Vapor-liquid equilibria in the ternary system acetone-benzene-cyclohexane
by Pu-Sheng Ting
A THESIS Submitted to the Graduate faculty in partial fulfillment of the requirements for the degree of
Master of Science In Chemical Engineering
Montana State University
© Copyright by Pu-Sheng Ting (1949)
Abstract:
The purpose of this investigation was the determination of binary and ternary equilibria in the system
acetone-benzene-cyclohexane. Othmer equilibrium stills were used. Vapor and liquid compositions
were obtained from refractive index-composition curves for the binary and ternary systems, which had
been previously determined. Data for the three binary systems were checked with those appearing in
the literature. Ternary equilibrium diagrams were obtained from benzene and cyclohexane equilibria
curves in the ternary system at constant weight percent of acetone in liquid. The ternary mixture
formed no azeotrope, although both the acetone-cyclohexane and the benzene-cyclohexane binary
systems formed minimum azeotropes. VA PO P-LXQTJID EQUILIBRIA IIJ THE TERIjArar SYSTEM
ACETON > B J I J IIH-C'TCLC Q,-JlNE
by
PU-SQLHO TIHO
A THESIS
Submit tod. to the Graduate Faculty
in
partial fulfillment of the requirements
for the degree of
Easter of Science In Chemical Engineering
at
Montana State College
Approved:
Chairman,
S a m i h i h g 'Corsai ttee
ian, ^ r adudte
^ivislon
Bozeman, Montana
August, 1949
V
2
Table of Contents
Page
!•
Uwmary
.
.
4
lie
Introduction
,
5
IIIe
ocpori.tental
•
7
IV.
V.
VI.
xiocults
.
.
10
Literature Cited
13
Appendix
14
Table
Table
Table
.
Ie
II.
.
- n r CU v
at
J. in
ujjaary Lys tem . c e tone -uenzene
u
Lefrrctslve Index at CO' 0. in the
M n a r y Lyster L cetone-Cyclobcxtme
Table
Table
IV.
V.
Vie
(j
Table
18
VIie
Analysis t nd Uquillbi i m )cta in
the M n t r y ye ten ce tone - Wncene
19
nalysis and B q u i l i m Ium Jata in
the Binary System Acetone-Cyclohex&ne
.
.
.
.
.
.
30
Analysis and Bquilibrium Jata in
The Binary Jystern Benzene-Gyclo-jOXanc
.
.
. . . . .
21
.kof.Uv vl.... Index t --t J. in ua©
ie m a z y r jystem a c e tone -Benzene ...................
Table VIII.
I
5
FigUi*e
17
I :.
y
Table
16
Analysis and equilibrium Jata in
the Ternary yst c m Acetono-Benzene
Cyclohexane
.
.
.
.
.
Ie
s
.
.
.
.
.
92538
22-24
Lt-CC
30
3
F i qure
Figure
Blguro
Figure
Figure
Figure
■I JVO
2.
3.
4.
5.
6.
7.
Ge
Veror-LiqulI Equilibrium Diagrams
s .
.
,
31
Boilinq a mints in the Ginar - Svat e a s ..........................
32
. ctivity CoeiTiciente in the ncetone-3enzene- System
.
,
.
33
.ctivity CoeTficicnto in the Acetone-Cyelauex. :i© bys tea
.
.
34
Activity Coefficients in the Ben.
.
35
Aefraetive Inde at 20°C. in the
Ternary Gystom he©tono-BenseneCyclohexane at Constant eight
I or Cent Acetone
. . . .
36
Gonzene equilibria In t _u Gerimry
S t s tem ee cone- ienzeno- C lohexene
a J von:.fc tic .c i 'y it I v..' G ent A c e to n e
,.
hi ,CUiO ICe
in the L i c u i d ................
57
Cyclonexane ,quiH b r i a in the Tern&ry b^ste:.. ce tone-Lenxer.e -C /elohex no at Ca Istant o' ^ht or Cent
, c e t o n e i n c ie . I q a i u
.
.
,
53
Vapor-a Iqui d equilibria In the Ter­
nary
•s ter; lcetone -Gengene -Ct c Io hexc no. Constant ..el he *or Gent
Benzene
Figure 11*
•
•
•
•
.
,
V k or-..!quid equilibria In the Ter­
nary oyateai i cetone-benzene-GycIoh OXanee Oonfctmt .eight i er Cent
Cyolohexane
.
.
.
.
.
39
40
4
I.
Sunmary
The purpoae of this investigation w s the determination
of binaz*y and ternary equilibria in the system acetone-benzenecyclohexane. Othmer equilibrium stills were used.
Vapor and
liquid compositions were obtained from refractive index-compo­
sition curves for the binary and ternary systems, which had"
been previously determined.
Data for the three binary systems
were checked with those appearing in the literature.
Ternary
equilibrium diagrams were obtained from benzene and cyclohexane
equilibria curves in tho ternary system at constant weight per
cent of acetone in liquid.
The ternary mixture formed no azeo­
trope, although both the acetone-cyclohexane and the benzenecyclohexane binary systems formed minimum azeotropes.
5
II.
Introducticm
i.ios u hydrooaruons occur in nature or ai-o produced as mix­
tures, and tne separation of one compound Ii-om another closely
boiling compound is a problem of coneIde ‘ab3 e importance.
At
present, a number of aromatic hydro carbons are manufactured
from petroleum since the recent introduction of eye?.!action
and hydroforming processes, in m i c h cycloparaffins are formed
as Intermediate products.
The economical separation of hydro­
carbons thus produced becomes a significant subject in research.
In the case of mixtures of benzene and cyclohexane, the
separation of benzene from cyclohexane by rectification is im­
possible because of their close boiling noInts and the forma­
tion of an azeotrope.
At 760 mm. pressure, benzene boils at
80.103°C.(13), and cyclohexane at 80.738°C,(13).
