J. Chem. Eng. Data 1981, 26, 323-332
Table IV. Henry’s Constants of H, in 9-Methylanthracene, 2-Ethylant hraq uinone, and Dibenzofuran Henry’s constant, atm temp, “C 100 125 150 200 250
9-methylanthracene
2-ethylanthraquinone
4140 3240 2525 2025
dibenzofuran 3750
3520 3175 2550
2925 2395 1920
where subscript 2 stands for the solute and 1 for the solvent: x2 is the mole fraction of the solute in the solvent; f2 is the fugacity of the solute in the gas phase. Henry’s constants for hydrogen in the three aromatic compounds were evaluated by extrapolating a plot of fH,lxHl to xH = 0. The fugacity of hydrogen in the gas phase, fw was calculated from the Soave-Redlich-Kwong equation of state (4). Figure 2 shows the plot of Henry’s constants vs. temperature. The values of
323
these constants are tabulated in Table IV. For comparison purposes, the Henry’s constant of hydrogen in 9,lOdihydrophenanthrene, calculated from data of Sebastian et al. (3),are also shown in Figure 2.
Acknowledgment Thanks are due Mr. Tor Kragas for zone purifying the polyaromatic compounds.
Llterature CRed (1) Cukor, P. M.; Prausnitz, J. M. J . phys. Chem. 1972, 76, 598-601. (2) Nasir, P.; Martin, R. J.; Kobayashi, R., submltted for publlcatlon In Fhkj
.
W s e EquiUb (3) Sebastian, H. M.; Sknnick, J. J.; Lin, H. M.;Chao, K. C. J. Chem. Eng. Deta 1879, 24, 343-5. (4) Soeve, G. Chem. Eng. Sci. 1872, 27, 1197-203. Received for review December 1, 1980. Accepted February 16, 1981. Funding for thls work was provlded by the U S . Department of Energy.
Density and Surface Tension of 83 Organic Liquids GBbor Karosi and E. sz. Kovlts” Laboratoire de Chimie Technique de I’Ecole Polytechnique F6d6rale de Lausanne, 10 15 Lausanne, Swkzerland
Densltles and surface tenslons of organlc llqulds of known purlty were measured In the temperature range of 20-80 OC. In many cases llterature data from apparently reliable sources conflicted with each other. Our measurements were conducted wlth the alm of maklng a choice. Also Included are data of a few compounds of hlgher molecular welght measured In a broader temperature range. In the present paper densities and surface tensions are given for 75 pure liquids and 8 purified polymers. The surface tensions of about half of the substances have been reported in the excellent critical review of Jasper ( I ) , and his recommended values are compared with our data in Table 11. In most cases the surface tensions agree within the experimental error, but, where significant deviations were found, the substances were reexamined with special care in order to obtain the most reliable values.
1. Compounds In Table Iinformation is given about origins, methods of purification, purities, refractive indexes, and melting points of the compounds examined. Compounds 16-24 are branched hydrocarbons of the general structures A1 and A2 with following formulas:
A1 A1-C,, R = hexyl AI-C,,, R = decyl AL-C,,, R = tetradecyl AI-C,,, R = octadecyl
A2 A2-C, ,,R = hendecyl A2-C,,, R = tridecyl A2-C,,, R = pentadecyl A2-C,,, R = octadecyl A2-C2,, R = docosy1
Squalane (15) is a mixture of the diastereomers of 2,6,10,15,19,23-hexamethyttetracosane. Compounds 69-76 are poly(ethy1ene glycols) (PEGS) and their methoxylated derivatives (PEGM) with nominal molecular masses of 600, 1000, 2000, and 20000. The average molecular masses of the HO(CH,CH,O),H
