10,000

Equation
Data

Solubility of water in compound, ppm(wt)

Feature Report
Engineering Practice
1,000

Solubility of Water in 100

Benzene Derivatives 10

Solubility and Henry’s Law constants for water 1

200 250 300 350 400 450 500 550 600
in benzene and its derivatives Boiling point, K

Figure 1. Solubility correlation with

boiling points for benzene derivatives.

Carl L. Yaws and Manish Rahate, Correlation for water solubility shown in Figure 1 for benzene deriva-
Lamar University In earlier work by Yaws and coworkers tives. The data of Englin [4] and Polak
[22, 25], the solubility of hydrocarbons and Lu [9], which are applicable at

T
he solubility of water in the hy- and other chemicals in water was cor- ambient temperature, were selected
drocarbons that comprise crude related as a function of the boiling point for the graph. The graph reveals favor-
oil is an increasingly important of the compound. In this present work, able agreement between correlation
issue in view of processing, safety it was determined that the boiling point values and experimental data.
and environmental considerations sur- method was also applicable for correla-
rounding product quality and equip- tion of solubility of water in benzene Henry’s Law constant
ment sustainability. Water in the re- derivatives: The results for solubility of water and
acting hydrocarbon species may result Henry’s Law constant are given in
log10(S) = A + B × TB (1)
in the formation of undesirable by- Table 1. In the tabulation, the results
products. The presence of water in the where: for Henry’s Law constant are based on
product may be detrimental to quality. S = solubility of water in compound water solubility and vapor pressure at
Water content at high enough levels at 25°C, ppm by weight ambient conditions using the appropri-
in the products of a given hydrocarbon TB = boiling point temperature of ate thermodynamic relationships [22].
process may render the products unu- compound (K) A compilation by Yaws [24] was used
seable by the customer. When chemi- A = 3.780 for vapor pressure. The presented val-
cal processes involve lowering tem- B = –2.720 × 10–3 ues are applicable for water in a wide
peratures to values near the freezing The correlation applies to boiling variety of benzene derivatives (normal
point of water, solids (ice or hydrates) point temperatures in a range from and branching).
can form. Such solid formation will about 280K to 590K. The tabulated values are based on
affect both the fluid flow in piping as The coefficients (A and B) for the both experimental data and estimates.
well as the operational characteristics correlation were determined from re- In the absence of data, the estimates
of process equipment. For catalytic re- gression of the available data. In pre- for isomers and large-sized compounds
