Journal of Molecular Liquids, 5 0 ( 1 9 9 1 ) 39-,52

39

E l s e v i e r S c i e n c e P u b l i s h e r s B.V., ~ , r n

Thermodynamic

Studies

Furan

on

the

Derivatives:

Binary

Liquid

Furfural

Hixtures

t Allphatic

Containing

Ketches

Homendra
Naorem
and Sushll
K. S u r i ~
Department
of Chemistry,
Indian
Institute
of Chemistry,
Delhi
Hau~
Khas.
New Delhi
- 110016.
(India)

(Received

22 October

1990)

ABSTRACT
The
K E ,

and

of

excess

viscositles,

fu~fural

over

the

be

it

with

The

was

been

were

the

range

for
E

the

compressibillties,

binary

2-butanone,

all
the

mixtures

over

the

entire

the

2-pentanone

in

the

light

between

the

component

been

mixtures

for

the

determined

containing

were

found

range

The

and
while

results

specific
in

and

acetone

composition

molecules

mixtures

2-penta.one

studied

mixtures.

of

liquid
and

have

the

for

discussed

interactions

KE

positive

negative

for

acetone,

and

and

E . isentroplc

mixing

composition

VE

negative

2-butanone

volumes,V

R E , of

entire

reported.
to

molar

have

intermolecular
the

mixtures_

INTRODUCTION
Thermodynamic
liquid

studies

mixtures

hydrocarbons

of

have

between

interactions

were

of

furan

expect

or
with

for

aromatic

the

0167-7322/91/$03.D0

solution

presence

component

to

be

behavlour

hydrocarbons
of

the

of

(THF)

with

strong

unlike

molecules

stronger

dlpole-dlpole

weakening

the

the

found

induced

~he

tetr~hydrofuran

reveal~d

interactions

dlsper~lon

on

than

The

exhibited
unlike

5-~

binary
various
speelflc

(I-ii).

those

forces.

of

These

expected
binary

mixtures

similar

behavlour

interactions

1991 m E l s e v i e r S c i e n c e P u b l i s h e m B.V.

from

All rights reserved

in

the

furan

mixtures

due

furan

molecule

(12).

furan

the
the

ring

or

unlike

viz.

than

were

the

alcohol

and

the

of

to

liquid

the

our

mixtures
the

compresaibilitias.
furfural

wfth

three

butanona.

and

2-pentanone

purpose
Oil

the

organic

of

these

solvents

understanding
interactions

excess

over

behavior
of
of

present

of

varying
the
in

to

polarities

in

these

the

the

more

of

we

have

mixtures

of

acetone,

2-

range.

The

informations
furfural

to

nature

decrease

isentropic

of

order

the

behaviour
furan.

provide

of

increases_

composition

mixtures

and

to

alcohol

namely,

binary

type

found

for

These

group

BXC6SS

entire
is

relatively

interactions

waa

substittited

of
self

(14.16).

aolution

ketones
the

be

-08

the

visoosities

aliphatlc

with

the

volumes,

investigations

solution

of

the

strength

bond

and

on
a

excess

The

the
of

furfural

interaotion

containing

and

associatea

hydrogen

group

by

determined

to

overall

the

mixtures

investigations

molar

aloohol

of

furfural

alkyl

containing

observed

of

the

ln

(11-15).

were

presence

of

change

dipolar

mixtures

of

significant

was

molecules

the
in

furfural

the

In
group

mixtures

hydrocarbon

group

length

determined

the

stre,ngth

continuation

of

binary

the

carbonyl

chain

binary

mixtures

cloud

a functional
a

binary

alcohola

to

about

the

of

fl-alctron
of

or

alcohol

those

the

In

in

attributed

between

bring

effect

furfuryl

of

furfural

aliphatic

stronger

to

of

interaotions

associated

presence

introduction

found

breaking

furfural

In

The

behaviour

struoture

the

behavfour.
furan

solution

as

was

s01uti0a

substituted

to

of

have

the

with
better
unlike

mixtures.