Azeotroplo
distillation with suitable entrainers usually provide favor­
able means of separating closely boiling pairs.
Acetone is a
suitable ontrainer, but no data have appeared in the litera­
ture for the acetone-benzene-cyclohexane system as yet.
A
thorough knowledge of the vapor-liquid equilibria involved is
essential in designing equipment* for the azeotropic opera­
tions, and It is the purpose of this thesis to provide such
data.
Acetone was chosen as the enbraincr, because it forms a
6
binary minimum, azeotrope with cyclohexane only (7)(S), which
is sufficiently lower than the original minimum azeotrope (3)
(7)(9)(12).
In addition, acetone has many other desirable
properties, such as its complete solubility in benzene and
cyclohexane, its ease of separation from the hydrocarbons by
water extraction and distillation (0), low cost, availability,
chemical stability and absence of reaction with the hydrocar­
bons or the column material.
7
III.
Experimental Ltterlalc, Equipment and Irocedixre
Acetone (0.P., Commercial Solvents Co.) and eyeloiiexane
(Doy / Chemical Co.) were subjected to rectification in a one
inch diaxsi©tcr, four feet long glass laboratory column, packed
with 1/16" stainless s beel Fenske helices and calibrating about
thirty theoretical plates at total reflux,
fhe refractive In­
dex of the acetone at 20°C . was 1.3537, compared with 1.3588
given by Hodgman (C), and that of the cyclohexane was 1.4262
as given by Rossini, et al (13).
Benzene (% & A Tested Purity)
Fisher Scientific Ce.) was shaken three tines with C. P. con­
centrated sulfuric acid, and washed three times with C.F. so­
dium bicarbonate solution.
After the final acid wash, there
was only a very slight tinge of coloration in the acid layer.
After washing with distilled water, the benzene was dried with
calcium chloride and subjected to rectification.
Its purity
was checked by determining the reTractive Inaex to be 1.5008,
compared with 1.5009 given by Griswold and Bowden (4).
Rossini,
et al, give 1.5011 for pure uenzene (15).
Vapor-Iiqula equilibrium determinations were made in two
glass CtlMer stills (10), which, were connected to a pressure
system.
The stills were constructed of Pyrex glass, and each
had a still pot capacity of approximately 120 ml.
Cn external
electrical heating coil surrounding the still pot provided heat
for the distillation.
A second external electrical heating
8
coil surrounding the vapor space served to minimize heat loss
from this section of the still.
The stills were insulated
with asbestos tape fee prevent temperature fluctuations in the
still due to outside Influences.
All heating colls were sepa-
SBte (Sn
Ioi
I :cbl iC Jo. ).
The pressure system consisted of two five gallon surge tonics,
one of which was connected through, a hand valve to a nitrogen
tank and served as a pressure reservoir at about 5 pounds
gage.
-ctrolt Lubricator Co,, Ko , 603-5. Solenoid valve
was placed in the line between the surge tanks.
The valve
was activated by a mercury contact pressure regulator through
a Pisher-Serfasa electronic relay (P. S. Co. 13-991), and main­
tain ^B pressure of 760 mm, in the second tank.
Operating pres­
sure was read from a mercury nanometer connected to t^e system.
Vapor liquid equilbrium determinations were m a :c accor­
ding to the following procedure:
A 75-12C ml, sample of either
a binary or ternary mixture prepared from acetome, Denzene and
cyclohexane was charged tc the still.
The still was then
slowly pressurized to 7 GCncu mercury.
The heat was adjusted
to give a distillation rate of about one drop per second.
The
d i s t i nctions were allowed more than one half an hour to at­
tain equilibrium.
Then the powerstats were turned off and the
pressure slowly dissipated.
Va or condensate and liquid sam­
ples were taken and their composition determined by refractive
index in a Valentine Abbe type refractoraeter, capable of being
9
read to 9.'001,
Hafractive indices had previously buen deter­
mined lor the three binary mixtures and the ternary mixture.
The refractive index data are presented in Tables J-XII and
VlX and Figures I
ternary system v/ere
acetone.
nd 7.
Jho refractive index data for the
.eten Ineu at constant weight
er cent of
In the case of ternary mixtures, compositions were
obtained from the refractive indices determined before and af ­
ter water extraction of acetone from the mixtures and drying
with calcium chlorine.
Calibrated precision thermometers v/ere
used to determine the vapor temperatures in the atills.
%
10
IV.
n©suits
Txie vapor--I I quid equilibria for vho t,,roe binary systems
are presented in Tables IVwVI and gTSij nically in figure 2.
The oyaten rce tone-bon z e m ex iibits no constant boiling mix­
ture.
Its equilibrium curve agrees closely v.ith that given by
Helnders and Do Vlnjer (11), except 5ca middle portion.
The
system acetone-cyclohexane exhibits an azeotrope containing
75*2 mole ^ (or 57.6
/t.
rhlle Leant -avo < 9 5 wt.
) of acetone and boiling at 53.8°C.,
at < 5 4 . u°C.
(7)(9).
The
ucm
bon sene-cyclohexfne exhibits cn azootrope containing 52.0
mole % (cr 49.6 wt.
) of benzene and boiling at 7G.S°C.,
v*ill6 Lecat gave 55 wt. % at 77.5°C. (7)($), and Richards and
Hargreaves gave 51.5 mole % at 77.4°C.
(12).
The azeotropic
points obtained in this research may be considered in ggod
check with the literature.
Boiling points of the bin&ry systo. .s ,are rlotted against
composition in Figure 3.
Activity coefficients were calculated
with temperatures read from these curves, so as to obtain
somewhat smoother curves in Figures 4-6.
Vapor pressures of
each pure component at various temperatures vere taken from
references (8)(13).
All three binary e u i l l b r i u n curves were
checked favorably by comparison of the slopes of the activity
coefficient curves with theoretical values from the GibbsDuhem relations (I)(2).
