J Therm Anal Calorim (2013) 111:943–949

DOI 10.1007/s10973-012-2384-5

Study on thermodynamic properties of glyphosate

by oxygen-bomb calorimeter and DSC
Xin Yu • Cai-Rong Zhou • Xue-Wei Han •

Guo-Peng Li

Received: 24 October 2011 / Accepted: 5 March 2012 / Published online: 28 March 2012
Ó Akadémiai Kiadó, Budapest, Hungary 2012

Abstract The combustion enthalpy of glyphosate was R The universal gas constant, 8.314 J mol-1 K-1
determined by XRY-1C oxygen-bomb calorimeter at a T Kelvin temperature, K
constant volume. The standard mole combustion enthalpy U Energy of thermodynamics, kJ mol-1
and the standard mole formation enthalpy have been cal-
Greek symbol
culated to be -1702.19 and -1478.36 kJ mol-1, respec-
u DSC output signal
tively. For testing the reliability of instrument, glycine and
naphthalene were used as reference materials by comparing Superscript
the measured values with the literature values, the absolute h Standard state
error and relative error are 2.58 kJ mol-1 and 0.26 % for
Subscripts
glycine, respectively, and these of naphthalene are
c Combustion
4.08 kJ mol-1 and 0.08 %, respectively. Moreover, the
f Reaction
constant-pressure heat capacities cp of glyphosate were
m Material, or melting enthalpy
measured by differential scanning calorimetry in the tem-
p Constant pressure
perature range 303.15–365.15 K, and the relationship
s Sample
between cp and temperature was established. These related
std Standard sample
studies can provide a thermodynamic basis for their further
v Constant volume
application.
e Zero line of DSC
Keywords Glyphosate  Standard mole combustion
enthalpy  The constant-pressure heat capacity Introduction

List of symbols Glyphosate [N-(phosphonomethyl)glycine, CAS RN

c The heat capacity of calorimeter, J K-1 or the
constant-pressure heat capacity of sample,
J g-1 K-1
DSC DSC signal value for sample at temperature, mW
H Enthalpy, kJ mol-1 or J mol-1
m Mass of sample, mg
n Molar number
Q Quantity of heat, J mol-1 or kJ mol-1
X. Yu  C.-R. Zhou (&)  X.-W. Han  G.-P. Li
School of Chemical Engineering and Energy, Zhengzhou
University, Zhengzhou 450001, China
e-mail: zhoucairong@zzu.edu.cn
1071-83-6] is a phosphonic and amino acid group-con-
taining chemical that constitutes an important category of
pesticides, formula of which is (HO)2P(O)CH2NHCH2-
COOH, and the relative molecular mass is 169.07. Pure
glyphosate has the characteristics of white solid, non vol-
atile, and odorless. Glyphosate has been widely used as a
herbicide in many countries including China because it has
such characteristics and properties of inhibiting the enzyme
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase
which produces EPSP from shikimate-3-phosphate and
phosphoenolpyruvate in the shikimic acid pathway, and
EPSP synthase inhibition leads to a depletion of the aro-
matic amino acids tryptophan, tyrosine, and phenylalanine,

