Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Separation of binary mixtures hexane/hex-1-ene, cyclohexane/cyclohexene and ethylbenzene/styrene based on limiting activity coefficients

Domanska, U.[Urszula], Wlazlo, M.[Michal], Karpinska, M.[Monika], Zawadzki, M.[Maciej]
J. Chem. Thermodyn. 2017, 110, 227-236
ABSTRACT
The measurements of a limiting activity coefficients, c1 13 at infinite dilution for 63 solutes including wide spectra of alkanes, alkenes and alkynes as well as aromatic hydrocarbons, alcohols, water, ethers, ketones, acetonitrile, pyridine, 1-nitropropane, thiophene, and esters in the 1-(3-hydroxypropyl)pyridinium dicyanamide, [N-C3OHPY][DCA], determined by gas-liquid chromatography at temperature range of (298.15 368.15) K are developed. The synthesis and thermochemical characteristic of the ionic liquid (IL) is described. The density and viscosity of the IL was measured as a function of temperature in a range of (298.15 368.15) K. The comparison of c1 13 for selected solutes in ionic liquids (ILs) with [N-C3OHPY]+ cation and [TCM] , [DCA] , [TCB] and [SCN] -anions at one temperature, T = 328.15 K is shown. The gasliquid partition coefficients, KL at infinite dilution and the limiting fundamental thermodynamic functions, the partial molar excess Gibbs energy, enthalpy and entropy were calculated for all solutes. The values of selectivity and capacity for three separation problems hexane/hex-1-ene, cyclohexane/cyclohexene and methylbenzene/styrene were calculated from c1 13 and compared to literature values for [N-C3OHPY]-based or [DCA]-based ILs for the same separation problems. The data presented here shows that [N-C3OHPY][DCA] reveals large selectivity 2.34, 2.79 and 2.27 in three of discussed separation problems. However, the comparison to the measured earlier [DCA]-based ILs shows the low capacity for the hex-1-ene and cyclohexene. The Abraham solvation parameter model was also presented for all solutes. On the bases of the results the intermolecular interactions of the chosen IL and solutes was discussed.
Compounds
# Formula Name
1 C10H12N4O N-(3-hydroxypropyl)pyridinium dicyanamide
2 C6H14 hexane
3 C6H14 3-methylpentane
4 C7H16 heptane
5 C8H18 octane
6 C8H18 2,2,4-trimethylpentane
7 C9H20 nonane
8 C10H22 decane
9 C5H10 cyclopentane
10 C6H12 cyclohexane
11 C7H14 methylcyclohexane
12 C7H14 cycloheptane
13 C8H16 cyclooctane
14 C5H10 1-pentene
15 C6H12 hex-1-ene
16 C6H10 cyclohexene
17 C7H14 1-heptene
18 C8H16 oct-1-ene
19 C10H20 1-decene
20 C5H8 1-pentyne
21 C6H10 1-hexyne
22 C7H12 1-heptyne
23 C8H14 1-octyne
24 C6H6 benzene
25 C7H8 toluene
26 C8H10 ethylbenzene
27 C8H10 1,2-dimethylbenzene
28 C8H10 1,3-dimethylbenzene
29 C8H10 1,4-dimethylbenzene
30 C9H12 propylbenzene
31 C9H12 isopropylbenzene
32 C8H8 styrene
33 C9H10 (1-methylethenyl)benzene
34 C4H4S thiophene
35 C5H5N pyridine
36 CH4O methanol
37 C2H6O ethanol
38 C3H8O propan-1-ol
39 C3H8O propan-2-ol
40 C4H10O butan-1-ol
41 C4H10O butan-2-ol
42 C4H10O 2-methyl-1-propanol
43 C4H10O 2-methylpropan-2-ol
44 C5H12O pentan-1-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
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
  • Triple point temperature, K ; Glass
  • Glass
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 15
  • POMD
  • 1
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Falling or rolling sphere viscometry
  • 7
  • POMD
  • 1
  • 2
  • Activity coefficient - 2 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 4
  • POMD
  • 1
  • 3
  • Activity coefficient - 3 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 4
  • POMD
  • 1
  • 4
  • Activity coefficient - 4 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 5
  • Activity coefficient - 5 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 6
  • Activity coefficient - 6 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 4
  • POMD
  • 1
  • 7
  • Activity coefficient - 7 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 7; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 8
  • Activity coefficient - 8 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 8; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 9
  • Activity coefficient - 9 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 9; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 10
  • Activity coefficient - 10 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 10; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 11
  • Activity coefficient - 11 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 11; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 12
  • Activity coefficient - 12 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 12; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 13
  • Activity coefficient - 13 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 13; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 14
  • Activity coefficient - 14 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 14; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 4
  • POMD
  • 1
  • 15
  • Activity coefficient - 15 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 15; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 16
  • Activity coefficient - 16 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 16; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 17
  • Activity coefficient - 17 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 17; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 18
  • Activity coefficient - 18 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 18; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 19
  • Activity coefficient - 19 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 19; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 20
  • Activity coefficient - 20 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 20; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 21
  • Activity coefficient - 21 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 21; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 22
  • Activity coefficient - 22 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 22; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 23
  • Activity coefficient - 23 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 23; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 7
  • POMD
  • 1
  • 24
  • Activity coefficient - 24 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 24; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 25
  • Activity coefficient - 25 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 25; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 26
  • Activity coefficient - 26 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 26; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 27
  • Activity coefficient - 27 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 27; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 28
  • Activity coefficient - 28 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 28; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 29
  • Activity coefficient - 29 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 29; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 30
  • Activity coefficient - 30 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 30; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 31
  • Activity coefficient - 31 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 31; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 32
  • Activity coefficient - 32 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 32; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 33
  • Activity coefficient - 33 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 33; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 34
  • Activity coefficient - 34 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 34; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 35
  • Activity coefficient - 35 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 35; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 36
  • Activity coefficient - 36 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 36; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 37
  • Activity coefficient - 37 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 37; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 38
  • Activity coefficient - 38 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 38; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 39
  • Activity coefficient - 39 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 39; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 40
  • Activity coefficient - 40 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 40; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 41
  • Activity coefficient - 41 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 41; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 42
  • Activity coefficient - 42 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 42; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 43
  • Activity coefficient - 43 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 43; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 44
  • Activity coefficient - 44 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 44; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 45
  • Activity coefficient - 45 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 45; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 4
  • POMD
  • 1
  • 46
  • Activity coefficient - 46 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 46; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 47
  • Activity coefficient - 47 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 47; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 48
  • Activity coefficient - 48 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 48; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 49
  • Activity coefficient - 49 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 49; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 50
  • Activity coefficient - 50 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 50; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 51
  • Activity coefficient - 51 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 51; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 52
  • Activity coefficient - 52 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 52; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 53
  • Activity coefficient - 53 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 53; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 54
  • Activity coefficient - 54 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 54; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 55
  • Activity coefficient - 55 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 55; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 56
  • Activity coefficient - 56 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 56; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 57
  • Activity coefficient - 57 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 57; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 58
  • Activity coefficient - 58 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 58; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 59
  • Activity coefficient - 59 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 59; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 60
  • Activity coefficient - 60 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 60; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 61
  • Activity coefficient - 61 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 61; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 62
  • Activity coefficient - 62 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 62; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 63
  • Activity coefficient - 63 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 63; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6
  • POMD
  • 1
  • 64
  • Activity coefficient - 64 ; Liquid
  • Temperature, K; Liquid
  • Mole fraction - 64; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Chromatography
  • 6