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The Separation of Acetone-Methanol Mixture

by Extractive Distillation

Article in Chemical Engineering Communications · June 1988

DOI: 10.1080/00986448808940398

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THE SEPARATION OF ACETONE-METHANOL MIXTURE BY

EXTRACTIVE DISTILLATION
a a a
AN-I YEH , LLOYD BERG & KARL J. WARREN
a
Department of Chemical Engineering , Montana State University , Bozeman, MT, 59717|
Published online: 05 Apr 2007.

To cite this article: AN-I YEH , LLOYD BERG & KARL J. WARREN (1988) THE SEPARATION OF ACETONE-METHANOL MIXTURE BY
EXTRACTIVE DISTILLATION, Chemical Engineering Communications, 68:1, 69-79, DOI: 10.1080/00986448808940398

To link to this article: http://dx.doi.org/10.1080/00986448808940398

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 Chem. Eng. Comm. \988, Vol. 68, pp. 69-79
Reprints available directly from the publisher.
Photocopying permitted by license only.
© \988 Gordon and Breach Science Publishers S.A.
Printed in the United States of America

THE SEPARATION OF ACETONE-METHANOL

MIXTURE BY EXTRACTIVE DISTILLATION
AN-I YEH, LLOYD BERG and KARL J. WARREN
Department of Chemical Engineering,
Montana State University, Bozeman, MT 59717
Downloaded by [National Taiwan University] at 20:48 14 May 2015

(Received June 15, 1987); in final form November 4, 1987)

Acetone and methanol can not be readily separated by ordinary distillation because of the presence of
the minimum boiling azeotrope. Either acetone Or methanol can be the overhead product when an
appropriate agent is applied in extractive distillation. An unusual phenomenon, "temperature
inversion" I was observed when ketones were used as the extractive distillation agents. The dissolving
of the vapors into the liquid phase could be the cause for the overhead at a temperature higher than
that of the stillpot.
KEYWORDS Separation Acetone Methanol Extractive Distillation.

INTRODucnON

Extractive distillation is the method of carrying out a rectification in the presence

of an added higher boiling liquid(s). Its presence on each plate in the column
changes the relative volatility of the compounds to be separated. The
effectiveness of the extractive agent depends principally on the quantity
employed. This is usually in the range of one to two parts of extractive agent per
part of mixture to be separated. The change in composition of the mixture to be
separated usually has little effect on the efficiency. For example, Berg (1981)
showed that in ethylbenzene-p-xylene separation, varying the concentration of
ehtylbenzene from 20% to 95% changed the relative volatility from 1.23 to 1.18.
Recovery and recycle of the extractive agent is done in another column. The ease
of this operation is largely dependent upon the temperature difference between
the less volatile component and the extractive agent. Twenty or more Centigrade
degrees temperature difference are required. This adds additional heat input both
to the extractive distillation column and the recovery column but often this is less
than the additional heat required in an azeotropic distillation. Usually the largest
single cost occasioned by the use of extractive distillation is the expense of
replacement of extractive distillation agent. Most of the effective agents are
priced at $1-2 per pound. Effective agents are selected from compounds that are
heat stable and non-reactive with the materials being separated. All the agents
presented below have been subjected to 24-72 hours of continuous boiling
without showing decomposition. Interest in extractive distillation as a method of
separating close boiling mixtures and azeotropes is increasing as information on
successful operations has appeared, e.g. formic acid from acetic acid (Berg,

69
 70 A.-I. YEH, L. BERG AND K.J. WARREN
1987). Yeh, (1986) indicated the extent to which chemical and physical properties
of potential extractive compounds can be used in the selection of effective agents.
The most likely correlation appears to be between polar interaction and hydrogen
bond parameter. This leaves much to be desired in explaining some of the strange
results occuring in extractive distillation.