11
I?iie vC-x>r-!i u." d oqulllovluzu data for tiho torriBZ1^ ays ten
are presented In table VIII in twenty two sets.
nearly the stone amount of acetone in the liquid,
LJach h a s
fhe values
of weight por cent of borscno in the vapor v;e *o • lottod
against wol^it per oont of benzene in the liquid for these
twenty two seta, or.ch sot yielding an equilibrium cu.-ve m%
weight por cent acetone.
The cyclohexane equilibria at con­
stant. vie.ityit per cent acetone wore plotted in the sane manner.
In Figures 8-9, only u few sots were graphed together in order
to avoid confusion and yet illustrate the general feature
clearly.
The end points of these curves were taken from ace­
tone-benzene or acetone-cyclohexane equilibrium curves.
Tne triangular charts of Figures 10-11 wore drawn from
the benzene and c rcloiiaxene equilibrium diagram*.
The curved
phase lines represent constant weight per cent of benzene or
cyclohexane in the equilibria a vapors.
The end points of
these carves were taken directly from figure 2.
The composi­
tions of tiie boiling liquid are represented by the coordinates
of the triangle.
From these two triangular charts, equilibrium vapor compo­
sitions can be obtained for any ternary liquid mixture of ace­
tone, benzene and cyclohexane.
ing 20.0
For example, a liquid contain-
acetone, ' i .0 j benzene and 50.0
of cyclohexane
will be in equilibrium with a vapor containing 13,4 % of ben-
12
zeno (from Firnire 10), 38.3 , of cyclohexane (from Figure 11)
and 45.3 % of acetone (by difference).
Bolling point data indicated no ternary azeotrope forma­
tion.
All boiling points determined for tornax'y mixtures
were higher than that of the binary azeotrope of acotono-cyclohexano.
13
V. Literati!:© Cited
(I)
CO--Isoil, H.C., and Colburn, a. ., Ind. .,Inge Chem*, 54,
581 (1342).
>
• '•
•
• >
> 1st,
,, .,,cu-i-cv/--!ill .Jack Co,, Sew 'fork
(1944).
(3)
?leld, E., I. . .c ;ent C,012,310 (1940).
(4)
Griswold, J., m d
Bowden,
.H., lnd. I nr-. Chem,, 38,
509 (1946).
(5)
(S)
derington, #.?.&*, Trane. Faraday ^oc., 40, 401 (1944).
Iodyaan, C.
‘’handbook of Chen.
: Ihge,", 32nd Cd.,
Chemical Rubber Iublichlng Co., Cleveland, Ohio,
(1957-
58).
(7)
Horsley, L.F., lnd. Ln;. CZiea.
nal.
-d., 19, 300 (1343).
(3)
Lanyo, N»A., "Handbooh of Chemistry", Handbook Iublishers, Inc., Cle/eland, Ohio (I f 3 ) .
(3)
Lee at, "Aaootro- issic", Brussels, Lsaaertin (191 j),
*
• •-
(II) Ho Indore,
*
•
.
4#
-nd Do M in Jcr, C.::., ..ov, Trav. Chin, 59,
369 (12.10),
(12) .Jlcharde , A.K., and Hargreaves, k., lnd,
jrt .. Chci:,.,
30. Jo5, (1944),
(13; .scasLij, - . /*, ct : J., ltSGleute i values of properties of
Hydrocarbons," Hat. Bni-. Std. 0461 (1947).
14
VI.
Appendix
Page
Table
Table
Table
Table
Table
Table
I.
21,
III.
IV.
V.
<
H
»
Table
VII,
Table VIII,
Firure
Figure
I.
2.
Kefroctive Index at 20°C. in the Binary
System Acetone-Benzene
. . . .
16
Refractive Index at 2C°C. in the Binary
S y s t m Acetone-Oyclohexrne
.
17
Refractive Index at CO0G. in the Binary
System Benzene-Cyclohexane
18
Analysis and equilibrium. Data in the
Binary By 3 te..: ^cetcno-Benzene
,
.
19
Analysis and Equilibrium Data in the
Binary System Acetone-Cyclohexane
.
,
20
Analysis and equilibrium Bata in the
Binary System Benzene-Cyclohexane
.
.
21
Refractive Index at 2tv°C. in the Ternary
System Ace tone -Benzene -Cyclohexane
22-24
Analysis and equilibrium. Data in the
Ternary System A cetone-Benzene-Cyclo­
hexane
•
«
*
«
•
•
• •
25-29
Refractive Index at SO0C. in the Bi­
nary Systems
30
Vapor-LI quid hqulljbrium Dla trems of
the Binary Systems
.................
31
Figure
3.
Boiling Points in the Binary systems
32
Figure
4.
Activity Coefficients in the AcetoneBenzene S y s t e m ......................
33
Activity Coefficients in che AcetoneCyclohexane System
.
.
.
.
.
34
Activity Coefficients in the BenzeneCycloliexane System
.
.
.
.
.
35
Refractive Index at CO0C. in the Ter­
nary >ysten Aico tone -Benzene -Cyclohexane
at C stant Reight Ier Cent Acetone
36
Figure
Figure
Figure
5,
6.
7.
15
Figure
Figure
8.
9,
Figure 1C.
Figure 11«
Beneone Equilibr*a in the Ternary System
4 cetone-Bonzane-C clohexano at Constant
VieiFnt Per Cont . cetono I i the Liquid
.
57
Cyclohexane equilibria in tlio Ternary
System Ace tone-Benzene -Cyclohexane at
Constant '.Voight For Cent Acetone in
t— £ iqu-'-d
«
«
«
•
«
*
•
•
53
Vapor-Liquid equilibria in the Ternary
System Acetone-Benstene-Cyclohexane*
Constant eight For Cent Benzone.
.
Vapor-Liquid equilibria in t ie Ternary
System £icetone-Benzene-Cyclohexane.
Constant Weiglit Fer Cent Cyclohexane
.
