Saturation vapor pressures and vaporization enthalpies of esters of ethylene glycol and lower carboxylic acids

Article abstract of DOI:10.1134/S0036024411100116

Saturation vapor pressures and vaporization enthalpies of ethylene glycol and C₁-C₅ carboxylic acid disubstituted esters of normal and branched structures are determined by the transfer method in the tem-perature range of 295 to 327 K. Dependences of vaporization enthalpies versus the number of carbon atoms in a molecule and the retention indices are determined. An analysis of existing calculation schemes is given to help predict the vaporization enthalpy of the compounds under study.

Full text of DOI:10.1134/S0036024411100116

ISSN 0036ꢀ0244, Russian Journal of Physical Chemistry A, 2011, Vol. 85, No. 10, pp. 1695–1700. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © A.S. Maslakova, E.L. Krasnykh, S.V. Levanova, 2011, published in Zhurnal Fizicheskoi Khimii, 2011, Vol. 85, No. 10, pp. 1822–1827.
CHEMICAL THERMODYNAMICS
AND THERMOCHEMISTRY
Saturation Vapor Pressures and Vaporization Enthalpies of Esters
of Ethylene Glycol and Lower Carboxylic Acids
A. S. Maslakova, E. L. Krasnykh, and S. V. Levanova
Samara State Technical University, Samara, 443100 Russia
eꢀmail: kinterm@samgtu.ru
Received June 4, 2010
Abstract—Saturation vapor pressures and vaporization enthalpies of ethylene glycol and C1–C5 carboxylic
acid disubstituted esters of normal and branched structures are determined by the transfer method in the temꢀ
perature range of 295 to 327 K. Dependences of vaporization enthalpies versus the number of carbon atoms
in a molecule and the retention indices are determined. An analysis of existing calculation schemes is given
to help predict the vaporization enthalpy of the compounds under study.
Keywords: vaporization enthalpy, vapor pressure, ethylene glycol esters, retention indices.
DOI: 10.1134/S0036024411100116
INTRODUCTION
EXPERIMENTAL
Ethylene glycol disubstituted esters were syntheꢀ
sized by the aseotropic etherification of ethylene glyꢀ
col and С1–С5 carboxylic acids in an alcoholꢀtoꢀacid
ratio of 1/(4–5) mol/mol, in analogy with the proceꢀ
dures given in [9].
In a continuation of our investigations of triol (i.e.,
glycerol) esters [1], we studied the thermodynamical
properties of esters of diols (i.e., ethylene glycol). The
latter find application as organic solvents and can serve
as solvents in the purification and recrystallization of
explosive substances [2], as curing agents for sand
blends in foundries [3], and are of interest as promising
oxygenating additives for fuels [4].
The reaction of ethylene glycol with acids is
described by the following reaction:
H2C OH
H2C OH
+
H2C OOCR
H2C OOCR
H
+ 2R–COOH
+ 2H2O,
Despite the wide use of ethylene glycol esters, their
thermodynamic properties (particularly their vaporꢀ
ization enthalpies) remain insufficiently studied. Ethꢀ
ylene glycol diethanoate is the disubstituted ester most
commonly studied: several experimental values have
been obtained by various authors for its vaporization
enthalpy at 298 K; the difference between these is
6 kJ/mol [2, 5–8]. There are also calorimetric data on
the vaporization enthalpies of ethylene glycol diproꢀ
panoate and dibutanoate of linear structure at 298 K
[7]. The thermodynamic properties of other comꢀ
pounds of this homologous series cannot be found in
the literature. To fill this vacuum, we performed a sysꢀ
tematic study of ethylene glycol and С1–С5 carboxylic
acid disubstituted esters with normal and branched
structures.
where R is H, CH3, С2Н5, C3H7, С4Н9, and С5Н11
with normal and branched structures.