EXPERIMENTAL

A preliminary investigation to determine the effectiveness of potential extractive

agents was done on the acetone-methanol azeotrope by the use of an Othmer
Downloaded by [National Taiwan University] at 20:48 14 May 2015

type vapor-liquid equilibrium still, Figure 1. To demonstrate the effectiveness of

some of the compounds that appeared to be attractive in the vapor-liquid still,
runs were made in an Oldershaw perforated plate column containing 4.5
theoretical plates, Figure 2. The relative volatility reported in the tables is the
average value for each plate based on overhead and bottoms composition as
calculated by the Fenske equation. These results are presented below in the
tables pertaining to the rectification column.

Thermometer

Thermocouple

Still

Sampling
Il-~---Tube - - - - i l

FIGURE 1 Othmer-type vapor-liquid equilibrium still.

 ACETONE-METHANOL SEPARATION 71

Cooling wafer oat»-

Thermocouple - -

B-
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Thermocouple -~L­
Sampling
C-""\ - Tube

FIGURE 2 Diagram of the batch-wise extractive distillation column.

RESULTS AND DISCUSSION

Vapor-Liquid Equilibrium
Figure 3 is a plot of the vapor-liquid equilibrium for the acetone-methanol system
with and without the agent, dimethylsulfoxide (DMSO). When no agent was
added, the minimum boiling azeotrope with a composition of 86.1 wt% acetone
existed in the system. The azeotrope was negated by adding DMSO. The relative
volatility of acetone to methanol was increased by DMSO.

Perforated Plate Rectification Column

The column was operated at ambient pressure which varied from 630-645 mm.
Hg. The pressure drop in the column is small. A semi-batch wise technique was
used to simulate a continuous process and to reduce the quantity of extractive
agents used. Yeh (1983) has demonstrated that the agent affects the separation
only when it exists in the column. The change of agent concentration in the
stillpot does not change the effect of the agent. It has been found that either
acetone or methanol can be the overhead product in extractive distillation even
though methanol has s higher boiling point than acetone.
 72 A.-I. YEH, L. BERG AND K.J. WARREN
IOO.-------,,.-------,----r---r--.~

Ql
VI
o
s:
Cl. 80
....
o
a.
o
>
c 60
Ql

-
C
o
Ql 40
u
o
....o
Downloaded by [National Taiwan University] at 20:48 14 May 2015

-0- No agent
o~
- e - Witll OMSO

60 80 100
in liquid phase
FIGURE 3 Vapor-liquid equilibrium data from methanol-acetone systems. Compositions on
agent-free basis

Acetone as Overhead Product

Acetone has a lower boiling point than methanol and normally is expected as the
overhead product. Table, I lists the results of the initial evaluation of extractive
distillation agents made in the vapour-liquid equilibrium still. Glycerine and
DMSO are two effective agents which cause the relative volatility of acetone to
methanol to be higher than 3.0. In addition to the single agents, some mixtures
of agents are also effective in enhancing the separation of acetone from methanol.
The mixture glycerine and ethylene glycol is the most effective. Mixtures of
ethylene glycol-DMSO and glycerine-DMSO-diethylene glycol are also very
effective and yield a relative volatility higher than 3. Glycerine, glycols and
DMSO have a polarity similar to methanol and bring the methanol down the
column. This leaves acetone as the overhead product. When these agents are
mixed with another agent having low polarity, the effectiveness will be reduced.
For example, DMSO mixed with isophorone yields a relative volatility of 2.1. The
apparatus shown in Figure 2 was used to demonstrate the effect of several agents
in extractive distillation. The results in Table II are the average of three runs. In
each case, the overhead contains more than 86% wt. % acetone, the azeotrope
composition which indicates the disappearance of the azeotrope. With DMSO as
the agent, the relative volatility of acetone to methanol is 3.1.

