J. Chem. Eng. Data 2002, 47, 761-764
761
Critical Point and Vapor Pressure Measurements for Nine Compounds by a Low Residence Time Flow Method Grant M. Wilson, David M. VonNiederhausern,* and Neil F. Giles Wiltec Research Company, Inc., 488 South 500 West, Provo, Utah 84601
Critical point measurements consisting of critical temperatures and critical pressures have been performed on nine compounds by a flow method with ultralow residence times. These compounds along with their Chemical Abstract Service Registry Numbers (provided by the author) are bis(2-aminoethyl)amine (11140-0), 2-(2-aminoethylamino)ethanol (111-41-1), 1,4-butanediol (110-63-4), 2-(2-butoxyethoxy)ethyl acetate (124-17-4), 2-(2-ethoxyethoxy)ethyl acetate (112-15-2), 2-methyl-1,3-propanediol (2163-42-0), phenyl acetate (122-79-2), 1,3-propanediol (504-63-2), and propylene carbonate (108-32-7). Vapor pressure measurements are also included for these nine compounds.
Introduction
Temperatures were measured on the ITS-90. Temperature and pressure measurement devices were calibrated to within (0.1 K and (0.7 kPa, respectively. The reported critical temperatures and pressures are estimated to have uncertainties of (2 K and (2%, respectively. The vapor pressure measurements are estimated to be uncertain to within (2%.
This work is part of an ongoing investigation of the critical properties for compounds of industrial interest selected in 1997 by sponsors of Project 851 of the Design Institute for Physical Property Data (DIPPR) of the American Institute of Chemical Engineers. This paper reports experimental measurements of the critical properties for nine compounds studied in a flow apparatus with ultralow residence times. Vapor pressure measurements on these nine compounds are also reported.
Results and Discussion Table 2 presents the measured critical point properties for the nine compounds included in this study. When available, values are compared with values from the literature. Table 2 also lists the estimated critical properties for these compounds. These estimates were made using Joback’s method2 and the boiling points measured as part of this project. Due to the lower residence times possible with this method, these newly measured values are believed to be more reliable than the previous values. Gas chromatographic analyses performed on many of the compounds after the measurements were performed showed no signs of significant decomposition.
Experimental Section The flow apparatus and procedures used for these measurements have been described previously.1 Table 1 reports measured purities and water contents for the compounds studied in this work. The purities were measured at Wiltec by means of gas chromatography. The water analyses were performed by Karl Fischer titration. Care was taken to purchase the compounds at high purity. Water and dissolved gases were removed by distilling off a small amount of material under vacuum, but no further attempts were made to purify the chemicals. The supplier and Chemical Abstract Service Registry Numbers (CASRN) of each chemical are also listed.
Tables 3-11 present vapor pressure data on the nine compounds included in this study. These tables list the measured temperature and the measured and correlated pressures. The reported correlations of the measured data demonstrate the internal consistency of the measured data and show, when applicable, that these data agree with data previously measured on these compounds. The Riedel
* Corresponding author [e-mail
[email protected]; fax (801) 374-6674].
Table 1. Source and Purity of Materials analyzed purity/mass %a
a
compound
CASRNb
Wiltec
supplier
water/mass %
supplier
bis(2-aminoethyl)amine 2-(2-aminoethylamino)ethanol 1,4-butanediol 2-(2-butoxyethoxy)ethyl acetate 2-(2-ethoxyethoxy)ethyl acetate 2-methyl-1,3-propanediol phenyl acetate 1,3-propanediol propylene carbonate
111-40-0 111-41-1 110-63-4 124-17-4 112-15-2 2163-42-0 122-79-2 504-63-2 108-32-7
99.7 98.8 99.4 99.6 98.8 99.0 99.9 99.6 99.8
99.8 99.9 99c 99c 98c 98.5 99.3 98.8 99.99
0.13 0.07 0.04 0.05 0.07 0.01 0.01 0.13 0.00
Aldrich Aldrich Aldrich Aldrich Aldrich Aldrich Aldrich Aldrich Aldrich
On a water-free basis. b Provided by the author. c These are product specifications instead of actual analyses.