H,CO(CH,CH,O),CH,
PEGM
PEG
PEGSdetermined by the method of ref 2 are as follows: PEG 600, 6.10 X lo2: PEG-1000, 1.13 X lo3: PEG2000, 2.15 X lo3: PEG20000, 1.71 X 10‘. The derivatives PEGM were prepared from the PEGS: consequently, their average molecular masses are MW(PEGM) = MW(PEG) 24. Under the synthetic conditions no degradation is to be expected. 1. I . Or@n. In the third column of Table I,the origin of the compounds is indicated by using the following abbreviations: FI, Fluka AG, Buchs, Switzerland: EGA, EGA-Chemie, Steinheim, Germany: Sh, Shell Research Laboratories, Amsterdam, Holland: Me, Merck AG, Darmstadt, Germany; Syl, Synthetized in our laboratory, see ref 3: Sy2, Synthetized in our laboratory, see ref 2. 1.2. Purlflcatlon. Commercially available research-grade compounds have been further purified. The method of purlfication is indicated in the fourth column of Table I by using the following abbreviations. Di: Distillation of the product in a Vigreux column discarding a forerun and a residue, each representing 25 % of the distilled material. This operation was capable of removing other members of homologous series to less than 0.2%. Di/Na: Distilled over sodium. Di/Hg: Distilled over mercury. Cr: Recrystallization from diethyl ether (DE), propanol (Pr), cyclohexane (CH), ethanol (E), or nhexane (H) or from a mixture of them. For example, the symbol “Di: 3XCr(E/DE)” means that the middle fraction of the distillation was recrystallized three times from a mixture of ethanol and diethyl ether. Fi: Filtration on a silica gel column (Merck: Kieselgel 60)
0021-95681811I726-0323$01.25fO 0 1981 American Chemical Society
+
324
Journal of Chemical and Engineering Data, Vol. 26, No. 3, 198 1
Table I
No
Compounds.
Compound
For a d e t a i l e d d e s c r i p t i o n o f t h e t a b l e see s e c t i o n 1 .
I
20
Gas c h r w t o g r a p k i c a n a l y s i s
M o l e c u l a r O r i - Method o f lxeioht l o i n wri f i c a t i o n .
Tc C
total Main Inlpurities cmoo1mpunent ities IA r e t e n t i o n i n d e x ( I A ) / X i n chromatogram 7;
OC
Hydrocarbons. Alkanes
04 63
,412
11
,422
14
,426
1370/.20;
47
,428
1500
324/ .02; 1386/ .02; 1599/ .02h
06
,431
1601
399/.02h;
1499/.03h;
1701/.02h
07
.434
50
1696
!00/.05h; j99/..02/;
1301/.07h; 1801/.04h
1402/.04h;
22
22.0[27
)i;F i
6U
1300
501/ .02h; 1600/ .Olh; 1739/ . 2 2 ; '72/ .25; 1862/ .02
52
26.21 27
I
li; F i
60 1901
598/.04h; 1648/.02; 1744/.02; )33/ .06; 1950/ .02; 1962/. 11
29
32.1[ 27
282.56
I
)i;F i
60 2000
564/.05; )36/ .02
1841/.03; 1933/.06;
18
36.8L ?7
12. 3,8-Di e t h y l decane
196.40
Y1
Ii; F i
80 1324
30/, 04; 1099/. 02; 1232/. 10; 1 301/. 10; 385/ .09
,35
,434
13. 2,6,10,14-Tetramethyl, pentadecane
268.53
1
2i; Fi
60
1686
!73/.01; j31/.01;
.38
. 4 38
226.45
1
li; F i
10
1337
34/.05;
.35
,439
422.83
1
li; F i
422.83
Yl
!xCr( OE/E)
647.26
Yl
l x C r ( OE/E )
6.0-46.
871.69
Yl
I x C r ( DE)
5.0-66.
1096.12
VI
I x C r ( CH)
72-76
829.61
Yl
Zr( Pr/H/E)
5.5-7
941.83
Yl
:r( Pr/H/E)
3,5-14.
1054.04
Yl
:r( Pr/H/E)
'2.5-23.
1222.37
Yl
Cr( P r / H / E )
i7.5-38,
1446.80
Yl
cr(Pr/H/E)
.7.5-48.