Methanol as Overhead Product

When certain ketones and their mixtures were used as the agents, methanol
became the overhead product despite its high boiling point. Table III lists the
initial evaluation of ketones. Ketones are homologs of acetone. The ketones have
 TABLE I

Effective agents for removing acetone as overhead

Downloaded by [National Taiwan University] at 20:48 14 May 2015

Relative volatility Relative volatility

Compounds acetone to methanol Compounds acetone to methanol ;>
n
DMSO, Methyl-n-propyl ketone 2.1 Glycerine 3.3 tTl
DMSO, Isophorone
DMSO, Ethylene glycol diacetate
2.1
2.0
Dimethylsulfoxide (DMSO)
Ethylene glycol
3.2
2.8 dz
DMSO, Diethylene glycol 2.0 1,4-Butanediol 2.5
DMSO, Ethylene glycol phenyl ether 2.0 Propylene glycol 2.4 tp
Glycerine, Ethylene glycol, Diethylene glycol 3.3 1,5-Butanediol 2.4 3:
Glycerine, DMSO, Diethylene glycol 3.2 1,3-Butanediol 2.2 rn
Glycerine, Ethylene glycol, 1,5-Pentanediol
Glycerine, Ethylene glycol, Diisobutylphthalate
3.1
3.1
Glycerine, Ethylene glycol
Ethylene glycol, DMSO
3.6
3.3
~
;>
Glycerine, Ethylene glycol, I A-Butanediol 3.0 Glycerine, 1,4-Butanediol 2.9 z
Glycerine, DMSO, 1,4-Butanediol 3.0 Glycerine, Propylene glycol 2.8 o
Glycerine, DMSO, Diisooctylphthalate 2.9 Glycerine, 1,5-Pentanediol 2.8 r-
Glycerine, DMSO, Triethylene glycol 2.8 Glycerine, Dimethylsulfoxide (DMSO) 2.8 en
Glycerine, DMSO, 1,5-Pentanediol 2.8 Ethylene glycol, Diethylene glycol 2.7 m
Glycerine, DMSO, 1,3-Butanediol
Glycerine, Ethylene glycol, Triethylene glycol
2.8
2.8
Ethylene glycol, IA-Butanediol
Ethylene glycol, 1,5-Pentanediol
2.6
2.6 '",0
;>
Glycerine, Ethylene glycol, Tetraethylene glycol 2.8 Ethylene glycol, Propylene glycol 2.5
Glycerine, DMSO, Ethylene glycol 2.7 DMSO, Propylene glycol 2.5 ~
Glycerine, Ethylene glycol, 1,3-Butanediol
Glycerine, Ethylene glycol, Dipropylene glycol
2.6
2.5
DMSO, Hexylene glycol
DMSO, Dipropylene glycol
2.2
2.2
sz
Glycerine, Ethylene glycol, Hexylene glycol 2.5 DMSO, Triethylene glycol diacetate 2.1
Glycerine, DMSO, Propylene glycol 2.5 DMSO,4-Methoxy-4-methylpentanone-2 2.1

-..l

'"
 74 A.-I. YEH, L. BERG ANDK.J. WARREN
TABLE Il

Data from rectification column

wt% Acetone Relative volatility

Agents Overhead Bottom acetone to methanol

DMSO 99.8 25 3.1

1,4-Butanediol 96.8 25 2.7
1,5-Pentanediol 95.0 25 2.5
Propylene glycol 98.0 50 2.4
DMSO, Glycerine 99.8 50 4.0
Ethylene glycol, 1,5-Pentanediol 99.0 25 3.5
DMSO, Butoxypropanol 99.0 50 2.8
Downloaded by [National Taiwan University] at 20:48 14 May 2015

DMSO, Propylene glycol 96.7 25 2.7

Glycerine, Ethylene glycol 96.5 25 2.7
Dimethylformamide (DMFA) Diethylene 97.8 50 2.3
glycol
DMFA, Diethylene glycol 94.0 30 2.2
DMSO, Glycerine 90.3 25 2.1
DMSO, Cellosolve acetate 92.4 50 1.7
Glycerine, Ethylene glycol,
Triethylene 98.1 25 3.1
Glycerine, Ethylene glycol,
Diethylene glycol 96.8 25 2.7
Glycerine, Ethylene glycol,
DMSO 91.5 50 2.0

