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197208

www.elsevier.nlrlocaterfluid

K of the ternary system tert-amylmethyl ether

TAME . q n-heptaneq methanol 1

Cesar

R. Chamorro, Jose J. Segovia, Mara

C. Martn,

Miguel A. Villamanan

Laboratorio de Termodinamica,

Depto. Ingeniera

E.T.S. de Ingenieros Industriales,

Energetica

y Fluidomecanica,

Received 12 October 1998; accepted 29 June 1999

Abstract

Experimental isothermal Px data at 313.15 K for the ternary system tert-amylmethyl ether TAME. q nheptaneq methanol. and for one of the unmeasured constituent binary systems, tert-amylmethyl ether

TAME. q methanol. are reported. Data reduction by Barkers method provides correlations for g E using the

Margules equation for the binary systems and the Wohl expansion for the ternary system. Wilson, NRTL and

UNIQUAC models have been applied successfully to both the binary and the ternary systems. The presence of

azeotropes in the ternary system and constituent binaries are studied as well as the presence of immiscible

zones. q 1999 Elsevier Science B.V. All rights reserved.

Keywords: Data; VLE low pressure; Hydrocarbons; TAME; Excess Gibbs energy; Azeotropes; Correlations

1. Introduction

tert-amylmethyl ether TAME. complements the use of methyl tert-butyl ether MTBE. as an

alternative oxygenate additive in unleaded gasolines. This work will contribute with an experimental

investigation of the thermodynamic parameters of VaporLiquid Equilibrium VLE. at 313.15 K of

the ternary system TAMEq n-heptaneq methanol and the binary system TAMEq methanol.

Methanol is present in the catalytic reaction to synthesize TAME from the isoolefine isopentene.

To design separation processes properly in the purification of TAME from methanol impurities,

acurate VLE data are necessary. Thermodynamic phase behaviour of both components with gasoline

)

1

This paper is part of the Doctoral Thesis of C.R. Chamorro.

0378-3812r99r$ - see front matter q 1999 Elsevier Science B.V. All rights reserved.

PII: S 0 3 7 8 - 3 8 1 2 9 9 . 0 0 2 6 8 - X

198

measurements of the corresponding generated ternary system whose data are reported here Chamorro

w1x, Chamorro et al. w2x.. A similar study has been done by our group concerning MTBE Segovia w3x,

Segovia et al. w48x..

2. Materials

All the chemicals used here were purchased from Fluka Chemie and were of the highest purity

available, chromatography quality reagents of the series puriss. p.a.. with a stated purity ) 97.0%

GC. for TAME, ) 99.5% GC. for n-heptane and ) 99.8% GC. for methanol. Only TAME was

distilled, at atmospheric pressure, through a packed column, the first and last portions of the distillate

were discarded and the intermediate fraction distilling at constant temperature was collected.

All reagents were thoroughly degassed using a modified distillation method based on the one

suggested by Van Ness and Abbott w9x. The purity of the products after degassing was checked in our

laboratory by gas chromatography, and the values obtained were ) 99.8% GC. for all the

compounds.

In Table 1, the vapor pressures of the pure constituents measured in this work are compared with

those reported in the literature to check for complete degassing.

Table 1

Average values of experimental vapor pressures Pisat . for the pure compounds measured in this work and literature values

Pisat . lit.., molar volumes of pure liquids Vi L . and the second virial coefficients Bii , Bi j . at 313.15 K used for the data

reduction of the measured systems

Pisat

Pisat

kPa.

lit. kPa.

Vi L cm3rmol.

Bi1

Bi2

Bi3

a

TAME is1.

n-Heptane is 2.

Methanol is 3.

