Fluid Phase Equilibria 384 (2014) 89–94

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Fluid Phase Equilibria

j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / fl u i d

Thermodynamic behaviour of second generation biofuels:

Vapour–liquid equilibria and excess enthalpies of the binary
mixtures 2-pentanol and n-heptane or 2,2,4-trimethylpentane
Alejandro Moreau, José J. Segovia, Rosa M. Villamañán, M. Carmen Martín *
Research Group TERMOCAL, Thermodynamics and Calibration, University of Valladolid, Escuela de Ingenierías Industriales, Paseo del Cauce 59,
E-47011 Valladolid, Spain

A R T I C L E I N F O A B S T R A C T

Article history: Accurate experimental data of vapour–liquid equilibria (VLE) and excess enthalpies are reported for the
Received 24 July 2014 binary systems (2-pentanol + 2,2,4-trimethylpentane) and (2-pentanol + n-heptane). An isothermal total
Received in revised form 26 September 2014 pressure cell was used for measuring the VLE at T = 313.15 K. The data were correlated using Margules,
Accepted 8 October 2014
Wilson, NRTL and UNIQUAC equations. The excess enthalpies were measured at two different
Available online 13 October 2014
temperatures T = (298.15 and 313.15) K using an isothermal flow calorimeter and were correlated by the
Redlich–Kister equation. Both binary systems exhibit a positive deviation from the ideality with
Keywords:
azeotropes, and an endothermic behaviour has been observed when the 2-pentanol is mixed with these
VLE
Excess enthalpies
hydrocarbons.
2-Pentanol ã 2014 Elsevier B.V. All rights reserved.
2,2,4-Trimethylpentane
n-Heptane

1. Introduction 2. Experimental

The European target of decrease the dependency on the 2.1. Materials

petroleum is been achieved by the use of biofuels and it also
reduces CO2 emissions and supports the agricultural community.
There is a wide variety of biogenic products that can be added to
fuels and the quality of these products becomes more and more
important, requiring an accurate knowledge of the thermodynamic
properties of the new fuel blends.
The 2-pentanol is considered a compound for the second
generation of biogasolines due to its high octane rating (up to
100 Research Octane Number-RON), better water tolerance and
very high heat of combustion.
Continuing with the study of the behaviour of this component,
the paper reports accurate experimental data of vapour–liquid
equilibria and excess enthalpies of the mixtures (2-pentanol +
2,2,4-trimethylpentane) and (2-pentanol + n-heptane).
In previous papers [1,2], binary mixtures of hydrocarbons with
1-pentanol were measured; this paper will continue the contribu-
tion to a better knowledge of second generation biofuels.
* Corresponding author. Tel.: +34 983 423756.
E-mail addresses: alejandro.moreau@eii.uva.es (A. Moreau),
jose.segovia@eii.uva.es (J.J. Segovia), rvillama@dce.uva.es (R.M. Villamañán),
mcarmen.martin@eii.uva.es (M. C. Martín).
The compounds were purchased from Sigma–Aldrich and were
of the highest purity available, chromatography quality reagents
with a purity >0.99 (GC) for 2-pentanol, >0.995 (GC) for 2,2,4-
trimethylpentane and n-heptane. Their purities were also checked
by gas chromatography and all were found to be >0.997. The details
are summarized in Table 1.
2.2. Experimental techniques
An isothermal total pressure cell has been used for measuring
the vapour–liquid equilibrium of the binary mixtures, and it has
been described in a previous paper [3]. Experimental values were
obtained in two overlapping runs starting from opposite ends of
the composition range. The equilibrium properties measured
directly and their uncertainties are injected volume
0.03 mL,
temperature
10 mK and total pressure
5 Pa. The overall mole
fraction is determined accurately from the volumetric displace-
ment of the injector pistons, the temperature of the injectors and
the densities for the pure components. The estimated uncertainties
for mole fractions are
0.0005.
Excess enthalpies have been measured with a quasi-isothermal
flow calorimeter, developed in our laboratory [4]. It is based on the
accurate measurement of the energy required to maintain the

http://dx.doi.org/10.1016/j.fluid.2014.10.016
0378-3812/ã 2014 Elsevier B.V. All rights reserved.
90 A. Moreau et al. / Fluid Phase Equilibria 384 (2014) 89–94

