For the same type of ester, a low molecular
weight always means a low boiling point. So, when the tempera-
ture reaches the boiling point of compound in the pyrolysis process,
it will lead to part of the compound thermal cracking, there is also
some compound escaping in the form of molecule at the same time.
Carbon residue rate of CABE is very low, only 1%, which also partially
supported above results.
Compared with CABE, the thermal pyrolysis process of SABE is
more complicated. SABE has two major thermal pyrolysis steps.
Once SABE was heated up to 210 ◦C, the pyrolysis proceeded into
the first pyrolysis stage. As can be seen in Fig. 4(b), there were
plenty of CO2 and tiny amount of H2O in the spectra of gaseous
products at 321 ◦C. Combining with the BDE data of SABE in Fig. 5,
this indicates the main reaction is the C C, C O bonds breakage of
bond nearby cyclic carbonate fracture to produce linear ester in the
form of fragment.
Acknowledgements
This work was financially supported by the National Natural Sci-
ence Foundation of China (Grant No. 21373150). The authors would
like to thank software application engineer Xuju Jiang at Bruker
Company for her help on TG–FTIR measurement and the use of the
software OPUS 6.0.
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