a r t i c l e i n f o
a b s t r a c t
Article history:
Received 6 May 2016
Received in revised form
2 September 2016
Accepted 2 September 2016
Available online 4 September 2016
A group contribution method for predicting the surface tension of alkanes at various temperatures, based
on Guggenheim-Katayama-van der Waals equation, has been developed. The constants of this equation
evaluated from TRC Tables data for surface tension were used as a basis to determination contributions of
structural units. With knowledge of critical temperature of the liquid alkane it is possible to predict value
of its surface tension at various temperatures (from 273.15 to 333.15 K, or to temperature below the
normal boiling point). The data for 50 compounds were processed: 30 of them to determine contributions of structural units (main set), and remaining 20 compounds (denoted as test set) to verify the
proposed method. On the whole, 394 data points were used, 235 in the main set and 159 in the test set.
2016 Elsevier B.V. All rights reserved.
Keywords:
Surface tension
Alkanes
Group contribution method
Guggenheim-Katayama-van der Waals
equation
1. Introduction
The efcient design of the processes in chemical, petroleum,
pharmaceutical, or polymer industries can be performed if the
values of the thermophysical, physicochemical, and/or thermodynamic properties of the involved liquids are available. One of these
important physical properties is surface tension. Even though the
experimental data for surface tensions are plentiful nowadays, the
rapid development of industry needs large amounts of experimental data of surface tensions for a variety of substances at
different temperatures. Therefore, it is very useful to develop estimating methods with a wide range of applicability and good prediction accuracy. This work pays attention to the prediction of
surface tension of liquid alkanes by group contribution method.
(A.
http://dx.doi.org/10.1016/j.uid.2016.09.007
0378-3812/ 2016 Elsevier B.V. All rights reserved.
Randov
a),
bartovsl@vscht.cz
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
Table 2
Characterization of compounds by structural units.
g g0 $ 1
T
Tc
n
(1)
Group
Group
Group
Group
167
Compound
Linear alkanes
1
Hexane
2
Heptane
3
Octane
4
Nonane
5
decane
6
Undecane
7
Dodecane
8
Tridecane
Alkylbutanes
9
2-methylbutane
10
2,2-dimethylbutane
11
2,3-dimethylbutane
Alkylpentanes
12
2-methylpentane
13
2,2-dimethylpentane
14
2,3-dimethylpentane
15
2,2,3-trimethylpentane
16
2-methyl-3-ethylpentane
17
3-methyl-3-ethylpentane
18
2,2-dimethyl-3-ethylpentane
19
2,4-dimethyl-3-ethylpentane
20
3,3-diethylpentane
Alkylhexanes
21
2-methylhexane
22
2,2-dimethylhexane
23
2,3-dimethylhexane
24
3-ethylhexane
25
2,2,3-trimethylhexane
26
2-methyl-3-ethylhexane
27
3-methyl-3-ethylhexane
Alkylheptanes
28
2-methylheptane
29
2,2-dimethylheptane
30
2,3-dimethylheptane
Alkyloctanes
31
2-methyloctane
Alkylcyclopentanes
32
Methylcyclopentane
33
Ethylcyclopentane
34
Propylcyclopentane
35
Decylcyclopentane
36
1,1-dimethylcyclopentane
37
Isobutylcyclopentane
Alkylcyclohexanes
38
Methylcyclohexane
39
Ethylcyclohexane
40
Propylcyclohexane
41
Butylcyclohexane
42
Pentylcyclohexane
43
Hexylcyclohexane
44
Heptylcyclohexane
45
Octylcyclohexane
46
Nonylcyclohexane
47
Decylcyclohexane
48
1,1-dimethylcyclohexane
49
(1-methylpropyl)cyclohexane
50
(1,1-dimethylethyl)cyclohexane
CH3
CH2
2
2
2
2
2
2
2
2
4
5
6
7
8
9
10
11
3
4
4
1
1
3
4
4
5
4
4
5
5
4
2
2
1
1
2
3
2
1
4
3
4
4
3
5
4
4
3
3
2
4
2
3
4
3
4
4
4
4
3
1
2
2
1
1
1
1
2
2
4
5
6
13
4
5
1
1
1
1
1
2
3
10
2
4
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
2
2
3
5
6
7
8
9
10
11
12
13
14
5
6
5
1
1
1
1
1
1
1
1
1
1
1
2
3
4
5
6
7
8
9
10
2
4
4
1
1
1
1
1
1
1
1
1
1
1
1
1
CH
1
2
2
1
2
1
1
2
1
2
1
3
1
1
1
1
1
1
2
1
1
2
1
1
1
1
1
2
1
2
1
1
2
2
3
3
3
4
4
4
1
2
2
2
3
3
3
2.3. Errors
The contributions of the structural units were determined by
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
168
the GCM constants were compared with TRC surface tension values
and with other data found in literature (Chapter 4).
