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共Received 8 May 2006; revised manuscript received 7 July 2006; accepted 4 September 2006; published online 6 July 2007兲
The mutual solubilities and related liquid–liquid equilibria of C8 – C17 alcohols with
water are exhaustively and critically reviewed. Reports of experimental determination of
solubility in 21 chemically distinct binary systems that appeared in the primary literature
prior to the end of 2004 are compiled. For 12 systems sufficient data are available to
allow critical evaluation. All data are expressed as mass percent and mole fraction as well
as the originally reported units. In addition to the standard evaluation criteria used
throughout the Solubility Data Series, a new method based on the evaluation of the all
experimental data for a given homologous series of saturated alcohols was used. © 2007
American Institute of Physics. 关DOI: 10.1063/1.2391321兴
Key words: C8–C17 alcohols; critical evaluation; liquid–liquid equilibria; reference data; solubilities; water.
0047-2689/2007/36„3…/685/47/$42.00 685 J. Phys. Chem. Ref. Data, Vol. 36, No. 3, 2007
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686 A. MACZYNSKI AND D. G. SHAW
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IUPAC-NIST SOLUBILITY DATA SERIES 687
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688 A. MACZYNSKI AND D. G. SHAW
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IUPAC-NIST SOLUBILITY DATA SERIES 689
Experimental Values
TABLE 4. Solubility in the 2,6-dimethylcyclohexanol/water system.40 2.5. 2-Ethyl-1-hexanol ⴙ Water
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690 A. MACZYNSKI AND D. G. SHAW
FIG. 1. All the solubility data for 2-ethyl–1-hexanol 共1兲 in water 共2兲. FIG. 2. All the solubility data for water 共2兲 in 2-ethyl–1-hexanol 共1兲.
The reference solubility values of 共1兲 in 共2兲 were calcu- TABLE 6. Sources of solubility data for water 共2兲 in 2-ethyl–1-hexanol 共1兲.
lated by the equation:
Author 共s兲 T共K兲 Author 共s兲 T共K兲
11 30
Cabezas et al. 298 Moriyoshi et al. 298
Ghanadzadeh et al.16 298–303 Ratkovics et al.32 293
ln x1 = ln x1,min + C1关T1,min/T − 1 − ln共T1,min/T兲兴, 共1兲 Hlavaty and Linek19 298 Ratkovics et al.33 293
McBain and Richards27 273 Stephenson et al.41 283–364
where T1,min = 306.4 K, ln x1,min = −9.24, and C1 = 40.0. The reference solubility values of water 共2兲 in alkanol 共1兲
T1,min, ln x1,min, and C1 were calculated with Eqs. 共7兲, 共9兲, were determined by liquid–liquid equilibrium 共LLE兲 calcula-
and 共10兲, where constants defined by Eqs. 共12兲 were used. In tions described in the Preface to Part 2.26 The concentrations
these equations number of carbon atoms 共Nc兲 was replaced of 共1兲 in 共2兲 predicted from Eq. 共1兲 were used as the input
by an effective value N*c = 7.68, which was calculated from data. The reference values obtained from the LLE calcula-
Eq. 共13兲. All the mentioned equations are given in the Pref- tions were afterward regressed by Eq. 共2兲
ace to Part 226 共see Table 6兲. ln x2 = ln x2,min + C2关T2,min/T − 1 − ln共T2,min/T兲兴, 共2兲
The criteria used to assign data to categories listed in
Table 7 are also described in the Preface to Part 2.26 All the where T2,min = 263.2 K, ln x2,min = −1.875, and C2 = 7.99.
experimental data and reference values are listed in Table 8 The criteria used to assign data to categories listed in
and shown in Fig. 1. Some data used in this evaluation were Table 9 are described in the Preface to Part 2.26 All the ex-
compiled for an earlier version of this work.8 Those compi- perimental data and reference values are listed in the Table
lations are not reprinted here. New compilations are pre- 10 and shown in Fig. 2.
sented following this evaluation.
References for 2-ethyl–1-hexanol/water system
Critical evaluation of the solubility of water (2) in 8
A. F. M. Barton, Editor, IUPAC Solubility Data Series, Vol.
2-ethyl–1-hexanol (1) 15, Alcohols with Water 共Pergamon, New York, 1984兲.
The experimental solubility data for 共2兲 in 共1兲 have been 11
J. L. Cabezas, L. A. Barcena, J. Coca, and M. Cockrem, J.
investigated by the authors listed in Table 6 together with Chem. Eng. Data 33, 435 共1988兲.
16
temperature range. H. Ghanadzadeh, A. Ghanadzadeh, and R. Sariri, J. Chem.
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IUPAC-NIST SOLUBILITY DATA SERIES 691
30
Thermodyn. 36, 1001 共2004兲. T. Moriyoshi, T. Sakamoto, and Y. Uosaki, J. Chem. Ther-
19
K. Hlavaty and J. Linek, Collect. Czech. Chem. Commun. modyn. 21, 947 共1989兲.
38, 374 共1973兲. 32
F. Ratkovics, B. Palagyi-Fenyes, E. Hajos-Szikszay, and A.
26
A. Maczynski and D. G. Shaw, Editor, “IUPAC-NIST Solu-
Dallos, J. Chem. Thermodyn. 22, 129 共1990兲.
bility Data Series. 82. Alcohol with Water – Revised and 33
F. Ratkovics, B. Palagyi-Fenyes, E. Hajos-Szikszay, and A.
Updated. Part 2. C6 alcohols with water,” J. Phys. Chem.
Ref. Data 36, 191 共2007兲. Dallos, J. Chem. Thermodyn. 23, 859 共1991兲.
27 41
J. W. McBain and P. H. Richards, Ind. Eng. Chem. 38, 642 R. Stephenson, J. Stuart, and M. Tabak, J. Chem. Eng. Data
共1946兲. 29, 287 共1984兲.
TABLE 7. The data categories for solubility of 2-ethyl–1-hexanol 共1兲 in water 共2兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±10% 兲 with the reference values兴 共⬎10% 兲 with the reference values兴
Experimental values x1
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x1
TABLE 9. The data categories for solubility of water 共2兲 in 2-ethyl–1-hexanol 共1兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±5 % 兲 with the reference values兴 共⬎5 % 兲 with the reference values兴
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692 A. MACZYNSKI AND D. G. SHAW
TABLE 9. The data categories for solubility of water 共2兲 in 2-ethyl–1-hexanol 共1兲.—Continued
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±5 % 兲 with the reference values兴 共⬎5 % 兲 with the reference values兴
TABLE 10. Experimental values for solubility of water 共2兲 in 2-ethyl–1-hexanol 共1兲.
Experimental values x2
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x2
Auxiliary Information
Components: Original Measurements:
共1兲 2-Ethyl-1-hexanol; C8H18O; 11
J. L. Cabezas, L. A. Barcena, Method/Apparatus/Procedure:
关104-76-7兴 J. Coca, and M. Cockrem, J. The analytical method was used. Alcohol 共1兲 and water 共2兲 were brought
共2兲 Water; H2O; 关7732-18-5兴 Chem. Eng. Data 33, 435 共1988兲. into equilibrium at a given temperature in an equilibrium still and samples
of each layer were removed for analysis. Compositions were obtained
Variables: Prepared by: from densities and refractive indexes measured at either 24 or 26 ° C, to
One temperature: 25 ° C B. Wisniewska-Goclowska avoid turbidity and phase separation. Densities were measured with a
calibrated U-pycnometer and refractive indexes with a PZO-RL2 Abbe
Experimental Values
refractometer 共see Table 11兲.
TABLE 11. Solubility in the 2-ethyl–1-hexanol/water system.11
Source and Purity of Materials:
Solubility of 2-ethyl–1-hexanol in water 共1兲 Source not specified; reagent grade; distilled.