Table 2
Nomenclature Total pressure VLE data for the binary system 2-pentanol (1) + 2,2,4-trimethylpen-
tane (2) at 313.15 K.a
List of symbols
x1 y1, calc P (kPa) x1 y1, calc P (kPa)
Ai adjustable parameters of Red-
0.0000 0.0000 12.973 0.5008 0.1353 11.787
lich
0.0499 0.0560 13.256 0.5502 0.1436 11.461
Aij, Aji adjustable parameters of the 0.0988 0.0740 13.231 0.5509 0.1438 11.463
VLE correlation models, Eqs. 0.1490 0.0839 13.162 0.6001 0.1533 11.058
(2) 0.1996 0.0917 13.041 0.6007 0.1535 11.085
Bii, Bij, Bjj second virial coefficients 0.2501 0.0991 12.904 0.6508 0.1652 10.636
0.2999 0.1063 12.694 0.7008 0.1797 10.110
C adjustable parameter of Red-
0.3501 0.1134 12.526 0.7512 0.1987 9.449
lich 0.4002 0.1205 12.320 0.8012 0.2248 8.640
GmE excess molar Gibbs energy 0.4006 0.1205 12.288 0.8513 0.2642 7.612
HmE excess molar enthalpy 0.4500 0.1276 12.059 0.9009 0.3314 6.302
0.4506 0.1277 12.054 0.9501 0.4749 4.596
i, j constituent identification 1id=6#or 2
0.5001 0.1352 11.784 1.0000 1.0000 2.305
lit. literature value
a
max maximum value of the indi- Standard uncertainties (k = 1): u(x1) = 0.0005, u(y1, calc) = 0.0005, u(P) = 5 Pa, u
cated quantity (T) = 10 mK.

P total pressure
Pis vapour pressure of pure con-
after the second term. The pure-component and interaction second
stituent i
virial coefficients (Bii, Bij) were calculated by the Hayden and
R universal gas constant
O’Connell method [8] using the parameters given by Dymond and
rms root mean square
Smith [9].
SmE excess molar entropy
VLE data were correlated by the Margules equation up to six
T absolute temperature
parameter [10]:
ViL molar volume of pure liquid
i = 1, 2 GEm h i
x mole fraction, liquid phase ¼ Aji xi þ Aij xj  ðlji xi þ lij xj Þxi xj þ ðhji xi þ hij xj Þx2i x2j xi xj (1)
RT
y mole fraction, vapour phase
also Wilson [11], NRTL [12] and UNIQUAC [13] models were used
Greek letters for the correlation, which expressions are given by Eqs. (2)–(4),
D signifies difference respectively:
aij adjustable parameter in NRTL model, Eq.id=6#(3)  
GEm
lij, lji adjustable parameters in Eq.id=6#(1) ¼  S xi ln S xj Aij (2)
RT
hij, h adjustable parameters in Eq.id=6#(1) i j