3. Results of calculation
3.1. The contributions of structural units, the input data and data
predicted by GCM
Fig. 1. The examples of compounds and their structural units (left) 2,2-dimethyl-3ethylpentane: C-group units (5xCH3, 2xCH2, 1xCH, 1xC), , main skeleton, geometry
unit (B b 4 number of C-group units attached to the main skeleton of molecule)
(right) 1,1-dimethylcyclohexane: C-group units (2xCH3, 5xCH2, 1xC), geometry unit
(, c 1, B b 2 number of C-group units attached to the cycle).
minimization function S.
X
X j X GCM;j
2
(2)
GCM;j
Xj
X
$100
Xj
Dj X
(3)
P
Dj X
dX
(4)
2.4. Procedure
The input data, g0 and n, were obtained by processing the surface tension data from TRC Tables [50] according to Eq. (1) using the
average values of critical temperatures (the data on critical temperatures together with corresponding references are cited in the
Appendix e Table A1). These values of g0 and n were used to
evaluation of the contributions of structural units. Next step was to
calculate the g0 and n of each compound under study using these
contributions and to compare them with the input data (Chapter 3).
To demonstrate the applicability of the proposed approach, one
substance from each of the eight groups was taken and its surface
tension values calculated at various temperatures from Eq. (1) using
Table 3
Main and test sets.
Main set
1
5
6
8
9
10
12
13
16
19
Test set
20
21
23
24
25
27
28
29
31
32
33
35
36
38
40
41
44
46
47
49
2
3
4
7
11
14
15
17
18
22
26
30
34
37
39
42
43
45
48
50
Table 4
Statistics of the proposed GCM.
Number of compounds
Total points of surface tension
Number of compounds in main set
Points of surface tension in main set
Number of compounds in test set
Points of surface tension in test set
Number of structural unit
50
394
30
235
20
159
6
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
169
Table 5
Contributions of structural units.
Structural unit
C-group unit
CH3
CH2
CH
C
Geometry unit
b
c
g0
30
30
20
7
24.40
0.56
22.89
47.71
0.562
0.017
0.527
1.079
17
11
0.56
54.67
0.005
1.138
Compound
Main set
1
Hexane
5
Decane
6
Undecane
8
Tridecane
9
2-methylbutane
10
2,2-dimethylbutane
12
2-methylpentane
13
2,2-dimethylpentane
16
2-methyl-3-ethylpentane
19
2,4-dimethyl-3-ethylpentane
20
3,3-diethylpentane
21
2-methylhexane
23
2,3-dimethylhexane
24
3-ethylhexane
25
2,2,3-trimethylhexane
27
3-methyl-3-ethylhexane
28
2-methylheptane
29
2,2-dimethylheptane
31
2-methyloctane
32
Methylcyclopentane
33
Ethylcyclopentane
35
Decylcyclopentane
36
1,1-dimethylcyclopentane
38
Methylcyclohexane
40
Propylcyclohexane
41
Butylcyclohexane
44
Heptylcyclohexane
46
Nonylcyclohexane
47
Decylcyclohexane
49
(1-methylpropyl)cyclohexane
Test set
2
Heptane
3
Octane
4
Nonane
7
Dodecane
11
2,3-dimethylbutane
14
2,3-dimethylpentane
15
2,2,3-trimethylpentane
17
3-methyl-3-ethylpentane
18
2,2-dimethyl-3-ethylpentane
22
2,2-dimethylhexane
26
2-methyl-3-ethylhexane
30
2,3-dimethylheptane
34
Propylcyclopentane
37
Isobutylcyclopentane
39
Ethylcyclohexane
42
Pentylcyclohexane
43
Hexylcyclohexane
45
Octylcyclohexane
48
1,1-dimethylcyclohexane
50
(1,1-dimethylethyl)cyclohexane
g0
g0(GCM)
n(GCM)
51.88
53.73
53.90
54.25
50.46
47.43
50.04
48.61
51.36
52.88
52.36
50.28
50.25
51.41
50.88
53.12
50.47
51.28
53.21
60.26
56.79
58.00
54.60
60.37
58.00
59.00
58.59
57.95
57.52
58.47
1.204
1.264
1.274
1.294
1.199
1.168
1.189
1.198
1.195
1.229
1.208
1.191
1.189
1.192
1.223
1.225
1.206
1.269
1.272
1.246
1.199
1.332
1.201
1.296
1.245
1.315
1.368
1.353
1.339
1.310
51.04
53.27
53.83
54.94
50.31
49.33
50.87
49.89
51.26
51.66
49.88
51.43
51.82
51.43
50.84
