Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Activity coefficients at infinite dilution of organic solvents and water in 1-butyl-3-methylimidazolium dicyanamide. A literature review of hexane/hex-1-ene separation

Domanska, U.[Urszula], Wlazlo, M.[Michal], Karpinska, M.[Monika]
Fluid Phase Equilib. 2016, 417, 50-61
ABSTRACT
The work presented focused on the experimental data of the activity coefficients at infinite dilution of several solutes in ionic liquid of 1-butyl-3-methylimidazolium dicyanamide, [BMIM][DCA]. The values of activity coefficient at infinite dilution for 64 solutes, including alkanes, cycloalkanes, alkenes, alkynes, aromatic hydrocarbons, alcohols, water, ethers, ketones, acetonitrile, pyridine, 1-nitropropane, thiophene, and esters in [BMIM][DCA] were determined by gas liquid chromatography at six temperatures in range of (318.15 368.15) K. The gas-liquid partition coefficients were calculated for all solutes. The partial molar excess Gibbs energy, enthalpy and entropy at infinite dilution were calculated from the experimentalactivity coefficient at infinite dilution values. The [BMIM][DCA] was discussed as a solvent for the different types of separation problems with special attention to the separation of hexane/hex-1-ene, cyclohexane/cyclohexene and ethylbenzene/styrene. This work discuss a particular type of mixture made up of small hydrocarbons (alkanes) and their unsaturated counterparts (alkenes). The separating ability of the investigated ionic liquid was compared with the previously investigated 1-butyl-3-methylimidazolium-based, and dicyanoamide-based ILs for three chosen separation problems. Additionally, a literature review of activity coefficient at infinite dilution for the hexane/hex-1-ene separation problem at T = 323.15 K is presented for the years 2010 2015. It was found that several ILs may replace conventional solvents. The proposed [BMIM][DCA] may be used as an alternative solvent for the separation of alkenes from alkanes.
Compounds
# Formula Name
1 C5H12 pentane
2 C6H14 hexane
3 C6H14 3-methylpentane
4 C6H14 2,2-dimethylbutane
5 C7H16 heptane
6 C8H18 octane
7 C8H18 2,2,4-trimethylpentane
8 C9H20 nonane
9 C10H22 decane
10 C5H10 cyclopentane
11 C6H12 cyclohexane
12 C7H14 methylcyclohexane
13 C7H14 cycloheptane
14 C8H16 cyclooctane
15 C5H10 1-pentene
16 C6H12 hex-1-ene
17 C6H10 cyclohexene
18 C7H14 1-heptene
19 C8H16 oct-1-ene
20 C10H20 1-decene
21 C5H8 1-pentyne
22 C6H10 1-hexyne
23 C7H12 1-heptyne
24 C8H14 1-octyne
25 C6H6 benzene
26 C7H8 toluene
27 C8H10 ethylbenzene
28 C8H10 1,2-dimethylbenzene
29 C8H10 1,3-dimethylbenzene
30 C8H10 1,4-dimethylbenzene
31 C9H12 propylbenzene
32 C9H12 isopropylbenzene
33 C8H8 styrene
34 C9H10 (1-methylethenyl)benzene
35 C4H4S thiophene
36 C5H5N pyridine
37 CH4O methanol
38 C2H6O ethanol
39 C3H8O propan-1-ol
40 C3H8O propan-2-ol
41 C4H10O butan-1-ol
42 C4H10O butan-2-ol
43 C4H10O 2-methyl-1-propanol
44 C4H10O 2-methylpropan-2-ol
45 H2O water
46 C3H6O2 methyl ethanoate
47 C4H8O2 methyl propanoate
48 C5H10O2 methyl butanoate
49 C4H8O2 ethyl acetate
50 C4H8O tetrahydrofuran
51 C4H8O2 1,4-dioxane
52 C5H12O 2-methoxy-2-methylpropane
53 C6H14O 2-ethoxy-2-methylpropane
54 C6H14O 2-methoxy-2-methylbutane
55 C4H10O diethyl ether
56 C6H14O dipropyl ether
57 C6H14O diisopropyl ether
58 C8H18O dibutyl ether
59 C3H6O acetone
60 C5H10O pentan-2-one
61 C5H10O pentan-3-one
62 C4H8O butanal
63 C2H3N acetonitrile
64 C3H7NO2 1-nitropropane
65 C10H15N5 1-butyl-3-methylimidazolium dicyanamide
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • 65
  • Activity coefficient - 1 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 1; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 2
  • 65
  • Activity coefficient - 2 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 2; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 3
  • 65
  • Activity coefficient - 3 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 3; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 4
  • 65
  • Activity coefficient - 4 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 4; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 5
  • 65
  • Activity coefficient - 5 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 5; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 6
  • 65
  • Activity coefficient - 6 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 6; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 7
  • 65
  • Activity coefficient - 7 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 7; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 8
  • 65
  • Activity coefficient - 8 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 8; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 9
  • 65
  • Activity coefficient - 9 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 9; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 10
  • 65
  • Activity coefficient - 10 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 10; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 11
  • 65
  • Activity coefficient - 11 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 11; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 12
  • 65
  • Activity coefficient - 12 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 12; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 13
  • 65
  • Activity coefficient - 13 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 13; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 14
  • 65
  • Activity coefficient - 14 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 14; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 15
  • 65
  • Activity coefficient - 15 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 15; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 16
  • 65
  • Activity coefficient - 16 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 16; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 17
  • 65
  • Activity coefficient - 17 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 17; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 18
  • 65
  • Activity coefficient - 18 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 18; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 19
  • 65
  • Activity coefficient - 19 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 19; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 20
  • 65
  • Activity coefficient - 20 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 20; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 21
  • 65