actions, water in the hydrocarbon may paring the correlation, a literature (compounds larger than C10) should
poison the catalyst that promotes the search was conducted to identify data be considered rough values, useful for
desired reaction. source publications [1–25]. Excellent initial analysis. If initial analysis is fa-
To illustrate the importance of water compilations by Englin and others vorable, follow-up experimental deter-
solubility in hydrocarbons, we offer [4], Glasoe and Schultz [5], Jones and mination is recommended.
the results of solubility studies involv- Monk [6], Polak and Lu [9], IUPAC The results are presented in a tab-
ing water in benzene derivatives. The [10–14] and Sorensen and Artl [16] ular format, which is especially ap-
results for both solubility and Henry’s were consulted for solubility of water. plicable for rapid engineering usage
Law constant for water are provided The compilation by Yaws [23] was with the personal computer or hand
in an easy‑to‑use tabular format for used for boiling point temperature. calculator. The tabulation is arranged
a wide variety of benzene derivatives The publications were screened and by carbon number (C6, C7, C8...). This
contained in crude oil. copies of appropriate data were made. provides ease-of-use in quickly locat-
A new correlation for solubility of These data were then keyed into the ing data using the chemical formula.
water is also presented. It provides computer to provide a database for
reliable solubility values down to which experimental data are avail- Applying the data
low concentrations (parts per million able. The database also served as a The results for solubility and Henry’s
range). The correlation is based on basis to check the accuracy of the cor- Law constant are useful in engineer-
the boiling point temperature of the relation. ing applications involving water in
hydrocarbon. Correlation values and The solubility of water versus boil- benzene derivatives. Examples are
experimental data agree favorably. ing point temperature of compounds is shown below.
44 Chemical Engineering www.che.com March 2010
 Table 1. Solubility of Water In Benzene Derivatives
Solubility of Water (S),
      Henry’s Law Constant (H)
parts per million (ppm)
S @25°C, S @25°C, H @ 25°C,
H @ 25°C,
No. ID FORMULA NAME CAS No. TB (K) ppm ppm code atm/mol code
atm/mol/m3
(wt) (mol) frac
1 7339 C6H6 benzene 71-43-2 353.24 691.88 3000.00 1 10.45 1.8804 × 10–4 1,2
2 11216 C7H8 toluene 108-88-3 383.78 541.78 2771.00 1 11.31 2.0358 × 10–4 1,2
3 14332 C8H10 ethylbenzene 100-41-4 409.35 441.01 2599.00 1 12.06 2.1706 × 10–4 1,2
4 14333 C8H10 o-xylene 95-47-6 417.58 454.93 2681.00 1 11.69 2.1042 × 10–4 1,2
5 14334 C8H10 m-xylene 108-38-3 412.27 431.17 2541.00 1 12.33 2.2201 × 10–4 1,2