Esterification was performed using benzene as
azeotropeꢀforming agent upon catalysis with phosꢀ
phoric acid for 8 h. The reaction mixture was then subꢀ
jected to neutralization and rectification. The purity of
the obtained diesters was not lower than 95 wt %. Furꢀ
ther purification to 99 wt % was performed directly on
the unit for determining the saturation vapor pressure.
The products were analyzed using the Kristallꢀ
2000M chromatographic complex with the following
parameters: OVꢀ101 capillary column with grafted
phase, 100 m × 0.25 mm; temperature of evaporator,
623 K; temperature of detector, 573 K; carrier gas,
helium; flux split, 1/40.
The aim of this work is to determine the vapor presꢀ
sures and vaporization enthalpies of ethylene glycol
disubstituted esters, to reveal correlations describing
the dependences of vaporization enthalpy versus the
number of carbon atoms and retention indices, and to
analyze the prediction capabilities of existing calculaꢀ
The retention indices for the obtained esters were
determined according to the standard procedure in
[10]. Measurements were performed in the isothermal
mode in the temperature range of 363 to 473 K. Samꢀ
ples of mixtures of the esters under study with a purity
tion schemes for compounds with two carboxylic of no less than 95% (1
µ
l) were dissolved in methanol
groups in a molecule. (1 ml) with ꢀalkanes (1
n
µ
l) and introduced into the
1695

1696
MASLAKOVA et al.
Table 1. Retention indices of ethylene glycol disubstituted esters
T,
°
C
1
2
3
4
5
6
7
8
90
797.9
797.0
795.7
795.0
100
110
120
130
140
150
160
170
180
190
200
150*
956.3
954.7
953.9
951.9
1146.2
1142.5
1141.2
1139.9
1316.3
1315.7
1315.1
1314.4
1234.3
1233.9
1233.6
1233.3
1507.3
1507.4
1507.5
1507.8
1507
1418.6
1418.9
1419.3
1419.8
1418
1296.1
1296.6
1297.1
1300
792
952
1139
1316
1234
1293
Note: (1) ethylene glycol dimethanoate, (2) ethylene glycol diethanoate, (3) ethylene glycol dipropanoate, (4) ethylene glycol dibutanoate,
(5) ethylene glycol di(2ꢀmethylpropanoate), (6) ethylene glycol dipentanoate, (7) ethylene glycol di(2ꢀmethylbutanoate), and (8) ethꢀ
ylene glycol di(2,2ꢀdimethylpropanoate). Asterisks denote the values of the indices calculated for a temperature of 150°C.
evaporator using a microsyringe (1.0 µl). The retenꢀ stance under study (error, 0.1–0.2%), l; Vi is the volꢀ
tion indices were calculated by the Kowach equation: ume of the substance transferred, l; and
R is the uniꢀ
versal gas constant, 8.314 J/(mol K).
Saturation vapor pressures versus temperature were
determined according to the following equation:
log(tx) − log(tN )
(1)
Jx =
100 +100N,
log(tN +1) − log(tN )
where tx, tN, and tN + 1 are the corrected retention time
⎛
⎞
g
b
T
T
T
of the ester and ꢀalkanes with numbers of carbon
n
(3)
Rlnpi = a + + Δl Cpln
,
⎜
⎝
⎟
⎠
atoms and + 1, respectively.
N
N
0
g
The experimental values of the retention indices
determined from 5–7 measurements are given in
Table 1. The confidence interval of the indices did not
exceed 0.5 index units (i.u.). On the basis of the experꢀ
imental values, the retention indices were calculated
for compounds at 423 K (150°С): J150, which served as
the reference for further correlation of the vaporizaꢀ
tion enthalpy and retention indices.
where
a
and
b
are normalized parameters;
is the
Δl Cp
difference in the molar heat capacity between gas and
liquid phases, respectively; is the temperature of the
Т
study; and Т0 is the temperature 298.15 K.