EXPEEIMMTAL
The
pentanone

laboratory
supplied

reagent
by

grade

Merck,

samples

India

were

of

X-butanone

treated

(17.18)

and

2with

potassium

aqueous
distilled

to

4-5

over

days

anhydrous

carbonate

remove

most

distilled

Spectroscopic

grade

such

without

one

the

was

purified

liquids

refractive
accepted
The

molar

the

excess

volumes

liuuid

mixtures

density

meter

experimental

l_

data.

were
(UMA

measured
60/602.

techniques

Densities

and

have

and

are

in

1,

Table

mixing

were
of

been

Refractive

of

the

used

sample

of

The

the

with

the

from

the

and

the

liquids
tube

digital

details

of

the

earlier(l2)_

described

indexes

was

and

computed

The

and

fractionally

vibrating

Paar).

over

(13).

compared

the

for

column.

densities

solvents

Anton

decanted

studies

The

using

was

The

use.

IJenaities

stored

treatment.

bottles

of

then

EMerck

previous

(17,181

dried

by

brown

purified

values

density

experimental

in

was

was

fractionating

supplied

our

mixture

sample

and

long

acetone

In

the

liquid

Im

before

of

literature

stored

were

indexes

sulfate

purification

used

immediately

distilled

Table

further

The

The

through
of

and

water.

sodium

sample

any

furfural

the

uarbonate.

fractionally

as

of

anhydrous

potassium

solution

liquiLds

used

298,15K,
-_--_------_----_______~-___-~______---____---_--_---_~~--~----Denfsitfea
-----------------_---LIquida
our value
lit,
value*

Refract+ve

Indexes

___-__---_____--____---lit, value*
our value

__---_----_-----________------_--_____-________--~~---~~---__---~
Furfural

l-15493

l-1545

l-5236

l-52345

Acetone

O-78451

o-7844

l-3569

l-3661

2-Butanonet

O-79981

O-7997

l-3670

l-3761

2-Pentanone

O-80158

1-3857

--

Ibference

17

--

at

42

Duplicate

density

agreed

measurement
+

within

to

uncertainty

of

3.008

of

the

liquids

5x10-5

g-cm -3 . This

cm3.mol

-'

in

the

and

mixtures

liquid

propagates
values

VE

maximum

reported

in

this

paper.
The
the

experimental

liquids
k,
Tha

the

relation

and

were

ultrasonic

calculated

sound

speed

speeds

New

The

where

#i

and

and

in

the

this

k,i

the

using

liquids.

Kinetic

The

of

of

being

single

fixed

Mittal

frequency

ICE, of

the

of

mixtures

'u'

in

was

the

mixtures.

estimated
of

+2

isentropic

and

to

TPa-'

be

The

maximum

0.15

percent

Lhe

in

k,

values

(2)the

of

the

The

liquids

Ubbelohde

benzene.

were

toluene

level

and

water

were

values

viscositY

measured

suspended

corrections

energy

using
viscometer

as

reference

applied

were

to

reproducible

the
to

centipoise.
were

the

more

Y'

unaertainty

purified

with

of

at

F-81.

fraction

volume

component

to

solutions
tightly

operating

the

(7)

data.

preparation

the

(2) -

an

similar

0.002

of

relation:

visaosities

experimental

using

(Model

compressibility.

equation

calibrated

Ketones

India)

measurement

viscometer

covered

interferometer

are

of

using

The

measured

were

-+s2

propagates

calculated

within

the

-&k,1

compressibility
error

sound

isentropic

from

KE= ks

of

Delhi,

excess

computed

(u)

variable

path

Ml%.

from

(1)

ultrasonic

Enterprise,

were

(p)

(k,)

