Fluid Phase Equilibria, 81 (1992) 261-212 261

Elsevier Science Publishers B.V., Amsterdam

Vapour-liquid equilibria. VI. The ternary system

acetone - hexane -cyclohexane at 313.15 K

M. G&-al, P. Oracz and S. Warycha

Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw (Poland)
(Received October 8, 1991; accepted in final form May 18, 1992)

ABSTRACT

G&al, M., Oracz, P. and Warycha, S., 1992. Vapour-liquid equilibria. VI. The ternary
system acetone-hexane-cyclohexane at 313.15 K. Fluid Phase Equilibria, 81: 261-272.

Total vapour pressure measurements made by the modified static method for the ternary
system acetone-hexane-cyclohexane and two constituent binaries (acetone-cyclohexane
and hexane-cyclohexane) at 313.15 K are presented. The different expressions for GE
suitable for the correlation .of these data are tested, the system acetone-hexane, published
previously, is also discussed again from the point of view of the present ternary system. The
prediction of ternary ,vapour-liquid equilibria from constituent binaries is studied. Our
results are compared with literature data.

INTRODUCTION

The acetone-hexane-cyclohexane system is the next to be investigated

within our project on measurements, correlation and prediction of the
ternary vapour-liquid equilibrium of non-electrolytes. The shapes of the
(GE, X) curves for both binary systems containing acetone are nearly the
same as are the shapes of the molar enthalpy of mixing (HE) curves. The
hexane-cyclohexane system is nearly ideal with endothermic and symmetric
HE.
In this paper we report the results of total vapour pressure measurements
at 313.15 K.

MATERIALS

The chemicals used were of the highest purity available from the suppli-
ers. Acetone (analytical reagent grade, POCh) was purified as a sodium

Correspondence to: S. Warycha, Department of Chemistry, Warsaw University, Pasteura 1,

02-093 Warsaw, Poland.

037%3812/92/$05.00 0 1992 - Elsevier Science Publishers B.V. All rights reserved

262 M. G&al et al. / Fluid Phase Equilibria 81 (1992) 261-272

TABLE 1
Vapour pressures, P, and second virial coefficients, fi,,, of pure substances at 313.15 K

Compound P(313.15 K) (kPa) - /?,(313.15 K)

This work Literature (dm’ mol - I) a

Acetone 56.603 56.617 + 0.012 b 1.612

56.594 + 0.023 b
56.583 ’
Hexane 37.270 37.255 + 0.008 b 1.664
37.260 c
Cyclohexane 24.625 24.623 + 0.037 b 1.659

a Calculated according to Tsonopoulos (1974).

b Calculated according to Boublik et al. (1973).
c Calculated according to Dykyj and Repas (1979) and Dykyj et al. (1984). (Note: molar
liquid volumes were calculated according to Yen and Woods ( 1966))

iodide addition compound in accordance with the recommendations of

Vogel (1961). The product obtained was then rectified on an efficient
column and dried with 3A molecular sieves. It is very important to use
neither basic nor acidic dehydrated reagents owing to formation of the enol
form of acetone. Hexane and cyclohexane (both analytical reagent grade,
POCh) were recrystallized three times, fractionated on an efficient column
having 80 theoretical plates, and stored over 4A molecular sieves.
Impurities were determined chromatographically. The water content was
checked using Fischer’s reagent and was on the limit of detectability. All the
materials had a purity of not less than 99.95%. Table 1 gives the vapour
pressures of the pure substances, measured both here and by other authors,
and the second virial coefficients.

METHOD

The vapour pressures of the mixtures were determined by a modified

static method. The apparatus and experimental procedure have been de-
scribed previously (Janaszewski et al., 1982). During our measurements the
temperature was constant to within 0.004 K and was controlled up to
0.001 K; the absolute deviation is estimated to be equal to +0.03 K
(ITS-go). The cathetometer readings contribute less than 0.004 kPa to the
error of a single pressure measurement. This is a major part of the error in
pressure if errors in both temperature and pressure are treated separately.
The binary samples, about 2.5 cm3 in volume, were prepared by weighing.
The errors in the mole fractions were less than 0.0005. The ternary samples
were prepared from mixtures of hexane and cyclohexane, to which acetone
M. G6ral et al. / Fluid Phase Equilibria 81 (1992) 261-272 263

was added. The mole fractions in the vapour phase were not determined
analytically.