50.44
51.99
51.01
52.55
57.86
57.85
57.82
56.88
58.41
58.41
58.40
58.39
58.38
58.37
58.80
1.193
1.262
1.279
1.313
1.170
1.175
1.187
1.192
1.211
1.223
1.216
1.205
1.217
1.216
1.221
1.221
1.222
1.227
1.239
1.236
1.248
1.342
1.241
1.253
1.277
1.289
1.324
1.347
1.359
1.289
52.03
52.42
53.19
54.05
50.09
51.35
49.34
51.30
53.07
48.49
53.06
53.57
56.34
55.10
60.55
58.61
56.26
57.58
55.66
58.30
1.214
1.223
1.245
1.285
1.200
1.198
1.185
1.193
1.255
1.189
1.222
1.268
1.215
1.257
1.301
1.339
1.280
1.345
1.214
1.331
51.59
52.15
52.71
54.38
50.71
51.27
50.29
49.89
50.28
50.45
51.82
52.38
57.85
58.24
58.41
58.40
58.39
58.40
57.43
57.82
1.210
1.227
1.244
1.296
1.182
1.199
1.204
1.204
1.216
1.209
1.228
1.234
1.260
1.272
1.265
1.300
1.312
1.338
1.258
1.282
170
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
Fig. 3. Calculated and literature surface tension of heptane and 2-methyl-3ethylhexane as a function of temperature.
Fig. 4. Calculated and literature surface tension of 2,2-dimethylbutane and 1,1dimethylcyclohexane as a function of temperature.
Fig. 5. Calculated and literature surface tension of 2-methylpentane and 2methylheptane as a function of temperature.
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
171
critical temperature (Tc 599.6 K) from the eight selected compounds. But other physico-chemical properties (acentric factor,
boiling point, van der Waals volume) are not of extreme values. The
literature data (capillary rise method [28], data compilations
[68,71]) are in very good agreement with our data (see Fig. 6), just
like in case of 2-methyloctane [28,68,71]. This substance boiling
point is the highest from our eight selected compounds (416.43 K
[37]), and so is also the acentric factor.
4.3. Calculation methods for surface tension determination
4.3.1. Parachor
The parachor belongs to the most known quantities which are
denoted as additive. At temperatures sufciently distant from the
critical state, where the vapour density can be neglected, the parachor is almost independent of temperature and can be calculated
from individual atomic and structural contributions [73]. Knowing
the molar mass of liquid M and its density r, this value of parachor
can be used to estimate the surface tension:
Fig. 6. Calculated and literature surface tension of 2-methyloctane and propylcyclopentane as a function of temperature.
g
calculation [67] and experimental (maximum bubble pressure
method) [70]. Viscosity of this substance (h 0.28 mPa s at 25 C) is
the smallest of all eight compounds under consideration. Also its
acentric factor (0.28) and van der Waals volume (68.3 cm3 mol1)
are very low. The main chain of 2-methylheptane consists of an
odd number of carbon atoms (7) like 2-methylpentane (5). The
properties of 2-methylheptane are approximately by 25% higher
than those of 2-methylpentane, and so are their surface tensions.
Fig. 5 points out to very good agreement between the surface
tension values calculated by GCM and literature data (in case of 2methylpentane: [28] and [68] e data compilations, [67] e correlation method, [70] e capillary rise and bubble pressure methods,
and in case of 2-methylheptane: [28] and [68] e data compilations,
[72] e maximum bubble pressure, [58] e measurement by pendant
drop method).
Propylcyclopentane has the highest solubility parameter (16.4),
the highest viscosity (h 0.65 mPa s at 25 C), and also the highest
r$P
4
(5)
Table 7
Comparison of calculation methods with method presented in this work, the values of surface tension are in mN m1, the values of percentage difference are in %.