TABLE 111

Effective agents for removing methanol from actone

Relative volatility
Compounds Ratio methanol to acetone

3-Hexen-2-one 4/3 3.0

Acetophenone 5/3 2.3
Ethylacetoacetate 5i3 2.2
o-Hydroxyacetophenone 2 1.9
2,4-Pentanedione 5/3 1.9
Ethyl butyl ketone 2 1.8
2-0ctanone 2 1.8
3-Heptanone 4/3 1.8
Phenyl ethyl ketone 1 1.7
Acetonylacetone 5/3 1.7
Methyl isobutyl ketone 4/3 1.5
Methylacetoacetate 5/3 1.5
2-Heptanone 2 1.4
Methyl isoamyl ketone 4/3 1.4
3-Pentanone 4/3 1.4
Diisobutyl ketone 2 1.4
Phorone 2 1.4
Methyl ethyl ketone 5/3 J.3
2-Pentanone 4/3 J.3
Cyclopentanone 2 J.3
Benzophenone, Acetophenone 1 1.8
Methyl ethyl ketone, Benzil 3/2 1.7

Note: The ratio is .the ratio of agent to agent to the binary mixture.
 ACETONE-METHANOL SEPARATION 75
TABLE IV

Data from rectification column

wt% Methanol Relative volatility

Agents Overhead Bottom methanol to acetone

Blank 10.0 7.0 1.09

Methyl ethyl ketone 31.1 6.2 1.53
2-Pentanone 43.6 7.3 1.66
3-Pentanone 43.9 5.8 1.76
Methyl isobutyl ketone 24.7 5.3 1.48
Methyl isoamyl ketone 30.9 4.6 1.64
2,4-Pentancdione 51.6 5.5 1.91
Downloaded by [National Taiwan University] at 20:48 14 May 2015

Diisobutyl ketone 31.8 4.8 1.64

Acetophenone 38.3 5.3 1.71
Ethyl acetoacetate 34.8 5.9 1.77
Methyl ethyl ketone,
Benzil 43.2 6.8 1.68

Notes: Mixture used comprised 7 wt% methanol and 93 wt% acetone. The agents were added at
20 ml/min and 25°C. The boil-up rate was controlled at 10-16 ml/min. The weight ratio of MEK to
benzil was 1.5. The analysis was based on agent free.

a stronger affinity for acetone than methanol and extract acetone down to the
bottom of the column. This leaves methanol as the overhead product. 3-Hexen-2-
one was the: most effective agent among the ketones.
Again, the extractive rectification column was used to confirm the effectiveness
of the agents, ketones. Table IV lists the relative volatility of methanol to acetone
when ketones were the agents. 2,4-Pentanedione was the most effective agent
among the ketones. The "blank" was made to demonstrate the result from
conventional distillation. The relative volatility is very close to one.
To assure that the agent, methyl ethyl ketone (MEK), is an effective agent, the
effectiveness of MEK was examined by using the methanol-acetone mixtures with
different compositions. Table V verifies that MEK is effective. In every case the
azeotrope is negated and the overhead product is richer in methanol than the
stillpot. This shows that the extractive distillation agent, MEK, is effective over a
broad range of concentration.
Temperature Inversion
When ketones were used as the agents, not only did methanol become more
volatile but also "temperature inversion" was observed. The temperature
TABLE V

The effectiveness of MEK at several compositions of the binary mixture

Composition of mixture wt% Methanol Relative volatility

wt% Methanol Overhead Bottom methanol to acetone
7 31.1 6.2 1.53
25 72.4 29.2 1.51
55 84.5 64.7 1.27
80 97.6 94.4 1.21
 76 A.-I. YEH, L. BERG AND K.J. WARREN
inversion was when overhead temperature was higher than the stillpot tempera-
ture. The thermocouples and temperature indicator were recalibrated against a
mercury thermometer. The reading was correct. The measurement was checked
by measuring the boiling point of methanol. At an atmospheric pressure of
643.5 mmHg, the boiling point of methanol was measured as 60.4°C using the
same apparatus. Interpolating from the data reported by Smith (1948) yielded a
boiling point of 60.6°C. A value of 60SC was calculated from the Antoine
equation provided by Reid et al. (1977). The measurement was assured.
Figure 4 shows a typical example of the progress of the overhead and stillpot
temperature. The initial binary mixture contained 15 wt% methanol and 85 wt%
acetone. Before the addition of the agent, MEK, the overhead temperature was
Downloaded by [National Taiwan University] at 20:48 14 May 2015