共2兲 Not specified.
t共°C兲 g共1兲 / 100 g sln x1共compiler兲
25 0.07 0.0001 Estimated Error:
Solubility of water in 2-ethyl–1-hexanol Solubility: 0.1% 共relative accuracy兲.
t共°C兲 g共2兲 / 100 g sln x2共compiler兲
25 2.27 0.1438
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IUPAC-NIST SOLUBILITY DATA SERIES 693
Experimental Values
Components: Original Measurements:
TABLE 13. Solubility in the 2-ethyl–1-hexanol/water system.30
共1兲 2-Ethyl-1-hexanol; C8H18O; 16
H. Ghanadzadeh, A.
关104-76-7兴 Ghanadzadeh, and R. Sariri, J. Solubility of 2-ethyl–1-hexanol in water
共2兲 Water; H2O; 关7732-18-5兴 Chem. Thermodyn. 36, 1001
共2004兲. g共1兲 / 100 g sln
T共K兲 P共MPa兲 共compiler兲 x1
Variables: Prepared by:
Temperature: 298.2– 313.2 K B. Wisniewska-Goclowska 298.15 0.1 0.66 0.001
100 0.66 0.001
Experimental Values
TABLE 12. Solubility in the 2-ethyl–1-hexanol/water system.16 200 0.66 0.001
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694 A. MACZYNSKI AND D. G. SHAW
Estimated Error:
Method/Apparatus/Procedure:
Solubility: ⱕ0.1 mass %.
The cloud-point method was used. No details were reported in the paper.
The results reported above are part of various ternary solubility
measurements 共see Table 15兲.
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IUPAC-NIST SOLUBILITY DATA SERIES 695
Critical evaluation of the solubility of 1-octanol (1) in investigated by the authors listed in Table 17 together with
water (2) temperature range and pressure range if reported:
The experimental solubility data for 共1兲 in 共2兲 have been
TABLE 17. Sources of solubility data for 1-octanol 共1兲 in water 共2兲.
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696 A. MACZYNSKI AND D. G. SHAW
TABLE 18. Sources of solubility data for water 共2兲 in 1-octanol 共1兲.—Continued
4
A. Arce, M. Blanco, and A. Soto, J. Chem. Eng. Data 43,
255 共1998兲.
5
A. Arce, M. Blanco, and A. Soto, Fluid Phase Equilib. 146,
161 共1998兲.
6
A. Arce, M. Blanco, A. Soto, and I. Vidal, J. Chem. Ther-
modyn. 28, 3 共1996兲.
8
A. F. M. Barton, Editor, IUPAC Solubility Data Series, Vol.
15, Alcohols with Water 共Pergamon, New York, 1984兲.
9
J. S. Brown, J. P. Hallett, D. Bush, and C. A. Eckert, J.
Chem. Eng. Data 45, 846 共2000兲.
10
J. A. V. Butler, D. W. Thomson, and W. H. Maclennan, J.
Chem. Soc. 674 共1933兲. 共IUPAC - SDS, Volume 15兲.
12
E. D., Jr. Crittenden and A. N. Hixon, Ind. Eng. Chem. 46,
265 共1954兲. 共IUPAC - SDS, Volume 15兲.
13
L. Erichsen, Brennst.-Chem. 33, 166 共1952兲. 共IUPAC -
SDS, Volume 15兲.
15
J. C. Galan, J. M. M. Moreno, R. T. Valle, and A. R. Se-
gado, An. Quim. Ser. A, 85, 273 共1989兲.
21
K. Kinoshita, H. Ishikawa, and K. Shinoda, Bull. Chem.
Soc. Jpn. 31, 1081 共1958兲. 共IUPAC - SDS, Volume 15兲.
22
M. Janado, Y. Yano, Y. Doi, and H. Sakamoto, J. Solution
Chem. 12, 741 共1983兲.
24
O. A. Lavrova and T. M. Lesteva, Zh. Fiz. Khim. 50, 1617
共1976兲. 共IUPAC - SDS, Volume 15兲.
26
A. Maczynski and D. G. Shaw, Editor, “IUPAC-NIST Solu-
bility Data Series. 82. Alcohol with Water – Revised and
Updated. Part 2. C6 alcohols with water,” J. Phys. Chem.
FIG. 4. All the solubility data for water 共2兲 in 1-octanol 共1兲.
Ref. Data 36, 191 共2007兲.
27
J. W. McBain and P. H. Richards, Ind. Eng. Chem. 38, 642
The reference solubility values of water 共2兲 in alkanol 共1兲 共1946兲. 共IUPAC - SDS, Volume 15兲.
30
were determined by LLE calculations described in the Pref- T. Moriyoshi, T. Sakamoto, and Y. Uosaki, J. Chem. Ther-
ace to Part 2.26 The concentrations of 共1兲 in 共2兲 predicted modyn. 21, 947 共1989兲.
from Eq. 共3兲 were used as the input data. The reference val- 31
K. S. Rao, M. V. R. Rao, and C. V. Rao, J. Sci. Ind. Res.,
ues obtained from the LLE calculations were afterward re- Sect. B 20, 283 共1961兲. 共IUPAC - SDS, Volume15兲.
gressed by Eq. 共4兲 33
F. Ratkovics, B. Palagyi-Fenyes, E. Hajos-Szikszay, and A.
Dallos, J. Chem. Thermodyn. 23, 859 共1991兲.
ln x1 = ln x2,min + C2关T2,min/T − ln共T2,min/T兲 − 1兴 35
I. Sanemasa, Y. Miyazaki, S. Arakawa, M. Kumamaru, and
+ D2 exp关␣2共1 − T/T2c兲兴 共4兲 T. Deguchi, Bull. Chem. Soc. Jpn. 60, 517 共1987兲.
37
K. Shinoda, T. Yamanaka, and K. Kinoshita, J. Phys.
where T2,min = 277.2 K, ln x2,min = −1.359, C2 = 6.250, D2 Chem. 63, 648 共1959兲. 共IUPAC - SDS, Volume 15兲.
= 0.647, ␣2 = −50, and T2c = 545 K. 38
H. Sobotka and D. Glick, J. Biol. Chem. 105, 199 共1934兲.
The criteria used to assign data to categories listed in 共IUPAC - SDS, Volume 15兲.
Table 21 are described in the Preface to Part 2.26 All the 41
R. Stephenson, J. Stuart, and M. Tabak, J. Chem. Eng. Data
experimental data and reference values are listed in Table 22 29, 287 共1984兲.
and shown in Fig. 4. 43
S. Tokunaga, M. Manabe, and M. Koda, Mem. Niihama
Technical College, Sci. Eng. 16, 96 共1980兲. 共IUPAC - SDS,
References for the 1-octanol/water system
Volume 15兲.
1 45
V. Ababi and A. Popa, An. Stiint. Univ. “Al. I. Cuza” Iasi 6, R. Vochten and G. Petre, J. Colloid Interface Sci. 42, 320
929 共1960兲. 共IUPAC - SDS, Volume 15兲. 共1973兲. 共IUPAC - SDS, Volume 15兲.
2 46
C. C. Addison, J. Chem. Soc. 98 共1945兲. 共IUPAC - SDS, I. K. Zhuravleva, E. F. Zhuravlev, and N. G. Lomakina, Zh.
Volume 15兲. Fiz. Khim. 51, 1700 共1977兲. 共IUPAC - SDS, Volume 15兲.
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IUPAC-NIST SOLUBILITY DATA SERIES 697
TABLE 19. The data categories for solubility of 1-octanol 共1兲 in water 共2兲.