196.38
Di; Fi
252.49
1 1
27. Cyclohexane
84.15
28. - < - - D e c a l i n
138.25
29. - r ; c - - D e c a l i n
1. 3ecane
142.29
I
)i;F i
40
1000
134/.02;
1065/.02
2. tI end ec a ne
156.32
I
)i;F i
40
1100
)99/ .37h; 1ZOO/.19h; 1300/ .04h; 399/ .03h
3. Dodecane
170.34
40
1201
)01/ .02h; 1099/.04h;
4. T r i d e c a n e
)i;F i
60
1300
)99/ .10h; 1146/ .02; 11 73/ .02
5. Tetradecane
196.40
1 I I
)i;F i
184.37
)i;F i
10
1399
!99/.02h; 1346/.04; 161/.02; 1499/ 19h
6 . Pentadecane
212:42
I
)i;F i
10
7. Hexadecane
226.45
1
li; F i
10
6. heptadecane
240.48
1
)i;F i
9. Octadecane
254.51
I
10. Nonadecane
266.53
11. Eicosane
1299/.05h
,417
I s m lkanes
133U.01; 1648/.03; 1382/.23;
1469/.04 1792/.25 1404/.04; 1500/.03
,452
k lkenes
2 5 . 1-Tetradecene 2 6 . 1-Octadecene
'1 c
1388
0961.02;
1299/.04;
1355/.02;
1324/.07
.15
.43L
Di; Fi
'5C
1784
598/.03;
1691/.09;
1754/.01;
1900/.05
.18
.44!
e
Di; F i
8C
678
.03
.42L
1
Di; Fi
4c
1162
119/.52;
1198/.05;
.56
.48'
138.25
1
D i ; Fi
4c
1121
000/.01;
1108/.01
.02
.46!
78.12
e
Di/Na
8C
66 3
97/.01;
.09
.50'
Di/Na
8r
769
64/ .02
.n2
.49(
C y c l i c hydrocarbcxs
30. 3enzene 31. Toluene
92.15
ie
99/ .02;637/ .01
739/.08
1225/.01
see section 1.5.
Journal of Chemical and Engineering Data, Vol. 26, No. Table I
No
Compound
3, 198 1 325
( continued)
M o l e c u l a r O r i - Method o f weight gin purification
20 nd
Gas c h r m t o g r a p h i c a n a l y s i s Tc OC
Main Impurities total impucomponent ities IA r e t e n t i o n index ( I A ) / i n% chranatogram %
m.p.
see OC
A I kane d e r iva t i ves
I-ha logeno alkanes 32. 1-Chl orotetradecane
232.85 F1
O i ; Fi
40
33. 1-Chlorohexadecane
260.90
2xCr( DE/E) ; Di
50
878
34. 1-Chlorooctadecane
288.95 F1
2xCr ( OS/ E ) Di
60
080 1781/.01h; 1878/.16h; 1940/.14; 1981/. 25h ; 1991 / .05; 2026/. 15; 2051/. 11
35. 1-Branotetradecane
277.30 F1
Di; Fi
50
380/ .07h ; 1579/. 23h; 1630/ $02; .09h ; 1697/ .02; 1823/ .02; 1883/ .03
36. 1-Branohexadecane
305.35 rl
2xCr( M/E) Oi
60
37. 1-8ranoijctadecane
333.41 F1
2xCr( D U E ) Di
60
1
1
1595;. 12 f 1616; .Os; 1631) .03; 1774; .05h 1805/. 03
I
15841.03;
17771. i a h ; 1840/.32;
19401.07
.38
a
.60
.4503
.90
.4511 28.61271
.48
.4609
.54
.4620
447 5
129/.03
986
1584/. 13h ; 1784/ .O5h; 1877/. 15; 1847/.07; 1935/.07; 194W.07 2119/.02;
2129/.25;
214W.09;
.52
-
28.2[271
209/. 05
1-Cyanoalkanes
38. A c e t o n i t r i l e
41.06 le
sp. r e f . [ 4
39. Cyanoethane
55.08 F1 83.13 71
Di Di
30
721
i95/. 45
.45
,3970
41. 1-Cyanohendecane
181.33 F1
Di
425
I 2 2 5 / . 39h; 1327/. 17h; 1483/ .04
.60
.4361
42. 1-Cyanotridecane
209.38
Oi
30 50
541
l097/ .02; 1332/.05h; 1420/ .05; l530/ .08h; 1595/ .02; 1833/ .03h