Vaporization enthalpy versus temperature was
determined according to the following equation:
g
(4)
ΔvapH°m(T) = −b + Δl CpT.
The saturation vapor pressures and vaporization
enthalpies were determined using the transfer method
(transpiration) described in [1, 11, 12]. Using Dalꢀ
ton’s law as it applies to the Mendeleev–Clapeyron
law, the saturation vapor pressure of substance at defiꢀ
nite temperature was calculated according to the folꢀ
lowing equation:
The random error of vaporization enthalpy was
determined by regression analysis, based on the recꢀ
ommendations in [13].
In Eqs. (3) and (4), the heat capacity of the liquid–
g
gas transition
was determined by the method
Δl Cp
suggested by Chickos [14], using the following equaꢀ
tion:
mRT
(2)
p =
, V = VN2 +Vi, VN2 ӷVi,
g
VM
is the saturation vapor pressure of the subꢀ
stance under study (error, 1%), Pa; is the mass of
(5)
is the heat capacity of the liquid at 298.15 K
Δl Cp = (Cpl − Cp g) = 10.56 + 0.26Cpl,
where
p
where
Cpl
determined additively, J/(mol K).
≤
m
the transferred component (determined chromatoꢀ
graphically by internal standard method; error,
0.05%), g;
g/mol; is the temperature at which the consumption
of nitrogen was measured ( 0.05 К), К; VN2 is the volꢀ
ume of nitrogen lost in transferring the of the subꢀ mentally for all the esters under study are given in
М is molecular mass of the component,
RESULTS AND DISCUSSION
The saturation vapor pressures determined experiꢀ
Т
m
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SATURATION VAPOR PRESSURES
1697
Table 2. Saturation vapor pressures and vaporization enthalpies of glycerol and C1–C5 carboxylic acid esters (
ν
is the rate
g
b
T
T
Rlnp = a + + Δl Cpln
of the carrier gas flow),
i
(
)
298.15
VN , dm3
VN , dm3
2
T, K
m
, mg
p, Pa
T
, K
m, mg
p, Pa
2
g
Ethylene glycol dimethanoate (a = 265.370, b = –68212
,
= –60.032)
Δl Cp
1.876
1.846
1.909
303.0
305.0
307.0
309.0
3.074
2.035
2.048
2.004
0.594
0.350
0.297
0.262
112.53
126.02
148.53
164.38
321.0
325.0
325.0
0.122
0.092
0.094
325.46
425.83
432.56
g
Ethylene glycol diethanoate (a = 310.060, b = –83476
,
=
–78.18)
Δl Cp
295.3
297.5
298.4
301.4
303.4
305.4
308.5
311.4
1.806
1.857
1.724
1.331
1.643
2.126
3.383
1.517
1.075
0.905
0.792
0.498
0.531
0.570
0.735
0.259
29.91
36.34
38.51
47.45
54.81
65.79
80.50
102.44
313.4
315.4
317.4
319.4
321.4
323.3
325.3
1.623
1.642
2.332
1.708
1.648
2.783
3.153
0.230
0.210
0.249
0.169
0.141
0.197
0.197
123.44
137.33
164.13
176.52
204.27
246.13
278.78
g
Ethylene glycol dipropanoate (a = 325.260, b = –91323
,
Δl Cp
=
–94.768)
295.5
297.5
299.5
301.4
303.4
305.4
307.4
309.4
0.514
0.500
0.534
0.462
0.488
0.504
0.494
0.509
0.989
0.806
0.696
0.536
0.482
0.422
0.355
0.302