T/K
[50]
Heptane
293.15
20.14
298.15
19.65
2-methyl-3-ethylhexane
293.15
22.80
298.15
22.34
2,2-dimethylbutane
293.15
16.30
298.15
15.81
1,1-dimethylcyclohexane
293.15
24.12
298.15
23.61
2-methylpentane
293.15
17.38
298.15
16.87
2-methylheptane
293.15
20.60
298.15
20.14
2-methyloctane
293.15
21.88
298.15
21.41
Propylcyclopentane
293.15
24.95
298.15
24.46
This work
4.3.1
4.3.2
4.3.3
dthis work
d4.3.1
d4.3.2
d4.3.3
20.03
19.54
19.25
18.78
19.79
19.99
19.47
0.55
0.56
4.40
4.45
1.74
0.74
0.90
22.20
21.74
23.42
22.91
22.7
22.53
22.05
2.63
2.69
2.73
2.57
0.44
1.20
1.30
16.83
16.33
16.61
16.14
17.02
16.50
16.00
3.27
3.28
1.91
2.06
4.42
1.21
1.23
24.25
23.75
23.94
23.43
0.53
0.56
0.76
0.76
17.70
17.18
17.03
16.55
17.45
17.35
16.83
1.81
1.85
2.04
1.91
0.40
0.18
0.23
21.00
20.52
19.96
19.50
20.87
20.68
20.20
1.93
1.87
3.10
3.17
1.31
0.39
0.30
22.15
21.68
21.01
20.57
22.17
22.13
21.66
1.22
1.24
3.95
3.92
1.33
1.15
1.18
24.83
24.33
24.10
23.60
0.46
0.55
3.41
3.53
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
172
gcalc g50
$100%
g50
Acknowledgement
Authors thank to UCT (University of Chemistry and Technology)
Prague Institutional support e specic university research 2016.
Appendix
Appendix A. Input data
di
Table A1
Critical temperatures of liquids together with their references.
Hexane
C6H14
M 86.175 g mol
(6)
1
1
Nonane
C9H20
M 128.255 g mol
5. Conclusions
A group-contribution method for predicting the constants of
Guggenheim-Katayama-van der Waals equation describing the
temperature dependence of surface tension for alkanes has been
developed. The method is based on these constants values evaluated from the surface tensions of 30 alkanes, taken from TRC Tables.
The structural units were dened (units of C-group and units of
geometry) and their contributions were determined from the data
for 30 alkanes.
The proposed GCM method was veried on g0 and n data for
further 20 alkanes (test set). The average percentage errors in main
set are 1.8% (g0) and 1.5% (n), in test set are 2.2% (g0) and 1.7% (n).
The overall percentage errors (all 50 compounds considered) were
determined to be 2.0% in g0 and 1.6% in n. These values show that
our group contribution method is able to predict the constants of
the chosen equation.
To demonstrate the applicability of the method for the surface
tension determination, the comparison of the data for eight casually chosen compounds calculated by GCM method as a function of
temperature with those found in literature is shown. This comparison revealed that the surface tension values acquired by GCM
calculation were in good agreement with available literature data
1
1
1
Undecane
C11H24
M 156.308 g mol1
Average critical temperature
Tc 638.9 K
Dodecane
C12H26
M 170.335 g mol1
Tc/K
Ref
507.5
507.6
507.5
507.4
507.8
507.6
[50]
[77]
[78]
[79]
[80]
[37]
540.3
540.2
540.3
540.3
540.2
540.6
[50]
[77]
[78]
[79]
[37]
[81]
568.83
568.7
568.83
568.8
568.7
568.88
568.82
[50]
[77]
[78]
[79]
[37]
[82]
[65]
594.6
594.6
594.6
595.7
594.6
594.55
[50]
[77]
[78]
[79]
[37]
[82]
617.9
617.7
617.7
618.5
617.7
617.7
617.5
617.54
[50]
[77]
[78]
[79]
[37]
[82]
[83]
[84]
639
639
638.8
639
638.8
639
[50]
[77]
[78]
[37]
[82]
[85]
658.2
658
658.2
658
658.1
658.2
[50]
[77]
[78]
[37]
[82]
[85]
675.8
675
676
675
[50]
[77]
[78]
[37]
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
Table A1 (continued )
10
14
15
16
17
18
19
20
21
1
13
1
12
1
11
Table A1 (continued )
173
1
Tc/K
Ref
675.9
675.8
[82]
[85]
C7H16
M 100.202 g mol1
460.39
460.4
460.4
460.95
460.51
460.4
[50]
[78]
[37]
[86]
[87]
[79]
488.7
489