RESULTS AND DISCUSSION

The results of the total vapour pressure measurements are given in Table
2 for binary mixtures and in Table 3 for ternary mixtures.
The binary systems were correlated by various equations such as Redlich
and Kister (1948), Van Laar extended by Van Ness (1964), Myers and Scott
(1963), Marsh (1977), SSF (Rogalski and Malanowski, 1977), Wilson
( 1964), NRTL (Renon and Prausnitz, 1968) and UNIQUAC (Anderson
and Prausnitz, 1978) and the pseudo-volume-fraction Redlich- Kister (as

TABLE 2
Liquid mole fractions, x,, calculated vapour mole fractions, y,, total vapour pressures, P,
and deviations, dP, at 313.15 K

XC3 Ya Xii Y:
&Pa) &a) $Pa)

Acetone(a) + cyclohexane( b)
0.0000 0.0000 24.625 0.1477 0.5628 51.086 - 0.008
0.0060 0.0844 26.760 -0.012 0.1553 0.5694 51.686 0.012
0.0091 0.1209 27.792 - 0.026 0.1649 0.5771 52.353 -0.002
0.0131 0.1625 29.076 -0.033 0.2908 0.6376 57.755 -0.117
0.0187 0.2122 30.741 -0.071 0.2992 0.6402 58.030 - 0.068
0.028 1 0.2789 33.378 - 0.043 0.4224 0.6703 60.555 0.073
0.0362 0.3242 35.453 0.006 0.4819 0.6825 61.299 0.041
0.0464 0.3700 37.751 0.009 0.5222 0.6907 61.755 0.055
0.0566 0.4068 39.802 0.012 0.5823 0.7035 62.321 0.069
0.0665 0.4360 41.591 0.020 0.6235 0.7131 62.639 0.077
0.0779 0.4639 43.415 0.011 0.7434 0.7485 63.099 0.046
0.0881 0.4849 44.894 0.022 0.7589 0.7545 63.103 0.049
0.1001 0.5057 46.436 0.017 0.8179 0.7827 62.853 0.021
0.1134 0.5251 47.929 -0.008 0.8641 0.8131 62.232 -0.060
0.1264 0.5412 49.229 - 0.020 0.9277 0.8757 60.456 -0.188
0.1389 0.5545 50.357 -0.017 1.0000 1.OOOo 56.603

Cyclohexane( a) + hexane( b)
0.0000 0.0000 37.270 0.5026 0.4030 31.671 -0.003
0.0900 0.0666 36.324 -0.012 0.5946 0.4903 30.496 -0.024
0.2133 0.1606 35.033 0.019 0.7043 0.6042 29.088 0.018
0.3051 0.2335 33.982 -0.012 0.7933 0.7070 27.839 0.014
0.4068 0.3182 32.817 - 0.006 0.8756 0.8129 26.618 0.010
1Mm0 1.OOOo 24.625

a dP = P-P+
b ya calculated using eqn. (1).
264 hf. Gdral et al. 1 Fluid Phase Equilibria 81 (1992) 261-272

TABLE 3
Ternary system acetone(a) f hexane( b) + cyclohexane(c) at 3 13.15 K: experimental liquid
mole fractions x,, xs and total pressure P; vapour mole fractions y,, yt, and deviations dP
( = P - P,,,) calculated using eqn. (3) and having one ternary parameter fitted to the data

XFt xb Y, Yb
&a)