Recommended
关data in good Tentative
agreement with each 关data in good Doubtful
other and 共±10% 兲 agreement 关data in poor agreement
with the reference 共±10% 兲 with the 共⬎10% 兲 with the
T共K兲 values兴 reference values兴 reference values兴
TABLE 20. Experimental values for solubility of 1-octanol 共1兲 in water 共2兲.
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698 A. MACZYNSKI AND D. G. SHAW
TABLE 20. Experimental values for solubility of 1-octanol 共1兲 in water 共2兲.—Continued
TABLE 21. The data categories for solubility of water 共2兲 in 1-octanol 共1兲.
Recommended
关data in good Tentative Doubtful
agreement with each 关data in good 关data in poor agreement
other and 共±5 % 兲 with agreement 共±5 % 兲 with 共⬎5 % 兲 with the
T共K兲 the reference values兴 the reference values兴 reference values兴
273.2 Erichsen13
280.2 Zhuravleva et al.46
283.2 Erichsen13
Stephenson et al.41
288.2 Tokunaga et al.43
292.2 Stephenson et al.41
293.2 Ratkovics et al.33 Erichsen13
Tokunaga et al.43 Galan et al.15
296.2 Zhuravleva et al.46
298.1 Arce et al.4
298.2 Ababi and Popa1 Crittenden and Hixon12
Arce et al.5 Janado et al.21
Arce et al.6 Moriyoshi et al.30
Tokunaga et al.43
303.2 Erichsen13
Rao et al.31
Tokunaga et al.43
303.7 Stephenson et al.41
308.2 Tokunaga et al.43 Arce et al.6
Zhuravleva et al.46
313.2 Lavrova and Lesteva24 Erichsen13
Stephenson et al.41
Tokunaga et al.43
323.2 Stephenson et al.41 Erichsen13
325.2 Zhuravleva et al.46
333.2 Erichsen13
Lavrova and Lesteva24
333.4 Stephenson et al.41
343.2 Erichsen13
41
343.3 Stephenson et al.
347.2 Zhuravleva et al.46
353.2 Erichsen13
353.3 Stephenson et al.41
356.1 Brown et al.9
363.2 Erichsen13
363.7 Stephenson et al.41
373.2–413.2 Erichsen13
419.3 Brown et al.9
423.2–453.2 Erichsen13
9
461.2 Brown et al.
463.2 and 473.2 Erichsen13
9
480.5 Brown et al.
483.2 and 493.2 Erichsen13
9
501.9 Brown et al.
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IUPAC-NIST SOLUBILITY DATA SERIES 699
TABLE 21. The data categories for solubility of water 共2兲 in 1-octanol 共1兲.—Continued
Recommended
关data in good Tentative Doubtful
agreement with each 关data in good 关data in poor agreement
other and 共±5 % 兲 with agreement 共±5 % 兲 with 共⬎5 % 兲 with the
T共K兲 the reference values兴 the reference values兴 reference values兴
TABLE 22. Experimental values for solubility of water 共2兲 in 1-octanol 共1兲.
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700 A. MACZYNSKI AND D. G. SHAW
TABLE 22. Experimental values for solubility of water 共2兲 in 1-octanol 共1兲.—Continued
Experimental Values
Components: Original Measurements:
TABLE 24. Solubility of water 共2兲 in 1-octanol 共1兲.5
共1兲 1-Octanol; C8H18O; 6
A. Arce, M. Blanco, A. Soto,
关111-87-5兴 and I. Vidal, J. Chem. g共2兲 / 100 g sln
共2兲 Water; H2O; 关7732-18-5兴 Thermodyn. 28, 3 共1996兲. t共°C兲 共compiler兲 x2
Variables: Prepared by: 25 5.23 0.2691
Temperature: 298.15 and B. Wisniewska-Goclowska 5.20 0.2680
308.15 K
Auxiliary Information
Experimental Values
TABLE 23. Solubility study in the 1-octanol/water system.6 Method/Apparatus/Procedure:
The cloud-point method was used. The solubility cell was thermostatted to
Solubility of 1-octanol in water ±0.02 ° C. No more details were reported in the paper 共see Table 24兲.
Estimated Error:
Solubility: above ±0.001 mole % 共accuracy兲. Auxiliary Information
Method/Apparatus/Procedure:
The cloud-point method was used. The solubility was obtained using
Components: Original Measurements: jacketed cells thermostatted to ±0.02 ° C using a HetoTherm
1-Octanol; C8H18O; 关111-87-5兴 5
A. Arce, M. Blanco, and A. ultrathermostat 共see Table 25兲.
共2兲 Water; H2O; 关7732-18-5兴 Soto, Fluid Phase Equilib. 146,
161 共1998兲. Source and Purity of Materials:
共1兲 Aldrich; purity by glc 99.2%.
Variables: Prepared by: 共2兲 Obtained from a Milli-Q Plus system.
One temperature: 25 ° C B. Wisniewska-Goclowska
Estimated Error:
Temperature: 0.02 ° C.
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IUPAC-NIST SOLUBILITY DATA SERIES 701
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702 A. MACZYNSKI AND D. G. SHAW
Method/Apparatus/Procedure:
The analytical method 关T. Moriyoshi, T. Sakamoto, and Y. Uosaki, J. Components: Original Measurements:
Chem. Thermodyn. 20, 551 共1988兲兴 was used. The apparatus consisted of 共1兲 1-Octanol; C8H18O; 35
I. Sanemasa, Y. Miyazaki, S.
a high-pressure equilibrium cell, two hand operated pumps, a pressure 关111-87-5兴 Arakawa, M. Kumamaru, and T.
exchanger, two pressure gauges and auxiliary equipment. The equilibrium 共2兲 Water; H2O; 关7732-18-5兴 Deguchi, Bull. Chem. Soc. Jpn.
cell was a stainless-steel cylinder of about 50 mL capacity, equipped with 60, 517 共1987兲.
a mechanical stirrer and two pieces of pressure tubing connected to two
valves for the withdrawal of samples and immersed in a thermostat Variables: Prepared by:
controlled to ±0.02 K. Pressure was measured with an accuracy of One temperature: 25 ° C B. Wisniewska-Goclowska
±0.1 MPa with a Heise Bourdon gauge and a strain-gauge pressure
Experimental Values
transducer connected to a digital integrator. Samples were analyzed by a
TABLE 31. Solubility of 1-octanol 共1兲 in water 共2兲.35
Shimadzu gas chromatograph model GC-9APT with a
thermal-conductivity detector, equipped with an electronic integrator
Shimadzu Chromatopac C-R3A. The results reported above are part of g共1兲 / 100 g sln x1 · 105
various ternary solubility measurements 共see Table 29兲. t共°C兲 103 · mol共1兲 / L 共compiler兲 共compiler兲
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IUPAC-NIST SOLUBILITY DATA SERIES 703
The reference solubility values of 共1兲 in 共2兲 were calcu- and shown in Fig. 5. Some data used in this evaluation were
lated by the equation: compiled for an earlier version of this work.8 Those compi-
ln x1 = ln x1,min + C1关T1,min/T − 1 − ln共T1,min/T兲兴, 共5兲 lations are not reprinted here. New compilations are pre-
sented following this evaluation.
where T1,min = 324.5 K, ln x1,min = −8.92, and C1 = 41.3.
T1,min, ln x1,min, and C1 were calculated with Eqs. 共7兲, 共9兲,
and 共10兲, where constants defined by Eqs. 共12兲 and 共14兲 were Critical evaluation of the solubility of water (2) in
used. All the mentioned equations are given in the Preface to 2-octanol (1)
Part 2.26 共see Table 34兲. The experimental solubility data for 共2兲 in 共1兲 have been
The criteria used to assign data to categories listed in investigated by the authors listed in Table 34 together with
Table 35 are also described in the Preface to Part 2.26 All the temperature range.
experimental data and reference values are listed in Table 36
TABLE 34. Sources of solubility data for water 共2兲 in 2-octanol 共1兲.