123
944
all needed for protein synthesis or for biosynthetic path-
ways leading to growth [1, 2]. To study the thermodynamic
actions, thermal decomposition and the non-isothermal
decomposition kinetics of glyphosate had been studied [3],
but some thermodynamic properties such as the standard
mole combustion enthalpy, the standard mole formation
enthalpy, and the specific heat capacity have not been
reported by now. The thermodynamics basic date is helpful
for the development of new synthesis method, engineering
design, and industry production of glyphosate. In this
study, we use XRY-1C oxygen-bomb calorimeter (XBC)
and differential scanning calorimetry (DSC) analyses to
demonstrate that glyphosate has the thermodynamic data of
the standard mole combustion enthalpy, standard mole
formation enthalpy, as well as the specific heat capacities.
Experimental
Materials and apparatus
The crystals both 95 % glyphosate and 97.5 % glycine
(provided by a chemical factory in Zhejiang Province,
China) were purified by recrystallization with pure organic
solvents, respectively. Putting the crystals in absolute
alcohol for three times, the purity of over 99.5 % can be
obtained (mass fractions) by high performance liquid
chromatography. Absolute and guaranteed reagent grade
(99.8 %) ethanol from Tianjin Deen chemical reagent
company, China was used. Benzoic acid and naphthalene
purchased from the Shanghai chemical reagent company,
China were used as delivered without further purification.
The purity of all the chemicals is more than or equal to
99.5 % (mass fractions). a-Al2O3 powder is provided as
DSC standard material by the Japan Shimadzu Co. Indium
(purity = 99.99 %, Tm = 429.78 K, DmH = 28.45 J g-1)
and zinc (purity = 99.99 %, Tm = 419.58 K, DmH =
100.50 J g-1) used as materials calibrated are also provided
by Japan Shimadzu Co.
A precise adiabatic oxygen bomb calorimeter (XRY-1C,
shanghai changji geology apparatus Ltd., R. P. China, mea-
suring accuracy 0.001 ± 0.0005 °C), FA1004 electronic
precision balance is provided by the shanghai Precision
Instrument Company, minimum weighing unit is 0.1 ?
0.05 mg. DSC-60 DSC and DTG-60 thermogravimetric–
differential scanning calorimetry (TG–DTA) including
TA-60WS Collection Monitor software is used as data acqui-
sition and inline processing are provided by the Shimadzu
Company in Japan. The error of electronic balance and mic-
rothermometer are, respectively, 0.01 ± 0.005 mg and 0.01 ±
0.005 °C. SPN-500 nitrogen generator (the HP analysis tech-
nology research institute in Beijing, China) is used to provide
nitrogen atmosphere for the experiment of thermal analysis.
123
X. Yu et al.
Experimental procedure
Procedure of combustion enthalpy measured
A high-precision automatic adiabatic calorimeter was used
to measure the combustion heat capacity. The principle and
structure of the adiabatic calorimeter were described in
detail elsewhere [4–7]. Briefly, there is a sample cell, a
platinum resistance thermometer, an electric heater, an
inner and outer adiabatic shield, and two sets of differential
thermocouples, and a high vacuum can for the calorimeter.
The samples were cooled by liquid water, and the sample
cell was made of gold-plated copper and had an internal
volume of about 5 cm3. To promote heat distribution, six
stainless steel vanes of 0.2-mm thickness were put into the
inner water tank in which there is 3,200 mL water. The
platinum resistance thermometer soldered at the bottom of
the sample cell was inserted into the copper sheath. The
metal Ni–Cr igniting wire was wound on the side surface of
sample in the cell. Two sets of six-junction chromel–copel
thermocouples, and controlled by two sets of DWT-702
precision temperature controller (manufactured by Shang-
hai No. 6 Automated Instrumentation Works) are used to
monitor the temperature differences between the sample
cell and the inner shield, and between the inner and outer
shields. The electrical energy introduced into the sample
cell and the equilibrium temperature of the cell after the
energy input were automatically picked up by the use of
data acquisition, and processed on line by a computer. The
heat-capacity values measured of the reference standard
material (naphthalene, CAS RN 91-20-3) were made over
the same temperature range as that of the measurement of
experimental sample to verify the reliability of the calo-
rimeter. The deviation of our experimental results from the
recommended value [8] of the former National Bureau of
Standards lies within ±0.2 %, in the whole experimental
temperature range.
The energy equivalent of the adiabatic calorimetry
instrument was determined by the combustion enthalpy of
standard sample (usually, that is benzoic acid, CAS EN
65-85-0, Qv = -26,460 J g-1 in the literature [5]). After
the benzoic acid was accurately quantified (about 1 g) by
an electronic precision balance, it was pressed into circular
flake by a hand driven tablet machine, the piece pressed
was placed in the gold-plated copper sample cell, and a
10-mm length of metal igniting wire was bound on a
couple of electrode, and made it to contact with the sample
surface. A 10-mL volume of water was added to the bomb,
which was then sealed by the lid, pressure tested, and
purged with oxygen. The bomb was then charged with
oxygen to a pressure p = 3.00 ± 0.50 MPa and assembled
in the calorimeter can, which was fitted with a stirrer,
internal heater, and lid. A measured quantity of water
Study on thermodynamic properties of glyphosate 945