488.78
489.25
489
488.8
[50]
[37]
[78]
[88]
[89]
[79]
499.9
500
499.98
500.23
500
500
[50]
[37]
[78]
[88]
[89]
[79]
497.5
497.7
497.5
497.5
498.05
497.7
[50]
[37]
[78]
[79]
[88]
[89]
520.4
520.5
520.5
520.5
[50]
[37]
[78]
[89]
27
537.3
537.3
537.35
537.4
537.3
[50]
[37]
[78]
[79]
[89]
28
563.4
563.5
563.5
563.5
563.5
[50]
[37]
[78]
[79]
[89]
567
567
567.09
567.1
567
[50]
[37]
[78]
[89]
[79]
576.5
576.5
576.58
576.5
[50]
[37]
[78]
[89]
589.5
590
592.1
590.4
[50]
[37]
[71]
[68]
588.5
591
591.25
598
[50]
[37]
[71]
[68]
610.2
610.05
610.1
610
610
[50]
[37]
[79]
[71]
[68]
22
23
24
25
26
29
30
31
32
33
34
35
Tc/K
Ref
530.1
530.4
530.4
530.4
530.37
[50]
[37]
[89]
[79]
[78]
549.8
549.8
549.87
549.8
[50]
[37]
[78]
[89]
563.4
563.5
563.49
563.5
563.4
[50]
[37]
[78]
[89]
[79]
565.4
565.5
565.5
565.49
[50]
[37]
[89]
[78]
587
588
588.05
589.4
[50]
[37]
[68]
[71]
587.4
588.1
588.1
589.2
[50]
[37]
[68]
[71]
597.6
597.5
597.55
598.4
[50]
[37]
[68]
[71]
559.6
559.64
559.64
559.7
[50]
[78]
[37]
[89]
577.8
576.8
576.7
576.7
[50]
[78]
[37]
[89]
588.8
589.6
589.6
590.6
[50]
[37]
[68]
[71]
587
582.9
582.8
582.8
[50]
[78]
[37]
[89]
532.79
532.73
532.8
532.79
532.7
[50]
[78]
[79]
[37]
[89]
569.5
569.5
569.5
569.5
569.5
[50]
[78]
[79]
[37]
[89]
596.2
596
603.15
603
[50]
[37]
[68]
[71]
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
174
Table A1 (continued )
36
37
38
39
40
41
42
43
44
45
46
47
48
49
C15H30
M 210.399 g mol1
Average critical temperature
Tc 731.3 K
1,1-dimethylcyclopentane
C7H14
M 98.186 g mol1
Average critical temperature
Tc 547.7 K
Isobutylcyclopentane
C9H18
M 126.239 g mol1
Average critical temperature
Tc 622.8 K
Methylcyclohexane
C7H14
M 98.186 g mol1
Average critical temperature
Tc 572.2 K
Ethylcyclohexane
C8H16
M 112.213 g mol1
Average critical temperature
Tc 606.9 K
Propylcyclohexane
C9H18
M 126.239 g mol1
Average critical temperature
Tc 629.9 K
Butylcyclohexane
C10H20
M 140.266 g mol1
Average critical temperature
Tc 654.6 K
Pentylcyclohexane
C11H22
M 154.292 g mol1
Average critical temperature
Tc 677.8 K
Hexylcyclohexane
C12H24
M 168.319 g mol1
Average critical temperature
Tc 695.9 K
Heptylcyclohexane
C13H26
M 182.346 g mol1
Average critical temperature
Tc 712.3 K
Octylcyclohexane
C14H28
M 196.372 g mol1
Average critical temperature
Tc 728.5 K
Nonylcyclohexane
C15H30
M 210.399 g mol1
Average critical temperature
Tc 740.8 K
Decylcyclohexane
C16H32
M 224.425 g mol1
Average critical temperature
Tc 754.3 K
1,1-dimethylcyclohexane
C8H16
M 112.213 g mol1
Average critical temperature
Tc 589.8 K
(1-methylpropyl)cyclohexane
C10H20
M 140.266 g mol1
Average critical temperature
Tc 668.4 K
Table A1 (continued )
Tc/K
Ref
729.1
730.64
742.4
723.15
[50]
[37]
[71]
[92]
547
547
547
547
550
[50]
[78]
[37]
[68]
[71]
617.21
625.65
625.6
[37]
[68]
[71]
572.19
572.2
572.2
572.1
[50]
[78]
[79]
[37]
602.4
609.2
609.15
606.9
[50]
[79]
[37]
[90]
625.6
639.15
630.8
624
[50]
[37]
[90]
[91]
648.4
667
653.1
650
[50]
[37]
[90]
[91]
669
674.01
684
684
[50]
[37]
[68]
[71]
687.7
691.81
702
702
[50]
[37]
[68]
[71]
704.7
708.63
718
718
[50]
[37]
[68]
[71]
720.3
723.61
735
735
[50]
[37]
[68]
[71]
750
734.6
737.79
[71]
[50]
[37]
2-Methyl-3-ethylpentane
Heptane
Main set
4xCH32xCH22xCH3xb
Test set
2xCH35xCH2
764
747.7
751.25
[71]
[50]
[37]
g0
585.8
591.15
591.15
591
[50]
[37]
[68]
[71]
667
669
669.15
[37]
[68]
[71]
50
(1,1-dimethylethyl)cyclohexane
C10H20
M 140.266 g mol1
Average critical temperature
Tc 659.2 K
Tc/K
Ref
667
652
659
659.15
659
[37]
[90]
[93]
[68]
[71]
Table A2
Properties of eight sample compounds [37,94,95].
