Liquid-Liquid

Extraction of Benzoic
Acid
Experiment 3 Chem 31.1
Presented by Gene Gansit and Marlon
Valdez

Introduction

Extraction
The act of extraction involves the withdrawing or
pulling out of something from something else.

Important industrially and in everyday use

Oil Extraction, Brewing Tea and Coffee

Introduction

In chemistry, extraction is defined as the

separation process by which a substance is
taken from a matrix.

Liquid-Liquid Extraction
Relies on relative solubility of solute in two
different solvents.
Immiscibility of the two solvents

Experimentation

0.5g of benzoic acid was transferred to a 250mL beaker

containing 100mL distilled water and was then stirred.

The resulting solution was then filtered using a pre-weighed

filter paper. The filter paper was put in an oven at 80C until
the paper was completely dry.

The weight of the undissolved benzoic acid left in the filter

paper was determined.

The dissolved benzoic acid in the mixture was also determined.

An aliquot of 20mL from the filtrate was transferred to a

separatory funnel.

Experimentation

10mL organic solvent of ether, hexane or acetone was added. The

stopper was inserted securely and the funnel was inverted with the
stop cock on top.

Excess pressure was relieved by shaking the funnel gently and

opening the stop cock. This process was repeated until no excess
pressure builds up within the funnel.

Separatory funnel was shaken vigorously for 1 minute and was let to
sit upright in a rack. The stopper was removed on top of the funnel
and the mixture was allowed to separate into two sharply defined
layers.

The organic layer was drained and received with a pre-weighed 50mL
beaker and was evaporated with a hot plate. Finally, the retained
benzoic acid in the beaker was weighed.

Results
Amount of Benzoic acid in
saturated solution

0.198g

Amount of Benzoic acid in

aliquot

0.0396g

Solvent
Ether
Hexane
Acetone

Amount
recovere
d
0.02g
-

%
recovery
50%
-

Results

Liquid-Liquid extraction using hexane yielded 0.02g of

recovered benzoic acid from the 0.0396g of dissolved
benzoic acid per 20mL water, showing a 50% recovery.

Unfortunately, the lack of Ether and Acetone in the

laboratory prevented the comparison of the relative
efficiency of the three solvents in terms of extracting
benzoic acid from water.

Cyclohexane was used in place of the missing solvents

but the result did not yield benzoic acid, rather it
showed a dark-brown colored substance during
evaporation.

Discussion

Extraction takes advantage of the chemical

properties of the solute and the two immiscible
solvents

contact of the original solvent containing the solute

and the extracting solvent that has the capability to
dissolve the solute.

which solvents is the solute more soluble in (efficient

extraction)

Key property = Polarity of Molecules

Discussion

Theoretical Basis
like dissolves like
Solute - Solute

Solute

Solvent

Solvent

Solvent

Discussion

SoluteSolvent interaction should be stronger than solute

solute and solvent-solvent

Strength is based on IMF

Ion-dipole > H-bond > Dipole-dipole > Induced-dipoles > LDF
Dissolution will not occur with substances with great differences of
polarity
the supposed solute-solvent attraction would not be enough to break
the solute-solute and solvent-solvent bonds.

Similar polarities of substances results to a more possible breaking

of the initial bonds to form the product bonds (Therefore soluble)

Discussion

The extracting solvent should have an affinity with

the solute (similar polarities)
Solute = Benzoic Acid
Slightly Polar
Sparingly soluble in water

The extracting solvents should be immiscible

(different polarities)
Partial miscibility makes the solvents harder to separate
and may add impurities with the recovered benzoic acid

Discussion
Solvent
Diethylether
Hexane
Cyclohexane
Acetone

Solubility
of
Benzoic Acid
1.816M
0.075M
0.100M
2.355M

Distribution
of the solute between the two immiscible
solvents can be expressed by the following equation:

The higher the KD, the more efficient the extracting

solvent

Discussion

Hexane and Cyclohexane

solubility of benzoic acid in cyclohexane and
hexane is 0.100M and 0.075M, respectively.
low values are due to the non-polar characteristic
of both cyclohexane and hexane; both
hydrocarbons having no net difference of
electronegativity in their component
LDF

Discussion

Acetone and Ether

theoretical solubility of benzoic acid in acetone and ether is
2.355M and 1.816M respectively.
High solubility is due to similar polarity with benzoic acid
(dipole)
More soluble in Acetone because it is more polar due to the
ketone group
Also means that Acetone is partially miscible with water because it is
polar like water