10.1021/je0100995 CCC: $22.00 © 2002 American Chemical Society Published on Web 10/02/2001
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Journal of Chemical and Engineering Data, Vol. 47, No. 4, 2002
Table 2. Results of Critical Point Measurements Tc/K compound bis(2-aminoethyl)amine 2-(2-aminoethylamino)ethanol 1,4-butanediol 2-(2-butoxyethoxy)ethyl acetate 2-(2-ethoxyethoxy)ethyl acetate 2-methyl-1,3-propanediol phenyl acetate 1,3-propanediol propylene carbonate a
meas
previous
709.8 739.2 723.8 693.9 673.5 708.0 685.7 718.2 762.7
709b
Estimated according to the method of Joback.2
722b b
VonNiederhausern et al.3
T/K 370.50 385.13 391.62 401.30 408.56 414.36 420.46 425.52 432.15 432.16 432.18 438.82 445.53 452.26 459.04 465.86 472.72 479.62 486.55 493.52 500.54 507.61 514.70 521.83
meas 2.000b 3.995b 5.331b 7.990b 10.67b 13.31b 16.65b 19.94b 25.03b 25.03b 25.04b 31.17b 38.57b 47.36b 57.80b 70.10b 84.51b 101.3b 120.8b 143.2b 169.0b 198.5b 232.0b 270.0b
c
% dev
2.025 4.014 5.331 7.975 10.62 13.24 16.57 19.83 24.90 24.90 24.92 31.04 38.43 47.24 57.72 70.09 84.62 101.6 121.3 144.0 170.2 200.2 234.2 272.9
-1.27 -0.48 0.00 0.20 0.40 0.48 0.51 0.55 0.55 0.52 0.49 0.44 0.36 0.26 0.14 0.01 -0.12 -0.27 -0.40 -0.55 -0.69 -0.84 -0.98 -1.10
T/K 615.0 615.2 668.8 668.8 687.6 688.0 696.0 696.2 704.6 704.6 704.8 704.8 705.0 705.6 707.0 707.0 707.0 707.4 708.2 708.4 709.0 709.2 709.8
meas 1379 1380 2757 2758 3448 3448 3791 3793 4138 4138 4137 4137 4240 4240 4240 4240 4310 4309 4309 4309 4377 4378 4377
corra 1363 1369 2751 2754 3431 3451 3775 3788 4157 4157 4166 4166 4180 4203 4269 4273 4273 4273 4287 4330 4335 4364 4373
447.45 453.65 460.85 468.65 475.55 483.55 488.25 491.35 498.85 504.05 719.2 719.4 725.8 726.8 726.8
15.82b 20.94b 26.61b 34.34b 42.04b 50.30b 57.65b 66.47b 78.19b 3447 3446 3792 3791 3791
4.60 4.82 4.97 2.05 2.46 5.03 3.67 5.72 4.59
6.22c 3.15c 2.73c 6.3b
% dev 1.13 0.77 0.23 0.14 0.50 -0.08 0.43 0.12 -0.46 -0.46 -0.70 -0.70 1.43 0.88 -0.68 -0.80 0.85 0.85 0.50 -0.50 -0.62 0.31 0.11
T/K 416.30 421.03 428.02 437.15 445.54 447.23 448.76 450.22 452.35 454.19 456.27 462.38 466.65 475.96 479.95 501.43 501.49 522.0 525.4 546.4 546.8
meas 3.952b 4.961b 6.863b 10.24b 14.54b 15.53b 16.54b 17.49b 19.04b 20.46b 22.15b 27.79b 32.45b 48.84b 51.23b 100.5b 100.9b 176.5 193.7 311.0 311.0
P/kPa
corra
% dev
T/K
meas
corra
% dev
3.914 4.930 6.844 10.27 14.62 15.65 16.65 17.65 19.19 20.62 22.33 28.07 32.77 45.28 51.72 100.4 100.6 175.7 191.6 316.6 318.7
0.96 0.62 0.29 -0.29 -0.51 -0.81 -0.63 -0.88 -0.79 -0.77 -0.83 -1.02 -0.99 7.29 -0.95 0.13 0.33 0.45 1.10 -1.82 -2.51
561.8 562.2 584.6 585.0 603.2 602.8 602.4 624.4 625.2 626.0 624.6 624.8 689.8 691.0 697.2 698.4 703.4 704.4 714.0 715.2 723.8
437.1 437.8 692.9 692.9 969.4 965.3 966.0 1371 1379 1379 1378 1378 3446 3445 3792 3791 4136 4138 4826 4827 5516
441.4 445.1 689.1 695.5 961.3 953.2 946.6 1358 1375 1393 1363 1367 3461 3517 3817 3872 4134 4194 4753 4821 5390
-0.99 -1.67 0.56 -0.37 0.83 1.25 2.00 0.96 0.26 -1.00 1.14 0.78 -0.45 -2.08 -0.65 -2.13 0.04 -1.35 1.53 0.13 2.30
a Riedel parameters: a ) 154.7833, b ) -15978.3, c ) -17.9329, d ) 6.068987 × 10-18. b Palczewska-Tulinska et al.8 (used in correlation).