39
40
16
TABLE I
Rofractivo Index at SO0C . in the Binary System
Acetone-Benzene
Weight % Acetone
OvOO
4.74
5.00
8.39
9.14
10.00
10.93
12.44
14.20
15.00
20.00
25.00
25. G8
30.00
35.00
37.43
40.00
41.44
45,00
50.00
55.00
60.QOJ
65.00
70.00
75.00
00,00
85.00
• 09.02
90.00
93.48
100.00
Weight % Benzene
100.00
95.26
95,00
91.61
90.85
90.00
89.07
87.56
85.80
85.00 /
30.00/
75.00
74.31
70.00
65.00
62.57
60.00
56,56
65.00
50.00
45.00
40.00
35. CO
30.00
25.00
20.00
15.00
10.98
10.00
6,52
0.00
Refractive Index
1.5003
1.4941
1.4935
1.4881
1.4874
1.4360
1.4845
1.4820
1.4794
1.4784
1,4711
1,4635
1,4623
1.4560
1,4433
1.4451
1,4411
1.4338
1.4337
1.4266
1.4193
1.4122
1.4053
1.3933
1.3916
1,3846
1.3779
1.3728
1.3716
1.3671
1.3587
17
TABIS II
Bearactlve Indox at 20 G « In the Binary System
Acotone-Gyclohexane
it
Acetone
0.00
5.00
8.25
11.54
14.74
15.39
21.20
25.00
50.00
35.00
37.96
40.00
42.00
45.00
46.66
50. OC
50.03
54.66
58.93
62.51
65.23
68.03
70.00
70.87
78.75
78.07
79.32
84.62
85.05
87.11
90.80
94.17
94.81
95.38
100.00
.-Oijgtifc % Cycloiiexane
Refractive Index
ICC. C
1.4262
1,4221
1.4200
1.4172
1.-1145
I *4142
1.4095
1.4067
1.4030
1.3992
1.3976
1,3952
1.3938
1,3922
1.3906
1.3085
1.3875
1.3848
1.3816
1.3794
1.3776
1.3752
1.5750
1.3742
1.3693
1.3692
1.3690
1.3660
1.3656
1.5644
1.5626
1.3611
1.3609
1.3607
1.3587
95.00
91.75
88.46
85.26
84.61
78.72
75.00
70.00
65.00
62.04
60.00
58.00
55.00
53.54
50.00
49.17
45.34
41.07
37.49
34.77
31.97
30.00
29.13
21.25
21.13
20.68
15.38
14,95
.12.09
9.20
5.83
5.19
4.62
0.00
18
TABLij III
Refractive Index at 20°G. in the Binary Byatem
Bensene-Cyclohexane
tit /o Benzene
0.00
5.90
9.34
10.19
10.38
10. Gl
15.37
14.30
14.31
10.12
20.35
23.04
27.83
32.06
30.20
40.68
44.96
40,59
52.90
57.59
61.28
65.62
67.71
69*33
72.82
78.39
80.99
84.15
86.29
87.07
88.27
91.46
95.56
100,00
..eight
Cyclohexane
100,00
94.10
90.16
89.81
89.62 ^
89.39/T
86.13
85.70
85.19
00.88
79.65
76.36
72.17
57.94
65.80
59.32
55.04
51.41
47.10
42.41
58.72
54.38
52.29
50.67
27.18
21.61
19.01
15,85
13.71
12.93
11.73
8.54/
4.44/
0.00
Refractive Index
1.4262
1.4292
1.4311
1.4315
1.4312
1.4316
1.4334
1.4356
1.4338
1.4366
1.4370
1.4395
1.4420
1,4448
1.4475
1.4510
1.4539
1.4567
1.4591
1.4630
1,4661
1.4698
1.4710
1.4730
1.4754
1.4800
1.4827
1.4854
1.4874
1.4881
1.4894
1.4922
1.4963
1.5008
vf)
TABLE 17
Analysis
and Equilibrium Bata In the Blnar y System Acetone -Benzene
Refractive Index. 20°C.
Liquid
Vapor
1.4962
1.4918
1.4862
1.4750
1.4733
1.4556
1.4506
1.4340
1,4263
1.3988
1.3797
1.3666
1.3623
1.4861
1.4747
1.4622
1.4433
1.4448
1.4237
1.4194
1.4067
1.4023
1.3846
1.3730
1.3645
1.3614
!dole f Acetone
Liquid
Vapor
4.0
7.9
13.8
22.0
23.2
36.6
40.4
52.2
57.5
75.3
87.2
95.1
97.7
12.9
22.2
31.8
45.8
45.3
59.1
62.0
70.1
73.2
84.4
92.0
96.6
98.6
Boiling Boint. °C.
Observed Corrected
77.2
74.9
72.0
68.6
68.5
65.0
64.5
62.1
61.6
59.2
57.8
57.2
56.9
77.3
74.8
72.2
68.6
68.5
65.0
64.3
62.3
61.5
59.2
57.7
56.7
56.4
Activity Coefficient
Acetone Benzene
1.657
1.555
1.487
1.390
1.304
1.215
1.179
1.098
1.070
1.020
1.007
1.003
1.004
0.994
0.998
1,005
1.006
1.037
1.057
1.071
1.122
1.164
1.264
1.423
1.512
1.341
TABLS V
Analysis and Equilibfriuxa Data in the Binary System Acetone-Cyclohexane
Refractive Index.zoC.
Liquid
Vapor
1.4256
1.4255
1.4253
1.4349
1.4237
1.4304
1.4152
1.4074
1.3973
1.3696
1.3871
1.3792
1.3748
1.3638
1.3673
1.3668
1.3658
1.3617
1.3611
1.3605
1.3603
1.3592
1.4237
1.4233
1.4202
1.4155
1.4063
1.5961
1.5895
1.3347
1.3822
1.3804
1.3799
1.3774
1.5755
1.3725
1.3710
1.5704
1.3692
1.5641
1.3631
1.3621
1.3613
1.3596
%
Acetone
Mole
Liquid
Vapor
1.0
1.1
1.4
2.3
4.4
10.2
19.0
31.2
46.4
57.3
60.6
71.3
76.8
83.7
87.0
87.6
89.2
95.2
96.2
97.0
98.8
99.3
4.4
5.0
10.5
18.3
33.0
48.2
57.4
64.0
67.5
69.5
70.2
73.4
75.8
79.8
81.9
82.7
84.3
91.6
93.1
94.5
97.8
98.6
BoiliiUs Point. °C.
