IJPRD, 2014; Vol 6(10):December-2014 (005 - 014)
International Standard Serial Number 0974 – 9446
-------------------------------------------------------------------------------------------------------------------------------------------------EXCESS VOLUMES, DEVIATION IN VISCOSITIES AND IR STUDIES OF O-DICHLOROBENZENE AND OCHLOROPHENOL WITH ACETONE, ACETOPHENONE, CYCLOHEXANONE AND CYCLOHEXANE
V J NAUKUDKAR*1 and A. B. SAWANT2
1*
Department of Chemistry, K. V. N. Naik, Arts, Commerce & Science College, Nashik, Nashik 422 002,
Maharashtram, India
2
Department of Chemistry, M S G College, Malegaon Camp 423 105, Maharashtra, India
Both college affiliated to Savitribai Phule Pune University.
ABSTRACT
The densities and viscosities of binary mixtures of odichlorobenzene
and
o-chlorophenol
with
acetone,
acetophenone, cyclohexanone and cyclohexane have been
measured at room temperature. These binary mixtures also
studied by Infrared spectroscopy. The data have been utilized to
compute the excess volumes, deviation in viscosities and
correlate to Infrared spectroscopy. The results have been
interpreted in terms of molecular interactions existing between
the components of the mixtures.
Keywords- Excess molar volume, Viscosity deviation, Infrared
spectroscopy, o- Dichlorobenzene, o-Chlorophenol, Ketones,
Cyclohexane, Molecular Interactions.
Correspondence Author
V J NAUKUDKAR
Department of Chemistry, K. V. N.
Naik, Arts, Commerce & Science
College, Nashik, Nashik 422 002,
Maharashtram, India
Email: [email protected]
INTRODUCTION
The
composition
dependence
of
thermodynamic properties has proved to be very
useful tools in understanding the nature and extent
of pattern of molecular aggregation resulting from
intermolecular interaction between components1,
2
. In the present paper binary liquid mixture of odichlorobenzene (ODB) and o-chlorophenol (OCP)
with
acetone
(AC),
acetophenone
(AP),
cyclohexanone (CYNO) and cyclohexane (CYN) have
been studied. The thermodynamic and transport
properties of o-dichlorobenzene (ODB) and ochlorophenol (OCP) with above ketones have been
studied over the entire composition range at
298.15 K.
Experimental
The entire chemical used was of A. R. grade
with purity >99% are used as such. The purity of
liquid was checked by comparing experimental
values of densities and viscosities of these liquids
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International Journal of Pharmaceutical Research & Development
with those reports in the literature (Table 1)3-9.
Binary mixtures were prepared by mixing a known
mass of each liquid in an airtight, stoppered glass
bottle. The masses were recorded on digital
balance (SHIMANZU AUX 220) to an accuracy of ±
1× 10-4g. The estimated error in mole fraction was
< 1× 10-4. Care was taken to avoid contamination
during mixing. For present study a specific gravity
bottle10/single stem pycnometer11 was used for the
density measurements. The specific gravity bottle
was calibrated with freshly prepared triply distilled
water. The density measurements for each
experimental liquid were repeated three to four
times. This procedure enabled us to get an
uncertainty of ±5 x 10-4 gm/cm3 in density
measurements. The density measurements for
each experimental liquid were repeated at least
three to four times and the results averaged. This
procedure enabled us to get an uncertainty of
±0.0005 gm.cm-3 in density measurements.
I.R. measurement through liquid mixtures
provides an excellent tool to investigate inter and
intramolecular interactions between like and unlike
molecules. I.R. spectroscopy studies of pure and
binary mixtures of ODB and OCP with ketones have
been recorded over the whole composition range
at room temperature and atmospheric pressure.
ISSN: 0974 – 9446
Theory
The excess molar volume (VE) can be computed
from experimental density data using the
relationship.
