Thermodynamic characteristics of triphenylantimony diacrylate

Article abstract of DOI:10.1134/S0036024412080079

The heat capacity of triphenylantimony diacrylate Ph₃Sb(O ₂CCH=CH₂)₂ was studied in an adiabatic vacuum calorimeter at 6-350 K and differential scanning calorimeter at 330-450 K. Melting was revealed at these te

Full text of DOI:10.1134/S0036024412080079

ISSN 0036ꢀ0244, Russian Journal of Physical Chemistry A, 2012, Vol. 86, No. 8, pp. 1189–1195. © Pleiades Publishing, Ltd., 2012.
Original Russian Text © I.A. Letyanina, A.V. Markin, N.N. Smirnova, A.V. Gushchin, D.V. Shashkin, 2012, published in Zhurnal Fizicheskoi Khimii, 2012, Vol. 86, No. 8,
pp. 1329–1335.
CHEMICAL THERMODYNAMICS
AND THERMOCHEMISTRY
Thermodynamic Characteristics of Triphenylantimony Diacrylate
I. A. Letyanina, A. V. Markin, N. N. Smirnova, A. V. Gushchin, and D. V. Shashkin
Lobachevskii Nizhni Novgorod State University, Nizhni Novgorod, Russia
Eꢀmail: markin@calorimetryꢀcenter.ru
Received August 25, 2011
Abstract—The heat capacity of triphenylantimony diacrylate Ph3Sb(O2CCH=CH2)2 was studied in an adiꢀ
abatic vacuum calorimeter at 6–350 K and differential scanning calorimeter at 330–450 K. Melting was
revealed at these temperatures; the melting point was estimated at 428.4 0.5 K. It was accompanied by the
partial decomposition of the substance. The lowꢀtemperature (20 K
≤
T
≤
50 K) heat capacity was treated
using the Debye theory of the heat capacity of solids and its multifractal model. The type of the structure
°
topology was determined. The standard thermodynamic functions
(
T
),
(0) of the compound in the crystal state were calculated from the obtained experimental data in
the range from to 428 K. The standard entropy of the formation of the crystalline compound
Ph3Sb(O2CCH=CH2)2 at = 298.15 K was determined.
H°(T) – H°(0), S°(T), and
C p
G°(T) – H°
T
→
0
T
Keywords: thermodynamic properties, triphenylantimony diacrylate, calorimetry.
DOI: 10.1134/S0036024412080079
INTRODUCTION
diacrylate and methylmethacrylate having increased
fungal resistance are available [11, 12].
The chemistry of the organic derivatives of antiꢀ
mony has actively developed in recent years. The comꢀ
pounds of Sb(V) that include functional groups with
nitrogen, oxygen, sulfur, halogens, and other elements
were synthesized and identified based on their structure
and composition [1–3]. The thermodynamic characꢀ
teristics of the organic derivatives of pentavalent antiꢀ
mony were not sufficiently studied [4]. We examined
the standard thermodynamic properties of pentapheꢀ
nylantimony Ph5Sb [5], tetraphenylantimony benꢀ
zophenone oximate Ph4SbONCPh2 [6], tetraphenyꢀ
lantimony acetophenone oximate Ph4SbONCPhMe
[7], triphenylantimony bis(acetophenone oximate)
Ph3Sb(ONCPhMe)2 [8], and triphenylantimony
dimethacrylate Ph3Sb(O2CCMe=CH2)2 [9], at temꢀ
peratures from 0 to 350–450 K.
The aim of this work was to study the temperature
dependence of the heat capacity of triphenylantimony
diacrylate Ph3Sb(O2CCH=CH2)2 (I) by calorimetry at
temperatures of 6–450 K; examine the peculiarities of
its melting; determine its melting point; calculate the
°
standard thermodynamic functions
(
T
),
(0) of the crystal comꢀ
to 428 K from the experimental
data; calculate its standard formation entropy at
298.15 K; determine the fractal dimensionality ; and
H°(T)–
Cp
H°
(0),
S
°
T
(
T
from
)
, and
G°(T)–H°
0
pound at
T
→
T
=
D
evaluate the type of the structure topology from the
experimental lowꢀtemperature heat capacities.