(3,200 mL water at about 298.15 K) was added to the can expressed by Eq. 1 [4, 5] if the specimen is completely
to just cover the bomb. Stir was opened before the appa- combusted.
ratus records automatically. After 5 min, the metal wire DH ¼ Qp ¼ DU þ DnRT ¼ Qv þ DnRT ð1Þ
fuse was ignited. At the same time, because the sample
measured was burning, the temperature was rising rapidly. where Dn is the mole variation amount of gaseous sub-
Temperature readings were taken at 5-s intervals before stances between the reactants and products in a combustion
and after the ignition. The test could be stopped automat- reaction, R is the universal gas constant
ically after the temperature has reached the most high (R = 8.314 J mol K), and T is Kelvin temperature of
point, and continued for 10 min. These values of related reaction.
temperature and time were given by data acquisition, and When the specimen is combusted completely, the tem-
the energy of combustion of sample measured could be perature of both the XBC and the surrounding medium
calculated by the computer software. Similar method was (usually, that is 3,200 mL water in the experiment) can be
used to determine the combustion enthalpy of other risen. The temperature variation value (DT) can be deter-
solid chemicals such as glyphosate and glycine (CAS RN mined by calorimetry. According to energy balance prin-
56-40-6). ciple, we have
mQV ¼ ð3200cwater þ cÞDT þ Qf ð2Þ

Procedure of the constant-pressure heat capacity measured where m is the amount of the sample, g; cwater is the spe-
cific heat capacity of water, 4.18 J g-1 K-1; c is the heat
The experimental measurements were carried out on capacity of calorimeter, J K-1; Qf is an attached heat
apparatus DSC-60 simultaneously connected to a Lenovo quantity generated by air which is in the calorimeter, it is
computer under same experimental conditions, the heating 0 J at the ideal state. Qv is the quantity of heat released in a
rates 5 K min-1 from ambient temperature to a specified combustion reaction which can be obtained by Eq. 2 after
test temperature in nitrogen atmosphere (the dynamic dry the heat capacity of oxygen bomb calorimeter (c) is
nitrogen gas, 30 mL min-1) which came from SPN-500 determined.
nitrogen generator. Calibration of this instrument was According to Hess’ law, the standard mole combustion
performed with the standard samples of both indium and enthalpy of sample can be calculated by Eq. 3.
zinc known temperatures and enthalpies of melting. The Dc HmH ð298:15KÞ ¼ DHr þ Dc Hm ðTÞ þ DHf
metals possess over 99.99 % purity. The purity of organic ¼ DHr þ Qv þ DnRT þ DHf ð3Þ
compounds is over 99.5 %. The mass of each sample was
about 3–5 mg. Sealed aluminum crucibles were used for where DHr is the enthalpy change value of reactants from
DSC and TG–DTA experimental analysis into which could 298.15 K to the measured temperature, DHf is the enthalpy
be put into a sample measured or a-Al2O3 used as reference change value of products from the measured temperature to
compound. The DSC and TG–DTA curves were obtained 298.15 K. That is
under the same conditions overlapping with each other, ZT X
indicating that the reproducibility of test was satisfactory.  
DHr ¼ aj cp;j reactant
dT; DHf
298:15
Z
298:15
X
Results and discussions 
¼ bk cp;k product
dT ð4a; bÞ
T
Determination of the standard mole combustion
enthalpy when T = 298.15 K, DHr and DHf is 0.

