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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.
Introduction
Liquid-Liquid Extraction
Relies on relative solubility of solute in two
different solvents.
Immiscibility of the two solvents
Experimentation
Experimentation
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
0.0396g
Solvent
Ether
Hexane
Acetone
Amount
recovere
d
0.02g
-
%
recovery
50%
-
Results
Discussion
Discussion
Theoretical Basis
like dissolves like
Solute - Solute
Solute
Solvent
Solvent
Solvent
Discussion
Discussion
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:
Discussion
Discussion
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.
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.
3.
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
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
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.
References
College
Liquid-