(u2. p)-l

crystal

density

using

compressibilities

isentropic

prepared

by

teflon

septuma_

solutions

have

volatile

were

weight
Details
been

in

pyrex
of

described

introduced

into

glass

the

bottles

technique
earlier

the

bottle

for
(12)first

43

and

weighed,

content

Furfural

of

the

was

bottle

Corrections

for

RESULTS

DISCUSSION

AND

The
given

Table

Tables

introduced

were

applied

V E . KE
2-4

and

into

thoroughly

were

bouyancy

experimental

in

then

and?=
shown

the

bottle

mixed

and

to

all

the

for

the

binary

graphically

5 Molar
exaez3s volumes
of mm,
for
the
binary
mixtures
aliphatia
ketones-

are

Figures

l-3

in

308_15K

298_15K
furfund+
0,0827
O-1922
0,274o
O-3508
O-4264
O-5247
0_6096
0-8395
O-9236

acotona
0_0835
0.2293
O-2952
O-4181
O-4630
O-5401
Om6009
O-7445
O-8795

-0.25s
-0,438
-0-546
-0,627
-0,644
-0-625
-0,598
-0,296
-0,142
furfural

0_1070
O-1938
0.2776
O-4047
O-4843
0.5874
O-6605
O-7553
O-8714

-0,142
-0.273
-0,292
-0,487
-0-531
-0,529
-0-467
-0,382
-0,254
_-------

----__--

-0,258
-0,557
-0,649
-0,736
-0,725
-0.702
-0,656
-0-482
-0,235

2-lmAJ3noneJ
0.0948
O-1895
O-3447
O-4605
O-5703
0.6449
0.7336
O-8022
O-9132

-0.227
-0-366
-0,471
-0,542
-0,553
-0,521
-0,462
-0.368
-0,218
fu.rFuraI

O-0751
0.1497
O-2344
O-3351
O-4185
0.5071
0.6237
O-7186
O-8272
-_-___----------

V=

-0,229
-0,403
-0,562
-0-598
-0,570
-0,502
-0,408
-0,331
-0-162

2-pentanone
O-0898
O-2113
0,317o
O-4064
O-5338
O-5969
O-6886
O-7840
O-8674
,_-----_-_-_

weighed.

mIxt.ures

-_-_____-_-__-_-_____-__~~~_~~__~_-_---~-~-~-~-_--------

x
V=
_------_---_-_-_-____~---~-~-_---~-~-~~~-~~--~-~-~-~~~~~~

the

wsighings.

VE <am3aol-1)
with
furfural

of

and

-0,160
-0-343
-0,453
-0-490
-0,485
-0,444
-0-377
-0,285
-0-188
--_-a .-----w--s

44

Table

= Volums
fraction,
@.
density
comgreasibflity,
isentrophz
iSf3M2OpiC

.Qm

speed
of sound.
u.
k,,
mnd
BXc888
IACJ binary
BF.
for
aliphatic
ketones
at

aompm3saibility.

with
mix-txlrea
of
furfural
308-15
K_
__--_______---_--_----------~~~--_____~~--__-__--------_--_~k
TPa=-1
furfural
O-0

O-1381
0.2660
0,4057
O-4628
O-5731
O-6900
0_7311
O-8517
O-9562
1-O

o-77337
Q-82831
O-87839
O-93217
O-95373
o-99431
1103639
l-05093
1,093Ol
1.12882
l-14372

Oe78935
O-84022
0.87053
O-90653
o-s5390
O-96647
l-01482
l-06678
1,08810
l-12944
l-14372

O-0
O-0936
O-1227
0_2693
O-3812
O-4548
O-5351
O-7081
O-8364
O-9246
l-00

0.79047
0.82525
O-83566
0.88984
0.93018
O-95635
0_98460
1.04450
l-08958
l-11822
1.14372

1183
1202
1217
1246
1274
1291
1312
1343
1366
1385
1404

-70
-101
-114
-111
-98
-82
-72
-42
-13

z-butJ%none
950
833
765
713
642
626
564
509
489
455
444

1155
1195
1225
1244
1278
1286
1322
1357
1371
1395
1404
furfural

acetone

1040
888
780
684
653
600
547
532
490
457
444

1115
1166
1208
1264
1267
1295
1328
1338
1366
1392
1404
furfural

O-0
O-1350
0_2166
O-3149
O-4460
O-4814
O-6192
0.7705
0.8335
o_s570
1.0

-49

-74
-78
-82
-80
-73
-51
-39
-11

2-pentanon
901
839
808
724
662
627
590
531
492
466
444

-19
-37
-54
-65
-66
-66
-46
-27
-12

4s
Table

vlacosltlaa
excess
and
lDeslit*~
(p.&K+.
(92.
cp)
vimzositias
(q . cp) for the binary
mlxturea
of furfural
with
aU.phatic
Latin05
__--__-__________~_-_~---_--_------__--_---_--__--__--___-------_--_-----furfural

acotona

308.15E
0.0964
0*8159
0.414
O-022

O-1804
O-8517
O-524
o-041

0.2705
O-8891
O-634
O-054

O-3561
O-9232
O-735
O-063

O-4327
0.9527
0.819
0.064
303.15

3c

O-1083
O-8262
0,432
0.011

%s
'I.