Tb/K
Tc/K
Heptane
371.58 540.3 0.35
2-methyl-3-ethylhexane
411.16 588.2 0.378
2,2-dimethylbutane
322.88 488.9 0.234
1,1-dimethylcyclohexane
392.7
589.8 0.233
2-methylpentane
333.41 497.6 0.279
2-methylheptane
390.8
559.6 0.377
Propylcyclopentane
404.11 599.6 0.327
2-methyloctane
416.43 583.9 0.458
r/g cm3
Hvap/
kJ mol1
h/mPa s
d/
(25 C)
(25 C)
MPa1/2
Vvdw/cm3
mol1
0.68
31.731
0.395
15.213
78.49
0.73
35.982
0.433
15.253
98.93
0.64
26.416
0.337
13.766
68.24
0.78
32.443
0.527
15.677
81.82
0.65
24.942
0.278
14.414
68.25
0.7
33.436
0.463
15.373
88.71
0.77
34.593
0.653
16.394
80.62
0.71
36.426
0.426
15.326
98.94
Table B1
Calculations.
GCM
51.263
1.211
51.357
1.195
T/K
g (mN m1)
Literature
Calculated
273.15
283.15
293.15
298.15
303.15
313.15
323.15
333.15
23.4
22.5
21.5
21.1
20.6
19.7
18.7
17.8
23.1
22.2
21.2
20.8
20.3
19.4
18.4
17.5
g0
GCM
51.594
1.210
52.026
1.214
T/K
g (mN m1)
Literature
Calculated
273.15
283.15
293.15
298.15
303.15
313.15
323.15
333.15
22.1
21.1
20.1
19.7
19.2
18.2
17.2
16.2
22.0
21.0
20.0
19.5
19.1
18.1
17.1
16.2
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
References
[1] J.W. Jalowka, T.E. Daubert, Group contribution method to predict critical
temperature and pressure of hydrocarbons, Ind. Eng. Chem. Process Des. Dev.
25 (1986) 139e142, http://dx.doi.org/10.1021/i200032a021.
[2] D. Ambrose, Correlation and Estimation of Vapour-liquid Critical Properties. I.
Critical Temperatures of Organic Compounds, vol. 92, National Physical Laboratory, Teddington, 1978. NPL Rep. Chem.
[3] D. Ambrose, Correlation and Estimation of Vapour-liquid Critical Properties. II.
Critical Pressures and Volumes of Organic Compounds, vol. 98, National
Physical Laboratory, Teddington, 1979. NPL Rep. Chem.
[4] A.L. Lydersen, Estimation of Critical Properties of Organic Compounds, Eng.
Exp. Stn. rept. 3, University of Wisconsin, College of Engineering, Madison, WI,
1955.
[5] D. Dalmazzone, A. Salmon, S. Guella, A second order group contribution
method for the prediction of critical temperatures and enthalpies of vaporization of organic compounds, Fluid Ph. Equilib. 242 (2006) 29e42, http://
dx.doi.org/10.1016/j.uid.2005.12.034.
[6] Q. Wang, P. Ma, Q. Jia, S. Xia, Position group contribution method for the
prediction of critical temperatures of organic compounds, J. Chem. Eng. Data
53 (2008) 1103e1109, http://dx.doi.org/10.1021/je700641j.
, V. Svoboda, Prediction of the enthalpy of vaporization by the
[7] P. Basarova
group contribution method, Fluid Ph. Equilib. 105 (1995) 27e47, http://
dx.doi.org/10.1016/0378-3812(94)02599-V.
[8] C.H. Tu, C.P. Liu, Group-contribution estimation of the enthalpy of vaporization of organic compounds, Fluid Ph. Equilib. 121 (1996) 45e65, http://
dx.doi.org/10.1016/0378-3812(96)03008-7.
[9] P. Li, Y.H. Liang, P.S. Ma, C. Zhu, Estimations of enthalpies of vaporization of
pure compounds at different temperatures by a corresponding-states groupcontribution method, Fluid Ph. Equilib. 137 (1997) 63e74, http://dx.doi.org/
10.1016/S0378-3812(97)00094-0.
, V. R
[10] Z. Kolska
u
zi
cka, R. Gani, Estimation of the enthalpy of vaporization and
the entropy of vaporization for pure organic compounds at 298.15 K and at
normal boiling temperature by a group contribution method, Ind. Eng. Chem.
Res. 44 (2005) 8436e8454, http://dx.doi.org/10.1021/ie050113x.