The reference solubility values of water 共2兲 in alkanol 共1兲 were determined by LLE calculations described in the Pref-
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704 A. MACZYNSKI AND D. G. SHAW
FIG. 5. All the solubility data for 2-octanol 共1兲 in water 共2兲. FIG. 6. All the solubility data for water 共2兲 in 2-octanol 共1兲.
7
ace to Part 2.26 The concentrations of 共1兲 in 共2兲 predicted A. L. Bartolome, C. Pazos, and J. Coca, J. Chem. Eng. Data
from Eq. 共5兲 were used as the input data. The reference val- 35, 285 共1990兲.
8
ues obtained from the LLE calculations were afterward re- A. F. M. Barton, Editor, IUPAC Solubility Data Series, Vol.
gressed by Eq. 共6兲 15, Alcohols with Water 共Pergamon, New York, 1984兲.
12
E. D. Crittenden, Jr. and A. N. Hixon, Ind. Eng. Chem. 46,
ln x2 = ln x2,min + C2关T2,min/T − 1 − ln共T2,min/T兲兴, 共6兲 265 共1954兲. 共IUPAC - SDS, Volume 15兲.
26
A. Maczynski and D. G. Shaw, Editor, “IUPAC-NIST Solu-
where T2,min = 285.4 K, ln x2,min = −1.546, and C2 = 7.84.
bility Data Series. 82. Alcohol with Water - Revised and
The criteria used to assign data to categories listed in
Updated. Part 2. C6 alcohols with water,” J. Phys. Chem.
Table 37 are described in the Preface to Part 2.26 All the
Ref. Data 36, 191 共2007兲.
experimental data and reference values are listed in Table 38 29
S. Mitchell, J. Chem. Soc. 1332 共1926兲. 共IUPAC - SDS,
and shown in Fig. 6.
Volume 15兲.
30
T. Moriyoshi, T. Sakamoto, and Y. Uosaki, J. Chem. Ther-
References for the 2-octanol/water system
modyn. 21, 947 共1989兲.
2 40
C. C. Addison, J. Chem. Soc. 98 共1945兲. 共IUPAC - SDS, R. Stephenson and J. Stuart, J. Chem. Eng. Data 31, 56
Volume 15兲. 共1986兲.
TABLE 35. The data categories for solubility of 2-octanol 共1兲 in water 共2兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±10% 兲 with the reference values兴 共⬎10% 兲 with the reference values兴
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IUPAC-NIST SOLUBILITY DATA SERIES 705
TABLE 35. The data categories for solubility of 2-octanol 共1兲 in water 共2兲.—Continued
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±10% 兲 with the reference values兴 共⬎10% 兲 with the reference values兴
TABLE 36. Experimental values for solubility of 2-octanol 共1兲 in water 共2兲.
TABLE 37. The data categories for solubility of water 共2兲 in 2-octanol 共1兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±5 % 兲 with the reference values兴 共⬎5 % 兲 with the reference values兴
TABLE 38. Experimental values for solubility of water 共2兲 in 2-octanol 共1兲.
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706 A. MACZYNSKI AND D. G. SHAW
Auxiliary Information
Components: Original Measurements:
共1兲 2-Octanol; C8H18O; 7
A. L. Bartolome, C. Pazos, and Method/Apparatus/Procedure:
关123-96-6兴 J. Coca, J. Chem. Eng. Data 35, The analytical method 关T. Moriyoshi, T. Sakamoto, and Y. Uosaki, J.
共2兲 Water; H2O; 关7732-18-5兴 285 共1990兲. Chem. Thermodyn. 20, 551 共1988兲兴 was used. The apparatus consisted of
a high-pressure equilibrium cell, two hand operated pumps, a pressure
Variables: Prepared by: exchanger, two pressure gauges, and auxiliary equipment. The equilibrium
One temperature: 298.15 K B. Wisniewska-Goclowska cell was a stainless-steel cylinder of about 50 mL capacity, equipped with
a mechanical stirrer and two pieces of pressure tubing connected to two
Experimental Values
valves for the withdrawal of samples and immersed in a thermostat
TABLE 39. Solubility in the 2-octanol/water system.7
controlled to ±0.02 K. Pressure was measured with an accuracy of
±0.1 MPa with a Heise Bourdon gauge and a strain-gauge pressure
Solubility of 2-octanol in water transducer connected to a digital integrator. Samples were analyzed by a
Shimadzu gas chromatograph model GC-9APT with a
T共K兲 g共1兲 / 100 g sln x1 共compiler兲
thermal-conductivity detector, equipped with an electronic integrator
Solubility of water in 2-octanol Shimadzu Chromatopac C-R3A. The results reported above are part of
various ternary solubility measurements 共see Table 40兲.
T共K兲 g共2兲 / 100 g sln x2 共compiler兲
Source and Purity of Materials:
298.15 4.31 0.2456 共1兲 Wako Chemical Co., best grade material; twice distilled.
共2兲 De-ionized water distilled from alkaline KMnO4 and redistilled.
Auxiliary Information Estimated Error:
Temperature: ±0.02 K
Method/Apparatus/Procedure:
Pressure: ±0.1 MPa
The cloud-point method was used. No details were reported in the paper
共see Table 39兲. Solubility: ±0.1 mass %.
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IUPAC-NIST SOLUBILITY DATA SERIES 707
Auxiliary Information The analytical method was used. Alcohol 共1兲 and water 共2兲 were brought
into equilibrium at a given temperature in a thermostat and samples of
Method/Apparatus/Procedure: each layer were removed by syringe for analysis. To each sample a higher
The analytical method was used. Alcohol 共1兲 and water 共2兲 were brought boiling organic compound was added as a standard and the ratio of peaks
into equilibrium at a given temperature in a thermostat and samples of was measured by gas chromatography 关R. M. Stephenson, J. Stuart, and
each layer were removed by syringe for analysis. To each sample a higher M. Tabak, J. Chem. Eng. Data 29, 287 共1984兲兴. Temperature was
boiling organic compound was added as a standard and the ratio of peaks measured by a calibrated thermometer accurate to 0.1 ° C 共see Table 42兲.
was measured by gas chromatography 关R. M. Stephenson, J. Stuart, and
M. Tabak, J. Chem. Eng. Data 29, 287 共1984兲兴. Temperature was Source and Purity of Materials:
measured by a calibrated thermometer accurate to 0.1 ° C 共see Table 41兲. 共1兲 Commercial reagent; purity 99+ mass %.
共2兲 Not stated.
Source and Purity of Materials:
共1兲 Commercial reagent; purity 98 mass %. Estimated Error:
共2兲 Not stated. Temperature: ±0.1 ° C.
Solubility: 共a兲 0.008, 共b兲 0.03 共standard deviation兲.
Estimated Error:
Temperature: ±0.1 ° C
Solubility: 共a兲 0.002, 共b兲 0.04 共standard deviation兲.
2.9. 1-Phenyl–1-propanol + Water
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708 A. MACZYNSKI AND D. G. SHAW
Estimated Error:
Temperature: ±0.1 ° C.
Solubility: 共a兲 0.03, 共b兲 0.02 共standard deviation兲.
Components: Evaluators:
共1兲 2,6-Dimethyl-4-heptanol; A. Maczynski, M. Goral, and B.
C9H20O; 关108-82-7兴 Wisniewska-Goclowska,
共2兲 Water; H2O; 关7732-18-5兴 Thermodynamics Data Center,
Warsaw, Poland, March, 2006.