0.2488
O-8866
O-639
0.058

O-3465
O-9248
0.763
O-071

0_4336
0.9581
0.861
O-069

O-0927
0.8264
0.44s
0.020

0_1922
O-8677
O-591
0,052

0.2740
0.9012
O-702
O-066

O-5007
0_9833
0.9s4
O-066

O-3508
0_9320
0,804
0,076

0.1002
0.8245
0.460
O-010

O-2134
O-8643
O-587
0.022

0.3087
O-8980
0,694
0.031

O-4301
O-9409
O-822
0.036

0.1238
O-016
O-516
0.8378

0.2186
O-026
0.628
0.8714

O-3164
O-037
0,744
0.9059

0.4005
0-9357
0.839
0.042

O-1070
0.8373
0.517
O-015

O-1938
0_8879
0.625
O-026

O-2776
O-8976
0.729
O-036

O-4047
O-9426
O-881
O-046
fux-furel

O-8229
O-1062

0.1754
O-8439
O-548
-0,027

O-2946
0.8616
O-649
-0.041

0.3839
0.9108
O-729
-0.047

0.8403
l-0996
I-282
0.026

0.9253
l-1263
l-365
O-012

O-5247
O-9975
I.001
O-066

0.6038
l-0261
l-090
0.061

0.8S95
l-1051
1.328
O-018

O-9236
1.1315
1.424
O-014

O-5746
0_9921
0.967
0.033

O-6278
l_OllO
1.018
O-030

O-7079
l-0394
l-094
0,025

O-8414
l-0869
1.218
0.013

O-6332
O-032
1.021
1.0183

O-7244
O-026
1.104
1.0506

O-8024
0.019
l-174
1.0783

0.9061
O_OOB
l-285
l-1155

0.5874
l-0076
l-078
o-039

0.6605
1.0335
l_lS6
O-035

O-7553
1.0673
1.255
0.026

0.8714
l-1089
l-973
O-016

O-6837
1_0165
1.026
-0.037

0.7683
l-0487
I-115
-0,030

0.8639
l-0866
l-219
-0,017

O-4843
O-9709
O-969
0.046

+ 2-pentanonar
308.15

"p

O-7622
l-0742
l-203
O-036

0.5146
0,960
O_BY62
0.041

298-15
"p
h
5

O-6620
l-0267
1.081
o-054

0.5163
O-9715
o-911
0.037
303-15

b
3

0.8688
1.1088
l-263
O-018

2-butJxnona

308-15
:

O-7513
l-0653
l-136
0.037

O-4284
O-9618
0.893
O-073

furfural

O-6013
l-0142
O-993
0.056

288-15
x

O-5118
O-9822
0.903
0.063

O-4777
0.9426
0.813
-0-053

O-6010
O-9861
0.930
-0.046

46
K

303-1s
F
%c
"L

O-3042
O-8887
0,681
-0-047

O-1968
0.8556
O-587
-0-032

0_1134
0_8299
0_516
-0-018

O-4426
0_9357
0.813
-0.056

298-15
x

0_0896

O-2113
O-8652
O-621
-0.035
--------

r93pect1ve1y.
fitted

where
the

The

into
YE

O-8362
1.0807
l-246
-0,025

0-9118
l-1115
1.335
-0-013

0.5969
0.6886
0_9951
1_0289
l-013
l-120
-0.047
-0,056
--------_ _--a-P

0.7840
1.0657
l-233
-0.036
--------

O-8674
1.0991
1.337
-0,022
ll_-----

0.4064
0.5338
O-9287
O-9727
0.943
0,806
-0,060
-0.058
---1---------

experimental

smoothing

excess

equations

values,

of

the

YE(=VE

type

ortE),

were

= x1.x2CA0

+ A1(x1-x2)

+ A2(x1-x21'

+ A3(~1-x~)~l

(3a)-

KE=

1_

+ AIC+l-~)

+ A2(#'l-fi)2

+ A,(e-%)3l

(3b).

xi

and#i

2C%
are

the

'i'

in

component

values

of

the

given

in

Table

fit.