Table 6. Vapor Pressure of 2-(2-Butoxyethoxy)ethyl Acetate P/kPa
P/kPa 12.37b
4.38 4.65 5.52 2.15 2.59 5.35 3.59 6.55 4.14
P/kPa
Table 4. Vapor Pressure of 2-(2-Aminoethylamino)ethanol meas
esta
4.3b
Table 5. Vapor Pressure of 1,4-Butanediol
a Riedel parameters: a ) 77.31858, b ) -9473.84, c ) -7.46276, d ) 2.500214 × 10-18. b Steele et al.6 (used in correlation).
T/K
previous
Wilson et al.4
P/kPa
corra
meas
676.1 694.3 667.7 683.0 658.5 651.1 684.6 657.5 771.1
727c 681c 663c
Table 3. Vapor Pressure of Bis(2-aminoethyl)Amine P/kPa
Pc/MPa esta
P/kPa
corra
% dev
T/K
12.50 15.82 20.56 26.94 33.84 43.28 50.20 55.02 68.18 78.66 3400 3415 3744 3793 3799
-1.04 0.04 1.84 -1.24 1.45 -2.95 0.19 4.57 -2.57 -0.60 1.35 0.91 1.27 -0.07 -0.21
727.2 728.0 729.4 729.8 730.2 730.2 730.4 732.0 734.2 735.6 735.8 736.2 737.6 737.8 738.8
meas corra % dev 3793 3793 3962 3962 3962 3962 3964 4135 4151 4309 4308 4305 4482 4481 4655
3815 3865 3939 3962 3985 3991 4003 4098 4226 4320 4333 4352 4450 4463 4530
-0.59 -1.92 0.57 -0.01 -0.58 -0.73 -0.97 0.92 -1.81 -0.27 -0.58 -1.09 0.71 0.40 2.68
a Riedel parameters: a ) 170.2815, b ) -16653.1, c ) -20.2672, d ) 8.917558 × 10-18. b Taken from Daubert7 (used in correlation).
equation5 was used to correlate the data in this study and is
b ln(P/Pa) ) a + + c ln(T/K) + d(T/K)6 T/K
(1)
P/kPa
T/K
meas
corra
% dev
T/K
meas
corra
% dev
513.0 515.0 540.0 540.8 570.0 591.0 589.4 590.8
84.81 85.49 157.2 157.2 287.5 424.7 423.3 423.3
81.87 85.91 156.0 158.4 291.7 433.5 420.3 431.1
-3.46 -0.49 0.78 -0.78 -1.44 -2.06 0.71 -1.84
609.4 632.0 654.2 672.8 673.0 691.0 691.8 693.8
593.0 855.0 1179 1572 1571 2068 2068 2150
597.0 861.1 1203 1572 1577 2024 2046 2105
-0.68 -0.71 -2.07 -0.03 -0.36 2.14 1.06 2.11
a Riedel parameters: a ) 100.0441, b ) -11866.6, c ) -10.5249, d ) 4.255466 × 10-18.
where a, b, c, and d are parameters. The values obtained for these parameters by a least-squares regression are given as a footnote with each table. In the case of 1,3propanediol, some of the data reported by Stein10 were not used to obtain the correlation listed in Table 10. The deviations for the higher temperature data of Stein suggest that decomposition may have been occurring. Conclusion Reliable critical properties have been determined for nine compounds of industrial significance. These data are also
Journal of Chemical and Engineering Data, Vol. 47, No. 4, 2002 763 Table 7. Vapor Pressure of 2-(2-Ethoxyethoxy)ethyl Acetate P/kPa
Table 10. Vapor Pressure of 1,3-Propanediol P/kPa
P/kPa
T/K
meas
corra
% dev
T/K
meas
293.15 484.6 488.4 512.0 531.6 553.4 554.0 573.6 573.6
0.013b 94.46 100.7 177.2 267.5 406.8 407.5 570.9 571.6
0.013 95.74 104.8 180.4 270.3 406.6 411.7 575.9 576.8
1.71 -1.35 -4.14 -1.80 -1.04 0.06 -1.04 -0.88 -0.92
597.8 598.6 618.2 619.4 639.8 661.8 663.0 672.6
852.2 852.2 1162 1162 1550 2108 2105 2417
corra
T/K % dev
846.3 0.69 855.3 -0.37 1142 1.75 1161 0.06 1537 0.81 2052 2.63 2084 0.99 2355 2.59
a Riedel parameters: a ) 81.60059, b ) -9600.36, c ) -8.14715, d ) 4.242500 × 10-18. b Wikoff et al.9 (used in correlation).