[11] L. Constantinou, R. Gani, J.P. O'Connell, Estimation of the acentric factor and
the liquid molar volume at 298 K using a new group contribution method,
Fluid Ph. Equilib. 103 (1995) 11e22, http://dx.doi.org/10.1016/0378-3812(94)
02593-P.
[12] R.L. Gardas, J.A.P. Coutinho, Extension of the Ye and Shreeve group contribution method for density estimation of ionic liquids in a wide range of
temperatures and pressures, Fluid Ph. Equilib. 263 (2008) 26e32, http://
dx.doi.org/10.1016/j.uid.2007.09.016.
[13] H.S. Elbro, A. Fredenslund, P. Rasmussen, Group contribution method for the
prediction of liquid densities as a function of temperature for solvents, oligomers, and polymers, Ind. Eng. Chem. Res. 30 (1991) 2576e2582, http://
dx.doi.org/10.1021/ie00060a011.
[14] A. Fredenslund, J. Gmehling, M.L. Michelsen, P. Rasmussen, J.M. Prausnitz,
Computerized design of multicomponent distillation columns using the
UNIFAC group contribution method for calculation of activity coefcients, Ind.
Eng. Chem. Process Des. Dev. 16 (1977) 450e462, http://dx.doi.org/10.1021/
i260064a004.
[15] A. Fredenslund, R.L. Jones, J.M. Prausnitz, Group-contribution estimation of
activity coefcients in nonideal liquid mixtures, AIChE J. 21 (1975) 1086,
http://dx.doi.org/10.1002/aic.690210607.
[16] L. Constantinou, R. Gani, New group contribution method for estimating
properties of pure compounds, AIChE J. 40 (1994) 1697, http://dx.doi.org/
10.1002/aic.690401011.
[17] T. Oishi, J.M. Prausnitz, Estimation of solvent activities in polymer solutions
using a group-contribution method, Ind. Eng. Chem. Process Des. Dev. 17
(1978) 333e339, http://dx.doi.org/10.1021/i260067a021.
[18] J.Y. Park, D.R. Paul, Correlation and prediction of gas permeability in glassy
polymer membrane materials via a modied free volume based group
contribution method, J. Membr. Sci. 125 (1997) 23e39, http://dx.doi.org/
10.1016/S0376-7388(96)00061-0.
[19] R.S. Boethling, P.H. Howard, W. Meylan, W. Stiteler, J. Beauman, N. Tirado,
Group contribution method for predicting probability and rate of aerobic
biodegradation, Environ. Sci. Technol. 28 (1994) 459e465, http://dx.doi.org/
10.1021/es00052a018.
[20] D.T. Wu, Prediction of viscosities of liquid mixtures by a group contribution
method, Fluid Ph. Equilib. 30 (1986) 149e156, http://dx.doi.org/10.1016/
0378-3812(86)80050-4.
[21] R.L. Gardas, J.A.P. Coutinho, A group contribution method for viscosity estimation of ionic liquids, Fluid Ph. Equilib. 266 (2008) 195e201, http://
dx.doi.org/10.1016/j.uid.2008.01.021.
[22] E. Stefanis, C. Panayiotou, Prediction of Hansen solubility parameters with a
new group-contribution method, Int. J. Thermophys. 29 (2008) 568e585,
http://dx.doi.org/10.1007/s10765-008-0415-z.
[23] C. Gao, R. Govind, H.H. Tabak, Application of the group contribution method
for predicting the toxicity of organic chemicals, Environ. Toxicol. Chem. 11
(1992) 631e636, http://dx.doi.org/10.1002/etc.5620110506.
[24] T.A. Albahri, Structural group contribution method for predicting the octane
number of pure hydrocarbon liquids, Ind. Eng. Chem. Res. 42 (2003) 657e662,
http://dx.doi.org/10.1021/ie020306.
175
176
[54]
[55]
[56]
[57]
[58]
[59]
[60]
[61]
[62]
[63]
[64]
[65]
[66]
[67]
[68]
[69]
[70]
[71]
[72]
[73]
[74]
, L. Bartovska
/ Fluid Phase Equilibria 429 (2016) 166e176
A. Randova
the Theoretical and Measured Forms of Drops of Fluid, Cambridge University
Press Warehouse, 1883.
G. Jones, L.D. Frizzell, A theoretical and experimental analysis of the capillary
rise method for measuring the surface tension of solutions of electrolytes,
J. Chem. Phys. 8 (1940) 986e997, http://dx.doi.org/10.1063/1.1750615.
re, M.-N. Bellon-Fontaine, Measurement of the
J.-C. Michel, L.-M. Rivie
wettability of organic materials in relation to water content by the capillary
rise method, Eur. J. Soil Sci. 52 (2001) 459e467, http://dx.doi.org/10.1046/
j.1365-2389.2001.00392.x.
