2
0
2017
kea
har
0
journal
Original
Keating, L.[Leasa]
Harris, H. H.[Harold H.]
Chickos, J. S.[James S.]
J. Chem. Thermodyn.
2017
2020-09-29
Vapor pressures and vaporization enthalpy of (-) alpha-bisabolol and (dl) menthol by correlation gas chromatography
The vapor pressures and vaporization enthalpies of (-) alpha-bisabolol and (dl)-menthol, two GRAS chemicals (generally recognized as safe) are evaluated by correlation gas chromatography using a series of saturated primary alcohols as standards. Vaporization enthalpies of (96.6 +- 2.4) and (74.2 +- 2.8) kJ mol 1 and vapor pressures of p/Pa = (0.020 +- 0.003) and (4.5 +- 0.44) were evaluated at T = 298.15 K for (-) alpha-bisabolol and (dl)-menthol, respectively, and compared to literature values. The vapor pressures of both compounds from T = (298.15 to 500) K have been derived from correlations using vapor pressures of a series of 1-alkanols and corresponding gas chromatographic retention times at 10 K intervals. The results were fit to a second order polynomial. Calculated normal boiling temperatures of TB = (574.8 and 492.7) K are calculated for (-) alpha-bisabolol and (dl)-menthol, respectively. A normal boiling temperature of TB = (485.2, and 489.7) K has previously been reported for (dl)-menthol. Vapor pressures for both (l)-menthol and (dl)-menthol from a previous study and (dl)-menthol from this study are compared with literature values.
(-) alpha-Bisabolol
(dl) Menthol
Vapor pressure
Vaporization enthalpy
Correlation gas chromatography
Boiling temperature
10.1016/j.jct.2016.11.027
107
18-25
1
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
NOOLISFMXDJSKH-KXUCPTDWSA-N
DL-menthol
(.+-.)-menthol
racementhol
rel-(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol
rel-(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanol
C10H20O
1
Commercial source
1
92
2
Stated by supplier
2
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
RGZSQWQPBWRIAQ-CABCVRRESA-N
(-)-.alpha.-bisabolol
(.alpha.S,1S)-.alpha.,4-dimethyl-.alpha.-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol
(S)-6-methyl-2-((S)-4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
Levomenol
C15H26O
1
Commercial source
1
93
2
Stated by supplier
1
1
1
Principal objective of the work
AB
TRC
8/17/2017
1
Molar enthalpy of vaporization or sublimation, kJ/mol
Correlation gas chromatography
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Temperature, K
Liquid
1
298
3
1
75
3
1
4.5
2
1
1
Principal objective of the work
AB
TRC
8/17/2017
1
Vapor or sublimation pressure, kPa
Gas chromatography
Metastable liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Metastable liquid
Gas
1
Temperature, K
Metastable liquid
1
298.15
5
1
0.0045
2
1
0.0009
1
310
2
1
0.014
2
1
0.001
1
320
2
1
0.034
2
1
0.003
1
330
2
1
0.075
2
1
0.008
1
340
2
1
0.16
2
1
0.021
1
350
2
1
0.31
2
1
0.046
1
360
2
1
0.57
2
1
0.09
1
370
2
1
1
1
1
0.155
1
380
2
1
1.7
2
1
0.251
1
390
2
1
2.9
2
1
0.381
1
400
1
1
4.6
2
1
0.565
1
410
2
1
7
1
1
0.78
1
420
2
1
10
1
1
1.027
1
430
2
1
15
2
1
1.422
1
440
2
1
22
2
1
1.985
1
450
2
1
30
1
1
2.729
1
460
2
1
41
2
1
3.908
1
470
2
1
55
2
1
5.596
1
480
2
1
73
2
1
8.717
1
490
2
1
96
2
1
13.983
1
500
1
1
120
2
1
21.747
1
492.7
4
1
101.325
6
1
15.748
3
2
1
Principal objective of the work
AB
TRC
8/17/2017
1
Molar enthalpy of vaporization or sublimation, kJ/mol
Correlation gas chromatography
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Temperature, K
Liquid
1
298
3
1
96.6
3
1
5.1
4
2
1
Principal objective of the work
AB
TRC
8/17/2017
1
Vapor or sublimation pressure, kPa
Gas chromatography
Liquid
Direct value, X
1
Data file compiler
Propagation of evaluated standard uncertainties
95
Liquid
Gas
1
Temperature, K
Liquid
1
298.15
5
1
2e-05
2
1
6e-06
1
310
2
1
9.3e-05
2
1
8e-06
1
320
2
1
0.0003
2
1
2e-05
1
330
2
1
0.00086
2
1
0.0001
1
340
2
1
0.0023
2
1
0.0004
1
350
2
1
0.0056
2
1
0.0011
1
360
2
1
0.013
2
1
0.003
1
370
2
1
0.027
2
1
0.004
1
380
2
1
0.055
2
1
0.011
1
390
2
1
0.11
2
1
0.018
1
400
1
1
0.2
1
1
0.031
1
410
2
1
0.35
2
1
0.047
1
420
2
1
0.59
2
1
0.073
1
430
2
1
0.97
2
1
0.109
1
440
2
1
1.5
2
1
0.161
1
450
2
1
2.4
2
1
0.241
1
460
2
1
3.6
2
1
0.351
1
470
2
1
5.3
2
1
0.494
1
480
2
1
7.5
2
1
0.679
1
490
2
1
10.6
3
1
0.963
1
500
1
1
15
2
1
1.503
1
574.8
4
1
101.325
6
1
15.743