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IUPAC-NIST SOLUBILITY DATA SERIES 709
TABLE 44. The data categories for solubility of 2,6-dimethyl–4-heptanol 共1兲 in water 共2兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±20% 兲 with the reference values兴 共⬎20% 兲 with the reference values兴
TABLE 45. Experimental values for solubility of 2,6-dimethyl–4-heptanol 共1兲 Experimental Values
in water 共2兲. TABLE 47. Solubility in the 2,6-dimethyl–4-heptanol/water system.40
273.2 1.17⫻ 10−4 共T; Ref. 40兲 1.18⫻ 10−4 t共°C兲 g共1兲 / 100 g slna兲 x1共compiler兲
283.0 1.34⫻ 10−4 共D; Ref. 40兲 9.29⫻ 10−5
9.8 0.107 0.000134
288.2 5.6⫻ 10−5 共D; Ref. 45兲 8.41⫻ 10−5
20.1 0.066 0.000082
293.3 8.2⫻ 10−5 共T; Ref. 40兲 7.76⫻ 10−5
30.6 0.053 0.000066
298.2 1.0⫻ 10−4 共D; Ref. 12兲 7.29⫻ 10−5
40.0 0.043 0.000054
303.8 6.6⫻ 10−5共T; Ref. 40兲 6.90⫻ 10−5
50.0 0.052 0.000065
313.2 5.4⫻ 10−5 共T; Ref. 40兲 6.53⫻ 10−5
60.4 0.031 0.000039
323.2 6.5⫻ 10−5 共T; Ref. 40兲 6.44⫻ 10−5
70.3 0.038 0.000047
333.6 3.9⫻ 10−5 共D; Ref. 40兲 6.63⫻ 10−5
80.4 0.032 0.000040
343.5 4.7⫻ 10−5 共D; Ref. 40兲 7.08⫻ 10−5
90.5 0.036 0.000045
353.6 4.0⫻ 10−5 共D; Ref. 40兲 7.81⫻ 10−5
363.7 4.5⫻ 10−5 共D; Ref. 40兲 8.88⫻ 10−5 Solubility of water in 2,6-dimethyl–4-heptanol
Estimated Error:
Temperature: ±0.1 ° C.
Solubility: 共a兲 0.005, 共b兲 0.01 共standard deviation兲.
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710 A. MACZYNSKI AND D. G. SHAW
Components: Evaluators:
共1兲 1-Nonanol; C9H20O; A. Maczynski, M. Goral, and B.
关143-08-8兴 Wisniewska-Goclowska,
共2兲 Water; H2O; 关7732-18-5兴 Thermodynamics Data Center,
Warsaw, Poland, March, 2006.
The reference solubility values of water 共2兲 in alkanol 共1兲 Rejected and Inaccessible Data
were determined by LLE calculations described in the Pref- The data reported by Sazonov and Chernysheva,36 and
ace to Part 2 共see Tables 50 and 51兲.26 The concentrations of Zhuravleva et al.47 lack sufficient information to justify
共1兲 in 共2兲 predicted from Eq. 共9兲 were used as the input data. evaluation. Therefore these data are Rejected.
The reference values obtained from the LLE calculations
were afterward regressed by Eq. 共10兲 References for the 1-nonanol/water system
8
ln x2 = ln x2,min + C2关T2,min兴/T − 1 − ln共T2,min/T兲, 共10兲 A. F. M. Barton, Editor, IUPAC Solubility Data Series, Vol.
15, Alcohols with Water 共Pergamon, New York, 1984兲.
13
where: T2,min = 296.6 K, ln x2,min = −1.401, and C2 = 7.04. L. Erichsen, Brennst.-Chem. 33, 166 共1952兲. 共IUPAC -
The criteria used to assign data to categories listed in SDS, Volume 15兲.
21
Table 52 are described in the Preface to Part 2.26 All the K. Kinoshita, H. Ishikawa, and K. Shinoda, Bull. Chem.
experimental data and reference values are listed in Table 53 Soc. Jpn. 31, 1081 共1958兲. 共IUPAC - SDS, Volume 15兲.
26
and shown in Fig. 9. A. Maczynski and D. G. Shaw, Editor, “IUPAC-NIST Solu-
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IUPAC-NIST SOLUBILITY DATA SERIES 711
FIG. 9. All the solubility data for water 共2兲 in 1-nonanol 共1兲.
TABLE 50. The data categories for solubility of 1-nonanol 共1兲 in water 共2兲.
Recommended
关data in good
agreement with Tentative Doubtful
each other and 关data in good agreement 关data in poor agreement
共±20% 兲 with the 共±20% 兲 with the 共⬎20% 兲 with the
T共K兲 reference values兴 reference values兴 reference values兴
TABLE 51. Experimental values for solubility of 1-nonanol 共1兲 in water 共2兲.
Experimental values x1
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x1
283.0 4.50⫻ 10 −5
共D; Ref. 40兲 1.72⫻ 10−5
288.2 1.70⫻ 10−5 共T; Ref. 45兲 1.66⫻ 10−5
293.2 3.50⫻ 10−5 共D; Ref. 40兲 1.62⫻ 10−5
298.2 1.70⫻ 10−5 共R; Ref. 22兲, 1.328⫻ 10−5 共R; Ref. 42兲 1.61⫻ 10−5
302.8 3.90⫻ 10−5 共D; Ref. 40兲 1.61⫻ 10−5
312.8 4.20⫻ 10−5 共D; Ref. 40兲 1.68⫻ 10−5
323.0 4.00⫻ 10−5 共D; Ref. 40兲 1.83⫻ 10−5
333.3 4.20⫻ 10−5 共D; Ref. 40兲 2.07⫻ 10−5
343.7 4.10⫻ 10−5 共D; Ref. 40兲 2.44⫻ 10−5
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712 A. MACZYNSKI AND D. G. SHAW
TABLE 51. Experimental values for solubility of 1-nonanol 共1兲 in water 共2兲.—Continued
Experimental values x1
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x1
TABLE 52. The data categories for solubility of water 共2兲 in 1-nonanol 共1兲.
Recommended
关data in good Tentative Doubtful
agreement with each 关data in good 关data in poor agreement
other and 共±5 % 兲 with agreement 共±5 % 兲 with 共⬎5 % 兲 with the
T共K兲 the reference values兴 the reference values兴 reference values兴
TABLE 53. Experimental values for solubility of water 共2兲 in 1-nonanol 共1兲.
Experimental values x2
T共K兲 共R⫽recommended, T⫽tentative, D⫽doubtful兲 Reference values x2
273.2 0.1955 共D; Ref. 13兲, 0.2462 共T; Ref. 40兲 0.2525
283.0 0.2363 共T; Ref. 40兲 0.2484
283.2 0.2185 共D; Ref. 13兲 0.2483
288.2 0.262 共D; Ref. 43兲 0.2471
293.2 0.2410 共R; Ref. 13兲, 0.2343 共R; Ref. 40兲, 0.263 共D; Ref. 43兲 0.2465
298.2 0.265 共D; Ref. 43兲 0.2464
302.8 0.2463 共T; Ref. 40兲 0.2468
303.2 0.2630 共D; Ref. 13兲, 0.265 共D; Ref. 43兲 0.2468
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IUPAC-NIST SOLUBILITY DATA SERIES 713
TABLE 53. Experimental values for solubility of water 共2兲 in 1-nonanol 共1兲.—Continued
Experimental values x2
T共K兲 共R⫽recommended, T⫽tentative, D⫽doubtful兲 Reference values x2
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714 A. MACZYNSKI AND D. G. SHAW
Estimated Error:
Temperature: ±0.1 ° C.
Solubility: 共a兲 0.001, 共b兲 0.01 共standard deviation兲.