0.0866 0.1012 0.4612 0.0888 46.088 0.211

0.1572 0.0934 0.5531 0.0727 52.939 - 0.068
0.2457 0.0836 0.6056 0.0635 57.496 - 0.080
0.3211 0.0752 0.6317 0.0590 59.810 0.046
0.4248 0.0637 0.6576 0.0548 61.760 0.121
0.1699 0.1688 0.5486 0.1272 54.777 WI47
0.2536 0.1517 0.5963 0.1129 58.603 -0.159
0.5011 0.1014 0.6648 0.0936 63.563 0.010
0.5801 0.0854 0.6824 0.0893 64.293 0.044
0.6684 0.0674 0.7046 0.0840 64.762 0.032
0.0879 0.2522 0.4350 0.2092 47.832 0.189
0.1665 0.2305 0.5353 0.1709 55.238 0.049
0.3346 0.1840 0.6162 0.1400 61.660 - 0.096
0.4176 0.1610 0.6368 0.1318 63.251 -0.012
0.0941 0.3249 0.4349 0.2594 49.380 0.131
0.2519 0.2683 0.5767 0.1927 60.176 - 0.037
0.3379 0.2374 0.6085 0.1779 62.613 -0.031
0.5028 0.1783 0.6508 0.1590 65.112 -0.011
0.6042 0.1419 0.6746 0.1488 65.905 0.006
0.7540 0.0882 0.7202 0.1298 66.108 - 0.008
0.0829 0.3953 0.4035 0.3174 48.487 -0.004
0.1580 0.3629 0.5081 0.2609 56.130 0.062
0.2500 0.3233 ,0.5678 0.2287 60.804 - 0.043
0.4202 0.2499 06244 0.1985 64.798 -9.029
0.1652 0.4209 0.5063 0.2963 57.310 0.025
0.3381 0.3337 0.5943 0.2430 64.032 -0.036
0.4995 0.2524 0.6375 0.2174 66.466 - 0.003
0.6676 0.1676 0.6798 0.1930 67.424 0.020
0.8342 0.0836 0.7505 0.1522 66.280 - 0.054
0.0931 0.5081 0.4093 0.3851 51.236 0.095
0.1615 0.4698 0.4973 0.3274 57.616 0.034
0.2488 0.4209 0.5543 0.2901 62.044 -0.014
0.4195 0.3253 0.6128 0.2520 66.033 -0.016
0.0996 0.5813 0.4127 0.4261 52.890 +I.085
0.5021 0.3214 0.6266 0.2710 67.894 0.121
0.5827 0.2694 0.6464 0.2569 68.481 0.154
0.7539 0.1589 0.6990 0.2195 68.377 .0.08 1
0.7539 0.1589 0.6990 0.2195 68.364 0.067
0.0956 0.6637 0.3984 0.4800 53.175 - 0.076
0.1546 0.6203 0.4753 0.4187 58.722 -0.119
0.3392 0.4849 0.5749 0.3395 66.226 - 0.052
0.4166 0.428 1 0.5978 0.3213 67.604 - 0.005
0.0985 0.7193 0.3988 0.5101 54.181 - 0.098
M. G&al et al. / Fluid Phase Equilibria 81 (1992) 261-272 265

TABLE 3 (Continued)

xb Yb p dP
@Pa) @Pa)

0.1755 0.6579 0.4886 0.4341 60.805 -0.102

0.2692 0.5831 0.5435 0.3877 64.997 -0.083
0.4974 0.4010 0.6136 0.3283 69.110 0.043
0.5802 0.3350 0.6344 0.3108 69.671 0.082
0.6664 0.2662 0.6580 0.2909 69.870 0.123
0.1061 0.7933 0.4054 0.5453 55.907 -0.202
0.1590 0.7464 0.4684 0.4877 60.368 -0.394
0.2501 0.6656 0.5283 0.4330 65.184 -0.143
0.3321 0.5928 0.5608 0.4032 61.562 -0.013
0.4300 0.5059 0.5896 0.3768 69.233 0.071

suggested by Scatchard and Hamer ( 1935) and Asmanova and G&al

(1980)). Coefficients of these equations were obtained by a modified Bark-
er’s method (Goral, 1977; Gbral and Janaszewski, 1977; Kolasinska and
Oracz, 1979). The values of the second virial coefficients for the pure
substances and for the mixtures were calculated according to Tsonopoulos
( 1974). Table 4 shows the efficiency of these equations applied to our data.
Table 4 also contains the results of calculations for the acetone-hexane
system, which were measured previously by Kolasinska et al. (1982). These
are included for completeness.
The results presented demonstrate that the expressions for GE based on
the local composition concept do not provide a sufficiently accurate descrip-
tion of systems with skewed (GE, x) curves. This conclusion agrees with the
literature and with the results of our previous studies. The near-ideal
system hexane-cyclohexane can be described by any equation with approx-
imately the same accuracy. Therefore, for correlation of our binary mea-
surements, we chose the pseudovolume fraction Redlich-Kister (RK)
equation