lower than that of the stillpot. After the addition of MEK, the overhead
temperature rose rapidly to 69°C in about ten minutes and then stayed at about
70.0-70.8°C during the rest of the operation. The stillpot temperature rose
gradually due to the addition of agent, MEK. After two hours running time, the
addition of MEK was stopped. The stillpot temperature did not change but the
overhead temperature dropped rapidly to about the temperature at time zero.
The difference of the temperature of overhead and stillpot, AT = To - T., is an
indication of the reversed temperature. Temperature inversion exists when A Tis
positive. Figure 5 illustrates the change of A T with time and the normal boiling
points of ketones. The numbers on the curves are the minutes during which the
operation proceeded. At time zero, the dashed line, AT was negative and almost
the same for all agents. The overhead temperature was lower than the stillpot
temperature. The same A T's at time zero was due to the same initial binary
mixture. Once the agent was added, the AT rose in all the cases studied. Then
A T decreased gradually due to the gradual rise of the stillpot temperature. This
figure shows that the agent with lowest normal boiling point gives the greatest
A T. As the normal boiling point of the ketones increases, A T becomes smaller
and the period for positive AT becomes shorter. The value of normal boiling

U
o

C
1
oi 65

...
73

:; _0-
6

/0
0.......
0_0
Overhead
~-6_6-6_6-6-6-6-6-6_A_o_o_0
_0-0-0-0-0-0-

Slit/pol
0

~ 57V

~ 1 6-6-6

:: [-~~--'----'---'----'----'--'------'--~-'--~~-~~
6

o 30 60 90 120 150

Time, min
FIGURE 4 Batch extractive distillation data for methanol-acetone using methyl ethyl ketone as
agent.
 ACETONE-METHANOL SEPARATION 77

10

~
• -10
f-
<J -15
Downloaded by [National Taiwan University] at 20:48 14 May 2015

-20

-25
-30
-35 L.._ _-':-_ _-'--_ _---'-_ _- - ' .L-_ _--'-_.:..-~
70 90 110 130 150 170 190 210
Normal B.P., °C
FIGURE 5 Change in difference of column temperature for several batch extractive distillations.

point is an indication of the volatility of the compound. MEK is most volatile

compound among the ketones used and has the greatest Ii. T.
Heat of mixing was the first reason suggested. However, no significant
temperature rise was observed when MEK was mixed with the acetone-methanol
mixture. It has been reported by Christensen et al. (1982) that the heats of mixing
between methanol and acetone, methanol and MEK, and acetone and MEK are
positive values. No exothermic heat of mixing can occur. MEK can hardly react
with acetone or methanol under the operating conditions. A piausable hypothesis
has been proposed by Yeh (1986). Based on his hypothetical calculation, the
dissolving of the vapor into the liquid phase could be the reason for temperature
inversion. The key components corning up the column as a vapor dissolve into the
liquid phase on the plate and give up their latent heats. The latent heats given up
by the vapor would partially evaporate the liquid and partially increase the
temperature of the liquid. From the calculation, it is possible to heat the liquid
MEK from 45 to 70°C by the latent heats given up by the vapors of methanol
and acetone. Further studies are needed to verify this hypothesis.
The methodology proposed by Yeh and Berg (1986) has been used to select
effective extractive distillation agents. The solubility parameters of acetone and
methanol are listed in Table VI (Barton, 1983). The difference in solubility
parameters for the key compounds, acetone and methanol, is slight in dispersion
force, only 1.4 (J/cm 3 ) 112, larger for polar interaction, 3.2 (J/cm 3 ) 112 and large for
hydrogen bonding, 13.0 (J/cm 3)1I2. The difference in specific volume is appreci-
able too, 34 cm 3/mo!.
 78 A.-I. YEH, L. BERG AND K.J. WARREN
TABLE VI