Experimental Values
TABLE 55. Solubility of 1-nonanol 共1兲 in water 共2兲s.42
Auxiliary Information
Method/Apparatus/Procedure:
A generator column method was used as described by De Voe et al. 关H.
De Voe, M. M. Miller, and S. P. Wasik, J. Res. Natl. Bur. Stand. 共USA兲
86, 361 共1981兲兴 and May et al. 关W. E. May, S. P. Wasik, and D. H.
Freeman, Anal. Chem. 50, 175 共1978兲兴. A column was coated with 共1兲 by
pulling about 2 mL of liquid through the clean dry support 共Chromosorb
FIG. 10. All the solubility data for 2-nonanol 共1兲 in water 共2兲.
W-HP兲. A saturated solution was generated by pumping water into the
inlet of the coated column and was then analyzed by glc. The column was
thermostated by pumping water from a bath through a column jacket. An T1,min, ln x1,min and C1 were calculated with Eqs. 共7兲, 共9兲
average of at least three measurements is reported 共see Table 55兲. and 共10兲, where constants defined by Eqs. 共12兲 and 共14兲 were
used. All the mentioned equations are given in the Preface to
Source and Purity of Materials:
共1兲 Source not specified; purity ⬎99 mole % checked by high-temperature
Part 2.26
glc. The criteria used to assign data to categories are also de-
共2兲 Source not specified. scribed in the Preface to Part 2.26 All the experimental data
and reference values are listed in Table 56 and shown in Fig.
Estimated Error:
10. The data of Stephenson and Stuart40 at 273, 293, and
Temperature: ±0.1 ° C.
303 K are in good agreement 共within ±20%兲 with the refer-
Solubility: 1% 共estimated by the authors兲.
ence values and are Tentative. All the remaining data are in
poor agreement 共greater than 20%兲 with the reference values
2.12. 2-Nonanol + Water and are Doubtful. Some data used in this evaluation were
compiled for an earlier version of this work.8 Those compi-
Components: Evaluators: lations are not reprinted here. New compilation is presented
共1兲 2-Nonanol; C9H20O; A. Maczynski, M. Goral, and B. following this evaluation.
关628-99-9兴 Wisniewska-Goclowska,
共2兲 Water; H2O; 关7732-18-5兴 Thermodynamics Data Center, Critical evaluation of the solubility of water (2) in
Warsaw, Poland, March, 2006.
2-nonanol (1)
The experimental solubility data for 共2兲 in 共1兲 have been
Critical evaluation of the solubility of 2-nonanol (1) in investigated by Stephenson and Stuart40 at 273– 364 K.
water (2) The reference solubility values of water 共2兲 in alkanol 共1兲
The experimental solubility data for 共1兲 in 共2兲 have been were determined by LLE calculations described in the Pref-
investigated by Stephenson and Stuart40 at 273– 364 K, and ace to Part 2.26 The concentrations of 共1兲 in 共2兲 predicted
Vochten and Petre45 at 288 K. from Eq. 共11兲 were used as the input data. The reference
The reference solubility values of 共1兲 in 共2兲 were calcu- values obtained from the LLE calculations were afterward
lated by the equation: regressed by Eq. 共12兲
ln x1 = ln x1,min + C1关T1,min/T − 1 − ln共T1,min/T兲兴, 共11兲 ln x2 = ln x2,min + C2关T2,min/T − 1 − ln共T2,min/T兲兴, 共12兲
where: T1,min = 319.1 K, ln x1,min = −10.18, and C1 = 45.5. where: T2,min = 290.6 K, ln x2,min = −1.623, and C2 = 7.43.
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IUPAC-NIST SOLUBILITY DATA SERIES 715
TABLE 57. Experimental values for solubility of water 共2兲 in 2-nonanol 共1兲.
The criteria used to assign data to categories are described Components: Original Measurements:
in the Preface to Part 2.26 All the experimental data and 共1兲 2-Nonanol; C9H20O; 40
R. M. Stephenson and J.
reference values are listed in Table 57 and shown in Fig. 11. 关628-99-9兴 Stuart, J. Chem. Eng. Data 31,
共2兲 Water; H2O; 关7732-18-5兴 56 共1986兲.
The data of Stephenson and Stuart40 at 273– 293 K are in
good agreement 共within ±5%兲 with the reference values and Variables: Prepared by:
are Tentative. All the remaining data are in poor agreement Temperature: 0 – 90.5 ° C B. Wisniewska-Goclowska
共greater than 5%兲 with the reference values and are Doubt- Experimental Values
ful. TABLE 58. Solubility in the 2-nonanol/water system.40
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716 A. MACZYNSKI AND D. G. SHAW
TABLE 58. Solubility in the 2-nonanol/water system.40—Continued TABLE 59. Solubility in the 3,3,5-trimethyl–1-hexanol/water
system.40—Continued
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IUPAC-NIST SOLUBILITY DATA SERIES 717
TABLE 62. Sources of dolubility data for 1-decanol 共1兲 in water 共2兲.
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718 A. MACZYNSKI AND D. G. SHAW
TABLE 62. Sources of dolubility data for 1-decanol 共1兲 in water 共2兲.—Continued
TABLE 63. Sources of solubility data for water 共2兲 in 1-decanol 共1兲.
The reference solubility values of water 共2兲 in alkanol 共1兲 are Rejected.
were determined by LLE calculations described in the Pref-
ace to Part 2 共see Tables 64 and 65兲.26 The concentrations of References for the 1-decanol/water system
共1兲 in 共2兲 predicted from Eq. 共13兲 were used as the input data. 3
C. C. Addison and S. K. Hutchinson, J. Chem. Soc. 3387
The reference values obtained from the LLE calculations
共1949兲. 共IUPAC - SDS, Volume 15兲.
were afterward regressed by Eq. 共14兲 8
A. F. M. Barton, Editor, IUPAC Solubility Data Series, Vol.
ln x2 = ln x2,min + C2关T2,min/T − 1 − ln共T2,min/T兲兴, 共14兲 15, Alcohols with Water 共Pergamon, New York, 1984兲.
13
L. Erichsen, Brennst.-Chem. 33, 166 共1952兲. 共IUPAC -
where: T2,min = 306.7 K, ln x2,min = −1.410, and C2 = 6.98. SDS, Volume 15兲.
15
The criteria used to assign data to categories listed in J. C. Galan, J. M. M. Moreno, R. T. Valle, and A. R. Se-
Table 66 are described in the Preface to Part 2.26 All the gado, An. Quim., Ser. A 85, 273 共1989兲.
18
experimental data and reference values are listed in Table 67 W. D. Harkins and H. Oppenheimer, J. Am. Chem. Soc. 71,
and shown in Fig. 13. 808 共1949兲. 共IUPAC - SDS, Volume 15兲
22
Rejected and Inaccessible Data K. Kinoshita, H. Ishikawa, and K. Shinoda, Bull. Chem.
The data reported by Harkins and Oppenheimer18 lack suf- Soc. Jpn. 31, 1081 共1958兲. 共IUPAC - SDS, Volume 15兲.
26
ficient information to justify evaluation. Therefore these data A. Maczynski and D. G. Shaw, Editor, “IUPAC-NIST Solu-
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IUPAC-NIST SOLUBILITY DATA SERIES 719
FIG. 13. All the solubility data for water 共2兲 in 1-decanol 共1兲.
TABLE 64. The data categories for solubility of 1-decanol 共1兲 in water 共2兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±20% 兲 with the reference values兴 共⬎20% 兲 with the reference values兴
TABLE 65. Experimental values for solubility of 1-decanol 共1兲 in water 共2兲.
