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ABSTRACT
Recrystallization is a basic and widely used technique used for the purification of organic
solids through the difference of their solubility at different temperatures. It is also the process of
crystallizing solids by dissolving them in a hot solvent and then cooled at low temperature.
In this experiment, Crude acetanilide was formed through the acetylation of aniline
(C6H5NH2) and acetic anhydride (C4H6O3). Then by using a recrystallizing agent, namely water
(H2O), the crude acetanilide undergoes crystallization process. This process is done by dissolving
the crude acetanilide in a hot water until the solution is clear, but if there are coloration activated
charcoal should be added. After heating let it cool in an ice bath to produce pure acetanilide
[C6H5 NH(COCH3)] The weight of the crude acetanilide is 1.4g while the weight of pure
acetanilide is 1g. The percentage yield is 62.5%. The percent recovery is 71%
Introduction
Organic compounds, compounds made
up of Carbon (C), contain different
impurities. This impurities sometimes need
to be removed or purify for it can destroy
the experiment, thus people use different
purification methods to remove impurities.
For liquid solutions, Distillation is
commonly used, for it separates liquids
based on their boiling points. While on
solids, Sublimation or Recrystallization is
widely or commonly used. Sublimation is
the change of state of a solid to gas without
turning into liquid phase. While
Recrystallization is the process of purifying
organic solids base on their solubility rate. It
also is the process of heating solids and
cooling them to produce crystals.
In this experiment, we did crystallization
twice. In the first, we formed a crude
product. This means that there are some
impurities that is why a second
crystallization is needed to remove this
Methodology
3. Recrystallization of Pure
Acetanilide Crystals
After drying, 20 mL of the recrystallizing
agent, namely water, was added to the crude
acetanilide. It was then heated in a hot plate
until the solids were dissolved. Then small
amounts of activated charcoal were added,
for the solution was colored. This was done
to remove the color for the activated
charcoal will absorb the color impurities.
Afterwards, the solution was filtered while
hot using a fluted filter paper, (a circular
piece of filter paper folded in an accordion
style and used to filter solid impurities from
a liquid during gravity filtration) Fluted
filter paper was used because it has an
increased filter area and because fluting
creates gaps between the filter paper and the
funnel. These gaps then provide channels for
the solvent to flow through there for
increasing the solvent flow. Then after
filtration, the distillate was cooled in an ice
bath and then the crystals were collected by
filtration again. Dry the residue then and
take note and weigh.
Room
During
Upon
Temp.
heating
cooling
Water
Insoluble Soluble
Insoluble
Ethanol Soluble, Soluble
Soluble
Hexane Insoluble Insoluble Insoluble
The solubility rates are first, At room
temperature insoluble and at the same time it
should be very soluble in heating or at high
temperatures. And again should be
insoluble at cooling or low temperatures.
Table 1. Solubility of Acetanilide
In this part, three solvents were used,
namely water, ethanol and hexane to find
which solvent would be suitable for the
experiment. As indicated in the table,
Hexane was insoluble in all temperatures
while Ethanol is soluble to all temperatures.
This proves that Ethanol and Hexane should
not be used as a recrystallizing solvent. On
the other hand, Distilled Water was insoluble
in room temperature and also upon cooling.
It is also non flammable and volatile. This
means that water is the recrystallizing agent
to be used in this experiment.
The combining of aniline and acetic
anyhydride produced crude acetanilide or
crystals with impurities with the help of
heating and cooling. Then the residue was
collected through the process of Filtration.
Although crystals were now produced,
we still need to remove its impurities so the
recrystallization process should be done
now. The crude acetanilide and the
recrystallizing solvent or water was then
cimbined and heated in a hot plate. Then
with constant stirring, wait for the crude
acetanilide to be dissolved. When the crude
acetanilide was dissolve, take a look at the
solution and if it has color then add a small
amount of activated charcoal. This was done
because Activated Charcoal is highly
absorbent carbin and also used as an
References:
Books:
1. Brown, W., & Poon, T.
(2014). Introduction to organic
chemistry (5th ed.). Hoboken, NJ:
John Wiley & Sons, Inc.
2. Tung H.H. et. al. (2009)
Crystallization
of
Organic
Compounds:
An
Industrial
Perspective, Hoboken, NJ: John
Wiley & Sons, Inc.
3. Mullin, J.W. Crystallization.
Great Britain. Pitman, Press,
Bath
1.4g
1.0g
Websites:
1.4 g
100=62.5
2.24 g
Based on the solution we could say that
the % yield can be easily computed. Then
the next to be solved is the %error of crude
acetanilide and pure acetanilide.
Recovery =
Recovery =
% Recovery =71%
Conclusion
I therefore conclude that recrystallization
can make a substance purified but the
amount of substance may be decreased.