6 14335 C8H10 p-xylene 106-42-3 411.51 438.97 2587.00 1 12.11 2.1806 × 10–4 1,2
7 17591 C9H12 cumene 98-82-8 425.56 347.73 2320.00 1 13.51 2.4316 × 10–4 1,2
8 17592 C9H12 m-ethyltoluene 620-14-4 434.48 396.47 2645.23 2 11.85 2.1326 × 10–4 1,2
9 17593 C9H12 o-ethyltoluene 611-14-3 438.33 387.03 2582.21 2 12.14 2.1847 × 10–4 1,2
10 17594 C9H12 p-ethyltoluene 622-96-8 435.16 394.79 2633.99 2 11.90 2.1417 × 10–4 1,2
11 17595 C9H12 1,2,3-trimethylbenzene 526-73-8 449.27 361.40 2411.21 2 13.00 2.3396 × 10–4 1,2
12 17596 C9H12 1,2,4-trimethylbenzene 95-63-6 442.53 376.98 2515.17 2 12.46 2.2429 × 10–4 1,2
13 17597 C9H12 trimethylbenzene 25551-13-7 445.00 371.19 2476.56 2 12.65 2.2779 × 10–4 1,2
14 17598 C9H12 mesitylene 108-67-8 437.89 332.74 2220.00 1 14.12 2.5411 × 10–4 1,2
15 17599 C9H12 propylbenzene 103-65-1 432.39 401.70 2680.09 2 11.69 2.1049 × 10–4 1,2
16 20487 C10H14 butylbenzene 104-51-8 456.46 387.89 2890.00 1 10.84 1.9520 × 10–4 1,2
17 20488 C10H14 isobutylbenzene 538-93-2 445.94 369.01 2749.35 2 11.40 2.0519 × 10–4 1,2
18 20489 C10H14 sec-butylbenzene 135-98-8 446.48 370.58 2761.00 1 11.35 2.0432 × 10–4 1,2
19 20490 C10H14 tert-butylbenzene 98-06-6 442.30 339.71 2531.00 1 12.38 2.2289 × 10–4 1,2
20 20491 C10H14 cymene 25155-15-1 449.50 360.88 2688.73 2 11.66 2.0981 × 10–4 1,2
21 20492 C10H14 m-cymene 535-77-3 448.23 363.76 2710.20 2 11.56 2.0815 × 10–4 1,2
22 20493 C10H14 o-cymene 527-84-4 451.33 356.77 2658.09 2 11.79 2.1223 × 10–4 1,2
23 20494 C10H14 p-cymene 99-87-6 450.28 359.17 2676.00 1 11.71 2.1081 × 10–4 1,2
24 20495 C10H14 1-methyl-2-propylbenzene 1074-17-5 457.95 342.28 2550.13 2 12.29 2.2122 × 10–4 1,2
25 20496 C10H14 1-methyl-3-propylbenzene 1074-43-7 454.95 348.77 2598.50 2 12.06 2.1710 × 10–4 1,2
26 20497 C10H14 1-methyl-4-propylbenzene 1074-55-1 456.45 345.51 2574.20 2 12.17 2.1915 × 10–4 1,2
27 20498 C10H14 (S)-(1-methylpropyl)benzene 5787-28-0 457.10 344.11 2563.76 2 12.22 2.2004 × 10–4 1,2
28 20499 C10H14 diethylbenzene 25340-17-4 455.05 348.55 2596.87 2 12.07 2.1723 × 10–4 1,2
29 20500 C10H14 o-diethylbenzene 135-01-3 456.61 345.16 2571.62 2 12.19 2.1937 × 10–4 1,2
30 20501 C10H14 m-diethylbenzene 141-93-5 454.29 350.21 2609.26 2 12.01 2.1620 × 10–4 1,2
31 20502 C10H14 p-diethylbenzene 105-05-5 456.94 344.45 2566.31 2 12.21 2.1982 × 10–4 1,2
32 20503 C10H14 3-ethyl-o-xylene 933-98-2 467.11 323.19 2407.95 2 13.02 2.3428 × 10–4 1,2
33 20504 C10H14 4-ethyl-o-xylene 934-80-5 462.93 331.76 2471.82 2 12.68 2.2822 × 10–4 1,2
34 20505 C10H14 2-ethyl-m-xylene 2870-04-4 463.19 331.23 2467.80 2 12.70 2.2860 × 10–4 1,2
35 20506 C10H14 4-ethyl-m-xylene 874-41-9 461.59 334.56 2492.65 2 12.57 2.2632 × 10–4 1,2
36 20507 C10H14 5-ethyl-m-xylene 934-74-7 456.93 344.47 2566.48 2 12.21 2.1981 × 10–4 1,2