!
GEm Sj Aij Gji xj
¼ S xi (3)
mixing vessel at a constant temperature. To achieve this condition, RT i Sk Gki X k
a Peltier cooler removes, at constant rate, energy from the flow cell
and a control-heater compensates this energy and additionally the
energy liberated (exothermic mixing) or absorbed (endothermic        
GEm f z #
mixing) by the mixing process. The properties measured directly ¼ S xi ln i þ S qi xi ln i  S qi xi ln S #j Aji (4)
RT i xi 2 i qi i j
and their corresponding uncertainties are flow rate
0.15%
(10 mL/min); temperature
10 mK; the heating and cooling where, Gji = exp(ajiAji);#i ¼ qi xi = Sj qj xj ; fi ¼ ri xi = Sj rj xj and z = 10.
systems have an stability better than 2.4 mW, and it results in an Tables 2 and 3 give the experimental values of total pressure,
uncertainty of
0.0001 in the composition of the mixture and the the liquid phase composition and the calculated vapour phase
extended relative uncertainty in the excess molar enthalpy is composition by Margules equation for the binary systems (2-
better than
1% for a cover factor of 2 (k = 2) which means a pentanol + 2,2,4-trimethylpentane) and (2-pentanol + n-heptane)
confidence level of 0.95. at T = 313.15 K, respectively, and both sets of data have been
represented in Fig. 1. The average values of the experimental
3. Results vapour pressures (Pis) for the pure compounds and their
comparison with the literature, the molar volumes of pure liquids
The use of a static technique for measuring the equilibrium (ViL) and the second virial coefficients (Bii, Bij) are indicated in
means that the vapour phase need not be sampled for analysis and Table 4. The results of VLE data correlation are summarized in
the data are thermodynamically consistent “per se” [5]. Data Table 5; it contains the values of the adjustable parameters for the
reduction was done by Barker’s method according to well different models, the root mean square of the difference between
established procedures [6,7]. The non-ideality of the vapour phase the experimental and the calculated pressures (rms DP) and the
was taken into account with the virial equation of state, truncated maximum value of this difference (max |DP|).

Table 1
Material description.

Chemical name Source Mass fraction purity Purification method

2-Pentanol Sigma–Aldrich 0.997 None
2,2,4-Trimethylpentane Sigma–Aldrich 0.997 None
Heptane Sigma–Aldrich 0.997 None
 A. Moreau et al. / Fluid Phase Equilibria 384 (2014) 89–94 91

Table 3
Total pressure VLE data for the binary system 2-pentanol (1) + heptane (2) at Table 4
313.15 K.a Average values of the experimental vapour pressures (Pis) for the pure compounds
and literature values (Pis(lit.)), the molar volumes of pure liquids (ViL) and the
x1 y1, calc P (kPa) x1 y1, calc P (kPa) second virial coefficients (Bii,Bij) at T = 313.15 K used for the calculations.
0.0000 0.0000 12.311 0.4991 0.1399 11.291 2-Pentanol 2,2,4-Trimethylpentane n-Heptane
0.0493 0.0593 12.656 0.5491 0.1487 10.959 (i = 1) (i = 2) (i = 3)
0.0991 0.0776 12.656 0.5493 0.1487 10.979
0.1491 0.0870 12.573 0.5991 0.1589 10.602 Pis/(kPa) 2.295a 12.973 12.311
0.1989 0.0946 12.464 0.5994 0.1590 10.615 Pis(lit.)/(kPa) 2.260b 12.973f 12.309b
0.2490 0.1020 12.339 0.6494 0.1713 10.188 2.281c 12.981g 12.321j
0.2991 0.1094 12.181 0.6995 0.1866 9.678 2.298d 12.966h 12.331k
0.3490 0.1168 11.993 0.7499 0.2067 8.995 2.280e 12.960i 12.300f
0.3990 0.1243 11.785 0.8000 0.2342 8.269 ViL/(cm3 mol1)l 111.2 169.2 150
0.3990 0.1243 11.797 0.8502 0.2755 7.292 Bii/(cm3 mol1)m 2560 2511 2414
0.4490 0.1318 11.534 0.9001 0.3460 6.007 Bi1/(cm3 mol1)m 2560 2303 2240
0.4491 0.1319 11.554 0.9504 0.4972 4.392 a
Average of 7 runs.
0.4990 0.1398 11.248 1.0000 1.0000 2.296 b
Ref. [14].
c
a
Standard uncertainties (k = 1): u(x1) = 0.0005, u(y1, Ref. [16].
calc) = 0.0005, u(P) = 5 Pa; u d
(T) = 10 mK. Ref. [17].
e
Ref. [18].
f
Ref. [19].
For the same two binary mixtures the excess enthalpies were g
Calculated from Antoine equation using constants reported by Reid et al. [20].
h
measured at T = (298.15 and 313.15) K, these experimental data as a Calculated from Antoine equation using constants reported in TRC [21].
i
function of the composition are given in Table 6 and in Fig. 2. The Ref. [22].
j
Ref. [23].
data have been correlated using Redlich–Kister equation: k
Ref. [24].
l
Ref. [25].
HEm n
Ai ð2x  1Þi1
¼ xð1  xÞ S
m
(5) Calculated by Hayden and O’Connell [8] from Dymond et al. [9].
i¼1 ½1 þ Cð2x  1Þ
1
Jmol
the parameters of the equation and the standard deviations are (2-pentanol + n-heptane). In both cases, NRTL adjustment is better
summarized in Table 7, the optimal number of parameters was than Wilson and UNIQUAC, obtaining always the worst fit with
selected by examining F-test. UNIQUAC model.
The pressure versus composition of both phases behaviour is
4. Discussion plotted in Fig. 1, it is shown that both systems exhibit a positive
deviation from the ideality. Both systems present an azeotrope due
For both binary systems, the six-parameter Margules equation to alkanes and alcohols form highly non ideal mixtures. For the
gives the best results with a root mean square pressure residual of mixture 2-pentanol + isooctane, the molar fraction of the azeo-
16 Pa and a maximum deviation of 37 Pa for the mixture (2- trope is x1 = 0.062 at 13.257 kPa and for the system 2-pentanol +
pentanol + 2,2,4-trimethylpentane) and a root mean square heptane, the molar fraction of the azeotrope is x1 = 0.0683 at
pressure residual of 17 Pa and a maximum deviation of 33 Pa for 12.656 kPa. Only the Margules equation can give the best
[(Fig._1)TD$IG]
Table 5
Determined parameters of the models used for the correlation of the binary systems
2-pentanol (1) + isooctane (2) and 2-pentanol (1) + heptane (2) at T = 313.15 K,
together with the root mean square deviation of pressure (rms DP) and the
maximum value of the deviation (max |DP|). The DP term is defined as the
difference between the experimental and calculated pressure.