Observed Corrected
78.2
78.1
76.9
74.4
69.2
62.2
58.9
56.0
54.7
54,2
54.0
54.4
53.7
55,9
53.8
54.0
54.2
55.1
55.3
55.4
56.0
56.2
77.7
77.4
76.7
74.4
69.2
62.2
58.3
56.0
54.7
54.2
54.0
53.8
53.8
53.9
54.1
54.2
54.3
55.0
55.3
55.4
55.8
55.9
Activity Coefficients
Acetone Cycloheiene
2.230
2.318
3.918
4.447
5.106
3.883
2.828
2.077
1.551
1.301
1.249
1.118
1.073
1.033
1.014
1.015
1.012
1.003
1.001
1.001
1.003
1.005
1.061
1.066
1.028
1.019
1.007
1.046
1.084
1.174
1.431
1.707
1.819
2.244
2.526
2.992
3.339
3.336
3.463
4.044
4.170
4.180
4.112
4.482
T-JJLi VI
Analysis and Equilibrium
RefraetiTe Index. 20°C.
Liquid
Vapor
1.4277
1.4290
1.4296
1.4315
1.4314
1.4329
1.4358
1.4389
1.4392
1.4477
1.4505
1.4551
1.4612
1.4702
1.4797
1.4832
1.4974
1.4985
1.4997
1.4286
1.4301
1.4307
1.4327
1.4328
1.4347
1.4379
1.4412
1.4414
1.4492
1.4515
1.4554
1.4603
1,4678
1.4763
1.4847
1.4959
1.4975
1.4990
Data in the Binary System Benzene -Cyclohexane
t
Hole
Benzene
Liquid
Vapor
3.5
6.1
7.2
10,5
10.7
13.8
19.1
24.3
34.7
37.6
41.7
48.3
57.0
68.4
79.2
88.1
97.0
98.1
99.0
5.2
8.2
9.5
13.5
13.7
17,0
22.7
28.0
28.5
40.0
43.4
48.9
55.8
65.4
75.3
84.5
95.6
97.0
98.4
Boiling Point, 0C.
Obeerred Corrected
80.0
79.8
79.8
79.4
79.2
78.9
78.6
77.6
78.0
77.3
77.1
77.1
77.0
77,1
77.5
78.2
79.1
79.3
79.4
80.2
79.9
79.7
79.3
79.3
79.0
78.5
78.0
78.0
77.3
77.1
77.0
77.0
77.1
77.5
78.2
79.1
79.3
79.5
Activity Coefficient
Benzene Cyclohexane
1.481
1.351
1.335
1.317
1.311
1.272
1.248
1.229
1.230
1.160
1.144
1.115
1.079
1.409
1.031
1.016
1.016
1.013
1.011
1.001
1.003
1.008
1.031
1.011
1.015
1,035
1.035
1.035
1.070
1.087
1.110
1.155
1.225
1.312
1.410
1.542
1,651
1.661
TABLE VII
Refractive Index at 20°C. in the Ternary System Acetone-Benzene-Cyclohexane
Weight /a Acetone
10
30
20
Wt*
Benzene
in Hydrocarbons
Refractive
Index
Yft•
Benzene
in Hydrocarbons
Refractive
Index
Wt. %, Benzene
in Hydrocarbons
Refractive
Index
5.56
11.11
16.67
22.22
27.78
33.33
38.89
44.44
50.00
55.56
61.11
66.67
72.22
77.78
83.73
88.89
94.44
1.4219
1.4243
1.4276
1.4294
1.4336
1.4366
1.4404
1.4442
1.4474
1.4513
1.4558
1.4592
1.4617
1.4677
1.4719
1.4768
1.4806
6.25
12.50
18.75
25.00
31.25
37.50
43.75
50.00
56.25
62.50
68.75
75.00
81.25
87.50
93.75
1.4137
1.4166
1.4201
1.4233
1.4265»
1.4304
1.4330
1.4370
1.4404
1.4445
1.4484
1.4532
1.4575
1.4612
1.4659
7.15
14.29
21.43
28.57
35.71
42.86
50.00
57.14
64.29
71.43
78.57
85.71
92.85
1.4063
1.4092
1.412&
1.4159
1.4197
1.4229
1.4267
1.4298
1.4340
1.4381
1.4420
1.4462
1.4511
*
TABLE V H
Weight
(Contd.)
i»Acetone
60
50
40
Wt.
Benzene
In Hydrocarb oos
Itofraetive
Index
Wt. 5», Benzene
in Hyorooarbona
Refractive
Index
Wt.
Benzene
in Hydrocarbons
Refractive
Index
8.33
16.67
25.00
33.33
41,67
50,00
58.33
66.67
75.00
63.33
91.67
1.3980
1.4019
1.4051
1.4033
1,4123
1.4159
1.4197
1.4237
1.4278
1.4320
1.4362
10.00
20.00
30.00
40.00
50.00
60.00
70.00
80.00
90.00
1.3914
1.3945
1.3982
1.4020
1.4056
1.4094
1.4033
1.4174
1.4219
6. S
12.50
25.00
37.50
50.00
62.50
75.00
87.50
93.75
I.3830
1.3847
1.3884
1.3919
1.3957
1.3996
1.4035
1.4079
1.4096
TABLE VII
(Conta.)
% ifeiit $ Aeetone
70
80
90
Itefractiva
Index
Mt.