EXPERIMENTAL
Characteristics of the sample. Sample
sized by the procedure of [13]. The oxidative synthesis
was a oneꢀstage reaction of triphenylantimony, tert
butyl hydroperoxide, and an excess of acrylic acid
I was syntheꢀ
This study is a continuation of our integrated
research of the standard thermodynamic properties of
a number of pentavalent antimony compounds. Here,
we studied the thermodynamic properties of triphenyꢀ
lantimony diacrylate Ph3Sb(O2CCH=CH2)2. It conꢀ
tains two double bonds in its molecule, due to which it
can be used for polymerization filling of polymethylꢀ
methacrylate. This results in metalꢀcontaining organic
glass. The participation of both acrylate groups in
polymerization leads to crossꢀlinking in space, conꢀ
siderably decreasing the thermooxidative destruction
of the resulting polymer [10, 11]. Patents on the proꢀ
ꢀ
(1 : 1 : 9) in ether at
of air.
T = 298 K for 1 day in the presence
The compound is a white crystalline substance,
which is stable against oxygen and air moisture. It is
readily soluble in chloroform, acetone, and benzene.
The molecular mass determined cryoscopically in
benzene and the analytical data on the metal content
agree well with the calculated values. Molecular mass:
found 503, calculated for С24Н21О4Sb: 495; metal conꢀ
duction of organic glass based on triphenylantimony tent: found 25.52%, calculated 24.60%. The structure
1189

1190
LETYANINA et al.
an ironꢀrhodium resistance thermometer (
R
≅
100 )
Ω
calibrated in accordance with ITSꢀ90. The temperaꢀ
ture difference between the ampule and the adiabatic
shell was controlled with a quaternary copper–iron–
chromel thermocouple. The reliability of the calorimꢀ
C3
C2
C1
°
Cp
eter operation was checked by measuring the
of the
reference sample of extrapure copper, corundum refꢀ
erence, and benzoic acid of Kꢀ3 grade, and the meltꢀ
C15
C13
C16
C18
O1
C14
O2
ing points and enthalpies of
nꢀheptane. As a result, it
was found that the apparatuses and the measurement
C17
°
Cp
procedure gave
of the substances with an error of
2% below 15 K, 0.5% at 15–40 K, and 0.2% at
40–350 K and phase transition temperatures with an
error of 0.01 K according to ITSꢀ90.
Sb1
O4
C24
C19
C23
C22
C12
C7
The heat capacity of sample
measured with a Phoenix DSC204F1 differential
scanning calorimeter (Netzsch Ger tebau, Gerꢀ
many). The design of the DSC204F1 calorimeter and
the working procedure are described, for example, in
[16, 17]. The reliability of its operation was checked by
performing the standard calibration measurements of
the thermodynamic characteristics of melting of
I at 330–450 K was
C11
C10
C20
C21
C4
ä
O3
C5
C8
C6
C9
Fig. 1. Structure of the triphenylantimony diacrylate molꢀ
nꢀheptane, mercury, indium, tin, lead, bismuth, and
ecule.
zinc. As a result, it was found that the apparatuses and
the measurement procedure allow measurements with
an error of 0.5 K for phase transition temperatures
and 1% for transition enthalpies. The heat capacity
was determined by the ratio method. Corundum was
used as a reference sample. The procedure for deterꢀ
of the compound was determined by XRD (Fig. 1) and
1H NMR and IR spectroscopy. The corresponding
data are given in [13].
According to the analytical data, the content of the
main substance in the sample was determined (within
the experimental error) to be at least 99.0 mol %. The
impurities were not identified, but their amount
(~1 mol %) in the sample was thought to be irrelevant
to the accuracy of the thermodynamic values (taking
into account the experimental error of the calorimetꢀ
ric methods used).
°
Cp
mining
from differential scanning calorimetry
(DSC) data is described in detail in [8, 16] and
Netzsch Software Proteus.
°
Cp
The error of
determined by this procedure was
not worse than 2%. The thermophysical measureꢀ
ments were carried out at an average rate of heating of
the ampule with the substance of 5 K/min under
argon.
The thermodynamic stability of I was studied with
a TG209F1 (Netzsch Gerätebau, Germany) thermoꢀ
microbalance. A pronounced mass loss was observed
at
T = 430 K due to the sample decomposition and
increased to 2% when the temperature increased by
10 K. The triphenylantimony diacrylate sample is thus
thermally stable to 430 K in inert media.