0_3170
0_8991
0.720
-0.049
-------

O-7580
1_0499
l-157
-0.034

O-6634
l-0141
l-052
-0.043

0_5830
O-9848
0_961
-0.052

Since

mole
the

constants

the

the

experimental

the

constants

fraction
mixture

determined

5 along
6(YE)

with
values

uncertainty
Ai's

can

and
and

Ai's

by

method

the

standard

for

all

used

of

fraction

the

The

smxares

least

6(YK)
are

of

less

measurement

represent

of

constants.

are

mixtures
in

to

volume

deviation

ths

involved

be

the

the

are
the
than

of

YE.

experimental

results.
It
values

is
for

from

observed
all

composition

the

mixtures

range.

containing

acetone

The
and

containing

2-pentanone

composition

range

more
(or

or

less

minima)

figures

1 and

studied

are

for

binary

q"

2-butanone

(Figure

found

to

3).

The

symmetrical

to

at

x=0.45

around

the

2 that

negative

the

VE

over

the

mixtures

are

positive

while

be

negative

over

plota

of

YE

composition
to

0.55.

vs.
axis

To

the

and

KE

entire

of

furfural

for

mixtures

the

entire

composition
with
best

are
maxima

of

our

Table

5,

values
of
deviation

p"pm
6<~

eters
Zm Eqs.<3a
) of exp~~imtmtal

and

3bl

results

and

at

standard
308-15E-

Furfural
+

Acetone
2-butanone
z-_pentanone

-2-8860

Acetone
L-butanone
2-p43ntanona

-433
-325
-264

Aaetona
P-butanone
2-Pent.anona

O_ 2525
O-1440
-0,200Q

O-5963
O-5346
-0.0641

-2,354o
-2.0867

163
102
83

0.2068
0_0069
O-5320

-52
-58
57

-0.0956
-0wO328
O-0335

0,2155
-0-2278
O-6292

23
14
36

-0,056O
-0-0718
O-0764

0.0731
O-Q284
-0.0224

0,006
0,006
0.008

3
3
4

O-001
0.001
0_.002

x
00

0.2

0-L

0.0

on

-0.2

; ;

-u
E

-Q6

+.I~
Fig.1

-VE

Vs. x for the

systems
turfural+
+ 2-pentanoneto
1 at 308.15K (broken

acetone(o),
+ Zbutanone(v)
lines at 298_15K I.

Fig.2

KEVs.@

f or

2-butanOne

the
(v),

binary
mixtures
of turfural
with
and 2-pentonone(a1
at 308.15.

acetone

?,
I-

!
Fig.3.$

at

Vs. x for
29&15(O),

+ acetone (0 1. 2-buta none{ b), 2-pentononek)

303_15(fi), and 308.15K(0)
respectively.

turfural

(0

1,

48
there

knowledge
considered

here

The

the

to
As

gohf3

from
'structure

in

the

breaking'
of

The

the

solvent

to

an

aluohol)

and

as

the

unlike

exist

to

a5

of

of
is

mixtures

results-

addition

breaking

the

of

our

known

to
of

hydrocarbon

strength

binary

leads

any

compare

are

state(l9).

polarity

for

to

furfural

pure

the

available

literature

furfural

associates.

the

data

of

the

in

solvent

dipolar
non-polar

dipclar

these

increased

there

is

consequence

Ii-e.
decrease

thereof

interactions

in

on

an

in

increase
resultant

the

mixtures(l3.16)_
The

m;>lecules

through

dipolar

reported

breaking

of

strong

binary

of

unlike

view

binary

of

in

of

the

an

in

of

the

the

state.
to

between

an

the

assouiated

Radojkovic

However,

and

an

et

al<201

ketone

leads

the

component

form

presence

molecules

aromatic

of

hydrocarbon

(20-22).

overall

solution

investigation

may

effects

effects

the

aliphatic

the

ketone

opposing

making'

in

associates.

above,

two

pure

literature

under

the

exist

alkane

dipclar

containing

'structure

binary

also

interaction

mixtures

resultant
and

UP

reported

In

ketones

addition

mixtures

been

of

interactions

that

to

in

be

namely

each

of

behaviour
envisaged
'structure

the

of

the

as

the

breaking'

components

of

the

mixtures_
The

fairy

1.)
strong

the

suggest
and

mixtures.