19.567

19.587 a

19.540 b

12.351

12.331c

12.348 d

12.335e

12.300 f

12.363 g

150 j

y2211k

y2521k

y622 k

35.463

35.475 c

35.431f

35.445a

35.453 h

35.470 i

42 j

y923 k

y622 k

y1964 k

136 j

y1988 k

y2211k

y923 k

Calculated from the Antoine equation using constants reported by Cervenkova and Boublik w29x.

c

Reported by Segovia w3x.

d

Reported by Montero w30x.

e

Calculated from the Antoine equation using constants reported in Ref. w31x.

f

Calculated from the Antoine equation using constants reported by Reid et al. w32x.

g

Reported by Reid et al. w33x.

h

Reported by Goral

et al. w34x.

i

Reported by Boublik et al. w35x.

j

Reported in Ref. w36x.

k

Calculated by Hayden and OConnell w18x from Dymond and Smith w19x.

b

199

3. Experimental method

A static VLE apparatus, consisting of an isothermal total pressure cell, has been employed for

measuring the VLE of binary and ternary mixtures. The apparatus and measuring technique are based

on that by Van Ness et al. Gibbs and Van Ness w10x; DiElsi et al. w11x. and whose performance has

been described in a previous paper Lozano et al. w12x..

The piston injectors are three 100-cm3 positive displacement pumps Ruska, mod. 2200-801. with

a resolution of 0.01 cm3 and an estimated total uncertainty of "0.03 cm3, allow the injection of

known volumes of the pure components, previously degassed, into the cell immersed in a high

precision water bath Hart Scientific model 6020. assuring an stability of 0.5 mK and thermostated at

313.15 K.

The cell is a cylindrical stainless steel piece with a capacity of about 180 cm3 and provided with a

magnetic stirrer externally operated. An initial amount of about 50 cm3 of one component is injected

into the evacuated cell, the vapor pressure is recorded, and successive increases in composition of a

second or a third component are generated until we nearly fill the cell completing a desired

composition range. The total amount of mass injected is accurately determined from the volume

differences read between two stop-points of the piston, the temperature of the injector and the value of

the density for that pure component allowing us assuring four digits in the value of the mole fraction.

The stop-point for advancing the piston is in all cases determined by an accurate break-point torque

wrench, set to overbalance the frictional effect of the packing around the piston.

Experimental values of total vapor pressure for the binary mixtures were obtained with two

different runs, the first one adding the second component to the first one up to a concentration close to

x 1 s 0.4, and the second run adding the first component to the second one up to x 1 s 0.6, completing

in this way the whole concentration range. For the ternary mixtures data were obtained by addition of

a pure species to a mixture of the other two at a fixed temperature. Six runs dilution lines. were done

starting the corresponding binary system at mole fractions close to 0.3 or 0.7 and adding the third

pure component up to a mole fraction of 0.5.

Table 2

Total-pressure VLE data for TAME 1.qmethanol 2.. at 313.15 K

x1

y 1,calc

P kPa.

x1

y 1,calc

P kPa.

0.0000

0.0487

0.1002

0.1506

0.1989

0.2493

0.2996

0.3499

0.3990

0.3999

0.4496

0.4498

0.4995

0.0000

0.0967

0.1616

0.2055

0.2368

0.2628

0.2845

0.3036

0.3209

0.3212

0.3380

0.3381

0.3548

35.467

37.574

38.860

39.555

39.910

40.060

40.061

39.939

39.751

39.740

39.456

39.459

39.082

0.5003

0.5498

0.5504

0.5977

0.6006

0.6508

0.6988

0.7466

0.7997

0.8469

0.9003

0.9494

1.0000

0.3550

0.3722

0.3724

0.3897

0.3908

0.4111

0.4332

0.4595

0.4968

0.5419

0.6186

0.7396

1.0000

39.066

38.598

38.603

38.048

38.019

37.296

36.433

35.376

33.822

31.998

29.113

25.353

19.573

200

Table 3

Total-pressure VLE data for TAME 1.q n-heptane 2.qmethanol 3.. at 313.15 K

x1

x2

y 1,calc

y 2,calc

P kPa.