Principle of determination of combustion enthalpy The standard mole combustion enthalpy of glyphosate

The thermodynamic process is at constant volume in
oxygen bomb calorimeter. According to the first law of
thermodynamics, the energy change value of sample is
equal to the quantity of heat released in the process of
compound combustion, that is DU = Qv. On the other
hand, a combustion enthalpy (DH) is equal to Qp, when
thermodynamic change process is at constant pressure.
Therefore, the relationship between DH and Qv can be
The standard mole combustion enthalpy of glyphosate was
determined by the detailed procedure mentioned above.
Freshly circular sheet solid samples were prepared for
determining the combustion heat of substances. Smooth
curves (see Fig. 1) were fitted to the pre and after-period
temperatures and the corrected temperature rise was cal-
culated by means of data processing software in the oxygen
bomb calorimeter working station, in which DT was the

123
946 X. Yu et al.

28
principle, the standard molar combustion enthalpy of pure
substance is given by Eq. 3.
The individual values of both the standard molar com-
h
27 bustion enthalpy Dc Hm are listed in Table 2. The reaction
equations of combustion of glyphosate can be written by
Eq. 5:
T/°C

26
15 1
C3 H8 NO5 PðsÞ þ O2 ðgÞ ! 3CO2 ðgÞ þ N2 ðgÞ
4 2 ð5Þ
Glyphosate 5
25 Glycine þ H2 OðlÞ þ H3 PO4 ðcryÞ
Naphthalene 2
In which, the combustion product of phosphorus element is
24 usually appointed to be H3PO4 (cry) [9]. The mole
0 5 10 15 20
t/min variation amount of gaseous substances (Dn) between the
reactants and products is -0.25 in Eq. 5. Such that, the
Fig. 1 Curves of temperature tendency versus time value of standard mole combustion enthalpy of glyphosate
could be gotten to be -1702.19 kJ mol-1 by Eqs. 2, 3. The
results are shown in Table 2.
Table 1 The heat capacity of XPY-1C calorimeter Glycine and naphthalene were used as the reference
materials to confirm the experimental data’s authenticity.
Sample m/g (3200cwater ? c)/ c/ caverage/
J K-1 J K-1 J K-1 The results of measurement are given in Table 2. The stan-
dard mole combustion enthalpies are -975.68 and
Benzoic 1.0145 15,298 1,922 1917.5 -5157.98 kJ mol-1 for glycine and naphthalene, respec-
acid 0.9952 15,309 1,933 tively. By comparing with literature values (-973.1 kJ mol-1
1.0015 15,279 1,903 [10] and -5153.9 kJ mol-1 [7]), the absolute error and relative
0.9951 15,248 1,872 error are 2.58 kJ mol-1 and 0.26 % for glycine, respectively.
0.9953 15,270 1,894 And those of naphthalene are 4.08 kJ mol-1 and 0.08 %,
1.0126 15,357 1,981 respectively. These values indicate that the determination
result of glyphosate is reliable.

ordinate that encloses equal areas above and below the

reaction curve. The energy equivalent of the calorimeter
c could be determined with a standard reference sample of
benzoic acid, and it is that its value was calculated to be
1904.7 J K-1 from six experimental dates of benzoic acid
by Eq. 2 (see Table 1). On the basis of thermodynamics’
The standard mole formation of glyphosate
The standard mole formation of glyphosate was calculated
by Hess’ law [11] to be -1478.36 kJ mol-1 according to
the thermo-chemical Eq. 6:

Table 2 The standard combustion of samples

Compound m/g DT/K DcUm/kJ mol-1 DcHmh /kJ mol-1 Average/kJ mol-1 Error/%

Glyphosate 0.9112 0.598 -1696.97 -1697.89 -1702.19 –

0.8904 0.586 -1701.77 -1702.74
0.8862 0.581 -1695.24 -1696.2
0.8946 0.592 -1711.12 -1711.91
Glycine 1.0369 0.881 -975.5 -974.93 -975.68 0.26
1.0508 0.896 -978.98 -978.43
1.0124 0.856 -970.75 -970.18
0.9539 0.814 -979.74 -979.19
Naphthalene 1.0175 2.679 -5161.54 -5166.57 -5157.98 0.08
1.006 2.643 -5150.39 -5155.39
0.9968 2.613 -5138.93 -5144.01
1.0032 2.641 -5160.86 -5165.95

123
Study on thermodynamic properties of glyphosate 947

Df Hmh ðC3 H8 NO5 P; sÞ ¼ 3Df Hmh ðCO2 ; gÞ Table 3 Experimental values and literature values of specific for
a-Al2O3
þ 5=2Df Hmh ðH2 O; lÞ þ Df Hmh ðH3 PO4 ; cryÞ
T/K cp/J g-1 K-1 Error/%
 Dc Hmh ðC3 H8 NO5 P; sÞ ð6Þ
Experimental value Literature value [7]
In which, Df Hmh ðCO2 ; gÞ ¼ ð393:51ÞkJ mol1 ; Df Hmh 308.15 0.8075 0.7975 1.25
ðH2 O; lÞ ¼ ð285:83Þ kJ mol1 ; Df Hmh ðH3 PO4 ; cryÞ ¼ 313.15 0.8130 0.8089 0.51
ð1284:40Þ kJ mol1 [10, 12]. 318.15 0.8319 0.8215 1.27
323.15 0.8400 0.8326 0.89
Determination of specific heat capacity 328.15 0.8435 0.8434 0.01
333.15 0.8497 0.8536 0.46
Principle of determination 338.15 0.8646 0.8635 0.13
343.15 0.8700 0.8729 0.33
Differential scanning calorimetery (DSC) is a heat analysis 348.15 0.8790 0.8820 0.34
method which studies materials’ thermodynamic properties 353.15 0.8883 0.8907 0.27
according the measured energy differential by temperature 358.15 0.8944 0.8990 0.51
scanning under the control of linear temperature pro-
363.15 0.8960 0.9071 1.22
gramme. For example, it can be used for the determination
ARD 0.60
of heat capacity of materials [13–16], it can be used on the
research of materials’ thermal stability [17–19], and
investigation on the crystallization behavior of some sub-
stances [20]. According to the first law of thermodynamics, them; DSCs, DSCs, e, DSCstd, and DSCstd, e are the scan-
when the sample is under linear temperature programming, ning output signals of heat flow rate of the tested sample,
heat flow from the sample is measured by DSC. The corresponding empty crucible, standard crucible, and cor-
relationship between a constant-pressure heat capacity and responding empty crucible, respectively.
heat absorbed can be represented by Eq. 7,
dH 1 Constant-pressure heat capacity of glyphosate
cp ¼  ð7Þ
dT m
For the sake of determining the reliability of the instru-
In practical, it is difficult to measure the value of dH/
ment, a reliability verification test of measurement was
dT precisely because of the limitation of an instrument
done by taking powdered alumina (a-Al2O3) as a standard
itself and the operating conditions. So, we used an indirect
reference material, the constant-pressure heat capacity was
method to get the value of the constant-pressure heat
measured at least three times. Compared to the value of the
capacity of the sample by the instrument of DSC, The
literature [12], the average relative error of a-Al2O3 is not
constant-pressure heat capacity of the sample determined is
more than 1 % (see Table 3). Relationship of the constant-
accomplished according to three-step technique process at
pressure heat capacity of glyphosate changing with tem-
a linear heating rate by DSC-60, That is
perature was studied at constant pressure and the results are
First, it is necessary that empty sample crucible is shown in Table 4. The results indicate that the higher
scanned to get DSC sign of zero line. temperature is, the bigger the constant-pressure heat
Then, zinc or indium used as the substance of calibration capacity is for glyphosate at solid phase state. Figure 2
is scanned to obtain DSC sign of either standard sample. shows the relationships between the constant-pressure heat
Finally, to scan sample crucible which contains the specific and temperature for the solid glyphosate, and Eq. 9
sample measured. are obtained with the least square method.
The experiments were done for each of them at least five cP ¼ 0:0038T
 