RESULTS AND DISCUSSION
The heat capacity of
method at 6–350 K (Table 1) and DSC methods at
330–450 K. The masses of the sample placed in the
calorimetric ampules were 0.6279
measurements and 0.025
I was studied by the AVC
Apparatuses and measurement procedure. To study
the temperature dependence of the heat capacity
10–3 kg for AVC
°
Cp
= f(T) at 6–350 K we used a completely automated
×
10–3 kg for DSC. In two
adiabatic vacuum calorimeter BKTꢀ3 (AVC) designed
and manufactured at Termis AOZT (Mendeleevo,
Moscow region). Liquid helium and nitrogen refrigerꢀ
ants were used. An ampule with the substance was
filled with dry helium (heatꢀexchange gas) to a presꢀ
sure of 40 kPa at room temperature. The design of the
calorimeter and the procedure were similar to those
described in [14, 15]. The calorimetric ampule was a
thinꢀwall cylindrical vessel of titanium with a volume
×
°
Cp
series of AVC measurements, 176 experimental valꢀ
ues were obtained. The heat capacity of the compound
was 25–60% of the total heat capacity of the caloriꢀ
metric ampule with the substance in all experiments.
°
Cp
The experimental
points were smoothed in the
form of power and semiꢀlogarithmic polynomials; the
corresponding coefficients were calculated by the least
of 1.5
×
10⎯6 m3. The temperature was measured with squares method using special programs.
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
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THERMODYNAMIC CHARACTERISTICS OF TRIPHENYLANTIMONY DIACRYLATE
1191
Table 1. Experimental heat capacities (J/(K mol)) of triphenylantimony diacrylate Ph3Sb(O2CCH=CH2)2 (
M
= 495.18 g/mol)
°
Cp
°
Cp
°
Cp
°
Cp
°
Cp
°
Cp
T
, K
T, K
T, K
T, K
T, K
T
, K
Series 1
22.79
23.60
24.50
25.40
26.27
27.08
27.88
28.68
29.51
30.32
31.12
31.91
32.68
33.56
34.64
35.52
36.72
37.91
39.10
40.16
41.25
42.28
43.30
44.35
45.49
46.58
47.60
48.54
49.71
50.99
46.42
48.89
51.62
54.35
56.96
59.40
61.80
64.25
66.79
69.30
71.76
74.16
76.43
79.02
82.24
84.63
88.09
91.36
94.42
97.40
100.2
103.0
105.4
108.0
110.9
113.5
116.0
118.5
121.2
124.4
52.16
53.20
54.25
55.27
56.30
57.35
58.40
59.68
60.90
62.05
63.26
64.49
65.69
66.98
68.04
69.34
70.60
71.80
73.07
74.19
75.39
76.75
77.65
78.62
79.75
81.00
82.29
84.03
86.03
88.12
127.3
129.9
132.5
135.0
137.5
139.9
142.2
145.1
147.7
150.1
152.7
155.2
158.0
160.6
162.9
165.7
168.6
171.3
173.9
176.2
178.6
181.1
182.6
184.4
186.2
188.5
190.5
193.4
196.6
200.3
90.24
204.0
165.89
169.45
173.01
176.57
180.12
183.68
186.80
189.80
192.45
195.80
199.58
203.00
206.47
209.62
213.17
216.73
220.27
223.82
226.95
230.04
233.56
237.08
240.60
244.11
247.61
251.10
254.58
258.05
261.52
264.98
324.8
329.2
334.4
339.0
344.3
348.9
353.6
356.9
360.4
365.0
370.2
375.3
379.4
384.1
388.5
392.9
397.3
402.3
406.8
412.0
417.2
421.5
426.3
431.4
436.6
441.3
447.2
452.4
457.9
462.7
268.43
271.87
275.31
278.73
282.12
285.52
288.91
292.10
294.74
297.62
300.43
303.28
306.59
309.89
313.17
316.09
319.01
321.75
324.98
328.18
331.37
334.53
337.68
340.80
343.88
346.96
349.98
353.01
467.9
472.3
477.1
482.2
488.0
491.7
496.5
501.2
505.3
509.3
513.3
518.0
522.6
528.1
533.3
538.0
542.4
546.2
552.0
556.6
561.1
566.1
572.1
577.5
582.5
588.7
594.0
600.7
6.13
6.81
2.72
4.01
5.21
6.43
7.58
8.71
9.92
Series 2
80.11
82.35
186.9
190.4
194.6
198.3
201.6
205.5
209.2
212.8
217.5
221.4
226.3
232.7
239.1
245.3
251.1
256.8
261.5
266.6
272.2
277.7
283.0
288.1
293.6
299.7
304.3
309.9
314.6
319.7
7.45
8.04
84.70
8.60
86.85
9.12
88.96
9.64
91.20
10.12
10.59
11.04
11.48
11.92
12.49
13.18
13.71
14.41
15.10
15.82
16.53
16.94
17.40
17.88
18.32
18.80
19.26
19.73
20.24
20.97
21.86
10.9
93.41
12.1
95.52
13.3
97.88
14.3
100.06
102.73
106.26
109.79
113.33
116.67
120.02
122.87
126.01
129.56
133.11
136.65
140.20
143.75
148.13
151.69
155.24
158.79
162.34
15.4
16.9
19.0
20.5
22.3
24.40
26.57
28.61
29.80
31.02
32.31
33.69
34.99
36.42
37.83
39.31
41.18
43.67
The experimental heat capacities of
I
and the
°
Cp
The mean square deviation of the experimental
°
smoothed curve
heat capacity of
= f
(
T
)
are presented in Fig. 2. The
increases smoothly with temperature
= 390 K. Then
it increases abruptly with temperature rising because
crystals start melting. The melting is accompanied by
Cp
I
°
points from the corresponding smoothed curve
=
Cp
f(T) was up to 0.4% at 20–90 K, 0.2% at 80–350 K,
rising and has no singularities below
Т
and 0.5% at 330–428 K. The molar mass of the comꢀ
pound was calculated using the IUPAC table of atomic
weights [18].