1.0000

0.6981

0.6780

0.6603

0.6275

0.5943

0.5584

0.5220

0.4884

0.4528

0.4186

0.3835

0.3497

0.0000

0.3008

0.2940

0.2888

0.2750

0.2564

0.2398

0.2258

0.2111

0.1960

0.1809

0.1655

0.1504

1.0000

0.7023

0.6859

0.6670

0.6303

0.5966

0.5619

0.5267

0.4914

0.4562

0.4209

0.3860

0.3510

0.0000

0.3046

0.2970

0.2896

0.2745

0.2590

0.2439

0.2286

0.0000

0.3019

0.2932

0.2856

0.2714

0.2570

0.2415

0.2257

0.2112

0.1958

0.1810

0.1658

0.1512

1.0000

0.6992

0.6836

0.6714

0.6392

0.5959

0.5573

0.5248

0.4908

0.4556

0.4204

0.3846

0.3497

0.0000

0.0000

0.0234

0.0505

0.1028

0.1508

0.2003

0.2505

0.3007

0.3508

0.4011

0.4507

0.5005

0.0000

0.0000

0.0252

0.0498

0.0996

0.1505

0.2002

0.2504

1.0000

0.7732

0.5753

0.4845

0.3927

0.3424

0.3086

0.2849

0.2681

0.2531

0.2403

0.2281

0.2168

0.0000

0.4202

0.2494

0.2016

0.1507

0.1265

0.1156

0.1091

0.1035

0.0983

0.0934

0.0886

0.0840

1.0000

0.4349

0.4186

0.4004

0.3671

0.3389

0.3118

0.2864

0.2626

0.2403

0.2192

0.1994

0.1803

0.0000

0.2864

0.2580

0.2353

0.1998

0.1732

0.1528

0.1357

0.0000

0.2268

0.1762

0.1539

0.1327

0.1226

0.1170

0.1142

0.1127

0.1119

0.1116

0.1115

0.1117

1.0000

0.5798

0.3621

0.3032

0.2444

0.2216

0.2145

0.2117

0.2103

0.2095

0.2090

0.2084

0.2077

0.0000

0.0000

0.0141

0.0297

0.0576

0.0807

0.1022

0.1219

0.1399

0.1563

0.1716

0.1859

0.1995

0.0000

0.0000

0.0355

0.0628

0.1031

0.1314

0.1522

0.1692

19.561

17.923

23.564

27.088

31.527

34.351

36.379

37.809

38.788

39.596

40.208

40.724

41.134

12.348

15.148

24.709

29.379

35.647

39.226

40.850

41.715

42.350

42.840

43.187

43.472

43.694

19.565

36.338

36.444

36.562

36.770

36.926

37.074

37.214

37.332

37.439

37.529

37.597

37.647

35.467

40.048

40.641

41.074

41.706

42.135

42.441

42.680

201

Table 3 continued.

x1

x2

y 1,calc

y 2,calc

P kPa.

0.2133

0.1984

0.1827

0.1674

0.1525

0.0000

0.0000

0.0244

0.0504

0.0992

0.1489

0.2014

0.2497

0.3002

0.3502

0.4004

0.4497

0.4999

0.0000

0.0000

0.0251

0.0503

0.0997

0.1502

0.2001

0.2500

0.3002

0.3500

0.4003

0.4502

0.5000

0.3008

0.3495

0.4011

0.4513

0.5002

1.0000

0.6962

0.6793

0.6612

0.6272

0.5925

0.5560

0.5223

0.4871

0.4523

0.4173

0.3829

0.3479

0.0000

0.3016

0.2940

0.2865

0.2716

0.2564

0.2414

0.2263

0.2112

0.1962

0.1810

0.1659

0.1509

0.1209

0.1081

0.0958

0.0848

0.0750

0.0000

0.0000

0.0108

0.0228

0.0460

0.0702

0.0963

0.1211

0.1479

0.1760

0.2063

0.2386

0.2745

0.0000

0.0000

0.0163

0.0325

0.0634

0.0938

0.1227

0.1506

0.1780

0.2048

0.2318

0.2588

0.2865

0.1836

0.1955

0.2063

0.2151

0.2224

1.0000

0.2552

0.2520

0.2481

0.2394

0.2295

0.2186

0.2083

0.1977

0.1871

0.1765

0.1660

0.1552

0.0000

0.2572

0.2447

0.2328

0.2117

0.1922

0.1745

0.1581

0.1426

0.1281

0.1144

0.1015

0.0895

42.889

43.053

43.214

43.345

43.452

12.358

45.572

45.254

44.823

43.927

43.012

42.028

41.081

40.064

39.016

37.926

36.785

35.572

35.456

45.611

45.266

44.915

44.274

43.628

43.002

42.396

41.776

41.140

40.479

39.771

39.020

Temperature was measured by a calibrated standard PRT-100 SDL model 5385r100. using as

indicator an AC resistance bridge ASL model F250. resolving 1 mK in the reading of temperature

and estimating an overall uncertainty of "10 mK. The measurement of the pressure was done

indirectly through a differential pressure cell and indicator Ruska models 2413-705 and 2416-711,

respectively.. Once air balances the vapor pressure of the cell a Bourdon fused quartz precision

pressure gauge Texas Instruments mod. 801. reads the pressure with an estimated uncertainty of "5

Pa for the 125 kPa range.