37 20508 C10H14 2-ethyl-p-xylene 1758-88-9 459.98 337.95 2517.92 2 12.45 2.2405 × 10–4 1,2
38 20509 C10H14 1,2,3,4-tetramethylbenzene 488-23-3 478.19 301.52 2246.52 2 13.95 2.5111 × 10–4 1,2
39 20510 C10H14 1,2,3,5-tetramethylbenzene 527-53-7 471.15 315.12 2347.79 2 13.35 2.4028 × 10–4 1,2
40 20511 C10H14 1,2,4,5-tetramethylbenzene 95-93-2 469.99 317.41 2364.91 2 13.25 2.3854 × 10–4 1,2
41 22958 C11H16 pentylbenzene 538-68-1 478.61 300.73 2474.77 2 12.66 2.2795 × 10–4 1,2
42 22959 C11H16 2-phenylpentane 2719-52-0 463.15 331.31 2726.38 2 11.50 2.0692 × 10–4 1,2
43 22960 C11H16 3-phenylpentane 1196-58-3 464.15 329.24 2709.36 2 11.57 2.0822 × 10–4 1,2
44 22961 C11H16 1-phenyl-2-methylbutane 3968-85-2 470.15 317.10 2609.44 2 12.01 2.1619 × 10–4 1,2
45 22962 C11H16 1-phenyl-3-methylbutane 2049-94-7 472.05 313.35 2578.57 2 12.15 2.1878 × 10–4 1,2
46 22963 C11H16 2-phenyl-2-methylbutane 2049-95-8 465.53 326.41 2686.04 2 11.67 2.1002 × 10–4 1,2
47 22964 C11H16 2-phenyl-3-methylbutane 4481-30-5 461.15 335.48 2760.75 2 11.35 2.0434 × 10–4 1,2
48 22965 C11H16 1-phenyl-2,2-dimethylpropane 1007-26-7 459.15 339.71 2795.55 2 11.21 2.0180 × 10–4 1,2
49 23006 C11H16 1,2,4-trimethyl-6-ethylbenzene --- 486.15 286.86 2360.62 2 13.28 2.3897 × 10–4 1,2
50 23007 C11H16 1,3,5-trimethyl-2-ethylbenzene 3982-67-0 485.55 303.80 2500.00 1 12.54 2.2565 × 10–4 1,2
51 23008 C11H16 pentamethylbenzene 700-12-9 504.55 255.64 2103.68 2 14.90 2.6816 × 10–4 1,2
52 25025 C12H18 hexylbenzene 1077-16-3 499.26 264.25 2380.29 2 13.17 2.3700 × 10–4 1,2
53 25026 C12H18 1,4-dipropylbenzene 4815-57-0 481.77 294.85 2655.92 2 11.80 2.1240 × 10–4 1,2
54 25027 C12H18 diisopropylbenzene 25321-09-9 473.60 310.32 2795.28 2 11.21 2.0182 × 10–4 1,2
55 25032 C12H18 1,2,3-triethylbenzene 42205-08-3 490.66 278.87 2512.01 2 12.48 2.2457 × 10–4 1,2
56 25033 C12H18 1,2,4-triethylbenzene 877-44-1 491.15 278.02 2504.32 2 12.51 2.2526 × 10–4 1,2
57 25034 C12H18 1,3,5-triethylbenzene 102-25-0 489.05 281.70 2537.47 2 12.35 2.2232 × 10–4 1,2
58 25043 C12H18 1,2,4-trimethyl-5-isopropylbenzene 10222-95-4 494.15 272.84 2457.70 2 12.75 2.2954 × 10–4 1,2
59 25044 C12H18 4-tert-butyl-o-xylene 7397-06-0 478.15 301.60 2716.75 2 11.54 2.0765 × 10–4 1,2
60 25046 C12H18 hexamethylbenzene 87-85-4 536.60 209.15 1883.93 2 16.64 2.9944 × 10–4 1,2
61 25049.1 C12H18 2,4,6-trimethyl-1-propylbenzene --- 494.15 298.24 2686.50 1 11.67 2.0999 × 10–4 1,2
62 26983 C13H20 heptylbenzene 1078-71-3 519.25 233.15 2281.72 2 13.74 2.4724 × 10–4 1,2
63 26984 C13H20 1-methyl-2,4-diisopropylbenzene 1460-98-6 497.15 267.76 2620.44 2 11.96 2.1528 × 10–4 1,2
64 28365 C14H22 octylbenzene 2189-60-8 537.55 207.90 2196.51 2 14.27 2.5683 × 10–4 1,2
65 28366 C14H22 1,2,3,4-tetraethylbenzene 642-32-0 524.16 226.09 2388.66 2 13.12 2.3617 × 10–4 1,2
(Continues on p. 46)

