Rationalization and prediction of the equivalent alkane carbon number (EACN) of polar hydrocarbon oils with COSMO-RS sigmamoments Thomas Lukowicz, Adrien Benazzouz, Véronique Nardello-Rataj, Jean-Marie Aubry* 1
Université Lille 1 and ENSCL, Unité de Catalyse et de Chimie du Solide, CNRS UMR 8181, Equipe
CÏSCO, Cité Scientifique F-59655 Villeneuve d’Ascq, France
*Corresponding author:
[email protected]
Supporting Information Experimental and predicted EACN of all relevant oils, as well as their σ-moments ܯ and ܯଶ , which were used to build up the QSPR-model. Compound
Structure
EACNexp EACNpred
ࡹࢄ
ࡹࢄ
595.55 516.26 436.48 396.57 356.86 316.59 276.64 236.78 216.79 196.84 176.89 156.90
25.79 22.54 19.27 17.64 16.00 14.42 12.80 11.14 10.36 9.50 8.67 7.92
n-Alkanes Octacosane Tetracosane Eicosane Octadecane Hexadecane Tetradecane Dodecane Decane Nonane Octane Heptane Hexane
C28H58 C24H50 C20H42 C18H38 C16H34 C14H30 C12H26 C10H22 C9H20 C8H18 C7H16 C6H14
28.0 24.0 20.0 18.0 16.0 14.0 12.0 10.0 9.0 8.0 7.0 6.0
29.1 24.7 20.1 17.9 15.7 13.4 11.1 8.9 7.7 6.6 5.5 4.3
Branched & Cyclic Alkanes Dodecylcyclohexane
17.3
16.6
367.61
15.50
Decylcyclohexane
14.4
14.3
327.82
13.95
Butylcyclohexane
7.0
7.5
207.97
9.18
Propylcyclohexane
5.7
6.3
186.65
8.34
Cyclodecane
5.5
6.4
191.14
8.83
cis-Decalin
5.3
6.1
180.73
7.64
Isopropylcyclohexane
5.3
5.9
183.19
8.65
1.4-Dimethylcyclohexane
4.4
5.1
168.79
8.04
Ethylcyclohexane
4.2
5.2
168.08
7.65
Cyclooctane
4.1
5.0
162.27
7.14
1.2-Dimethylcyclohexane
3.3
4.8
163.93
7.97
Methyl-cyclohexane
3.2
4.0
148.89
7.11
Cyclohexane
2.2
3.3
131.49
5.70
Halogenated Alkanes 1-Chlorohexadecane
9.8
10.6
375.07
35.19
1-Chlorotetradecane
8.0
8.6
336.98
33.19
1-Chlorododecane
5.6
6.1
295.24
31.95
3.5
3.7
252.91
30.08
-3.3
-3.1
136.50
26.17
14.1
391.54
27.99
1-Chlorodecane
1-Bromo-3-methylpropan
C9H19
Cl
Unsaturated Alkanes 1-Octadecene
14.2
1-Dodecene
8.1
7.4
272.29
23.10
1-Decene
5.5
5.1
232.04
21.54
1-Octene
3.9
2.8
192.22
19.99
cis-Cyclooctene
1.6
2.0
158.70
15.24
1-Methyl-1-cyclohexene
0.4
1.3
148.75
15.24
4-Methyl-1-cyclohexene
0.4
0.8
148.35
16.76
3-Methyl-1-cyclohexene
-0.1
0.9
148.04
16.54
Cyclohexene
-1.2
-0.2
129.65
15.91
1-Tetradecyne
3.9
4.4
308.41
39.76
1-Dodecyne
2.0
1.9
268.31
38.70
1-Decyne
0.1
-0.3
228.52
37.05
1-Octyne
-2.2
-2.5
188.67
35.41
Dodecylbenzene
7.9
9.0
357.91
36.21
Decylbenzene
6.2
6.8
317.88
34.65
Octylbenzene
4.3
4.5
278.05
33.05
Butylbenzene
0.4
0.0
198.60
29.91
p-Xylene
-2.3
-1.9
160.45
27.44
Phenyl-1-butyne
-3.3
-4.0
192.75
40.76
Terpenes Longifolene
6.5
6.1
234.48
18.96
p-Menthane
6.0
6.5
197.61
10.05
Caryophyllene
5.6
4.1
250.11
28.28
Pinane
4.0
5.5
185.99
10.57
α-Pinene
3.4
3.0
182.79
17.39
p-Menth-2-ene
3.3
3.6
199.01
19.12
∆-3-Carene
2.5
2.8
187.24
19.03
β-Pinene
2.2
2.2
182.98
19.97
Limonene
2.0
1.0
193.07
25.77
γ-Terpinene
1.8
1.5
197.46
25.18
α-Terpinene
1.3
1.2
193.84
25.23
Terpinolene
1.0
1.2
195.95
25.77
p-Cymene
-0.4
0.0
194.19
28.89