VE = x1M1[1/ρm – 1/ρ1] +
x2M2[1/ρm – 1/ρ2]
Where, xi, Mi and ρ i designate the mole fraction,
the molecular weight and the density of the
component i. ρm is the density of mixture. The
Ostwald viscometer was calibrated with triply
distilled water at 298.15 K. A viscometer was
selected having a flow time of approximately 100300 seconds at 298.15 K. The flow time
measurement was repeated a number of times
(usually 5-6 times). The difference reading did not
deviate from the mean by more than 0.2s. To
determine the influence of temperature on
viscosity, the time of out flow was measured at
298.15 K. From the densities and times of flow,
absolute viscosities of the liquid mixtures were
calculated. Deviations in viscosities (∆η) were
obtained as follows:
∆η = ηmix – (x1 η1 + x2 η2)
(2)
where η1 and η2 are the viscosities of pure
components 1 and 2, respectively and ηmix is the
viscosity of the liquid mixture.
Table 1. Comparison of experimental data of ρ and η with literature at 298.15 K.
Liquids ρ x 10-3 kg. m-3
Exp
η x 103 kg. m-1. s-1
Lit
3
Exp
Lit
1.326
1.3243
ODB
1.2995 1.3003
OCP
AC
AP
1.2577 1.25723 3.479
0.7846 0.78444 0.305
1.0231 1.02385 1.612
-0.30294
1. 6176
CYNO
CYN
0.9423 0.94227 1.895
0.7737 0.77388 0.881
-0.8869
RESULTS AND DISCUSSION
VE and ∆η studies:
The derived parameter data VE and ∆η at the
experimental temperamental are listed in Table 2
and 3.The density and viscosities for the binary
mixtures of ODB with AC, AP, CYNO, and CYN are
listed in Table 2 and OCP with AC, AP, CYNO, and
CYN are listed in Table 3 at atmospheric pressure
and at 298.15 K. Figures 1 to 4 exhibit the variation
of VE/∆η of ODB/OCP with ketones at 298.15 K and
atmospheric pressure.
ODB + Ketones: From Figure (1), VE are negative for
binaries ODB + AC, ODB + AP, ODB + CYNO, ODB +
CYN at 298.15 K and atmospheric pressure over the
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International Journal of Pharmaceutical Research & Development
ISSN: 0974 – 9446
to the formation of weak molecular complexes,
when compared to all remaining mixtures.
entire range of composition. ODB + CYN for which
the VE values are more negative, which may be due
Excess Molar Volume
Mole Fraction
0.00
-1.00 0.0
-2.00
-3.00
-4.00
-5.00
-6.00
-7.00
-8.00
-9.00
0.2
0.4
0.6
0.8
1.0
Figure 1. Variation of VE for for (x1) ODB + (1-x) AC (■), AP (X),
CYNO (●) and CYN (■) at 298.15 K.
values of ∆η generally follow the order: CYNO > AP.
Figure (2) shows the variation in ∆η for
The positive values of ∆η in these mixtures can be
binaries ODB + AC, ODB + AP and ODB + CYNO at
interpreted in terms of strong interactions
298.15 K. ODB + AC show negative deviation. ∆η
between unlike molecules, ODB + CYNO and ODB +
values shows negative due to dispersion forces are
12
AP.
dominat . ODB + PN show positive deviation. ODB
+ CYNO and ODB + AP show positive deviation. The
Table 2. ρ, η, VE and Δη of binary liquid mixture at 298.15 K.