GE/RT =vza(l -Z,) ~ Ki(2Z,- l)i (1)

i=O

where
lJ =xaua+(l -X&I, and z, =x,v,/v (la)
In eqn. (la), the pseudovolumes u, and z]bare not the molar liquid volumes
of the corresponding pure components but are adjustable parameters. One
can observe that GE in eqn. (1) depends on the ratio of the u parameters,
and one of them can be arbitrarily set to unity. For other components, the
3 parameters evaluated with trial-and-error methods remained constant and
common for all investigated binary and ternary mixtures. The values of the
266 M. G&al et al. / Fluid Phase Equiiibria 81 (1992) 261-272

TABLE 4
Comparison of the efficiency of different equations for binary systems at 313.15 R (number
of ~rameters n, average standard error of the total vapour pressure a(P)) a

Equation n a(P) Number Calculated azeotropic point

(kPa) of sign
changes b x, P(kPa)

Acetone (a) - hexane (b)

P~udovol~e fraction
Redlich-Kister 3 0.061 13 0.638 71.75
Redlich-Kister 3 0.064 10 0.639 71.75
Van Laar-Van Ness 4 0.063 13 0.636 71.73
Myers-Scott 4 0.065 13 0.639 71.73
Marsh 2+2 0.063 13 0.636 71.73
SSF 4 0.063 13 0.636 71.74
W&on 2 0.119 5 0.635 71.67
NRTL LX= 0.3 2 0.490 2 0.625 71.59
NRTL 3 0.085 13 0.636 71.68
UNIQUAC 2 0.553 2 0.624 71.57

Acetone (a) -cyclohexane (b)

Pseudovolume fraction
Redlich-Kister 3 0.056 6 0.751 63.07
Redlich-Kister 6 0.024 11 0.748 63.08
Van Laar-Van Ness 6 0.024 11 0.748 63.08
Myers-Scott 5 0.029 9 0.748 63.08
Marsh 2+3 0.023 9 0.751 63.08
SSF 6 0.023 9 0.751 63.08
Wilson 2 0.071 6 0.754 63.08
NRTL c1= 0.3 2 0.407 2 0.743 62.66
NRTL 3 0.088 3 0.755 63.09
UNIQUAC 2 0.441 2 0.742 63.61

Cyclohexane (a) - hexane (b)

Pseudovolume fraction
Redlich-Kister 1 0.013 4
Redlich-Kister 2 0.015 3
Van Laar 2 0.015 5
SSF 2 0.015 3
Wilson 2 0.015 5
NRTL a = 0.2 2 0.015 3
UNIQUAC 2 0.015 5

a a(P) = [Z(P,,, - P,kf2&n - n)]112, where m is the nwnber of points.

b When neighbouring points lie on opposite sides of an approximation curve, there is a sign
change in their deviations. The points should be scattered randomly with respect to the
correlating curve. An easy measure of the randomness is the number of sign changes, which
should be roughly equal to m/2 f (m/2)'12.
M. Gdral et al. 1 Fluid Phase Equilibria 81 (1992) 261-272 261

TABLE 5
Parameters KI of eqn. (1) with their standard errors cr&), correlation coefficients qil,
coefficients A,, B, and C, of eqn. (2) and cross second virial coefficients &,. fl,,., flbc at
313.15 K

Acetone(a) + hexane( b)
lJa= 1.00 ub= 1.00 Pab= -0.925 dm3 moi-’
i= 0 2 5
Ki = 1.6438 0.1586 - 0.0472
a&) = 0.0008 0.0034 0.0074
A, = 0.0082 - 0.0054 0.0089
3, = 0.0181 -0.0087 -0.0092
c, = 0.0219 - 0.0061 - 0.0024
pI2= -0.3681
9i5 = -0.3659 0.2244

