Recrystallization and Melting Point Determination

Sofia Padilla (Lueck, Brady, and Goldon)

September 17th, 2019
Aim: To purify crude benzoic and impure acetanilide through recrystallization in order to determine
the melting point for both substances as well as to determine the percent recovery.
Experimental:
Chemicals: Equipment:
Name Structure Physical
Acetanilide Solid,
M.P = Procedure:
114° A literature procedure was followed with the
Reagents: following
Capillaries modifications
NaCl (Salt), Sand, M.W =
135 a. a mixture that contains sand, salt and
Water acetanilide was used instead of activated
Mel-Temp Apparatus
g/mol
Benzoic Solid, charcoal.
acid M.P = b. a Hirsch funnel was used for the vacuum
122° filtration instead of a short-stem glass funnel
M.W =
122
Setup:
g/mol
Chemical Reaction/Mechanism:

5 6 5 6
4 7 4 7

3 8 3 8

2 9 2 9
1 11 1 10

Vacuum filtration,
Erlenmeyer flask,
Ice Bath,
Clamp and Stand
Hot Plate
Data:
After 1st filtration
Weighing Paper Only (g) 0.2377
Weighing Paper with Acetanilide (g) 1.2530
Acetanilide Only (g) 1.0153

After 2nd filtration

Weighing Paper Only (g) 0.2410
Weighing Paper with Acetanilide (g) 0.2422
Acetanilide Only (g) 0.0012

Melting Point Melting Point Range

Benzoic (pure) 120 119-121
Acetanilide (impure) 101 98-104

Results:
Acetanilide (impure)
Percent Recovery 0.12%
Moles of product 8.87 · 10-6 mol

Percent Recovery:
0.0012
∗100=0.11819 % ≈ 0.12%
1.0153

Moles of Product:
0.0012 g
=0.00000887=8.87 · 10-6 mol
135.17 g
Discussion:
The aim of this experiment was to purify crude benzoic and impure acetanilide through
recrystallization in order to determine the melting point for both substances as well as to determine the
percent recovery. Usually, an organic compound would have impurities either obtaining the compound
or being synthesized. Recrystallization is the technique that would be used in this experiment in order
to extract the impurities from the sold organic compound (based on concentration and solubility) in
order to purify it. For the 1st part of the experiment, a mixture of sand, salt, and acetanilide was a
solution in the Erlenmeyer flask, the sand was a solute and was reagent during the filtration because it
was removing the impurities from the mixture leaving the acetanilide and salt to pass through the filter
paper to the flask while the undesirable parts were left on the filter paper. The ice bath was then used
for the solution in order to recrystallized the product because the acetanilide and the salt were in an
aqueous state. A second filtration happened after the iced bath because the salt has to be separated
from the acetanilide in order to determine the purity of the substance. The crystals were left on the
filter paper and those crystals were placed in the capillaries in order to determine the melting point and
its range. The melting point helped to determine the purity of the product by taking the starting
temperature of the substance and the temperature when the substance started to “sweat” before turning
to liquid. The melting point for benzoic acid was revealed to be 119-121° and the melting point to be
120° and it was expected to be in that range because pure compounds tends to have stronger interaction
between molecules. As for the acetanilide, it was revealed that the melting point range was 98-104°
and the melting point to be 101° and it was lower than the expected value (109-114°) because the
intermolecular force for impure compounds tend to be weaker. It was upsetting that our crystals were
lower compared to other groups’ crystals which could have played a big role for the melting point and
the percent recovery. It could have the loss of the crystals during the second filtration when we have
the score lines to get as much crystals as we can. The percent recovery was calculated to be 0.12%, less
than 1% meaning that there were barely any crystals that were purified.
Conclusion:
The aim of this experiment was to purify crude benzoic and impure acetanilide through
recrystallization in order to determine the melting point for both substances as well as to determine the
percent recovery. After the first filtration, it was reported that the mass for impure acetanilide was
1.0153g. After the second filtration, the mass for acetanilide was reported to be 0.0012g. During the
experiment, the melting point range for benzoic acid was revealed to be 119-121° and the melting
point to be 120°. For the acetanilide, it was revealed that the melting point range was 98-104° and the
melting point to be 101°. The percent recovery was calculated to be 0.12% and the moles of product
was calculated to be 8.87 · 10-6 mol. A significant issue that was found during the experiment was the
loss of crystals during the second filtration, which caused a hassle to collect the leftovers for the
capillaries.
Reference:

Organic Laboratory Manual, Shanbhag & Veliz, pg. 15-23, Nova Southeastern University, 2012.

Question:
1. What happens to the impurities in a recrystallization? In other words, how are soluble
impurities removed during a recrystallization?
During recrystallization, the impurities are being removed and the soluble impurities are
removed by when the mixture is dissolved in the solvent during heating the mixture, the
solubility of the compound would decrease which leaves the purity of the product by itself.

2. Why is water a good solvent for the recrystallization of acetanilide?

Water is a good solvent for the recrystallization because acetanilide dissolve very easily when
the water is hot. However, if the water is cold, the product would be insoluble.

3. How did the melting point of your acetanilide change after

recrystallization?
 The melting point of the acetanilide change after recrystallization by the temperature
decreasing which means that the product is still impure (higher temperature indicates purity of
the product).
4. Why could you test the purity of your acetanilide by mixing it with
a known, pure sample of acetanilide and rechecking the m. p.?
I could test the purity of acetanilide by mixing it with a known, pure sample of acetanilide
because I can compare the values of the melting points to see if the melting point of impure
acetanilide is close to the expected range of the pure substance.

5. Why must the funnel be heated before the hot acetanilide solution
is filtered?
The funnel must be heated before the hot acetanilide solution is filtered because it won’t clog
the funnel. In other words, if the funnel wasn’t heated, then crystallization would occur before
it supposed to which would affect the crystals (in order to find the percent recovery).

6. What purpose does adding activated charcoal during

recrystallization serve?
The purpose of adding activated charcoal during recrystallization to remove the impurities in
the solution because the activated charcoal as a reagent.

7. What is the difference between percent recovery and percent yield?

The percent recovery is to measure the data from recrystallization while percent yield is to
measure the data from chemical reactions.

8. Melting “point” is a misleading term. Why?

Melting “point” is a misleading term because the melting point isn’t consistent once the solid
turns to liquid. For instance, the substance can start to sweat at 100° then it would turn to liquid
in 101° and then the temperature would continue to rise because of pressure changes.