7.79
9.26
311.4
313.4
315.4
317.4
319.4
321.3
323.3
0.525
0.505
1.024
0.495
1.042
0.633
0.852
0.261
0.221
0.384
0.159
0.301
0.157
0.177
29.24
33.21
39.14
44.84
50.75
58.85
70.37
11.42
12.82
15.00
17.43
20.08
24.33
g
Ethylene glycol dibutanoate (a = 356.190, b = –104894
,
= –111.356)
Δl Cp
0.393
0.389
0.396
0.406
0.405
0.771
0.418
0.421
297.5
299.4
301.4
303.4
305.4
307.4
309.4
311.4
0.527
1.061
0.367
0.351
0.382
0.357
0.373
0.382
4.211
6.797
2.069
1.625
1.412
1.129
0.941
0.816
1.59
1.97
2.24
2.73
3.38
3.95
4.95
5.85
313.4
315.4
317.4
319.4
321.4
322.8
325.3
327.3
0.739
0.625
0.504
0.438
0.371
0.646
0.282
0.250
6.68
7.76
9.79
11.30
13.60
14.67
18.07
20.50
g
Ethylene glycol di(2ꢀmethylpropanoate) (a = 346.320, b = –98793
,
=
–107.976)
0.342
0.274
0.241
Δl Cp
295.0
297.0
299.0
301.0
303.0
305.0
307.0
309.0
0.442
0.441
0.475
0.432
0.388
0.428
0.452
0.425
1.230
1.035
0.912
0.717
0.521
0.494
0.432
0.332
4.57
5.40
311.0
313.0
315.0
317.0
319.0
319.0
321.0
323.0
0.473
0.439
0.496
0.487
0.446
0.482
1.162
2.161
17.32
20.11
25.74
28.83
33.11
33.22
40.75
46.79
6.58
7.59
0.211
9.36
0.169
10.90
13.11
16.02
0.182
0.355
0.575
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MASLAKOVA et al.
Table 2. (Contd.)
VN , dm3
VN , dm3
2
T, K
m
, mg
p, Pa
T
, K
m, mg
p, Pa
2
g
Ethylene glycol dipentanoate (a = 388.040, b = –118295
,
=
–127.944)
Δl Cp
0.595
0.619
0.615
0.689
0.729
0.257
0.697
297.4
299.2
301.3
303.4
305.4
307.4
309.4
311.4
0.624
0.654
0.642
0.638
0.624
0.630
0.723
0.664
21.502
17.759
14.715
11.274
9.395
0.32
0.41
0.48
0.63
0.74
0.90
1.09
1.37
313.4
315.4
317.4
319.3
321.3
322.8
325.3
4.069
3.420
2.915
2.579
2.355
0.706
1.553
1.62
2.01
2.35
2.97
3.45
4.03
4.97
7.767
7.391
5.386
g
Ethylene glycol di(2ꢀmethylbutanoate) (a = 362.550, b = –108640
,
=
–124.564)
2.867
1.525
Δl Cp
297.4
299.5
301.4
303.5
305.4
307.4
309.4
311.4
0.552
0.582
0.577
0.551
0.662
0.560
0.607
0.628
8.319
6.991
5.720
4.703
4.358
3.178
2.838
2.521
0.73
0.91
1.10
1.28
1.66
1.91
2.34
2.73
313.4
315.4
317.4
319.4
321.3
323.3
325.3
327.4
0.822
0.530
0.543
0.551
0.568
0.534
0.551
0.561
3.13
3.77
4.38
5.12
6.19
7.04
8.63
10.03
1.354
1.173
1.004
0.829
0.698
0.611
g
Ethylene glycol di(2,2ꢀdimethylpropanoate) (a = 364.890, b = –105549
,
= –121.756)
Δl Cp
295.0
297.0
299.0
301.0
303.0
305.0
307.0
309.1
0.472
0.390
0.248
0.275
0.373
0.365
0.370
0.381
1.807
1.271
0.688
0.645
0.722
0.606
0.520
0.433
2.90
3.40
3.97
4.70
5.69
6.61
7.80
9.64
311.0
313.0
315.0
317.0
319.0
321.0
323.0
325.0
0.400
0.388
0.375
4.281
0.397
0.397
0.381
3.142
0.375
0.312
0.263
2.416
0.190
0.163
0.136
0.966
11.65
13.51
15.56
19.35
22.64
26.42
30.43
35.46
Table 2; the vaporization enthalpies of the compounds
at 398.15 K are given in Table 3.