3.1. Experimental results and correlations

The use of the measuring technique described above allows a static equilibrium between phases,

assuring a true thermodynamic equilibrium. Direct sampling, particularly of the vapor phase, upsets

the equilibrium, the mass of vapor in the cell is very small; yet an appreciable mass must be

202

withdrawn to yield an amount of condensate suitable for accurate analysis. However, as a consequence of Duhems theorem, sampling of the phases is not, in fact, necessary. Given a set of

equilibrium x, P data at constant T, thermodynamics allows calculation of the y-values. Thus, the

equilibrium vapor need not be sampled for analysis and the data are thermodynamically consistent

per se. Van Ness et al. w13x; Van Ness w14x.

Data reduction for the binary and ternary mixtures was done by Barkers method w15x according to

well established procedures Abbott and Van Ness w16,17x. developing a computer program described

in detail earlier. Lozano et al. w12x.

The non-ideality of the vapor phase was taken into account with the virial equation of state,

truncated in the second term. The second virial coefficients Bii . are indicated in Table 1. They were

calculated by the Hayden and OConnell method w18x using the parameters given by Dymond and

Smith w19x. Correction for the vapor phase was also applied to x.

The quality of the data of the present VLE technique for ternaries has been assessed previously and

reported in Refs. w38x.

The ternary system TAMEq n-heptaneq methanol has been measured together with the binary

system TAMEq methanol at 313.15 K. The other binary systems involved in this ternary TAMEq nheptane and n-heptaneq methanol have been already published Chamorro et al. w2x; Segovia et

al.w8x., using the same experimental procedure and data reduction.

Data for this ternary system are adequately correlated by the three-parameter Wohl equation, Eq.

1. Van Ness and Abbott w13x., which also includes the parameters of the corresponding binaries.

g 123 s

gE

g q g 13 q g 23 q C0 q C1 x 1 q C2 x 2 . x 1 x 2 x 3

1.

RT 12

Correlations for the g i j are given by Eq. 2.; parameters C0 , C1 and C2 are found by regression of

the ternary data. The Margules equation with three parameters, Eq. 2. , has been chosen for the

binaries.

gE

s A ji x i q A i j x j y l x i x j x i x j

2.

Rt

Binary and ternary systems have also been correlated using Wilson w20x, NRTL w21x and

UNIQUAC w22x models, whose expressions for the excess Gibbs energy are indicated by the Eqs.

3. 5., respectively.

gi j s

gE

RT

gE

RT

s y x i ln

i

/

x j Ai j

3.

A ji Gji x j

s xi

i

4.

Gk i x k

k

RT

s x i ln

i

wi

xi

qi

qi x i ln q

2

i

y qi x i ln

i

/

qj A ji

5.

203

Table 4

Summary of the data reduction results and azeotrope situation obtained for the binary system TAME 1.qmethanol 2.. at

313.15 K

Margules 3p.

A12

A 21

l

a 12

rms D P kPa.

max D P kPa.

x 1 azeotrope.

P azeotrope. kPa.

a

b

Wilson

1.5372

1.5096

0.5045

0.3996

0.4189

0.007

0.023

0.2737

40.076

0.081

0.180

0.2788

40.014

NRTLa

NRTLb

UNIQUAC

0.8593

0.9015

0.9723

1.0111

0.2146

1.2523

0.47

0.113

0.252

0.6138

0.007

0.014

0.2736

40.072

0.203

0.455

0.2870

39.948

This column contains a 12 s 0.47 as recommended, but the fitting is rather poor.

This column contains a simultaneous adjustment of the three parameters.

Table 2 gives experimental values of total pressure and the corresponding compositions of the

liquid and vapor phases for the binary system TAMEq methanol. , reduced by Margules equation.