NOTE: Ether is the most effective solvent because it exhibits

high dissolution of Benzoic acid and immiscibility with water

Conclusion
This experiment illustrated the idea of how organic
compounds are extracted from a liquid matrix, and how
a compound distributes itself in a mixture of two
solvents. Given the limitations of the experiment, it is
seen that hexane can be used as an extracting solvent,
but without any other samples that yielded results,
comparing the relative effectiveness of hexane as an
extracting solvent is not possible. Although
theoretically, ether is the most efficient of the three
supposed solvents as it has the greater affinity to
benzoic acid compared to hexane, and completely
immiscible in water unlike acetone.

Recommendation
Since the experiment took a lot of time to finish, further
experiments may also opt to attain more separatory
funnels to be able to do two or all three extractions
simultaneously, reducing the time required for each
extraction. The experiment may also be modified by
increasing or changing extracting solvents to show more
relative and comparative data, although the solvent
should not be reactive with benzoic acid or water. As
ether and acetone were unavailable, cyclohexane was
used as another solvent, and this proved to be fruitless as
it was not able to recover any amount of benzoic acid,
rather, a dark-brown colored substance. Also, the trials
may be increased to produce more accurate results.

Problems and Questions

1.

Suppose 20mL of the saturated solution was treated with 10% NaOH, which solvent
(hexane, acetone, ether) could extract most of the benzoic acid solution? Explain
C6H5OO- + Na+ C6H5COO-Na+
The presence of sodium in sodium hydroxide reacts with benzoic acid forming sodium
benzoate, an organic salt that is polar and therefore becomes more soluble in water.
This will decrease the overall percent recovery of all solvents since the K D value will
decrease as the solubility of benzoic acid in water increases. The new K D value may be
written as:

The most efficient extracting solvent would still be ether as benzoic acid is still more
soluble in ether than in hexane, and is still immiscible to water and NAOH solution
unlike acetone.

Problems and Questions

2.
What effect does partial miscibility of the two
solvents have on the efficiency of the
extraction?

Partial miscibility decreases the efficiency of

liquid-liquid extraction since the two layers
would be harder to separate. This in turn also
means that the recovered substance may have
impurities contained in the aqueous solution.

Problems and Questions

3.

A substance C can be isolated from its plant source by solvent extraction.

However, a minor component Y has an appreciable solubility in the solvents that may be use
Given below are the solubility of X and Y in different solvents:

Solvent

T,

Ethyl
methyl
ketone
Cyclohex
ane
Benzene
CCl4
Water

80

Solubility in
100g solvent at
6
5

81

80
78
100

5
8.75
2

1.8
1.25
1.0

Problems and Questions

A.
Which is the best extracting solvent?

KD values of X and Y given the solvents are

shown below.

Solvent
Ethyl
methyl
ketone
Cyclohex
ane
Benzene
CCl4

KDx
3.0

KDy
5.0

4.0

2.0

2.5
4.4

1.8
1.25

The best extracting solvent

would be the solvent
corresponding to a high KDx
value and a low KDy value.

The best extracting solvent

would be CCl4 having a KDx - KDy
ratio of 4.4:1.25.

Problems and Questions

B.
Given a saturated aqueous solution of X and Y
and using 100mL of solvent in (a), determine the
percent recovery of X in a single extraction.

Problems and Questions

C.
Repeat (b) using 50mL of solvent in each two
successive extractions. Determine the
percent recovery and compare this with (b).

Problems and Questions

D.
What is the percent recovery of the minor
component in a single extraction using
100mL solvent in (a)?

References

Alexandria, (n.d.) Extraction. Northern Virginia Community

College

Fijal, Z., Loukeris, C.,Naghibzadeh, Z. & Walsdorf, J., (n.d.).

Liquid extraction. University of Illinois in Chicago

Liquid-

Liquid/Liquid extraction (n.d.). Penn State Department of Chemistry

Solubility of benzoic acid in organic solvents (October, 2014)

Retrieved from http://lxsrv7.oru.edu/~alang/onsc/solubility/allsolv
ents.php?solute=benzoic%20acid

Solution and solubility (n.d.) Elmhurst College Retrieved from

http://www.elmhurst.edu/~chm/vchembook/170A solubility.html