Joint analysis of the results given in Table 3 allows
us to draw the following conclusions: The calorimetric
data on ethylene glycol diethanoate [6–8] and ethylꢀ
ene glycol dipropanoate [7] deviate from Eqs. (6) and
(7) by 3 to 4 kJ/mol, or ~6–7% of the value of their
vaporization enthalpy. The value obtained in [7] for
ethylene glycol dibutanoate corresponds to Eq. (6)
with an error of 1 kJ/mol (1%), but does not exceed
the experimental error; its deviation from Eq. (7),
however, is somewhat higher: 2.5 kJ/mol, or ~3%. At
the same time, the data on the vaporization enthalpy
of ethylene glycol diethanoate [2, 5] are described well
by the proposed equations.
It is known that the vaporization enthalpy of subꢀ
stances in one homologous series is a linear function of
the number of carbon atoms in a molecule (N) and the
chromatographic retention indices (J) [1, 12]. Equaꢀ
tions
ΔvapHm = 3.565N + 36.58, (R2 = 0.98),
ꢀ
(6)
ΔvapHm = 0.0367J150 + 22.37, (R2 = 0.95)
ꢀ
(7)
show these dependences for the compounds under
study.
The results from calculating the vaporization
enthalpies of esters according to these equations and
the experimental values’ deviation from linearity
We analyzed the prediction capabilities of the existꢀ
ing calculation schemes for estimating the vaporizaꢀ
tion enthalpy of ethylene glycol esters and lower carꢀ
boxylic acids. To accomplish this, we used the Benson
methodꢀbased additive [8, 15–18] and additive correꢀ
ꢀ
ꢀ
(
ΔΔ
H
=
Δvap
–
Δvap
) are given in Table 3.
Hm calc
Hm exp
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SATURATION VAPOR PRESSURES
1699
Table 3. Vaporization enthalpies of ethylene glycol and C1–C5 carboxylic acid esters
Dependence from Dependence from
N
°
ΔvapHm exp
kJ/mol
,
Ethyleneglycol
diesters
(6), kJ/mol
J150 (7), kJ/mol
N
J150
Method
Δ
T, K
°
°
ΔvapHm calc ΔΔ
H
ΔvapHm calc ΔΔH
Methanoate
4
792 50.3 1.4
952 55.2 [5]
transpiration 303–325
50.8
58.0
–0.5
–2.8
3.0
–0.4
3.4
2.2
3.7
2.5
–2
51.4
57.3
1.1
2.1
Ethanoate
6
tensimetry
311–464
298.15
61.0 0.1 [6] calorimetry
57.6 [2] tensimetry
61.4 0.2 [7] calorimetry
60.2 1.1
61.4 0.2 [8] transpiration 291–334
1139 67.6 0.5 [7] calorimetry 298.15
3.7
0.3
4.1
2.9
4.1
3.4
1.1
1.1
2.5
1.0
0.5
373–463
298.15
transpiration 295–325
Propanoate
8
65.1
64.2
63.1 1.0
10 1234 66.6 1.3
transpiration 295–323
transpiration 295–323
2ꢀMethylpropanoate
Butanoate
–
–
67.7
70.7
10 1316 73.2 0.6 [7] calorimetry
298.15
72.2
1.0
71.7 1.3
transpiration 297–327
transpiration 295–325
–0.5
–
2,2ꢀDimethylproꢀ
panoate
12 1293 69.3 1.1
–
69.8
2ꢀMethylbutanoate
Pentanoate
12 1418 71.5 1.1
12 1507 80.2 1.0
transpiration 297–327
transpiration 297–325
–
–
74.4
77.7
2.9
2.5
79.4
0.8
Table 4. Deviations in predicting vaporization enthalpies by various methods, kJ/mol
[15]
[16]
[17]
[18]
[8]
[19]
[20]
Ethyleneglycol diesters
Methanoate
additive
additiveꢀcorrelation
–5.9
2.4
4.7
3.3
7.8
5.0
–5.9
5.1
–2.2
4.9
–2.1
0.0
Ethanoate
1.2
7.0
Propanoate
7.7
0.3
3.0
3.4
0.6
–1.1
–2.3
–3.6
–4.9
–0.2
–8.2
3.8
Butanoate
7.1
–1.0
–2.5
–2.4
–
2.1
1.8
4.8
0.2
Pentanoate
6.4
1.0
0.1
5.9
–0.2
–1.5
–3.9
–2.5
2.6
2ꢀMethylpropanoate
2,2ꢀDimethylpropanoate