  • Activity coefficient - 21 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 21; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 22
  • 65
  • Activity coefficient - 22 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 22; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 23
  • 65
  • Activity coefficient - 23 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 23; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 24
  • 65
  • Activity coefficient - 24 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 24; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 25
  • 65
  • Activity coefficient - 25 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 25; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 26
  • 65
  • Activity coefficient - 26 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 26; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 27
  • 65
  • Activity coefficient - 27 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 27; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 28
  • 65
  • Activity coefficient - 28 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 28; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 29
  • 65
  • Activity coefficient - 29 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 29; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 30
  • 65
  • Activity coefficient - 30 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 30; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 31
  • 65
  • Activity coefficient - 31 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 31; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 32
  • 65
  • Activity coefficient - 32 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 32; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 33
  • 65
  • Activity coefficient - 33 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 33; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 34
  • 65
  • Activity coefficient - 34 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 34; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 35
  • 65
  • Activity coefficient - 35 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 35; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 36
  • 65
  • Activity coefficient - 36 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 36; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 37
  • 65
  • Activity coefficient - 37 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 37; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 38
  • 65
  • Activity coefficient - 38 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 38; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 39
  • 65
  • Activity coefficient - 39 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 39; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 40
  • 65
  • Activity coefficient - 40 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 40; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 41
  • 65
  • Activity coefficient - 41 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 41; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 42
  • 65
  • Activity coefficient - 42 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 42; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 43
  • 65
  • Activity coefficient - 43 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 43; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 44
  • 65
  • Activity coefficient - 44 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 44; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 45
  • 65
  • Activity coefficient - 45 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 45; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 46
  • 65
  • Activity coefficient - 46 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 46; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 47
  • 65
  • Activity coefficient - 47 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 47; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 48
  • 65
  • Activity coefficient - 48 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 48; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 49
  • 65
  • Activity coefficient - 49 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 49; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 50
  • 65
  • Activity coefficient - 50 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 50; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 51
  • 65
  • Activity coefficient - 51 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 51; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 52
  • 65
  • Activity coefficient - 52 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 52; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 53
  • 65
  • Activity coefficient - 53 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 53; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 54
  • 65
  • Activity coefficient - 54 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 54; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 55
  • 65
  • Activity coefficient - 55 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 55; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 56
  • 65
  • Activity coefficient - 56 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 56; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 57
  • 65
  • Activity coefficient - 57 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 57; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 58
  • 65
  • Activity coefficient - 58 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 58; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 59
  • 65
  • Activity coefficient - 59 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 59; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 60
  • 65
  • Activity coefficient - 60 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 60; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 61
  • 65
  • Activity coefficient - 61 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 61; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 62
  • 65
  • Activity coefficient - 62 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 62; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 63
  • 65
  • Activity coefficient - 63 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 63; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6
  • POMD
  • 64
  • 65
  • Activity coefficient - 64 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 64; Liquid
  • Liquid
  • Gas
  • Chromatography
  • 6