I
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1192
LETYANINA et al.
Cp°, J/(K mol)
1000
800
600
400
200
0
100
D
D'
50
C
E
B
А
0
20
, K
40
T
B
100
200
300
400
500
, K
T
°
C p
Fig. 2. Temperature dependence of the heat capacity of triphenylantimony diacrylate: AB are the
lation (3), BC is crystal, and CDD'E is the apparent heat capacity in the range of melting points.
values obtained by extrapoꢀ
the decomposition of the substance, preventing the where
k
is Boltzmann’s constant,
atoms in a molecule, + 1) is the gamma function,
+ 1) is the Riemann function, and Θmax is the
characteristic temperature. For a particular solid,
N is the number of
γ
(D
measurement of its heat capacity in the liquid state
and evaluation of the thermodynamic characteristics
of the melting. The melting point of the compound
ξ
(D
3D
(D
+ 1)kN
γ
(D
+ 1)
ξ
(D
+ 1)(1/Θmax)D =
A
is conꢀ
°
Tfus
was
= 428.4 0.5 K as evaluated by the standard
stant. Then (1) can be recorded as
Netzsch Software Proteus procedure. The substance
was thus in the crystalline state under the conditions of
the calorimetric experiment (Fig. 2, ABC region) and
then decomposed. According to the thermogravimetꢀ
ric analysis data, the thermal destruction of the comꢀ
pound starts at 430 K, which can explain the behavior
ln = ln Dln
C
A
+
T.
(2)
v
°
values can be set
For
T
< 50 K, the experimental
Cp
without a pronounced error. Using the corꢀ
equal to
C
v
responding experimental heat capacities for 20–50 K
and Eq. (2), we can obtain the fractal dimensionality
D
The error of these values was 0.6%. According to
Tarasov’s theory of the heat capacity of solids [21, 22],
°
Cp
of the dependence of
on Т (D'E region). This
. For I, D was evaluated at 1.4 and Θmax at 251.1 K.
behavior is also characteristic for the organic derivaꢀ
tives of pentavalent antimony that we studied earlier
Ph5Sb [5], Ph4SbONCPh2 [6], Ph4SbONCPhMe [7],
and Ph3Sb(O2CCMe=CH2)2 [9].
D
= 1, 2, and 3 corresponds to solids with a chain, layꢀ
ered, and spatial structure, respectively. The value
obtained in this study points to the chainꢀlayered
topology of structure . This conclusion is in good
D
It was interesting to calculate the fractal dimenꢀ
D
sionality
mental lowꢀtemperature heat capacities. The fractal
dimensionality is the exponent at the temperature in
the main equation of the fractal model of the treatꢀ
ment of the lowꢀtemperature heat capacity. The valꢀ
D [19, 20] for the substance from the experiꢀ
agreement with Xꢀray diffraction data [13]. Figure 3
shows a fragment of a oneꢀdimensional chain of
Ph3Sb(O2CCH=CH2)2 molecules observed in crysꢀ
tals. The organic derivatives of pentavalent antimony
studied earlier [5–9] also have a chainꢀlayered strucꢀ
ture topology.