Table 8. Vapor Pressure of 2-Methyl-1,3-propanediol P/kPa
P/kPa
T/K
meas
corra
% dev
T/K
meas
corra
% dev
489.2 487.8 489.6 487.8 521.6 521.8 536.6 537.2 553.2 553.4 571.8 572.2 592.8 593.6 612.8
114.4 114.4 113.8 111.0 262.0 263.4 359.2 363.4 518.5 521.2 755.0 757.0 1091 1092 1509
114.9 110.5 116.1 110.1 262.3 263.5 368.4 373.2 522.7 523.8 748.5 752.6 1085 1100 1501
-0.36 3.49 -2.09 0.78 -0.12 -0.06 -2.55 -2.72 -0.82 -0.49 0.86 0.58 0.54 -0.69 0.50
613.6 613.0 612.6 634.0 634.2 654.4 654.8 678.6 679.6 698.8 699.4 705.2 705.2 707.8 708.0
1513 1510 1509 2068 2068 2760 2760 3798 3797 4835 4837 5182 5180 5353 5354
1517 1503 1494 2060 2066 2738 2753 3759 3802 4822 4851 5206 5206 5363 5376
-0.31 0.44 0.97 0.38 0.13 0.78 0.25 1.00 -0.14 0.26 -0.28 -0.46 -0.50 -0.19 -0.41
a Riedel parameters: a ) 99.44587, b ) -11595.9, c ) -10.3564, d ) 3.127100 × 10-18.
Table 9. Vapor Pressure of Phenyl Acetate P/kPa T/K
meas
corra
465.8 490.2 490.6 513.6 514.0 539.4 539.6 561.4 562.0 585.2 585.4 605.2
93.08 171.7 171.7 281.3 281.3 457.1 457.1 670.9 670.2 972.2 972.2 1304
94.04 169.1 171.0 279.9 281.6 457.4 459.1 669.5 675.0 971.8 976.2 1299
P/kPa % dev
T/K
meas
corra
% dev
-1.04 1.51 0.39 0.52 -0.09 -0.07 -0.43 0.21 -0.72 0.04 -0.41 0.35
606.0 629.8 630.2 629.8 630.6 652.8 653.4 674.8 675.8 681.6 682.4 685.2
1303 1816 1816 1817 1817 2430 2430 3174 3174 3442 3442 3593
1314 1811 1823 1811 1833 2422 2443 3155 3192 3416 3452 3562
-0.82 0.27 -0.38 0.34 -0.83 0.33 -0.53 0.59 -0.59 0.75 -0.29 0.87
a Riedel parameters: a ) 71.29997, b ) -8616.02, c ) -6.73640, d ) 3.357878 × 10-18.
useful in the evaluation of the applicability of current predictive techniques as well as in developing better correlations for estimating critical temperatures and pressures. Accurate vapor pressures are also included for these nine compounds. Literature Cited (1) VonNiederhausern, D. M.; Wilson, G. M.; Giles, N. F. Critical Point and Vapor Pressure Measurements at High Temperatures by Means of a New Apparatus with Ultra-low Residence Times. J. Chem. Eng. Data 2000, 45, 157-160. (2) Joback, K. G. S.M. Thesis in Chemical Engineering, Massachussetts Institute of Technology, Cambridge, MA, June 1984.
meas 86.18b
480.65 489.65 113.1b 500.85 145.5b 511.85 201.3b 522.65 260.6b 532.15 326.1b 542.65 420.6b 551.65 482.6b 560.35 621.2b 562.55 622.6b 571.85 810.1b 571.95 764.6b 574.45 817.0b 578.45 854.3b 582.45 990.0c 591.65 1195c 601.45 1366c
P/kPa
corra
% dev
T/K
85.82 111.3 151.3 201.3 262.4 327.7 414.2 501.9 600.0 627.0 751.8 753.3 790.0 851.6 916.9 1082 1282
0.43 1.56 -4.02 0.03 -0.69 -0.49 1.51 -4.00 3.42 -0.70 7.20 1.49 3.31 0.31 7.40 9.47 6.19
611.45 621.15 624.95 653.25 656.65 700.8 701.8 704.0 705.4 705.4 706.8 709.4 715.2 715.4 716.6 716.0
meas corra % dev 1665c 1976c 2073c 3160c 3536c 5515 5516 5688 5688 5860 5860 6032 6205 6378 6378 6549
1515 1770 1879 2866 3008 5433 5503 5658 5752 5760 5862 6050 6513 6521 6619 6578
9.04 10.41 9.36 9.31 14.95 1.49 0.24 0.52 -1.13 1.71 -0.04 -0.29 -4.96 -2.25 -3.77 -0.44
a Riedel parameters: a ) 91.33574, b ) -11145.1, c ) -9.20254, d ) 3.140965 × 10-18. b Stein10 (used in correlation). c Stein10 (not used in correlation).
