ABSTRACT

This report presents the experimental results and analysis of the liquid-liquid extraction of
benzoic acid into two separate phases- aqueous and organic.

In the experiment, benzoic acid of varying concentrations: 15ml, 10ml and 5ml was
introduced into the benzene - demineralized water mixture to determine its distribution into
the extract and raffinate phases. By titrating 10ml samples of each layer with 0.5M NaOH,
the concentrations of benzoic acid in both phases were determined.

The resulting concentrations were used in the calculation of distribution coefficient, K .

The distribution coefficient, K is the ratio of the solubility of solute dissolved in the organic

layer to the solubility of material dissolved in the aqueous layer.

Results showed that the value of K for different benzoic acid volume is greater than 1, thus
benzoic acid dissociates more in benzene (i.e. organic phase) than in water (aqueous
phase).

With regards to the objectives of the experiment, the distribution coefficient K, as well as its
dependence on the initial concentration of benzoic acid, was ascertained.

The method in this experiment can also be applied to other ternary system where a

solute is added to two immiscible solvents.

INTRODUCTION

Liquid-liquid extraction or solvent extract uses the solubility differences to separate compounds

into two immiscible layers which are the organic and aqueous layer. Extraction can be used to

separate or “partition” ionic or polar low-molecular-weight substances into an aqueous phase and

less polar water-insoluble substances into an immiscible liquid organic phase. This is governed

by the distribution coefficient.

In this Liquid-Liquid Extraction experiment, molecules of benzoic acid are transferred across the

aqueous and organic phases, until equilibrium is established. However, the phase in which

benzoic acid is more soluble in will have the higher concentration of the acid at equilibrium.

Liquid-liquid extraction is a basic technique in chemical laboratories, where it is performed using

a separatory funnel.

Hence, the objective of the experiment is to ascertain the extent of solubility of the acid in the

extract layer with the help of the distribution coefficient, K and to show the dependence of the

distribution coefficient on the concentration of benzoic acid.

The distribution or partition coefficient is a quantitative measure of the how solute will

distribute between aqueous and organic phases. It is the ratio, K, of the solubility of solute

dissolved in the organic layer to the solubility of material dissolved in the aqueous layer.

Thus, the distribution coefficient is a property of the aqueous and organic solvents which gives

an idea of the relative extent of solubility of a particular constituent in both solvents.

Consequently from this experiment, we can know how best to select the extraction solvent so as

to suit the required preferential extraction in industrial situations.

DISCUSSION

In this experiment, we determined the relationship between the distribution

coefficient and concentration of benzoic acid in benzene and demineralized water.
The experiment was carried out under the principle of liquid-liquid extraction and
the concentrations of benzoic acid in the aqueous and organic layers were
calculated.

Having known that extract layer is the layer that contains greater fraction of the
desired solute (i.e. Benzoic acid) as compared with the raffinate (aqueous) layer
which contains the lowest fraction of Benzoic acid due to its polarity. It is
expected that for the titration of a given volume of extract phase, more of NaOH
will be needed to neutralize the Benzoic acid in this layer/phase.

From the result table, it can be observed that for an initial volume of 15ml of
benzoic acid, more NaOH solution was used to neutralize the acid (that is, 1.90ml
NaOH for the extract and 1.10ml NaOH for the raffinate).

Titrating with a volume of 5mL of benzoic acid, a titre of 1.25mL NaOH for the
extract and 1.15ml NaOH for the raffinate was recorded. This clearly showed the
concentration and volume relationship.
Comparing the titre values for both the extract and the raffinate phases, it was also
observed that the amount of base (NaOH) required to neutralize the acid (Benzoic
acid) in the extract phase was always larger than that required to neutralize the acid
left in the raffinate layer.

In addition, it was also noticed that there was a consistent increase in the values of
the distribution coefficients (K) as the volume of acid increased from 5mL –
15mL. When an initial volume of 15mL of benzoic acid was used, the distribution
coefficient (K) recorded was 1.7273, while that of 5mL volume of benzoic acid,
the distribution coefficient gave 1.0870. It can be seen that the Distribution
coefficient (K) for 5mL acid is relatively small as compared with that of 15mL
acid volume.

The possible sources of error are personal and instrumental errors. The
burette pipe that was used in the experiment has a leak problem, and the tip of the
burette was loosened, resulting in the inaccurate volume reading for NaOH.

This error can be attributed to the discrepancy observed in the tire values of Extract
which in turn affected the distribution coefficient. By distribution theory, an
increase in volume of Benzoic acid from 10mLto 15mL is expected to give an
increase in titre values of Extract. But from the result table, a decrease in titre value
was recorded for this acid volume change. This can be faulted to experimental
error during the course of titration. The loose end of burette stopcock resulted to
titration of the 10mL of acid with excess NaOH.

The data table showed that the concentrations of benzoic acid is higher when
it is in organic (extract) layer, and lower when it is in aqueous (raffintae) layer.
This phenomenon clearly implies that the solute (benzoic acid) is more soluble in
benzene than in water, since the distribution coefficient is equal to or greater than
one.

Having compared the distribution coefficient values at different Benzoic acid

volume (Concentration), we can include that most of the Benzoic acid was found
in the extract phase since a larger volume of NaOH was required to neutralize it
than was required for the raffinate phase. Hence, the added organic solvent
(Benzene) was an appropriate solvent for the extraction of benzoic acid from the
mixture of Benzoic acid and water. Another reason why Benzene served well as an
extraction solvent is that its density is lighter than that of water. Therefore, with a
lesser density, the organic layer which was the extract floated on the aqueous
(raffinate) layer, this led to the successful separation of the extract from the
raffinate.

CONCLUSION

In this experiment, the value for distribution coefficient was determined by

titration of 10mL sample of extract and raffinate phases with 0.5M NaOH and the
values are: 1.0870 for 5mL of benzoic acid, 2.4957 for 10ml benzoic acid and
1.7273 for 15ml benzoic acid.

The solute which is benzoic acid distributed itself between the two immiscible solvents

which are water and benzene at constant temperature and the solute is in the same molecular
condition in both solvents. The concentration of benzoic acid is greater in organic solvent

(benzene) than in water solvent, resulting in the K value greater than 1.

It was observed that the distribution coefficients of benzoic acid in the

extract and raffinate layers increased as the initial concentration of the acid

decreased in the entire mixture. Comparing the data result with the theory, it

is noticed that the experiment was carried out appropriately.

In conclusion, the use of benzene to extract benzoic acid from

The benzoic acid – water mixture was proven to be of high efficiency, considering
the high value of the distribution coefficient for the system. This experiment
illustrated accurately the behaviour of the distribution coefficient with respect to
varying solute (benzoic acid) concentrations (volumes) .

RECOMMENDATION

For future experimentation on liquid-liquid extraction of benzoic acid, there are a

few recommendations and precautions that should be considered so that better
results can be obtained with fewer errors.

Other extraction solvents (apart from benzene) should be used so that the results

obtained could be compared with themselves and also with the results obtained
from the experiment using benzene as extraction solvent.
The comparison of the results gotten from the above suggestion would help
provide an understanding of benzoic acid’s affinity for the different solvents. It
could also help in extraction solvent choice for industrial processes.

Also, there should be frequent checking of the burette pipe and separatory funnel
for leak problems, in order to ensure accurate readings during titration and
separation processes.