Acetone (a) + cyclohexane (c)

0, = 1.00 v, = 0.89 Bac = - 0.925 dm3 mol- *
j= 0 2 5
Ki = 1.7807 0.1494 -0.0351
a(&) = 0.001 I 0.0037 0.0059
,A, = -0.0001 - 0.0070 0.0047
B, = 0.0142 -0.0061 -0.0033
ci = 0.0156 - 0.0057 -0.0015
qt2 = -0.7550
6% = -0.5685 0.6195

Cyclohexane (c) + hexane (b)

v, = 0.89 ub= 1.00 ,!& = - 1.661 dm3 mol-’
K, = 0.1056
a(K,) = 0.0007
A, = 0.~
B, = -0.0054
C, = 0.0123

Ki coefficients in eqn. (l), together with their standard errors a(&) and the
correlation coefficients qti for pairs (1y,, IQ, are given in Table 5 for all the
binary systems (including the acetone-hexane system). The qfl values
together with the standard errors o(Ki) allow, if necessary, the estimation of
standard errors of all values which depend on K.
The coefficients Ai, Bi and Ci given in Table 5 may be used in the
equation
G - K = 4@B, - Paa) + 4 t&7 - P&J + Ci W’ - WI (2)
to show how the parameter Ki would change if the second virial coefficients
/&a, pbb and @ = 28ab - Paa - bbb used in this study were replaced by
another set of values j3&, &-, and a/?‘. Equation (2) clearly shows the
influence of the second virial coe~cients on the Ki values.
268 M. G&al et al. /Fluid Phase Equilibria 81 (1992) 261-272

440 ./

-T--
b ,*’
8 d

,” 400
d
/I’
s
360 n

3.0 32
1000/T

Fig. 1. Acetone + cyclohexane: comparison of equimolar value of Q = GE/RT with literature

data at various temperatures: x , Marinchev et al. (1965); W, Rao et al. (1957); 0, this
work. All literature data were taken from Maczynski et al. (1979).

The binary systems under consideration have been investigated by other

authors, who have measured VLE under isobaric or isothermic conditions,
as well as the molar enthalpy of mixing (HE). Therefore it is possible to
compare, simultaneously, various VLE and HE sets of data. For this
purpose, each VLE data set under comparison may be represented by the
value of GE/RT at, for example, equimolar concentration, henceforth de-
noted &. The Qo.5 values calculated from various data sets were plotted
against l/T. From the Gibbs-Hehnholtz equation, the slope of the resulting
line should be equal to HE,/R. Such plots for the acetone-cyclohexane and
hexane-cyclohexane systems are presented in Figs. 1 and 2. For the
acetone-hexane system, such a plot is presented in the paper of Kolasinska
et al. (1982). The slopes of the unbroken lines in these figures were
calculated using HE data from the literature. In ranges where HE data are
not available, broken lines are used. The HE data are taken from the
compilation by Belousov and Morachevskii (1970). The scattering of the
points in the figures results from experimental errors in the literature data.
The figures clearly show the mutual agreement of some GE data sets as well
as their consistency with HE.
In our opinion, the QO.s versus l/T test shows excellent agreement
between our results and those published in the literature.

w
1000/T

Fig. 2. Hexane + cyclohexane: comparison of equimolar value of Q = GE/RT with literature

data at various temperatures: +, Meixner et al. (1979); n , Ott et al. (1980); x , Gumpert
et al. (1980); 0, Martin et al. (1980); A, Mathot (1950); 0, this work; 0, unpublished data
of authors of this work. All literature data were taken from Maczynski et al. (1991).
M. Gdral et al. 1 Fluid Phase Equilibria 81 (1992) 261-272 269

TABLE 6
Comparison of different equations for the ternary system acetone(a) -hexane( b) -cyclohex-
ane( c) at 3 13.15 K, average standard error of the total vapour pressure a(P) and the relative
standard error of the total vapour pressure o(dP/P)”

Equation Number of parameters c(P) c(dPIP)

Binaryb Ternary &pa) (%)