Experimental values x1
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x1
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720 A. MACZYNSKI AND D. G. SHAW
TABLE 66. The data categories for solubility of water 共2兲 in 1-decanol 共1兲.
Recommended
关data in good Tentative Doubtful
agreement with each 关data in good 关data in poor agreement
other and 共±5 % 兲 with agreement 共±5 % 兲 with 共⬎5 % 兲 with the
T共K兲 the reference values兴 the reference values兴 reference values兴
273.2 Erichsen13
40
283.0 Stephenson and Stuart
283.3 Erichsen13
43
283.7 Zhuravleva et al.
288.2 Tokunaga et al.43
293.2 Erichsen13 Tokunaga et al.43
Galan et al.15
298.2 Tokunaga et al.43
40
302.8 Stephenson and Stuart
303.2 Erichsen13
Tokunaga et al.43
308.2 Tokunaga et al.43
313.2 Tokunaga et al.43 Erichsen13
313.5 Stephenson and Stuart40
323.2 Stephenson and Stuart40 Erichsen13
333.2 Erichsen13
333.5 Stephenson and Stuart40
335.7 Zhuravleva et al.46
343.2 Erichsen13
343.4 Stephenson and Stuart40
353.2 Erichsen13
40
353.4 Stephenson and Stuart
355.7 Zhuravleva et al.46
363.2 Erichsen13
363.6 Stephenson and Stuart40
373.2–533.2 Erichsen13
TABLE 67. Experimental values for solubility of water 共2兲 in 1-decanol 共1兲.
Experimental values x2
T共K兲 共R⫽recommended, T⫽tentative, D⫽doubtful兲 Reference values x2
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IUPAC-NIST SOLUBILITY DATA SERIES 721
TABLE 67. Experimental values for solubility of water 共2兲 in 1-decanol 共1兲.—Continued
Experimental values x2
T共K兲 共R⫽recommended, T⫽tentative, D⫽doubtful兲 Reference values x2
Experimental Values
Components: Original Measurements: TABLE 69. Solubility in the 1-decanol/water system.40
共1兲 1-Decanol; C10H22O; 15
J. C. Galan, J. M. M. Moreno,
关112-30-1兴 R. T. Valle, and A. R. Segado, Solubility of 1-decanol in water
共2兲 Water; H2O; 关7732-18-5兴 An. Quim., Ser. A 85, 273
共1989兲. t共°C兲 g 共1兲 / 100 g slna兲 x1共compiler兲
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722 A. MACZYNSKI AND D. G. SHAW
Estimated Error:
Temperature: ±0.1 ° C.
Solubility: 共a兲 0.001, 共b兲 0.03 共standard deviation兲.
Components: Evaluators:
共1兲 1-Undecanol; C11H24O; A. Maczynski, M. Goral, and B.
关112-42-5兴 Wisniewska-Goclowska,
共2兲 Water; H2O; 关7732-18-5兴 Thermodynamics Data Center,
Warsaw, Poland, March, 2006.
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IUPAC-NIST SOLUBILITY DATA SERIES 723
TABLE 71. Experimental values for solubility of water 共2兲 in 1-undecanol 共1兲. The analytical method was used. Alcohol 共1兲 and water 共2兲 were brought
into equilibrium at a given temperature in a thermostat and samples of
Experimental values x2 each layer were removed by syringe for analysis. To each sample a higher
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference valuesx2 boiling organic compound was added as a standard and the ratio of peaks
was measured by gas chromatography 关R. M. Stephenson, J. Stuart, and
288.2 0.255 共T; Ref. 43兲 0.2492 M. Tabak, J. Chem. Eng. Data 29, 287 共1984兲兴. Temperature was
293.0 0.2408 共T; Ref. 40兲 0.2467 measured by a calibrated thermometer accurate to 0.1 ° C 共see Table 72兲.
293.2 0.252 共T; Ref. 43兲 0.2466
Source and Purity of Materials:
298.2 0.254 共T; Ref. 43兲 0.2447
共1兲 Commercial reagent; purity 99 mass %.
303.1 0.2337 共T; Ref. 40兲 0.2433
共2兲 Not stated.
303.2 0.251 共T; Ref. 43兲 0.2433
308.2 0.250 共T; Ref. 43兲 0.2423 Estimated Error:
313.2 0.245 共T; Ref. 43兲 0.2418 Temperature: ±0.1 ° C.
313.5 0.2337 共T; Ref. 40兲 0.2418 Solubility: 共a兲 0.004, 共b兲 0.02 共standard deviation兲.
323.2 0.2295 共D; Ref. 40兲 0.2421
333.3 0.2343 共T; Ref. 40兲 0.2438
343.4 0.2420 共T; Ref. 40兲 0.2469
353.3 0.2501 共T; Ref. 40兲 0.2512 2.18. 1-Dodecanol ⴙ Water
363.7 0.2501 共T; Ref. 40兲 0.2569
Components: Evaluators:
共1兲 1-Dodecanol; C12H26O; A. Maczynski, M. Goral, and B.
Components: Original Measurements:
关112-53-8兴 Wisniewska-Goclowska,
共1兲 1-Undecanol; C11H24O; 40
R. M. Stephenson and J. 共2兲 Water; H2O; 关7732-18-5兴 Thermodynamics Data Center,
关112-42-5兴 Stuart, J. Chem. Eng. Data 31, Warsaw, Poland, March, 2006.
共2兲 Water; H2O; 关7732-18-5兴 56 共1986兲.
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724 A. MACZYNSKI AND D. G. SHAW
FIG. 15. All the solubility data for 1-dodecanol 共1兲 in water 共2兲. FIG. 16. All the solubility data for water 共2兲 in 1-dodecanol 共1兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±20% 兲 with the reference values兴 共⬎20% 兲 with the reference values兴
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IUPAC-NIST SOLUBILITY DATA SERIES 725
TABLE 74. Experimental values for solubility of 1-dodecanol 共1兲 in water 共2兲. TABLE 74. Experimental values for solubility of 1-dodecanol 共1兲 in water
共2兲.—Continued
Experimental values x1
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x1 Experimental values x1
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x1
289.2 1.6⫻ 10−7 共D; Ref. 23兲 2.67⫻ 10−7
298.2 4.2⫻ 10−7 共D; Ref. 34兲 2.77⫻ 10−7 333.7 1.5⫻ 10−4 共D; Ref. 40兲 4.91⫻ 10−7
302.7 4.0⫻ 10−5 共D; Ref. 40兲 2.88⫻ 10−7 343.7 9.0⫻ 10−5 共D; Ref. 40兲 6.35⫻ 10−7
307.2 2.8⫻ 10−7 共T; Ref. 23兲 3.02⫻ 10−7 353.5 1.4⫻ 10−4 共D; Ref. 40兲 8.45⫻ 10−7
313.2 5.0⫻ 10−5 共D; Ref. 40兲 3.27⫻ 10−7 364.0 1.7⫻ 10−4 共D; Ref. 40兲 1.18⫻ 10−6
322.2 3.5⫻ 10−7 共T; Ref.23兲 3.82⫻ 10−7
323.4 9.0⫻ 10−5 共D; Ref. 40兲 3.92⫻ 10−7
TABLE 75. The data categories for solubility of water 共2兲 in 1-dodecanol 共1兲.
Tentative Doubtful
关data in good agreement 关data in poor agreement
T共K兲 共±5 % 兲 with the reference values兴 共⬎5 % 兲 with the reference values兴
TABLE 76. Experimental values for solubility of water 共2兲 in 1-dodecanol Experimental Values
共1兲. TABLE 77. Solubilty in the 1-dodecanol/water system.40
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726 A. MACZYNSKI AND D. G. SHAW
The analytical method was used. Alcohol 共1兲 and water 共2兲 were brought
into equilibrium at a given temperature in a thermostat and samples of
each layer were removed by syringe for analysis. To each sample a higher
boiling organic compound was added as a standard and the ratio of peaks
was measured by gas chromatography 关R. M. Stephenson, J. Stuart, and
M. Tabak, J. Chem. Eng. Data 29, 287 共1984兲兴. Temperature was
measured by a calibrated thermometer accurate to 0.1 ° C 共see Table 77兲.