Benaene
in Hydrocarbons
Refractive
Index
Wfc. >>, Benzem
in Hydrocarbons
Refractive
Index
6.33
16.67
1.3764
1.3705
1.3808
1.3821
1.3861
1.3897
1.3917
1.3939
1.3953
6.25
12.50
35.00
37.50
50.00
62.50
75.00
87.50
93.75
1.3700
1.3708
1.3710
1.3745
1.3764
1.3784
1.3306
1.3323
1.3831
6.25
12.50
25.00
37.50
50.00
62.50
75.00
87.50
93.75
1.3641
1.3644
1.3654
1.3663
1.3673
1.3683
1.3695
1.3699
1.3708
8 8 8 3 8 8 8
Wt.
Bensaene
in Hyilrooorbona
TAHLS V i n
Analysis and SquilIbrium Data in the Ternary System Acetone-Benzene-Oyolohexane
n?
Weight Bari Gent Composition
Liquid
Vapor
Acetone Benzene Cyclohexane
Aoetone Benzene Cyclohexane
Ternary System
Liquid Vapor
Hydrocarbons
Liquid Vapor
1.4751 1.4636
1.4871 1.4770
1.4515 1.4365
1.4647 1.4522
1.4758 1.4593
1.4361 1.4250
1.4640 1.4459
1.4473 1.4322
1.4424 1.4276
1.4771
1.4896
1.4537
1.4677
1.4797
1.4381
1.4678
1.4506
1.4453
1.4727
1.4860
1.4533
1.4646
1.4741
1,4395
1.4649
1.4506
1.4464
1.7
1.8
2.5
2.9
3.2
3.3
3.5
3.6
3.6
73.5
87.1
43.8
61.6
75.3
20.8
61.3
39.0
31.6
24.8
11.1
53.7
35.5
21.5
75.9
35.2
57.4
64,8
8.0
6.9
17.3
12.3
12.2
17.3
17.3
19.5
20.8
64.0
79.0
36.6
52.1
62.6
19.4
49.5
32.6
27.2
28.0
14.1
46.1
35.6
25.2
63.3
33.2
47.9
52.0
1.4376 1.4216
1.4710 1.4512
1.4851 1.4664
1.4371 1.4213
1.4370 1.4184
1.4813 1.4619
1.4385 1.4149
1.4283 1.4091
1.4444 1.4252
1.4838 1.4601
1.4665 1.4454
1.4637 1.4404
1.4432 1.4210
1.4827 1.4615
1.4521 1.4303
1.4602 1.4384
1.4418
1.4771
1.4936
1.4418
1.4417
1.4887
1.4376
1.4325
1.4499
1.4926
1.4738
1.4712
1.4501
1.4926
1.4597
1.4684
1.4434
1.4733
1.4889
1.4434
1.4423
1.4841
1.4383
1.4331
I.4490
1.4885
1.4686
1.4660
1.4490
1.4890
1.4561
1.4634
5.1
5.2
5.4
5.6
5.6
5.6
5.9
6.0
6.1
6.3
6.4
6.9
6.9
7.0
7.3
7.6
26.1
70.9
87.0
24.0
25.8
82.9
19.2
11.8
37.1
86.3
66.4
63.0
37.0
85.6
49.1
59.4
68.8
23.9
7.6
70.4
68.6
11.5
74.9
82.2
56.8
7.4
27.2
30.1
56.1
29.0
17.8
16.5
26.0
27.2
16.9
27.8
29.8
25.1
20.8
20.0
22.7
30.3
20.2
56.7
73.5
21.6
20.5
68.7
15.8
9.1
28.6
69.4
51.6
47.3
26.6
50.8
25.5
10.0
52.4
52.3
14.4
56.4
61.1
46.3
9.8
28.4
30.0
43.1
7.4
43.6
33.0
20.0
25,3
22.8
70.6
36.0
44.8
9.4
38.7
32.4
a
Acetone
Plotted
CO
Oi
TABIE V U I
(Coatd4)
Weight Ber Cent Composition
Liquid
Vapor
Acetone Benaene Cyclohexane
Acetone Benaene Cyclohexane
a2;
Ternary System
Liquid
Vapor
Hydrocarbons
Liquid Vapor
1.4521
1.4406
1.4682
1.4744
1.4454
1.4446
1.4297
1.4461
1.4599
1.4777
1.4298
1.4191
1.4431
1.4496
1.4213
1.4231
1.4053
1.4232
1.4333
1.4489
1.4605
1.4481
1.4787
1.4858
1.4537
1.4532
1.4371
1.4559
1.4715
1.4924
1.4566
1.4469
1.4738
1.4804
1.4512
1.4506
1.4371
1.4527
1.4651
1.4866
8.1
8.5
8.6
8.7
8.8
9.2
9.4
10.0
10.3
10.6
49.6
33.8
70.1
77.3
40,9
40.1
18.1
43.1
61.2
81.9
42.3
57.7
31.3
14.0
50,3
50.7
78.5
46.9
38.5
7.5
36.1
29.7
25.2
24.1
30.4
89.3
37.7
29.6
28.0
28.0
36.1
24.7
53.0
59.6
28.7
28.7
12.5
30.6
43.2
61,6
37.8
45.6
21.8
16.3
40.9
42.0
49.8
39.8
28.8
10.4
1.4593
1.4571
1.4271
1.4554
1.4620
1.4490
1.4679
1.4533
1.4570
1.4135
1.4383
1.4011
1.4279
1.4338
1.4302
1.4384
1.4230
1.4270
1.4501
1.4714
1.4374
1.4681
1.4795
1.4639
1.4860
1.4079
1.4750
1.4470
1.4638
1.4364
1.4624
1.4711
1.4572
1.4789
1.4610
1.4660
11.8
13.4
13.6
13.1
13.4
13.4
13.6
13.9
14.3
35.9
59.6
17.6
55.5
67.1
50.7
73.4
54.8
62.0
52.3
28.0
69.8
31.4
19.5
35,9
13.0
31.3
23.7
35.9
31.9
42.0
31.5
32.4
35.5
32.8
35,6
34.6
22.6
39.8
10.8
38.7
45.8
32.1
52,8
35.8
40.5
41.5
28.3
47.2
29.8
21.8
32.4
15.0
28.6
24.9
1.4455
1.4690
1.4505
1.4564
1.4161
1.4353
1.4188
1.4254
1.4635
1.4932
1.4723
1.4811
1.4562
1.4874
1.4620
1.4722
16.4
17.1
18.4
IS. I
48.5
76.7
56.5
64.2
35.1
6.2
25.1
16.7
38.9
30.5
39.6
39.2
29.5
5 3.1
33.8
42.0
31.6
8.4
26.6
18.3
Wt. %
Aoetcme
Plotted
9.2
13.2
-
V.