Eqn. (3) 3/3/l + 2 0 0.218 ; 0.37

Eqn. (3) 3/3/l + 2 1 0.102 0.18
Eqn. (5) /I = 0
(Kohler) 1.352 2.231
Eqn. (5) fi = -0.05 0.993 1.574
0.615 0.957
0.425 0.680
SSF 1.342 2.300
Wilson 1.132 1.773
NRTL 1.160 1.774
UNIQUAC 1.187 1.828

a m =Lwe,, -Pcalc)‘l(m --n)]‘12 (n is the number of parameters, m the number of

points); a(dP/P) = [Z( 1 -PcaIc/Pexp)2/((m --r~)]‘/~.
b This column should be read: number of adjustable parameters for the mixture a + b/ for
the mixture a + cl for the mixture b + c. The parameters are those fitted to the binary data
(see Table 4).

The ternary system was correlated by eqns. (3) -( 6) below, as well as by

commonly used equations (SSF, Wilson, NRTL and UNIQUAC). Equa-
tion (3) is an extension of eqn. (1) to the ternary mixture. The extension
results from an assumption that the ternary mixture can be treated as a
pseudobinary mixture of acetone with a mixture of hexane-cyclohexane,
treated as one component with properties depending on concentration. This
explains why in eqns. (3) and (4), the mole fractions of methanol are treated
asymmetrically with respect to the two other components. Table 6 shows
that eqn. (3) predicts ternary VLE data better than the other equations. The
equation has the form

GE/RT = u Z,Zb C Ki(a, b)( 1 - 2Zb)’ + Z,Z, C Ki(a, C)(2zc - l)i

+ zbz&(b,
1
c) + GE(ter)/RT

where v = &a, + xbz)b-I-x,0,, z, = XiVi/U, subscript a denotes acetone and

(3)

subscripts b and c denote hexane and cyclohexane respectively. The

pseudovolumes u,, vb and u, are adjustable parameters kept constant for all
binary and ternary data, Ki are the corresponding binary parameters and
GE(ter)/RT is a ternary term, assumed to be zero, when eqn. (3) is used for
270 M. Gdral et al. /Fluid Phase Equilibria 81 (1992) 261-272

prediction of ternary VLE from constituent binaries. The ternary contribu-

tion GE(ter) has the form

GE(ter) = z,&,& Cl (4)

Equation (5) is the one discussed previously by Oracz (1987), to which
ternary terms were added. The equation has the form

GEIRT= i i (Xi + xj)2’PGF(xt)/RT + GE(ter)/RT

r=I j-i+1
where XT = xi/& + Xi). Gi is any equation suitable for the correlation of a
binary mixture (i +j). For this reason, eqn. (5) is much more general than
any other proposed in the literature. Parameter /I is adjustable. In this work
we used /.I = -0.05. This value is suitable for systems with medium positive
deviations from Raoult’s law. If /I = 0, then eqn. (5) is equivalent to
Kohler’s equation. For the ternary contribution GE(ter) in eqn. (5), we need
only one adjustable parameter:

GE(ter)/RT = x,&,x,Cr (6)

Table 6 shows the efficiency of various equations applied to the ternary
data.

ACKNOWLEDGEMENT

We appreciate the financial support provided for this work by the Polish
Academy of Sciences within project CPBP 01.16.

LIST OF SYMBOLS

coefficients in eqn. (2)

coefficient in eqns. (4) and (6)
excess Gibbs energy
enthalpy of mixing
Ki parameters in eqn. (1)
P vapour pressure (kPa)
Q value of GE/RT
QOS value of GE/RT at equimolar concentration
4v correlation coefficients between parameter pairs (Ki, K,)
R gas constant
5 overall relative deviation
T temperature (K)
&i, ub, %, v adjustable pseudovolumes in eqns. (l), (3) and (4)
X mole fraction in liquid
M. Gdral et al. 1 Fluid Phase Equilibria 81 (1992) 261-272 271

X* mole fraction in eqn. (5)

Y mole fraction in vapour
Z pseudovolume fraction in liquid

Greek letters

NRTL parameter
exponent in eqn. (5)
second virial coefficients
= 2Pab - /$a - hb
standard error

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