Estimated Error:
Temperature: ±0.1 ° C
Solubility: 共a兲 0.02, 共b兲 0.01 共standard deviation兲.
Components: Evaluators:
共1兲 1-Tetradecanol; C14H30O; A. Maczynski, M. Goral, and B.
关112-72-1兴 Wisniewska-Goclowska,
共2兲 Water; H2O; 关7732-18-5兴 Thermodynamics Data Center,
Warsaw, Poland, March, 2006.
Experimental values x1
T共K兲 共T⫽tentative, D⫽doubtful兲 Reference values x1 Critical evaluation of the solubility of 1-hexadecanol
(1) in water (2)
277.2 3.5⫻ 10−9 共D; Ref. 20兲 1.76⫻ 10−8 The experimental solubility data for 共1兲 in 共2兲 have been
298.2 2.6⫻ 10−8 共T; Ref. 34兲 1.92⫻ 10−8
investigated by Hoffman and Anacker20 at 316 and 334 K,
305.2 2.2⫻ 10−8 共T; Ref. 20兲 2.12⫻ 10−8
Krause and Lange23 at 307 and 328 K, and Robb34 at 298 K.
318.2 4.3⫻ 10−8 共D; Ref. 20兲 2.74⫻ 10−8
334.2 7.5⫻ 10−8 共D; Ref. 20兲 4.24⫻ 10−8
The reference solubility values of 共1兲 in 共2兲 were calcu-
lated by the equation:
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IUPAC-NIST SOLUBILITY DATA SERIES 727
ln x1 = ln x1,min + C1关T1,min/T − 1 − ln共T1,min/T兲兴, 共20兲 Critical evaluation of the solubility of 1-heptadecanol (1)
in water (2)
The experimental solubility data for 共1兲 in 共2兲 have been
where T1,min = 278.4 K, ln x1,min = −20.60, and C1 = 74.9. investigated by Robb34 at 298 K, and Upchurch and van
T1,min, ln x1,min, and C1 were calculated with Eqs. 共7兲, 共9兲, Winkle44 at 298 and 323 K.
and 共10兲, where constants defined by Eqs. 共12兲 were used. The reference solubility values of 共1兲 in 共2兲 were calcu-
All the mentioned equations are given in the Preface to Part lated by the equation:
2.26 ln x1 = ln x1,min + C1关T1,min/T − 1 − ln共T1,min/T兲兴, 共21兲
The criteria used to assign data to categories are also de-
where T1,min = 276.7 K, ln x1,min = −21.96, and C1 = 79.1.
scribed in the Preface to Part 2.26 All the experimental data
T1,min, ln x1,min, and C1 were calculated with Eqs. 共7兲, 共9兲,
and reference values are listed in Table 79. All the data are in and 共10兲, where constants defined by Eqs. 共12兲 were used.
poor agreement 共greater than 35%兲 with the reference values All the mentioned equations are given in the Preface to Part
and are Doubtful. The data used in this evaluation were 2.26
compiled for an earlier version of this work.8 Those compi- The criteria used to assign data to categories are also de-
scribed in the Preface to Part 2.26 All the experimental data
lations are not reprinted here. and reference values are listed in Table 80. All the data are in
TABLE 79. Experimental values for solubility of 1-hexadecanol 共1兲 in water
共2兲. poor agreement 共greater than 35%兲 with the reference values
and are Doubtful. Some data used in this evaluation were
Experimental values x1 compiled for an earlier version of this work.8 Those compi-
T共K兲 共D⫽doubtful兲 Reference values x1 lations are not reprinted here. A new compilation is presented
298.2 3.1⫻ 10 共D; Ref. 34兲
−9
1.35⫻ 10−9
following this evaluation.
307.2 6.0⫻ 10−10 共D; Ref. 23兲 1.61⫻ 10−9
316.2 2.8⫻ 10−9 共D; Ref. 20兲 2.03⫻ 10−9 Critical evaluation of the solubility of water (2) in
328.2 2.3⫻ 10−9 共D; Ref. 23兲 2.96⫻ 10−9 1-heptadecanol (1)
334.2 7.3⫻ 10−9 共D; Ref. 20兲 3.68⫻ 10−9 The experimental solubility data for 共2兲 in 共1兲 have been
investigated by Upchurch and van Winkle44 at 298 and
323 K.
References for the 1-hexadecanol/water system The reference solubility values of water 共2兲 in alkanol 共1兲
8 were determined by LLE calculations described in the Pref-
A. F. M. Barton, Editor, IUPAC Solubility Data Series, Vol.
15, Alcohols with Water 共Pergamon New York, 1984兲. ace to Part 2.26 The concentrations of 共1兲 in 共2兲 predicted
20
C. S. Hoffman and E. W. Anacker, J. Chromatogr. 30, 390 from Eq. 共21兲 were used as the input data. The reference
共1967兲. values obtained from the LLE calculations were afterward
23
F. P. Krause and W. Lange, J. Phys. Chem. 69, 3171 regressed by Eq. 共22兲
共1965兲. ln x2 = ln x2,min + C2关T2,min/T − 1 − ln共T2,min/T兲兴, 共22兲
26
A. Maczynski and D. G. Shaw, Editor, “IUPAC-NIST Solu-
where T2,min = 366 K, ln x2,min = −1.337, and C2 = 5.90.
bility Data Series. 82. Alcohol with Water - Revised and
The criteria used to assign data to categories are described
Updated. Part 2. C6 alcohols with water,” J. Phys. Chem. in the Preface to Part 2.26 All the experimental data and
Ref. Data 36, 191 共2007兲. reference values are listed in Table 81. All the data are in
34
I. D. Robb, Aust. J. Chem. 19, 2281 共1966兲. poor agreement 共greater than 5%兲 with the reference values
and are Doubtful.
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728 A. MACZYNSKI AND D. G. SHAW
TABLE 80. Experimental values for solubility of 1-heptadecanol 共1兲 in water 共2兲.
Experimental values x1
T共K兲 共D⫽doubtful兲 Reference values x1
298.2 1.8⫻ 10−9 共D; Ref. 34兲, 0.00016 共D; Ref. 44兲 3.60⫻ 10−10
323.2 0.00016 共D; Ref. 44兲 7.18⫻ 10−10
TABLE 81. Experimental values for solubility of water 共2兲 in 1-heptadecanol 共1兲.
Estimated Error:
Solubility: 0.2 mass %.
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IUPAC-NIST SOLUBILITY DATA SERIES 729
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730 A. MACZYNSKI AND D. G. SHAW
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IUPAC-NIST SOLUBILITY DATA SERIES 731
31
V. Krupina, Uch. Zap. Yarosl. Tekhnol. Inst. Khim. Khim. Tekhnol. 28, K. S. Rao, M. V. R. Rao, and C. V. Rao, J. Sci. Ind. Res. 20, 283 共1961兲.
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Ser. A 85, 273 共1989兲. Chem. Thermodyn. 22, 129 共1990兲.
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H. Ghanadzadeh, A. Ghanadzadeh, and R. Sariri, J. Chem. Thermodyn. F. Ratkovics, B. Palagyi-Fenyes, E. Hajos-Szikszay, and A. Dallos, J.
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I. Sanemasa, Y. Miyazaki, S. Arakawa, M. Kumamaru, and T. Deguchi,
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