Margules Wilson NRTL UNIQUAC

2-Pentanol (1) + 2,2,4-trimethylpentane (2)
A12 2.4687 0.1682 0.9293 1.6097
A21 1.4493 0.5719 1.8028 0.2652
l12 3.7768
l21 0.7752
h12 4.5840
h21 0.7769
a12 0.6184
rms DP/kPa 0.016 0.099 0.041 0.173
max |DP|/kPa 0.037 0.168 0.073 0.286
x1, az 0.0620 0.0535 0.0605
Paz/kPa 13.257 13.134 13.199

2-Pentanol (1) + n-heptane (2)

A12 2.5100 0.1563 0.8964 1.6432
A21 1.4014 0.5998 1.8494 0.2531
l12 3.9711
l21 0.7372
h12 4.7945
h21 0.8300
a12 0.6197
rms DP/kPa 0.017 0.093 0.042 0.162
Fig. 1. Experimental VLE data at T = 313.15 K for the systems: (4) 2-pentanol
max |DP|/kPa 0.033 0.150 0.077 0.263
(1) + 2,2,4-trimethylpentane (2) and (&) 2-pentanol (1) + n-heptane (2). (+)
x1, az 0.0683 0.0616 0.0675
Literature values 2-pentanol + n-heptane [14]. () Calculated values using Margules
Paz/kPa 12.656 12.533 12.598
equation with the parameters given in Table 5.
92 A. Moreau et al. / Fluid Phase Equilibria 384 (2014) 89–94
[(Fig._2)TD$IG]
Table 7
Parameters of Redlich–Kister equation, standard deviation of excess molar
enthalpies s and, absolute maximum deviation () for the measured systems.