M.-S. Zhu, C.-X. Lu, Surface tension of diuoromethane, J. Chem. Eng. Data 39
(1994) 205e206, http://dx.doi.org/10.1021/je00014a003.
H.T. Xue, Z.N. Fang, Y. Yang, J.P. Huang, L.W. Zhou, Contact angle determined
by spontaneous dynamic capillary rises with hydrostatic effects: experiment
and theory, Chem. Phys. Lett. 432 (2006) 326e330, http://dx.doi.org/10.1016/
j.cplett.2006.10.017.
G.W. Smith, The measurement of boundary tension by the pendent-drop
method. II. Hydrocarbons, J. Phys. Chem. 48 (1944) 168e172, http://
dx.doi.org/10.1021/j150436a002.
H. Kahl, T. Wadewitz, J. Winkelmann, Surface tension of pure liquids and binary liquid mixtures, J. Chem. Eng. Data 48 (2003) 580e586, http://dx.doi.org/
10.1021/je0201323.
L.I. Rolo, A.I. Cao, A.J. Queimada, I.M. Marrucho, J.A.P. Coutinho, Surface
tension of heptane, decane, hexadecane, eicosane, and some of their binary
mixtures, J. Chem. Eng. Data 47 (2002) 1442e1445, http://dx.doi.org/10.1021/
je025536.
K. Lunkenheimer, K.-D. Wantke, Determination of the surface tension of
surfactant solutions applying the method of Lecompte du Noy (ring tensiometer), Colloid Polym. Sci. 259 (1981) 354e366, http://dx.doi.org/10.1007/
BF01524716.
, Ann. Chim. Phys. 32 (1851) 5.
M. Simon, Recherches Sur La Capillarite
skov
s, Surface tension of binary solutions of non-electrolytes. III.
M. Si
a, E. Erdo
Verication of theoretical relations, Collect. Czechoslov. Chem. Commun. 31
(1966) 2327e2337, http://dx.doi.org/10.1135/cccc19662327.
skova
, Surface tension of binary solutions of non-electrolytes. IV. Relation
M. Si
between the surface tension and other properties of pure non-electrolytes,
Collect. Czechoslov. Chem. Commun. 35 (1970) 1641e1649, http://dx.doi.org/
10.1135/cccc19701641.
B.A. Grigoryev, B.V. Nemzer, D.S. Kurumov, J.V. Sengers, Surface tension of
normal pentane, hexane, heptane, and octane, Int. J. Thermophys. 13 (1992)
453e464, http://dx.doi.org/10.1007/BF00503882.
W. Gao, X. Zhao, Z. Liu, Surface tension of 2,2-dimethylbutane from (233 to
378) K, J. Chem. Eng. Data 54 (2009) 1761e1763, http://dx.doi.org/10.1021/
je8007952.
R.K. Dewan, S.K. Mehta, Correlation between topological features and surface
tension of binary liquid mixtures, Monatsh. Chem. 121 (1990) 593e600,
http://dx.doi.org/10.1007/BF00809761.
G. Liessmann, W. Schmidt, S. Reiffarth, Data Compilation of the Saechsische
Olenwerke Boehlen, Germany, Recommended Thermophysical Data, 1995.
D. Cherqaoui, D. Villemin, Use of a neural network to determine the boiling
point of alkanes, J. Chem. Soc. Faraday Trans. 90 (1994) 97e102, http://
dx.doi.org/10.1039/FT9949000097.
J.P. Wibaut, H. Hoog, S.L. Langedyk, J. Overhoff, J. Smittenberg, A study on the
preparation and the physical constants of a number of alkanes and cycloalkanes, Recl. Trav. Chim. Pays-Bas 58 (1939) 329e376, http://dx.doi.org/
10.1002/recl.19390580409.
D. Hopfe, Data Compilation of FIZ CHEMIE, 1990. Germany.
O.R. Quayle, R.A. Day, G.M. Brown, A study of organic Parachors. VII. A series of
saturated hydrocarbons, J. Am. Chem. Soc. 66 (1944) 938e941, http://
dx.doi.org/10.1021/ja01234a030.
J.J. Bikerman, Surface Chemistry, second ed., Academic Press, Inc., New York,
1958.
Y.-M. Dai, Y.-N. Liu, X. Li, Z. Cao, Z.-P. Zhu, D.-W. Yang, Estimation of surface
tension of organic compounds using quantitative structure-property relationship, J. Cent. South Univ. 19 (2012) 93e100, http://dx.doi.org/10.1007/
s1177101209776.