17.7
TABIS Vin
nl0
Ternary System
Liquid
Vapor
Ho0
Hydrocarbons
Liquid Vapor
1.4183 1.3952
1.4448 1.4132
1.4398 1.4100
1.4561 1.4222
1.4408 1.4110
1.4298 1.4042
1.4870 1.4012
1*4462 1.4153
1.4391
1.4750
1.4691
1.4930
1.4737
1.4572
1.4542
1.4017
(Contd.)
Vieisht Per Cent Composition
Liquid
Vapor
Acetosis Benzene Jyclobexane
Aeetona Benzene Cyclohexane
wt. #
Acetone
Plotted
1.4362
1.4516
1.4538
1.-1357
1.4592
1.4494
1.4471
1.4702
24.6
34.7
25.2
26.1
26.4
26.8
27.0
27.3
17,5
54.5
48.7
63.3
51,5
36.4
33.2
58.2
57.9
20.8
26.1
5.6
22.3
36.8
39.8
14.5
49.1
44.8
46.4
47.7
45.7
47.5
49.2
40.6
9.3
SC.6
27. S
44.2
28.4
20.4
18 .0
35.5
41.6
24.6
25.8
8.1
25.9
32.1
32.8
17.9
25.0
1.4401
1.4357
1.4374
1.4102
1.3994
1.4069
1.4745 1.4634
1.4563 1.4460
1.4739 1.4591
28.1
29.6
29.3
51,6
34.0
49.8
20.3
36.4
20.4
48.4
50.4
49.5
89.9
16.8
86,4
21.7
32.8
24.1
29.1
1.4490
1.4399
1.4 330
1.4363
1.4152
1.4104
1.3977
1.4058
1.4932
1.4801
1.4564
1.4762
1.4864
1.4699
1.4465
1.4631
30.7
31.4
32.0
38.1
63.4
53.7
38.9
50.1
5.9
14,9
35.1
17.8
52.4
51.1
52.7
52.5
39.8
32.3
16.4
27.3
6.8
16.6
30.9
20.1
31.6
1.4330 1.4031
1.4099 1.3911
1.4305 1.3975
1.4371 1.4004
1.4291 1.4021
1.4176 1.3957
1.4361 1.4079
1.4306 1.4017
1.4417 1.4107
1.4077 1.3888
1.4188 1.3952
1.4743
1.4396
1.4563
1.4669
1.4701
1.4521
1.4833
1.4753
1.4937
1,4396
1,4581
1.4584
1.4346
1.4422
1.4532
1.4566
1.4445
1.4727
1.4583
1.4878
1.4346
1.4417
33.8
34.5
34.7
34.8
34.8
35.0
35.9
36.3
36.7
37.1
37.5
47.4
15.7
31.6
40.6
43.3
27.8
52.5
46.3
58.8
15.1
31.8
18.8
49.8
33.7
24.6
21.9
37.2
11.6
17.4
4.5
47.8
30.7
52.9
53,0
54.5
53.5
53.1
58.5
54.5
54.3
57.5
56.0
52.8
24.1
7.3
12.8
20.7
22.9
13.1
31.6
23.4
36.9
6.9
12.9
23.0
29.7
52.7
26.0
24.0
28.4
15.9
22.3
5,6
37.1
34.3
35.6
TABIiS V I U
(Oontd,)
Weight Bar Oent Composition
Liquid
Vapor
,icetolio Benzene Oyclobexam
Acetone Benzene Cyclohexane
<
Ternary Syatem
Liquid Vapor
nr
Hydrocarbons
Liquid Vapor
1.4362
1.4136
1.4151
1.4255
1,4066
1.3935
1.3937
1,3996
1.4901
1.4539
1.4576
1.4765
1.4798
1.4437
1,4442
1.4614
59.1
40.0
40.3
41.3
54.4
27,1
29. 8
43.6
6.5
32.9
29.4
15.1
1.4240
1.4371
1.4189
1.4054
1.4153
1.4010
1.3995
1.4008
1.3943
1.3873
1.3939
1.3864
1.4781
1.4842
1.4698
1.4470
1.4673
1.4409
1.4636
1.4704
1.4532
1.4331
1.4507
1.4346
43.2
43.4
43.3
44.2
45.5
45.5
43,2
46.9
37.1
19.7
34.3
14.3
13.6
9.7
19.1
36.1
20.3
40,3
1.4151
1.4076
1.3967
1.4346
1.4034
1.3952
1.3943
1.3898
1,3846
1,3986
1.3884
1.3841
1.4705
1.4563
1.4393
1.4948
1.4523
1.4399
1.4532
1.4455
1.4343
1,4890
1.4429
1*4338
47.3
47.7
49.4
49.4
49.6
51.4
35.3
25.3
11.8
47.7
31.7
11.8
1.4101
1.4048
1.3931
1.3920
1.3904
1.3886
1.3832
1.3886
1.4759
1.4683
1.1417
1.4405
1.4576
1.4520
1.4331
1.4838
53.8
54,1
55.0
55.7
1,3943 1.3838
1.4009 .1.3855
1.4542 1.4410
1.4750 1.4548
1.3844
1.3847
1.3901
1.4377 1.4332
1.4396 1.4322
1.4552 1.4420
1.3796
1.3792
1.3812
53.3
55.9
55.9 ‘
57.9
32.5
13.4
13.7
23.3
9.2
30.7
30.4
18*8
53.7
60,0
. 69,0
59.5
53.8
59.0
24.0
26,6
18.8
6.7
16.8
6.4
17.3
13.4
21.3
31.8
24.4
34,6
17.4
27.0
38.8
2.9
28.7
36.8
59.7
61.1
61.1
67,4
61,3
61.7
17.8
12.9
5.3
28.7
11.3
5.4
22.5
26.0
33.1
5.9
27.4
32.9
33.9
29,4
13.2
11.3
12.3
16.5
32,8
33.0
65,5
65.0
62.2
63.5
17.4
14.9
4.9
5.2
17.1
20.1
32.9
31.3
60.0
61.6
18.3
27.8
21.7
10.6
66.0
69.6
8.9
14.1
25.1
16.3
63,5
64.1
64.8
7.7
8.5
16.5
28.8
27,4
18.7
67.2
67.3
69.5
4.3
3.7
8,5
28.5
29.0
22.0
Wt. *
Acetone
Plotted
40.3
44.3
49.1
54.7
60.8
64.1
TABUS VIII
n2,,0
Ternary System
Liquid
Vapor
no6
Hydrocarbons
Liquid Vapor
height Ber Cent Composition
Liquid
Vapor
Acetone Benaene O y c l o ii e x a n e
Acetone B e m a e n e Cyelobaxane
%
'At.