.25
.4413
43. 1-Cyanohexadecane
251.46 F1
2xCr(H); D i
60
937
l581/ .04; 1630/ .03h; 1777/.08; 1837/.25h;
.61
34 [27
.2
41 [27
.2
42
40. 1-Cyanobutane
265.49
45. 1 Cyanoectadecane
279.52 '1
46. Methanol
32.04
47. Ethanol
46.07
48. 2-Butanol
74.12
49. 1-Hexanol
102.17
Benzene and naphthelene d e r i v a t i v e s
.3658
EA LxCr(H); O i
44. 1-Cyanoheptadecane
A 1kano Is
.3442
1733/ .02h; 1985/.05; 2065/.14
i
PxCr(H); O i
e
.02
e
1
Oi
60
1
Di
40
563 311
1
64/.02;
..02 799/.08
:.02
.3976
.10
.4179
50. Fluorobenzene
96.11 F1
Fi
en
657
.02 1.4660
51. Chlorobenzene
112.56 F1
Fi
30
869
.02
1.5248
5 2 . Branobenzene
157.02 F1
Fi
40
963
.02
1.5601
53. Iodobenzene
204.01 F1 Oi/Hg;
80
122
54. Nitrobenzene
123.11 F1
Ii
40
077
Di
40
9 20
Fi
1091/.10
55. Methoxybenzene
108.15 F l
56. N , N - D i m e t h y l a n i l i n
121.18 F1 D i
57. O i m e t h y l p h t a l a t e
194.19 F1 O i
20
384 945/.02;
58. 1-Chloronaph t a l e n e
162.62 F1
20
497
60
509 605/.04; 663/.09
Di
1295/.12;
1156/.09; 1429/.07
1518/.01
.10
1.6201
.02
1.5521
.02
1.5172
.02
1.5582
.12
1.5150
.19
1.6321
.02
1.3817
.13
1.4246
Hethane d e r i v a t i v e s 59. N i t r a n e t h a n e
61.04 -1
3i
60. D i c h l o r m e t h a n e
84.93 -1
Sp. r e f . [ 4 l
Remarks
61. Tetrachloranethane
153.82 C D i ; F i
60
663
.02
1.4601
62. Dibrananethane
173.85 -1
3i; Fi
60
709
.02
1.5419
63. Diicdanethane
267.84 '1
Di/Hq; F i
.2
12.74251
section 1.5.
328 Journal of Chemical and Engineering Data, Vol. 26, No. 3, 1981 Table I
(continued)
No Compound
M o l e c u l a r O r i - Method o f weight gin purification Tc OC 1
nd20
Gas chromatographic a n a l y s i s Main component
I*
m.p.
Remarks
OC
see section 1.5.
Impurities
total impuities r e t e n t i o n index ( I A ) / % i n chromatogram % 1
1
01 igo-and poly- ( e t h y l enegl y c o l s 1 64
1,2-Ethanediol
62.07 F1
Oi
65
1.2-Oimethoxyethane
90.12 F1
Oi; Fi
60
601
579/. 27
.27
66
2,5,8-Trioxanonane
134.18 F1
O i ; Fi
140
867
797/ .01
.02 1.4090
67
2,5,8,11-Tetraoxadodecane
178.24 F1
Di; Fi
140
1126
600/.01;
68
2,5,8,11,14-Pentaoxapentadecane
222.29 F1
Di; Fi
180
1379
1004/ .01; 1102/ .01;
69
PEG-600
610
c.02 1.4281
776/.01;
829/.01;847/.01
1.3819
.05 1.4235
12191.02
.05
1.4326
F1
Sp r e f l 2 1
20-22
Sp r e f [ 2 ]
42-45
Sp r e f [ Z ]
52-55
71
PEG-2000
1.13.103 F1 3 2.15.10 F1
72
PEG-20000
1.71.104 F1
Sp r e f [ 2 ]
60-65
73 74
PEG-M-600 PEG-M-1000
638 Sy2 Sp r e f [ 2 ] 1.16.103 Sy2 Sp r e f [ 2 1
43-45
75
PEG-M-2000
2 . 1 8 . 1 0 ~sy2 ~p r e f [ 2 1
52-55
76
PEG-M-20000
1.71.104 Sy2 Sp r e f [ Z ]
60-66
?O PEG- 1OOO
22-25
Miscellaneous 77
Fommide
45.04 F1
Di