3ꢀMethylbutanoate
Rootꢀmeanꢀsquare deviation
|Δ|max
–2.2
2.1
0.8
–6.4
–2.7
–6.1
4.5
10.5
16.3
12.6
9.0
–0.9
–3.6
3.8
4.3
–8.5
4.1
5.2
7.7
8.5
7.8
6.4
16.3
4.9
8.2
lation schemes [19, 20]. We chose these methods
because they do not require any additional characterꢀ
istics for the initial data.
In calculating the vaporization enthalpies of linear
esters by additive methods [16–18], ΔΔ values fall to
H
values comparable to the experimental error, starting
with the third member of the homologous series.
Because the decline is systematic, the error will most
likely grow with an increase in the acidic residue.
Upon a transition to branched structures, the error
increases to 6 kJ/mol; in addition, the method in [16]
does not consider the contributions that describe the
structure of diꢀ2,2ꢀdimethylpropanoate molecule; i.e,
we are not allowed to calculate its properties.
The values of vaporization enthalpy obtained by
the above methods are given in Table 4, an analysis
of which shows that additive methods allow us to
calculate the vaporization enthalpies of ethylene
glycol esters only approximately. The deviation of
the calculated values from the experimental values
ꢀ
ꢀ
(
ΔΔ
H
=
ΔvapHm exp
–
Δvap
) vary from –8.5 to
Hm calc
16.3 kJ/mol, more than 10% of the vaporization
enthalpy value.
Additive correlation methods [19, 20] yield the
highest convergence with the experimental values,
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MASLAKOVA et al.
4. C.ꢀY. Lin and J.ꢀC. Huang, Ocean Eng. 30, 1699
starting with ethylene glycol dipropanoate; the error of
the method does not exceed 1 kJ/mol for linear strucꢀ
tures, which corresponds to the experimental error.
Calculations for the vaporization enthalpy of esters
with branched substituents are less effective, but their
deviation does not exceed 3.9 kJ/mol.
In comparing the results from calculations using
similar data for glycerol [1], it should be noted that if
the deviation of calculated data from experimental for
ethylene glycol esters is on average 5 kJ/mol, then this
value is 10 kJ/mol for glycerol esters, testifying to the
unconsidered interactions of multibasic alcohol esters.
(2003).
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I. K. Kukushkin, Izv. Vyssh. Uchebn. Zaved., Khim.
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CONCLUSIONS
Based on the above, we may conclude that the use
of additive methods for calculating the vaporization
enthalpies of polyatomic alcohol esters cannot be recꢀ
ommended. Of all the additive correlation methods,
we can recommend only the one in [19] (which yields
the smallest error).
Khim. 82, 2250 (2008) [Russ. J. Phys. Chem. A 82
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2025 (2008)].
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Moscow, 1970) [in Russian].
ACKNOWLEDGMENTS
The work was supported by the federal target proꢀ
gram Scientists and Science Teachers of an Innovative
Russia 2009–2013, State Contract no. 1660 of Sepꢀ
tember 15, 2009.
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RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A
Vol. 85
No. 10 2011