Table 3 gives the same type of information for the ternary system TAMEq n-heptaneq methanol.,

where Wohl expansion has been used in the data reduction.

Results of data correlation for the binary system TAMEq methanol are summarized in Table 4.

The results of the correlations for the other binaries involved in the ternary system TAMEq nheptaneq methanol. have been published previously Chamorro et al. w2x; Segovia et al. w8x.. For the

ternary system, the results of the correlation are given in Table 5. All these tables contain values of

the adjustable parameters of the different models which lead to the correlated results using Barkers

Table 5

Summary of the data reduction results obtained for the ternary system TAME 1.q n-heptane 2.qmethanol 3.. at 313.15

K

Wohl a

C0

C1

C2

A12

A 21

A13

A 31

A 23

A 32

a 12

a 13

a 23

rms D P kPa.

max < D P < kPa.

a

Wilson

NRTLb

UNIQUAC

0.7071

1.0561

0.4133

0.4044

0.0594

0.0296

0.4237

y0.1962

0.9958

0.9585

2.6495

2.7360

0.3

0.6138

0.4356

0.212

0.774

1.4011

0.5517

0.2205

1.2379

0.0616

1.1425

1.7416

2.6007

2.3999

0.159

0.470

0.118

0.407

0.620

2.096

The values for the correlation parameters of the two constituent binaries, not reported in this paper, were taken from Refs.

w2,8x.

b

The recommended value of a 12 s 0.3 has been taken, since it has been found that the outcome of the fitting was the same

using an adjusted ad hoc value.

204

Fig. 1. Comparison for the binary system TAME 1.qmethanol 2.. at 313.15 K of the pressure residuals, P y Pcalc ,

defined as differences between experimental pressures, P, and calculated pressures, Pcalc . A"0.1% band of the experimental pressure in each point is indicated on the diagram.

method. The root mean square of the difference between experimental and calculated pressures rms

D P . and the maximum value of these pressure residuals max < D P <. are indicators of the quality of

the agreement with data.

As an example of the fits of models to the data, Fig. 1 shows a plot of P y Pcalc . vs. x 1 for the

binary TAMEq methanol. using Margules equation with three parameters. It can be seen that both

branches, necessary to measure the binary, have a good match close to equimolar concentrations,

showing the figure at that point a comparison of the residual with 0.1% of the experimental pressure.

4. Discussion

The ternary system TAMEq n-heptaneq methanol. and its constituent binaries are specially rich

in a variety of fluid phase behaviour. The binary system studied TAMEq methanol. at 313.15 K

presents a positive deviation from the ideality and the results of the correlation give a root mean

square pressure residuals of 7 Pa with a maximum value of the absolute deviation of 14 Pa, using

NRTL model when the third parameter a i j is also adjusted. Table 4 also shows the result with the

recommended value of 0.47 providing a poor fitting of the data. The values obtained with Margules

equation of three parameters are rather similar and worse correlations are obtained with Wilson and

UNIQUAC models. This system exhibits an azeotrope in the alcohol rich region at x 1 s 0.2737 and

P s 40.076 kPa, which agrees with literature values of Gmehling et al. w23x and Coto et al. w24x which

situate it at x 1 s 0.2731 and x 1 s 0.2749, respectively. These literature azeotrope compositions in

fact does not come from direct experimental data at 313.15 K as ours, but have been obtained by

linear interpolation of reported data available at other temperatures, since it has been observed a linear

variation of the azeotrope composition value with temperature. A view of the results here discussed

together the ones obtained with the other reduction equations used in this paper are given in Table 6.

The quality of data are shown in Fig. 1 by the study of their dispersion in all the composition range

and Fig. 2 displays the azeotropic Pxy behaviour of the mixture.

In contrast to previous binary system, the TAMEq n-heptane. system shows a rather ideal

behaviour without any azeotrope and a very good miscibility as can be expected and was reported by

205

Table 6

Values of the azeotrope composition, x 1, and total vapor pressure, P, for the binary system TAME 1.qmethanol 2.. at

313.15 K, calculated with different correlation models, and comparison with values reported from literature

Margules

Wilson

NRTL

UNIQUAC

Reported by Gmehling et al. w23x

Reported by Coto et al. w24x

a

b

x1

P kPa.