ρ x 10-3 η x 103
kg.m-3 kg.m-1.s-1
ODB(x1) + AC(1- x1)
0.0681 0.8334 0.378
0.1412 0.8880 0.434
0.2199 0.9420 0.491
0.3048 0.9953 0.552
0.3967 1.0479 0.624
0.4966 1.0995 0.709
0.6054 1.1496 0.817
0.7245 1.1994 0.938
0.8555 1.2484 1.086
ODB(x1) + AP(1- x1)
0.1033 1.0527 1.570
0.2058 1.0850 1.565
0.3076 1.1154 1.554
0.4086 1.1438 1.535
0.5090 1.1709 1.512
0.6086 1.1976 1.479
0.7075 1.2240 1.439
x1
VE x 106 Δη x 103
m3.mol-1 kg.m-1.s-1
-0.191
-0.439
-0.624
-0.738
-0.801
-0.780
-0.634
-0.468
-0.227
-0.030
-0.041
-0.056
-0.073
-0.085
-0.092
-0.084
-0.072
-0.044
-0.244
-0.756
-1.040
-1.105
-1.045
-0.943
-0.821
0.030
0.057
0.077
0.089
0.098
0.095
0.086
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0.8057 1.2494 1.397
0.9032 1.2728 1.345
ODB(x1) + CYNO(1- x1)
0.0929 0.9848 1.992
0.1872 1.0267 1.942
0.2831 1.0678 1.886
0.3805 1.1082 1.827
0.4795 1.1436 1.763
0.5802 1.1775 1.690
0.6825 1.2096 1.613
0.7866 1.2414 1.525
0.8924 1.2704 1.400
ODB(x1) + CYN(1- x1)
0.0967 0.8349 0.888
0.1942 0.9080 0.916
0.2923 0.9779 0.946
0.3912 1.0467 0.979
0.4908 1.1128 1.019
0.5911 1.1727 1.064
0.6922 1.2185 1.111
0.7940 1.2553 1.159
0.8966 1.2742 1.214
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-0.614
-0.240
0.075
0.053
-0.940
-1.546
-2.033
-2.431
-2.349
-2.125
-1.763
-1.378
-0.759
0.159
0.168
0.172
0.174
0.173
0.163
0.150
0.128
0.069
-1.500
-3.858
-5.546
-6.905
-7.865
-8.176
-7.263
-5.653
-2.603
-0.013
-0.023
-0.033
-0.040
-0.039
-0.035
-0.028
-0.020
-0.008
Table 3. ρ, η, VE and Δη of binary liquid mixtures at 298.15 K.
x1
ρ x 10-3 η x 103
kg.m-3 kg.m-1.s-1
OCP(x1) + AC (1- x1)
VE x 106
m3.mol-1
Δη x 103
kg.m-1.s-1
0.0746 0.8311 0.421
0.1535 0.8871 0.543
0.2371 0.9388 0.707
0.3260 0.9898 0.936
0.4204 1.0397 1.258
0.5211 1.0866 1.708
0.6286 1.1309 2.158
0.7437 1.1717 2.581
0.8672 1.2104 2.988
OCP(x1) + AP (1- x1)
0.1127 1.0507
2.098
0.2223 1.0834
2.540
0.3289 1.1156
3.043
0.4325 1.1408
3.566
0.5334 1.1618
4.100
0.6317 1.1815
4.323
0.7274 1.1992
4.273
0.8206 1.2164
4.145
0.9114 1.2334
3.598
OCP(x1) + CYNO (1- x1)
-0.401
-1.167
-1.520
-1.807
-1.996
-1.949
-1.700
-1.177
-0.483
-0.158
-0.284
-0.382
-0.431
-0.405
-0.270
-0.158
-0.096
-0.075
-0.519
-1.535
-2.412
-2.554
-2.299
-1.945
-1.433
-0.901
-0.382
0.311
0.545
0.844
1.169
1.511
1.546
1.313
1.008
0.287
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International Journal of Pharmaceutical Research & Development
0.1028 0.9798
2.656 -0.850
0.2049 1.0188
3.393 -1.589
0.3064 1.0575
4.248 -2.250
0.4073 1.0949
5.064 -2.743
0.5076 1.1275
5.545 -2.796
0.6073 1.1576
5.560 -2.625
0.7064 1.1855
5.426 -2.290
0.8026 1.2104
4.958 -1.786
0.9027 1.2342
4.181 -1.107
OCP(x1) + CYN (1- x1)
0.1056 0.1056 0.1056 0.1056
0.2100 0.2100 0.2100 0.2100
0.3130 0.3130 0.3130 0.3130
0.4148 0.4148 0.4148 0.4148
0.5153 0.5153 0.5153 0.5153
0.6146 0.6146 0.6146 0.6146
0.7127 0.7127 0.7127 0.7127
0.8096 0.8096 0.8096 0.8096
0.9054 0.9054 0.9054 0.9054
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0.598
1.173
1.867
2.524
2.846
2.702
2.411
1.792
0.855
0.1056
0.2100
0.3130
0.4148
0.5153
0.6146
0.7127
0.8096
0.9054
Deviation in Viscosity
0.20
0.15
0.10
0.05
0.00
-0.05 0.0
0.2
0.4
0.6
0.8
1.0
-0.10
-0.15
Mole Fraction
Figure 2. Variation of ∆η for (x1) ODB + (1-x) CYNO (●), AP (X), CYN
(■) and AC (■) at 298.15.