D
D
ues allow us to draw certain conclusions about the type
of structure topology of solids and can be derived from
the plot of ln
C
vs ln
T
. In particular, this follows from
Standard thermodynamic functions. To calculate
v
the standard thermodynamic functions (Table 2), the
С
= 3
D(D
+ 1)kN
γ(
D
+ 1) + 1)(
ξ
(
D
T/
Θmax)D, (1)
temperature dependence of the heat capacity of I was
v
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
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THERMODYNAMIC CHARACTERISTICS OF TRIPHENYLANTIMONY DIACRYLATE
1193
O1
Sb1
O3
C5
C6
C3
C2
O1
Sb1
O3
C5
C6
C3
C2
O1
Sb1
O3
Fig. 3. Fragment of the chain of Ph Sb(O CCH=CH ) molecules in crystal.
3
2
2 2
extrapolated from 6 to 0 K using the Debye’s heat error of the calculated functions was set at 2% for Т <
capacity function of solids
15 K, 0.6% for 15–40 K, 0.3% for 40–350 K, and
2.0% for 350–428 K.
°
Cp
=
nD(ΘD
/Т),
(3)
The standard formation entropy of crystal
calculated using the absolute entropy of (Table 2) and
the simple substances carbon [25], hydrogen [26],
oxygen [26], and antimony [27]: Δf = –1383.5
= 298.15 K. The result corresponds
I was
I
where D is the Debye’s heat capacity function,
the number of the degrees of freedom, and ΘD
66.0 K is the characteristic Debye temperature. With
these parameters, Eq. (3) reproduces the experimental
n
= 6 is
=
S°
5.4 J/(K mol) at
Т
to the equation
°
heat capacities in the range 6–14 K with an error of
Cp
1.8%. For the range 0–6 K, we admitted that (3)
reproduced the heat capacities with the same error.
24С(gr) + 10.5H2(g) + Sb(cr) + 2O2(g)
Ph3Sb(O2ССH=CH2)2(cr),
(4)
→
The procedure for calculating the enthalpy
H°(T) –
H°(0), entropy
S°(T), and Gibbs function
G°(T) –
H°(0) is described in detail in [23, 24]. The where gr is graphite, g is gas, and cr is crystal.
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
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No. 8 2012

1194
LETYANINA et al.
Table 2. Standard thermodynamic functions of triphenylantimony diacrylate Ph3Sb(O2CCH=CH2)2 (
M
= 495.18 g/mol)
°
Cp
T, K
(T), J/(K mol)
H
°
(
T
) –
H°(0), kJ/mol
S°
(T
), J/(K mol)
–[
G
°
(
T
) – H°(0)], kJ/mol
5
10
1.68
10.7
0.00210
0.0303
0.1160
0.2727
0.5013
0.8045
1.184
0.562
4.10
0.000703
0.0107
0.04712
0.1230
0.2468
0.4239
0.6575
0.9506
1.304
1.719
2.731
3.985
5.479
7.205
9.158
11.33
13.72
16.33
19.15
22.17
25.39
28.81
32.43
36.23
40.23
44.41
48.77
53.31
58.03
62.93
68.01
73.26
78.69
84.28
88.97
90.05
95.99
15
24.18
38.48
53.05
68.34
83.24
96.87
109.7
122.1
145.7
167.3
186.9
203.4
221.2
239.4
256.7
272.9
288.0
302.4
316.3
330.1
343.9
357.5
371.0
384.2
397.5
411.4
425.8
440.3
455.0
469.6
484.1
498.7
510.5
513.3
528.1
543.3
559.3
576.2
593
10.88
19.78
29.92
40.95
52.61
64.63
76.79
88.99
113.4
137.5
161.1
184.1
206.4
228.4
249.9
271.1
291.9
312.3
332.3
351.8
371.1
390.1
408.7
427.2
445.3
463.3
481.1
498.8
516.4
533.8
551.1
568.4
582.4
585.5
602.6
619.6
636.6
653.5
670
20
25
30
35
40
1.635
2.151
45
50
2.731
4.072
60
70
5.638
7.411
80
90
9.362
100
110
120
130
140
150
160
170
180
190
200
210
220
230
240
250
260
270
280
290
298.15
300
310
320
330
340
350
360
370
380
390
400
410
428
11.48
13.79
16.27
18.92
21.72
24.68
27.77
31.00
34.37
37.88
41.52
45.30
49.21
53.25
57.44
61.77
66.24
70.86
75.63
80.55
84.66
85.61
90.81
96.17
101.7
107.4
113
102.1
108.4
114.8
121
609
625
119
125
687
704
128
135
641
657
132
138
721
738
142
150
673
689
145
152
755
772
157
165
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