0.2737

0.2788

0.2736

0.2870

0.2731a

0.2749 a

40.076

40.014

40.072

39.948

b

b

Not determined by the referred authors w23,24x at 313.15 K.

Chamorro et al. w2x. The remaining binary system methanolq n-heptane. presents a large immiscibility gap between x 1 s 0.2263 and x 1 s 0.8714 as has been determined by us Segovia et al. w8x..

The molar excess Gibbs function, g E , shows a positive deviation from ideality with maximum

values close to equimolar concentrations at 1672 Jrmol for methanolq n-heptane., 910 Jrmol for

TAMEq n-heptane. and 107.4 Jrmol for TAMEq n-heptane.. This behaviour of g E shows

quantitatively the strong gradation of the nature of the binary mixtures, ranging from nearly an ideal

solution in the case of TAMEq n-heptane. to the high non-ideality with separation for methanolq

n-heptane..

Concerning the measured ternary system, the results of the correlation give a root mean square

pressure residuals between 0.118 kPa for Wilson equation and 0.620 kPa for UNIQUAC, being the

Fig. 2. Total vapor pressure as a function of the liquid, x 1, and vapor composition, y 1, of TAME for the VLE of the binary

system TAME 1.qmethanol 2.. at 313.15 K. The azeotrope showed occurs at x 1 s 0.2737 and P s 40.076 kPa.

206

Fig. 3. Isobar lines in kPa as a function of the ternary liquid composition, x i , for the VLE at 313.15 K of the ternary system

TAME 1. q n-heptane 2.qmethanol 3...

former the best fit for all the miscible region. Figs. 3 and 4 show, respectively isobar and the iso-g E

lines as a function of the ternary liquid composition.

Fig. 4. Iso-g E lines in Jrmol as a function of the ternary liquid composition, x i , for the VLE at 313.15 K of the ternary

system TAME 1.q n-heptane 2.qmethanol 3...

207

The investigated ternary system TAMEq n-heptaneq mehtanol. shows good miscibility in the

whole range of our measurements, nevertheless, it is to expect a really very narrow immiscible zone

close to binary line of methanolq n-heptane. which is impossible to precise with our experimental

technique due to the very low concentrations of TAME at which it appears. In fact, very low

quantities of TAME representing according to our measurements values lower than 0.1 molar destroys

the immiscibility of the binary methanolq n-heptane..

The search for ternary azeotropes either homogeneous or heterogeneous using the calculation

procedures indicated by Gmehling and Menke w25x; Demirel w26x and Chapman and Goodwin w27x

have been negative in all the concentration range for the correlated data by Wilson, NRTL or

UNIQUAC. Concerning the g E function the maximum value occurs at the maximum value for the

binary methanolq n-heptane. already given.

5. Nomenclature

A i j , A ji

Bii , Bi j , Bj j

C 0 , C1 , C 2

gE

g

i, j

lit

max

P

Pisat

R

rms

T

Vi L

x

y

Greek letters

D

l

second virial coefficients

parameters in Eq. 1.

molar excess Gibbs energy

value of g ErRT for a binary or a ternary mixture

constituent identification: 1, 2 or 3

literature value

maximum value of the indicated quantity

total pressure

vapor pressure of pure constituent i

universal gas constant

root mean square

absolute temperature

molar volume of pure liquid i s 1,2,3

mole fraction, liquid phase

mole fraction, vapor phase

signifies difference

parameter in Eq. 2.

Acknowledgements

Support for this work came from the DGICYT, Direccion

y

General de Investigacion

Cientfica

Tecnica

of

the

Spanish

Ministery

of

Education,

Project

PB-95-0704

and

from

Junta

de

Castilla

y

Leon

Consejera

de Educacion

y Cultura. project VA 42r96.

208

References

w1x

w2x

w3x

w4x

w5x

w6x

w7x

w8x

w9x

w10x

w11x

w12x

w13x

w14x

w15x

w16x

w17x

w18x

w19x

w20x

w21x

w22x

w23x

w24x

w25x

w26x

w27x

w28x

w29x

w30x

w31x

w32x

w33x

w34x

w35x

w36x

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