Chemical Engineering www.che.com March 2010 45

 Table 1. Solubility of Water In Benzene Derivatives (Continued)
Solubility of Water (S),
      Henry’s Law Constant (H)
parts per million (ppm)
S @25°C, S @25°C, H @ 25°C,
H @ 25°C,
No. ID FORMULA NAME CAS No. TB (K) ppm ppm code atm/mol code
atm/mol/m3
(wt) (mol) frac
66 28367 C14H22 1,2,3,5-tetraethylbenzene 38842-05-6 522.00 229.17 2421.20 2 12.94 2.3300 × 10–4 1,2
67 28368 C14H22 1,2,4,5-tetraethylbenzene 635-81-4 523.16 227.51 2403.67 2 13.04 2.3470 × 10–4 1,2
68 28369 C14H22 1,4-di-tert-butylbenzene 1012-72-2 510.43 246.39 2603.16 2 12.04 2.1671 × 10–4 1,2
69 29455 C15H24 nonylbenzene 1081-77-2 555.20 186.15 2111.58 2 14.84 2.6716 × 10–4 1,2
70 29456 C15H24 1,2,4-triisopropylbenzene 948-32-3 517.15 236.24 2679.81 2 11.70 2.1051 × 10–4 1,2
71 29457 C15H24 1,3,5-triisopropylbenzene 717-74-8 511.15 245.29 2782.43 2 11.26 2.0275 × 10–4 1,2
72 29458 C15H24 3,5-di-tert-butyltoluene 15181-11-0 517.15 236.24 2679.81 2 11.70 2.1051 × 10–4 1,2
73 30357 C16H26 decylbenzene 104-72-3 571.04 168.57 2043.41 2 15.34 2.7607 × 10–4 1,2
74 30358 C16H26 pentaethylbenzene 605-01-6 550.16 192.12 2328.89 2 13.46 2.4223 × 10–4 1,2
75 30361 C16H26 (1-methylnonyl)benzene 4537-13-7 562.65 177.66 2153.65 2 14.55 2.6194 × 10–4 1,2
76 30361.1 C16H26 (2,4,6-trimethylheptane)benzene --- 562.65 202.52 2455.00 1 12.77 2.2979 × 10–4 1,2
77 31034 C17H28 undecylbenzene 6742-54-7 586.40 153.11 1975.20 2 15.87 2.8561 × 10–4 1,2
78 31730 C18H30 dodecylbenzene 123-01-3 600.76 139.94 1914.27 2 16.37 2.9470 × 10–4 1,2
79 31731 C18H30 hexaethylbenzene 604-88-6 571.16 168.44 2304.17 2 13.60 2.4483 × 10–4 1,2
80 31732 C18H30 1,2,4,5-tetraisopropylbenzene 635-11-0 532.15 215.06 2941.86 2 10.65 1.9176 × 10–4 1,2
Code: 1 = data, 2 = estimate TB — boiling point temperature, K

Example 1. In hydrocarbon pro- log10(S) = 3.780 – 2.720 × 10–3 × 383.78 From thermodynamics at low pressure,
cessing, toluene (C7H8) comes into = 2.73612 the vapor concentration is given by:
contact with water at ambient con- S = 544.65 ppm (wt.) y = H / (Ptot × X)
ditions (25°C, 1 atm). Organic and Example 2. Consider a toluene (C7H8) where:
aqueous phases are separated. Es- spill into a body of water at ambient H = Henry’s Law constant
timate the concentration of water conditions (25°C, 1 atm). After separa- X = mole fraction
at saturation in the toluene after tion, the concentration of water in the Ptot = total pressure
separation. toluene at the surface is 0.00277 mole Substitution of Henry’s Law con-
Substituting coefficients and boiling fraction. Estimate the concentration stant from the table, total pressure
Chemical Engineering e 86x123_2010.qxd:MuŴllerGmbh_e.qxd
points into Equation (1) yields: of water in the vapor at the surface. (Ptot= 1 atm) and liquid concentration
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46 Chemical Engineering www.che.com March 2010
 Engineering Practice