OCP + Ketones: Figures (3) shows the variation in
interaction takes place between a lone pair of
E
V for binaries OCP + AC, OCP + AP, OCP + CYNO,
electrons of the oxygen atom of ketone and Cl, O-H
OCP + CYN at 298.15 K. OCP + AC show less
group14. This may also be due to the formation of
negative deviation. The VE (x1 ≈ 0.5) shows the
weak molecular complexes due change of free
order: OCP + AC > OCP + AP > OCP + CYNO. OCP +
volumes in the real mixture because of interstitial
PN show less negative deviation and OCP + CYN
accommodation of ketone molecules into cluster of
shows more negative VE.
OCP molecules.
E
Negative V reveals the existence of specific
interaction between unlike molecules13. The
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International Journal of Pharmaceutical Research & Development
Mole Fraction
Excess Molar Volume
0.00
-2.00
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0.0
0.2
0.4
0.6
0.8
1.0
-4.00
-6.00
-8.00
-10.00
-12.00
-14.00
Figure 3. Variation of VE for (x1) OCP + (1-x) AC (■), AP (X), CYNO (●) and CYN
(■) at 298.15 K.
Figure (4) gives the variation of ∆η for binaries
dominating.OCP + CYNO and OCP + AP show
OCP + AC, OCP + AP, OCP + CYNO, OCP + CYN at
positive deviation. The positive values of ∆η in
these mixtures can be interpreted in terms of
298.15 K over the entire composition range. OCP +
AC and OCP + CYN show negative deviation. ∆η
strong interactions between unlike molecules, OCP
values shows negative due to dispersion forces are
+
CYNO
and
OCP
+
AP.
4.00
3.00
Deviation in
Viscosity
2.00
1.00
0.00
-1.00 0.0
0.2
0.4
0.6
0.8
1.0
Mole Fraction
Figure 4. Variation of ∆η for (x1) OCP + (1-x) CYNO (●), AP (X), AC (■)
and CYN (■) at 298.15 K.
Infrared studies:
observed at around 1680-1690 cm-1 due to
The FTIR absorption frequencies of the binary
conjugation effect. From Table 4.0, it is observed
mixtures of ODB and OCP with ketones over the
that C=O stretching frequency is almost same from
x1 ≈ 0.1- 0.9 for ODB + AC, ODB + AP (fig.6) and
entire range at room temperature are listed in
Tables 4.0-6.0.
ODB + CYNO. Lower C=O stretching frequency is
ODB + Ketones:
observed at x1 ≈ 0.1 and higher C=O stretching
C=O stretching vibrations: The band due to
frequency is observed at x1 ≈ 0.8 and 0.9 for all
C=O stretching vibration is observed in the region
systems. The frequency follows the order: ODB +
1650-1850 cm-1. For aliphatic ketone C=O
AC > ODB + CYNO > OCP + CYNO > ODB + AP.