Solubility parameters and specific volumes for acetone and methanol

0.
Component v, cm'/mol (J/cm 3) " 2

Acetone 74.0 13.0 9.8 11.0

Methanol 40.7 11.6 13.0 24.0

16 ,\MSO
Downloaded by [National Taiwan University] at 20:48 14 May 2015

Glj!cerine
o 0
Ethylene Glycol
14 1.4 -Butonediol
oOMFA
Metho 01 0 0
_oS:' _~ Propylene Glycol
..,
~

Acetophenone \ ol.5-Pentonediol
E 12 I> 1>2.4'P{ntoned~o.lJe/
~ I>Ethyl Ace.~ooc(Jfote
J
~

~IO e,2J;etone
o 1.3-Butonediol
2-Pentonone I>MEK
I>1>3-Pentanone
8 I>M/BK
b.MIAK
I>OIBK
6::------------,':--------,-1:--------'----------'
2 10 26 34

FIGURE 6 Polarity diagram for the methanol-acetone system.

According to the difference in solubility parameter, there exists two ways for
selecting agents. One is to find the agents having a polarity similar to acetone.
Another choice is to select the agents with a polarity close to methanol. Figure 6
is the polarity diagram for the acetone-methanol system. The effects of the agents
follow the trend predicted by Yeh and Berg (1986). One exception is DMFA
which falls on the acetone side in the diagram but yields acetone as the overhead
product. Ritchie et al. (1969) have shown that DMFA can induce the acidity of
alcohols. DMFA behaves as the base. There exists strong molecular interaction
between DMFA and methanol. This leaves acetone as the overhead product.

CONCLUSION
-
The polarity diagram has been verified as a useful tool to predict the effectiveness
of the extractive distillation agents. From there, the overhead product can also be
 ACETONE-METHANOL SEPARA nON 79
predicted. Temperature inversion has been observed when ketones were used as
the agents. The phenomenon could be due to the dissolving of vapors into the
liquid phase. The latent heat given up by vapors heats up the liquid phase. This is
worth further study.

REFERENCES

Barton, Allan E.M., Handbook of Solubility Parameters & Other Cohesion Parameters, CRC Press,
(1983).
Benedict, M., and Rubin, L.C., "Extractive and Azeotropic Distillation, I. Theoretical Aspects,"
Trans. AIChE, 41,353, (1945).
Berg, L., U.S. Patent 4,292,142, Sept. 29, (1981).
Berg, L., U.S. Patent 4,692,219, Sept. 8, (1987).
Downloaded by [National Taiwan University] at 20:48 14 May 2015

Bojnowski, J.H., and Hanks, D.L., "Low-Energy Separation Process," Chern. Eng., p. 67, May
(1979).
Brilton, E.C., Nutting, H.S., and Horsley, L.H., U.S. Patent 2,324,255, "Separation of Ketones and
Monohydric Alcohols from Mixtures Thereof," July 13, (1943).
Christensen, J.J., Hanks, R.W., and Izatt, R.M., Handbook of Heats of Mixing, John Wiley & Sons,
Inc., New York, (1982).
Reid, R.C., Prausnitz, J.M., and Sherwood, T.K., The Properties of Gases and Liquids, 3rd ed.,
McGraw-Hili Book Company, New York, (1977).
Ritchie, C.D., and Coetzee, J.E., Solute-Solvent Interactions, Marcel Dekker, Inc., New York,
(1969).
Smith, J.M., "Thermodynamic Properties of Methyl Alcohol," Chern. Eng. Prog., 44(7), 521, (1948).
Sucksmith, I., "Extractive Distillation Saves Energy," Chern. Eng., p. 91, (1982).
Treybal, R.E., Mass-Transfer Operations., 3rd ed., New York, McGraw-Hill, Inc., (1980).
Yeh, An-I, "The Separation of Three Azeotropes by Extractive Distillation," M.S. Thesis, Montana
State University, (1983).
Yeh, An-I, "A Study of The Reversing of Relative Volatility by Extractive Distillation," Ph.D.
Dissertation, Montana State University, (1986).
Yeh, An-I, and Berg, L., "Reversing The Relative Volatility by Extractive Distillation," Recent
Advances in Separation Techniques-Ill., AIChE Symposium Series No. 250, vol. 82, (1986).

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