Acetone
Blotted
68.3
68.8
69,7
70.3
24.6
23.7
9.9
7.4
7.1
7.5
20.4
22,3
75.3
73.2
70.5
70,6
12.9
13.9
4.7
3.4
11.8
12.9
24.8
26.0
1,4816 1.4621
1,4421 1.4324
73.6
75.0
21,1
7,0
5.3
18.0
78.7
75.2
12,0
3.1
9.3
23.7
74.3
1.3736
1.3747
1.4402 1,4332
1.4802 I. 45 99
77.0
78.7
5,8
16.7
17.3
4.6
75.9
82.3
3.1
9.2
21.0
8.5
77.9
1,3728
1,3731
1,3719
1,3716
1.4433 1,4336
1,4443 1.4352
%
80.5
80.6
5.8
6.2
13.7
13.2
78.7
79.6
3.0
3.4
18.3
17.0
80.6
1.3782
1.3707
1.3717
1.3694
1,4830 1.4615
1.4463 1.4355
82.8
84.2
14.0
5.4
3.2
10.4
85.8
02.9
7.9
3.0
6.3
14.1
83.5
1,3680
1.3717
1.3673
1.3676
1.4456 1,4360
1,4832 1.4622
•%-
87.5
83.5
4.2
9.4
6.3
2.1
86;2
90.4
2.5
5.4
11,3
4.2
88.0
1.3644
1,3639
1.4467 1.4343
92.4
2.6
5.0
91.0
1.4
7.6
92.4
I.3935
1.3970
1.3838
1.3798
1.3812
1,3832
1,3779
1,3768
1,4795
1,4782
1.4452
1.4402
1.3890
3.s3?69
1.3787
1.3750
1.3749
1,3826
1.4593
1.4588
1.43T47
I. 43,24
(Ccntd.)
-1
69.3
REFRACTIVE
IM O EX ^o
1.51
WEIGHT PER
Figure I.
CENT
Refractive Index at 20°G. in the Binary Systems.
mole
per
cent
in v a p o r
IOO
mole
Figure 2.
per
cent
in
liquid
Vapor-Liquid Equilibrium Diagrams of the Binary Systems.
BOILING POINT
BENZENE-CYCLOHEXANE
ACETONE-CYCLOHEXANE
MOLE PER CENT
Figure 3.
Boiling points in the Binary Systems.
•24
MOLE PER CENT
Figure 4.
ACETONE
Activity Coefficients in the Acetone-Benzene System.
.8
MOLE PER
Figure 5.
CENT ACETONE
Activity Coefficients inthe Acetone-Cyclohexane System.
24
MOLE PER CENT BENZENE
Figure 6.
Activity Coefficients in the Benzene-Cyclohexane System.
REFRACTIVE INDEX, 2 0 ° C.
90 %
100 %
WEIGHT PER CENT BENZENE IN HYDROCARBONS
Figure 7.
Refractive Index at 20°C. in the Ternary System Acetone-Benzene-Cyclohexane at Constant
Weight Per Cent Acetone.
LU50
END POINTS OF EACH LINE TAKEN
FROM ACETONE-BENZENE CURVE-
WEIGHT % BENZENE IN LIQUID
Figure 8.
Benzene Equilibria in the Ternary System Acetone-Benzene-Cyclohexane at Constant Weight
Per Cent Acetone in the Liquid.
100
END POINTS OF EACH LINE TAKEN FROM
ACETONE- CYCLOHEXANE
,v
30
40
50
60
70
CURVE.
80
90
WEIGHT % CYCLOHEXANE IN LIQUID
Figure 9.
Cyclohexane Equilibria in the Ternary System Acetone-Benzene-Cyclohexane at Constant
Weight Per Cent Acetone in the Liquid.
39
CYCLOHEXANE
pigure 10.
Vapor-Liquid Equilibria
in the Ternary System Acetone-BenzeneCyclohexane .
phase lines are constant
weight per cent benzene in vapor.
3 0 --
ACETONE
ENZENE
UO
CYCLOHEXANE
Figure 11.
Vapor-Liquid Equilibria in
the Ternary System Acetone-BenzeneCyclohexane.
phase lines are constant
weight per cent cyclohexane in vapor.
— -30
acetone
BENZENE
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