-1
stretching vibration is at 1710-1720 cm and for
OCP + Ketones:
aromatic ketone C=O stretching vibration it is
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International Journal of Pharmaceutical Research & Development
C=O stretching vibrations: From Table 5.0,
it is observed that C=O stretching frequency
decreases from x1 ≈ 0.1 to 0.9 for OCP + AC, OCP +
AP (fig.5) and OCP + CYNO. Higher C=O stretching
ISSN: 0974 – 9446
frequency observed at x1 ≈ 0.1 and lower for all
above systems except OCP + AC. The frequency
follows the order: OCP + AC > OCP + CYNO > OCP +
AP.
Table 4. IR stretching frequencies of C=O (cm-1) in (x1) ODB and (1-x1) ketones systems.
x1
0
ODB+AC
1714.6(w)
ODB +AP
1683.7(s)
ODB +CYNO
1710.7(s)
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1714.6(w)
1714.6(w)
1714.6(w)
1714.6(w)
1714.6(w)
1714.6(s)
1714.6(s)
1714.6(s)
1714.6(m)
1714.6(w)
1683.7(s)
1683.7(s)
1683.7(s)
1683.7(s)
1685.7(s)
1683.7 (s)
1685.7(s)
1685.7(s)
1683.7(m)
----
1712.8(s)
1712.8(s)
1712.8(s)
1712.8 (s)
1712.8(s)
1712.8(s)
1712.8(s)
1712.8(s)
1712.8(m)
----
Table 5. IR stretching frequencies of C=O (cm-1) in (x1) OCP and (1-x1) ketones systems.
x1
0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
OCP+AC
1714.6(w)
1714.6(s)
1706.9(s)
1701.1(s)
1701.1(s)
1701.1(s)
1705.0(s)
1699.2(s)
1697.2(s)
1701.1(m)
----
O-H stretching vibrations: The non
hydrogen-bonded hydroxyl group of phenol
absorbs strongly in the 3584-3650 cm-1 region. The
sharp free hydroxyl bands are observed in the
vapour phase and in dilute solution in non polar
solvent15. Intermolecular hydrogen bonding
increases as the concentration of solution increases
and additional bands appears at lower frequencies
3200-3500 cm-1. Hence in the present
investigations (Table 6.0); phenolic O-H frequency
OCP+AP
1683.7(s)
1679.9(s)
1679.9(s)
1678.0(s)
1676.0(s)
1674.1(s)
1672.2(s)
1670.0(s)
1668.3(s)
1668.3(s)
----
OCP+CYNO
1710.7(s)
1712.8(s)
1712.8(s)
1705.1(s)
1701.2(s)
1697.4(s)
1697.4(s)
1697.4(m)
1697.4(m)
1693.5(m)
----
decreases from x1 ≈ 0.1 - 0.6 and increases from x1
≈ 0.7 - 0.9 for OCP + AC. This frequency increases
from x1 ≈ 0.1 - 0.9 for OCP + AP (fig.7). The O-H
frequency decreases from x1 ≈ 0.1 - 0.4 and
increases from x1 ≈ 0.5 - 0.9 for OCP + CYNO. For
OCP systems the sharp band is due to free -OH,
while weak band is due to hydrogen bonded -OH.
Two bands are observed in OCP + CYNO in x1 ≈ 0.6 0.9 and one sharp band is recorded for OCP + AC
and OCP + AP over entire range of composition.
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International Journal of Pharmaceutical Research & Development
ISSN: 0974 – 9446
Table 6. IR stretching frequencies of O-H (cm-1) in (x1) OCP and (1-x1) ketones systems.