Table 11. Vapor Pressure of Propylene Carbonate P/kPa T/K 368.57 370.89 371.67 373.14 375.80 378.47 381.52 384.37 388.53 391.57 395.66 398.77 402.50 406.57 410.69 414.61 419.07 426.83
meas corra % dev 0.669b 0.732b 0.753b 0.835b 0.953b 1.066b 1.253b 1.433b 1.736b 1.990b 2.389b 2.739b 3.186b 3.775b 4.462b 5.201b 6.167b 8.202b
P/kPa T/K
meas
0.661 1.23 432.07 9.879b 0.744 -1.61 435.69 11.18b 0.774 -2.70 437.71 11.98b 0.833 0.24 441.97 13.80b 0.949 0.40 444.49 14.99b 1.081 -1.40 449.01 17.33b 1.250 0.26 455.60 21.28b 1.429 0.28 459.10 23.64b 1.729 0.38 462.07 25.84b 1.982 0.42 668.6 1380 2.372 0.74 668.6 1380 2.711 1.02 725.6 2758 3.172 0.43 762.0 3964 3.751 0.66 760.4 3966 4.426 0.81 762.2 3961 5.163 0.74 763.6 4135 6.125 0.67 762.2 4138 8.165 0.46 762.6 4137
corra
% dev
9.845 11.17 11.97 13.82 15.02 17.40 21.41 23.84 26.08 1407 1409 2741 4020 3959 4032 4091 4028 4045
0.35 0.07 0.06 -0.13 -0.23 -0.40 -0.63 -0.86 -0.92 -1.98 -2.11 0.62 -1.40 0.18 -1.80 1.07 2.64 2.22
a Riedel parameters: a ) 69.98825, b ) -9331.73, c ) -6.46065, d ) 1.726568 × 10-18. b Hong et al.11 (used in correlation).
(3) VonNiederhausern, D. M.; Wilson, L. C.; Giles, N. F.; Wilson, G. M. Critical Point Measurements for Nine Compounds by a Flow Method. J. Chem. Eng. Data 2000, 45, 154-156. (4) Wilson, L. C.; Wilson, H. L.; Wilding, W. V.; Wilson, G. M. Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method. J. Chem. Eng. Data 1996, 41, 1252-1254. (5) Poling, B. E.; Prausnitz, J. M.; O’Connell, J. P. The Properties of Gases and Liquids, 5th ed.; McGraw-Hill: New York, 2001; pp 7.9-7.11. (6) Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K. Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Dicyclohexyl Sulfide, Diethylenetriamine, Di-noctyl Sulfide, Dimethyl Carbonate, Piperazine, Hexachloroprop1-ene, Tetrakis(dimethylamino)ethylene, N,N′-Bis(2-hydroxyethyl)ethylenediamine, and 1,2,4-Triazolo[1,5-R]pyrimidine. J. Chem. Eng. Data 1997, 42, 1037-1052. (7) Daubert, T. E. Vapor Pressure of 13 Pure Industrial Chemicals. Experimental Results for Phase Equilibria and Pure Component Properties: DIPPR Data Series No. 1; American Institute of Chemical Engineers: New York, 1991; pp 80-95. (8) Palczewska-Tulinska, M.; Cholinski, J.; Szafranski, A.; Wyrzykowska-Stankiewics Experimental Vapor Pressures and MaximumLikelihood Antoine-Equation Constants for 1,1,1-Methoxydimethylpropane, Thiacyclopentane, and 1,4-Butanediol. Fluid Phase Equilib. 1984, 15, 295-307.
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(9) Wikoff, H. L.; Cohen, B. R.; Grossman, M. I. Production of Low TemperaturessA Simplified and Inexpensive Laboratory Procedure. Ind. Eng. Chem. Anal. 1940, 12, 92-94. (10) Stein, J. Structural Effects on Critical Properties B Vapor Pressure and Critical Property Measurement. M.S. Thesis, The Pennsylvania State University, University Park, PA, 1984.
(11) Hong, C. S.; Wakslak, R.; Finston, H.; Fried, V. Some Thermodynamic Properties of Systems Containing Propylene Carbonate and Ethylene Carbonate. J. Chem. Eng. Data 1982, 27, 146-148. Received for review March 21, 2001. Accepted July 10, 2001.
JE0100995