T(K) A1 A2 A3 A4 A5 C s
(J mol1)

2-Pentanol (1) + 2,2,4-trimethylpentane (2)

298.15 3804.08 2676.91 282.70 1068.04 353.86 0.86868 3.0 5.6
313.15 4479.62 3129.39 531.99 350.19 453.85 0.93255 3.3 6.0

2-Pentanol (1) + n-heptane (2)

298.15 3772.99 3074.63 224.90 905.49 620.02 0.95463 2.7 5.3
313.15 4504.06 3164.73 526.40 540.08 290.84 0.91287 3.2 7.5

correlation of these azeotropic mixtures. An addition of the alcohol

to the hydrocarbons produces a maximum pressure azeotrope and
then the vapour pressure decreases. It can be also observed the
good agreement of our experimental data with those found in the
literature for the system 2-pentanol + heptane [14].
The study of the energy behaviour of these mixtures shows that
both systems have a strong endothermic effect due to the mixing
process which increases at higher temperatures. The highest
excess enthalpies are observed for the systems 2-pentanol + 2,2,4-
trimethylpentane and 2-pentanol + n-heptane at 313.15 K with a
maximum value of HEm = 1143 J mol1 for a mole fraction of 2-
pentanol of 0.40, and HEm = 1142 J mol1 for a mole fraction of 2-
pentanol of 0.45, respectively. In addition, at T = 298.15 K the excess
Fig. 2. Experimental excess molar enthalpies as a function of the composition for
the binary systems: (^) 2-pentanol (1) + 2,2,4-trimethylpentane (2) at T = 298.15 K enthalpy for the system 2-pentanol + 2,2,4-trimethylpentane
and (^) at T = 313.15 K; (4) 2-pentanol (1) + n-heptane (2) at T = 298.15 K and (~) at decreases to HEm = 959 J mol1 for a mole fraction of 2-pentanol
T = 313.15 K. (+) Literature data for the system 2-pentanol (1) + heptane (2) at of 0.45. And the mixture 2-pentanol + n-heptane shows the
303.15 K [15]. The line represents the values calculated by Redlich–Kister equation. maximum excess enthalpy at a mole fraction of 2-pentanol of
0.45 and the corresponding value is HEm = 950 J mol1. We have not
Table 6 found literature values for both systems at the same conditions,
Experimental excess molar enthalpies HmE as a function of the mole fraction x1 for
the binary systems.a
but the system 2-pentanol + n-heptane were measured at 303.15 K
[15] showing the same tendency of our experimental data. All
x1 HmE/(J mol1) x1 HmE/(J mol1) x1 HmE/(J mol1) these data can be observed in Fig. 2.
2-Pentanol (1) + 2,2,4-trimethylpentane (2) at T = 298.15 K Finally, Figs. 3 and 4 represent the calculated excess functions of
0.0000 0.00 0.3503 921.54 0.7019 740.68 the binary systems at 313.15 K, 2-pentanol + 2,2,4-
0.0507 476.49 0.4011 951.03 0.7517 646.70
0.0997 643.78 0.4521 958.55 0.8009 536.84 [(Fig._3)TD$IG]
0.1498 725.78 0.5011 956.31 0.8510 417.34
0.2009 794.91 0.5521 921.47 0.9002 283.08
0.2500 847.17 0.6010 879.26 0.9500 141.44
0.3022 892.11 0.6517 818.59 1.0000 0.00

2-Pentanol (1) + 2,2,4-trimethylpentane (2) at T = 313.15 K

0.00 0.00 0.3502 1133.81 0.7018 883.26
0.0507 609.62 0.4010 1143.37 0.7516 774.81
0.0998 822.09 0.4520 1136.47 0.8008 659.89
0.1499 937.51 0.5010 1117.82 0.8510 512.00
0.2009 1016.71 0.5520 1086.31 0.9002 357.82
0.2499 1078.55 0.6010 1035.90 0.9500 184.65
0.3023 1120.63 0.6516 964.46 1.0000 0.00