binary

that

the

predominant
The

mixtures

large

of

indicative

of

interactions

in

the

trend.

expeuted

VE

negative

observed

(Figure

in

in

no

molecules

associates

has

are

the
the

unlike

over

presenae

VB
with

of

for

the

dipolar

the

negative

furfural

mixtures

value8

breaking
as

compared
alcohola

aliphatic
relatively

containing

ketones

mixtures

Interactions

structure
values

binary

are
effects
to

the
are

stronger

unlike

and

follow

hence

50

At

equimolar

acetone<
the

Z-butanonec

unlike

the

increase

group
in

the

(ii)

also

The

observed

appears

which

more

than

is

between

to

in

the

in

increasingly
the

for
strong

from

the

and

mutual

specifiu
for
of

the

the

the

volume

Ci)

an
and

mixtures(Figure

volume

molar

1)

of

the

interactions

changes

from

arising

interactions

dipolar

of

molecule

intermolecular

unlike

by

of

form

the

with

group

of

values
of

large

are

the

that
ketone

the

the

observed

presence

mixturas
to

KE

KE
in

which

is

arising

for

the
those

present

(16).
the

which

with

interactions

of

furfural

values

ketone

as

become

interactions

values

the

stronger

increases

to

aggregates

containing

increases

isentropic

unlike
KE

to
pO3itiVO

expected

contribution

unlike

exceaa

in

of

KS

to

suggest

comparison

relatively

leads

the

dipolar

that

mixtures

negative

positive
of

interactions

are

interaotions

reveals

the

KE

consideration

the

2.

liquid

specifio

negative

strength

mixtures

Figure

of

uontributing

and

The

other.

alcohol

in

thereby

The

as

each

presence

sound

under

systems

former

the

free-space

rupturing

an

alkyl

in

molecules

compensates

containing

the

decrease

dipole-dipole

binary

observed

of

VE

increases.

furfural

the

approach

of

t,he size

from

of

that

mixtures

ketones

arise

oo-effioient

(23-26).

unlike
than

may

in

temperature

speeds

mixture

more

increase

the

extent

negative

these

strength

the

in

aomponent

oompressibilities

in

that

order:

temperature.

the

&viation

the

interactions

the

established

decrease

follows

dispersive

from

the

the

This

olosest

compensates

in

in

It

in

due

with

ketone..
of

formed

decrease

increase

the

negative

mixture

binary

of

distance

be

indicating

decrease

decrease

to

VK 0.5

Z-pentanone

interactions

alkyl

the

ooacentration.

It

chain

is

in
also

len&h

of

indicative

of

61
relatively
higher

weaker

ketones.

conclusions

These

arrived

The

the

presence
unlike

butanone

positive

compared

tp

the

mixtures

decrease

in

mixtures

wherein

'2E

dipolar

at

resistance

to

temperature

co-efficient

indicates
over

the

and

for

:n

interactions

VE

and

KE

hence

predominance

decrease

unlike
the

flow

the

of

while

the

resistance

and

corroborates

an

into

TE.

the

due

the
The.

tend
a

The

to

lesser
positive

'2-pentanone

hindrance

flow

in

would

containing

increased

present.

are

in

,)LE

opposite

expected

resulting

of

2-

2-pentanone.
is

dearease

the

and

2-butanone

molecules

mixtures

between

acetone

and

interactions
the

the

2-pentanone.

temperature

temperature

that

Indicates

containing

acetone

between

higher

more

the

mixtures

containing

unlike

with

interactions

temperature

increasing

dissociate

the

containing

of

interactions

agreement

for

dipolar

ones

containing

2-pentanone

mixtures

strong

mixtures

studies.

containing

for

with

good

mixtures

increase

observed

was

in

values

stronger
binary

the

the

2-butanone>

relatively

with

strong

rE

acetone>

for

are

in

volumetric

in

Further
decreases

the

molecules
as

trend

from

trend

of

interactions

conclusions

observed

follows

the

unlike

to

of

rotation

decrease

conclusions

in

drawn

from

studies.

References
1.

s.
Jap.

Murakami.
1968.
a.

2.

A.W.

Andrews

3.

D.D.

Dsshpande

4.

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M.D.

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M.
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