into the above equation yields: References 14. Solubility Data Series, IUPAC-NIST, D. G.
Shaw and A. Maczynski, eds., 81. Hydrocar-
y = 11.31 / (1 × 0.00277) = 0.0313 1. Chen, H. and Wagner, J. J. Chem. Eng. Data,
39, 470. 1994. bons with Water and Seawater – Revised
y = 3.13 mol %  ■ 2. Chen, H. and Wagner, J. J. Chem. Eng. Data, and Updated. Part 11. C13-C36 Hydrocar-
39, 475. 1994. bons with Water, J. Phy. Chem. Ref. Data, 35,
Edited by Scott Jenkins 3. Chen, H. and Wagner, J. J. Chem. Eng. Data,
687-784. 2006.
39, 679. 1994. 15. Solubility Data Series, IUPAC-NIST, Shaw,
Authors 4. Englin, B. A. and others, Khim. Tekhnol. Topl. D.G. and Maczynski, A. eds., 81. Hydrocar-
Massel, 9, 42. 1965. bons with Water and Seawater – Revised
Carl L. Yaws is a professor and Updated. Part 12. C5-C26 Hydrocarbons
of chemical engineering at 5. Glasoe, P. K. and Schultz, S.D. J. Chem. Eng.
Data, 17, 66. 1972. with Seawater, J. Phy. Chem. Ref. Data, 35,
Lamar University in Beau- 785-838. 2006.
mont, Tex. (Email: clyaws@ 6. Jones, J. R. and Monk, C.B. J. Chem. Soc.,
2633. 1963. 16. Sorensen, J. M. and Artl, W. Liquid-Liquid
my.lamar.edu). Yaws holds Equilibrium Data Collection, Vol. V, part
bachelor’s, master’s and doc- 7. Marche, C., De Hemptinne, J.C. and Jose, J. J.
Chem. Eng. Data, 51, 355. 2006. 1, Dechema Chemistry Data Series, 6000
toral degrees from Texas A&I Frankfurt/Main, Germany. 1979.
University and University of 8. Moule, D. C. and Thurston, W.M. Can. J.
Houston. A registered profes- Chem., 44, 1361. 1966. 17. Stavely, L.A.K., Johns, L.G.S. and Moore,
sional engineer (Texas), he is 9. Polak, J. and Lu, B.C.Y. Can. J. Chem., 51, B.C. J. Chem. Soc., 2516. 1951.
the author of 30 books and 4018. 1973. 18. Tsonopoulos, C. and Wilson, G.M. AIChE J.,
has published more than 640 10. Solubility Data Series, IUPAC, Vol. 37, Hy- 29, 990. 1983.
technical papers. His research interests include drocarbons with Water and Seawater, Part 1 19. Tsonopoulos, C., Heidman, J.L. and others.
technology development, thermodynamic and – Hydrocarbons C5 to C7, Pergamon Press, AIChE J., 31, 376. 1985.
transport property data, environmental engi- Oxford, England. 1989. 20. Tsonopoulos, C., Economou, I.G. and others.,
neering and process simulation. 11. Solubility Data Series, IUPAC, Vol. 38, Hy- AIChE J., 43, 535. 1997.
Manish Rahate is a gradu- drocarbons with Water and Seawater, Part 1 21. Tsonopoulos, C., Fluid Phase Equilib., 186,
ate student working on a – Hydrocarbons C8 to C36, Pergamon Press, 185. 2001.
master’s degree in environ- Oxford, England. 1989. 22. Yaws, C.L. “Chemical Properties Handbook,”
mental engineering at Lamar 12. Solubility Data Series, IUPAC-NIST, Shaw, McGraw-Hill, Inc., New York, N.Y. 1999.
University. He is a recipient of D.G. and Maczynski, A. eds., 81. Hydrocarbons
with Water and Seawater – Revised and Up- 23. Yaws, C. L., “Yaws Handbook of Physical
an engineering scholarship in Properties for Hydrocarbons and Chemicals,”
the Civil Engineering Depart- dated. Part 9. C10 Hydrocarbons with Water,
J. Phy. Chem. Ref. Data, 35, 93-151. 2006. Gulf Publishing Co., Houston, Tex. 2005.
ment at Lamar. His research
interests are in thermody- 13. Solubility Data Series, IUPAC-NIST, Shaw, 24. Yaws, C.L. “Yaws Handbook of Vapor Pressu-
namics, environmental engi- D.G. and Maczynski, A. eds., 81. Hydrocar- ree — Antoine Coefficients,” Gulf Publishing
neering and water treatment. bons with Water and Seawater – Revised Co., Houston, Tex. 2007.
He earned a bachelor’s degree and Updated. Part 10. C11 and C12 Hydro- 25. Yaws, C.L., “Yaws Handbook of Properties
at Visvesvaraya National Institute of Technology carbons with Water, J. Phy. Chem. Ref. Data, for Environmental and Green Engineering,”
in Nagpur, India. 35, 153-204. 2006. Gulf Publishing Co., Houston, Tex. 2008.

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