OCP+AC
OCP+AP
OCP+CYNO
x1
0
---------0.1
3460.1(s)
3355.9(s)
3404.4(s) 3255.9(m)
0.2
3402.2(s)
3352.1(s)
3400.6 (s) 3255.9(s)
0.3
3442.7(s)
3354.0(s)
3277.1(s) 3265.5(s)
0.4
3400.3(s)
3392.8(s)
3265.5(s)
0.5
3394.5(s)
3398.3(s)
3369.7(s) 3294.5(s)
0.6
3386.8(s)
3404.1(s)
3369.7(s) 3302.2(m)
0.7
3444.6(s)
3409.9(s)
3400.6(s) 3381.3(s)
0.8
3454.3(s)
3425.3(s)
3524.0(m) 3431.4(s)
0.9
3427.3(s)
3438.8(s)
3524.0(s) 3448.84(m)
1.0
3456.2(s)
3456.2(s)
3456.2(s)
The position and breadth of an -OH
absorption band depends on the concentration of
the solution. The more concentrated solution and
the more -OH containing molecules form
intermolecular hydrogen bonds. It is easier to
stretch an O-H bond if it is hydrogen bonded,
because the hydrogen is attached to oxygen of a
neighboring molecule. Therefore, the stretch of a
concentrated (hydrogen bonded) solution of OCP
occurs at 3427.3 cm-1, whereas the stretch of a
dilute solution (with little or no hydrogen bonding)
occurs at 3460.1 cm-1 for OCP + AC system.
However no such dilution effect is observed in
other binary mixture. But other all systems show
hydrogen bond effect at higher concentration
Fig 5:
(x1 ≈ 0.1 to 0.6) of OCP.
It is seen that the O-H stretching frequency
increases when mole fraction of OCP decreases.
Higher values of O-H stretching frequency is
observed at high mole fraction and lower values of
O-H stretching frequency is recorded in between
0.2 to 0.5 mole fractions of OCP. This may be due
to hydrogen bonding between phenolic O-H group
and carbonyl group. The O-H stretching frequency
of OCP is 3456.2 cm-1, which gets decrease in
presence of ketone because of intermolecular
hydrogen bonding between them. The binaries
OCP + AP and OCP + CYNO show large decrease in
the O-H stretching frequency.
IR stretching frequencies of C = O (cm-1) for
OCP + AP system.
x1=0.1
x1=0.6
x1=0.2
x1=0.7
x1=0.3
x1=0.8
x1=0.4
x1=0.5
x1=0.9
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International Journal of Pharmaceutical Research & Development
ISSN: 0974 – 9446
Fig 6: IR stretching frequencies of C = O (cm-1) for
ODB + AP system.
x1=0.1
x1=0.5
x1=0.2
x1=0.6
Spectrum of some OCP + ketones show two
absorption bands -OH. The sharp band is due to
free -OH while weak band is due to hydrogen
bonded -OH. Presence of hydrogen bonding
between -OH of OCP with oxygen of studied
x1=0.3
x1=0.7
x1=0.8
x1=0.4
x1=0.9
ketones and absence of hydrogen bonding in
systems of ODB + ketones is confirmed by FTIR. In
case of ODB + Ketones, carbonyl stretching
frequency is not so affected.
Fig 7: IR stretching frequencies of O - H (cm-1) for OCP +
AP system.
x1=0.1
x1=0.6
x1=0.2
x1=0.7
The interesting behavior of intramolecular
hydrogen bonds both from the practical and
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x1=0.3
x1=0.4
x1=0.8
x1=0.5
x1=0.9
theoretical points of view has received increased
attention in recent years16-24. This can be attributed
13
International Journal of Pharmaceutical Research & Development
to the fact that the value of hydrogen bond energy
is only a few kilocalories per mole and can readily
perturb by any change in its environment. This is
especially important in studies of weekly bound
complexes of ketones and OCP.
ISSN: 0974 – 9446
9. Grunberg L, Trans. Faraday Soc., 1954, 50,
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Rao
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