times. Thus, the constant-pressure heat capacity Cp of the  0:06786 J g1 K1 ðT ¼ 303:15  365:15 KÞ
substance can be calculated by Eq. 8 [7]: ð9Þ
mstd DSCs  DSCs;e
cp;s ¼   cp;std ð8Þ Where the multiple correlation coefficient R is 0.9987, the
ms DSCstd  DSCstd;e
standard deviation SD is 0.00412. Comparing the values
where cp, s and cp, std are the constant-pressure heat calculated by Eq. 9 with the experimental values examined,
capacities of both the tested sample and the standard the relative deviation (RD) and average relative deviation
sample, respectively; ms and mstd are, respectively, mass of (ARD) are listed in Table 4. And ARD is defined as:

123
948 X. Yu et al.

Table 4 The specific heat capacity of glyphosate

6 50
T/K cp/J g-1 K-1 Error/%
Experimental value Calculation value
4

DTA/µV
303.15 1.0817 1.0842* 0.23

TG/mg
0
308.15 1.1015 1.1032 0.15
313.15 1.1143 1.1222 0.71 2
318.15 1.1410 1.1412 0.01
323.15 1.1640 1.1602 0.33 –50
328.15 1.1829 1.1792 0.32 0

333.15 1.1984 1.1982* 0.02

338.15 1.2145 1.2172* 0.22 0 100 200 300 400 500
343.15 1.2307 1.2362 0.44 T/°C
348.15 1.2568 1.2552 0.13
Fig. 3 DTA and TG curves of glyphosate
353.15 1.2754 1.2742 0.10
358.15 1.2902 1.2932 0.23
363.15 1.3087 1.3122 0.27 result of thermal analysis in Fig. 3 shows that glyphosate
365.15 1.3152 1.3198* 0.35 start to be decomposed at 484.15 K, and the mass loss of it
ARD 0.25
was about 41.9 % (from 484.15 to 773.15 K) in nitrogen
atmosphere.
 
1 X cpi  cpi ;cal 
ARD ¼ ð10Þ Conclusions
n Cpi
The results show that there is a good agreement between The value of standard mole combustion enthalpy of gly-
the experimental and calculated results for the specific heat phosate was measured using XRY-1C calorimeter to be -
capacity of glyphosate; it also indicates to be believable for 1702.19 kJ mol-1. Using DSC (differential scanning
them according to RD (to be 0.23, 0.02, 0.22, and 0.35 %, calorimetric), the thermodynamic basic data, such as the
respectively) of four experimental data (at 303.15, 333.15, constant-pressure heat capacity, was examined. Relation-
338.15, and 365.15 K) marked with an asterisk (*) in ship between the constant-pressure heat capacity of solid
Table 4 and in Fig. 2 which did not participate in the glyphosate and temperature was accomplished by DSC.
program regression. Using DTG-60 TG–DTA, thermal stability of glyphosate
Meanwhile, thermal stability of glyphosate was inves- was investigated, and heat decomposed temperature is
tigated by DTG-60 TG–DTA. The measurement was made 484.15 K. So, these thermodynamic basic data are avail-
under fixed conditions of which was the constant heating able for the exploiting new synthesis method, engineering
rate of 10 min-1 and under nitrogen (30 mL min-1). The design, and industry production of glyphosate.

1.35

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