2-Pentanol (1) + n-heptane (2) at T = 298.15 K

0.0000 0.00 0.3460 916.92 0.6963 759.17
0.0505 489.03 0.3967 939.42 0.7480 664.70
0.0997 630.23 0.4459 949.97 0.7981 554.04
0.1477 725.31 0.4958 946.25 0.8483 431.29
0.1969 795.45 0.5463 925.20 0.8985 295.40
0.2472 848.75 0.5972 888.71 0.9486 150.00
0.2962 882.04 0.6466 834.99 1.0000 0.00

2-Pentanol (1) + n-heptane (2) at T = 313.15 K

0.0000 0.00 0.3455 1130.70 0.6959 894.95
0.0504 611.71 0.3962 1143.90 0.7477 794.25
0.0996 825.47 0.4454 1142.21 0.7979 672.84
0.1475 933.45 0.4953 1130.35 0.8481 529.86
0.1967 1014.34 0.5458 1098.56 0.8984 368.06
0.2469 1069.73 0.5968 1051.04 0.9485 192.87
0.2956 1110.60 0.6462 992.58 1.0000 0.00
a
Fig. 3. Excess functions for the system 2-pentanol + 2,2,4-trimethylpentane at
Standard uncertainties (k = 1): u(x1) = 0.0001, u(T) = 10mK, ur(HmE) = 0.5%.
T = 313.15 K: () GmE; () HmE; (—) TSmE.
 A. Moreau et al. / Fluid Phase Equilibria 384 (2014) 89–94 93
[(Fig._4)TD$IG] [(Fig._6)TD$IG]

Fig. 6. Comparison between the excess entropy for the systems 2-pentanol + n-
heptane () and 1-pentanol + n-heptane (—) at 313.15 K.

increases from 0.905 kPa to 2.295 kPa for the 2-pentanol.

Concerning the excess entropy, it is positive in all range of
Fig. 4. Excess functions for the system 2-pentanol + heptane at T = 313.15 K: ()
compositions for the systems with 2-pentanol (Figs. 3 and 4) which
GmE; () HmE; (—) TSmE.
means that the excess enthalpy is higher than the excess Gibbs
energy. However, the excess entropy is negative for the alcohol
trimethylpentane and 2-pentanol + n-heptane, respectively. The
mole fraction from 0.15 to 1 for the system 1-pentanol + 2,2,4-
excess Gibbs energies were calculated using the Margules
trimethylpentane and from 0.13 to 1 for the system 1-pentanol + n-
equation, the excess enthalpies were fitted with the Redlich–
heptane and therefore the excess Gibbs energy is higher than the
Kister equation, and finally the excess entropies were obtained
excess enthalpy. This effect is plotted in Figs. 5 and 6 it is due to the
using the relation between them: GE = HETSE. These functions
effect in the excess enthalpies. The maximum excess enthalpies for
exhibit very close behaviours and values for both systems. Also
the mixtures with 1-pentanol are lower than those with 2-
they present positive excess entropy in all range of the composition
pentanol meanwhile the excess Gibbs energy is quite similar, these
due to the greater positive value of the excess enthalpies.
differences in the excess enthalpies are caused by a combination of
Their behaviours are completely opposite from those observed
chemical and physical effects [15] the self-association due to
for the binary systems with 1-pentanol previously published [1].
hydrogen bonding is higher for 1-pentanol than 2-pentanol as it is
When the alcohol group changes the position in pentanol isomers,
reflected in the vapour pressure but the disruption of this bonds
the properties of the mixture change as it has been observed in the
shows the opposite tendency resulting in a highest endothermic
literature [15]. The vapour pressure of the pure 1-pentanol
effect for the mixtures with 2-pentanol.
[(Fig._5)TD$IG]
Acknowledgments

The authors are grateful for financial support from the Spanish
Minister of Science and Innovation (MICINN) for Project ENE2009-
14644-C02-01 and Junta de Castilla y León for the Project
VA391A12-1. Alejandro Moreau thanks the support from European
Social Fund (ESF) and from Consejería de Educación de la Junta de
Castilla y León.

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