Recrystallization

January 18, 2016

Submitted to: Kevin
Submitted by: Erin Kadosa
Name of partner: Adriana Driesman

Recrystallization
Objective:
to obtain a pure organic acetanile compound through a separation method of
recrystallization using water as the solvent. To determine the melting points of the crude
and purified products to assess the purity of the newly formed organic compound and
determine the percent yield of the recovered pure compound to observe the
effectiveness of the recrystallization process.
Reagents/Safety: 2.0 g Acetanilide C6H5NH, Distilled water. Please refer to pre-lab chart
for safety information. Avoid skin and eye contact with acetanilide compound.
Equipment: Weight boat, 250 ml round-bottom flask, powder funnel, 2 rubber tubes,
reflux condenser, heating mantle, retort stand, arm clamp, Erlenmeyer flask, glass
funnel, filter paper, 50 mL graduated cylinder, melting point apparatus, Buchner funnel,
rubber stopper, ice bath, aspirator, plastic container, label.
References - For complete method details refer to Organic Chemistry 1, Durham
College Laboratory Manual, Experiment # 1 pages 1- 10.
Structures:
Acetanilide melting point - 1130c-1150c

First Image - Chemical Formula of Acetanilide.

Reaction Statements:
Reflux process.

Observations/Data:
Before starting the recrystallization process the melting point of the crude product
acetanilide was read for a comparison to the pure product. The melting point was
recorded as 1140c - 1160c. Prepare to perform a simple reflux distillation using 2.0g of
acetanilide and 35 mL of distilled water as the solvent. The acetanilide is a gray
crystalline solid and flake-like in texture. The reflux process was performed for forty
minutes and is used to dissolve the acetanilide into a solution and removing any
impurities in the crude acetanilide that may be soluble. Subsequently to the end of the
reflux process a hot filtration by gravity was performed using a hot a funnel, Erlenmeyer
flask, and filter paper. For the formation of crystals to occur an ice bath was used as a
catalyst. These crystals are the acetanilide compound. The flask containing the
acetanilide solution sat in the ice bucket for five minutes before being removed. A final
vacuum filtration technique was performed to remove and collect the pure compound
from the mother liquor. The melting point of the newly formed pure product was
determined to be 1130c - 1180C
Calculations Weight of crude acetanilide - 2.0 g
Weight of filter paper - 0.2170 g
Weight of plastic cup - 17.3495 g
Weight of product and cup - 18.2250 g
17.3495 g
- 18.2250 g
0.8775 g Amount of acetanilide produced in grams.
Percent Recovered = Weight of Purified Product
Weight of Crude Product
Percent Yield = 0.8775 g X 100
2g
Percent yield of acetanilide = 43.875 %

x100

Discussion:
The purpose of the reflux process used in recrystallization is to use a solvent that is able
to slowly dissolve the solute at low temperatures easily, have a low boiling points itself,
and not react with the solute. As a result the solute acetanilide has dissolved into an
aqueous solution and remove any impurities in the crude acetanilide that may be
soluble. The solution obtained will contain the acetanilide, the soluble impurities, and
any insoluble impurities. To continue the recrystallization process hot filtration by gravity
was performed to remove any insoluble impurities in the acetanilide solution. The use of
ice bath is to speed up the production of the precipitate. The crystals are able to form
because the temperature decreased which also decreases the solubility of the original
solute.Vacuumm filtration is the final step to obtain the solid purified compound. The
crystalline compound will be removed from the mother liquor containing the soluble
impurities. A final rinse using cold water allows for the removal of any leftover impurities
such as the mother liquor. According to the change in the melting point range, 114 Oc to
1130c the pure acetanilide compounds new melting point has decreased indicated that
the final product is a more purified compound. Recrystallization is a separation
technique used to purify and recrystallize a desired compound such as the crude
acetanilide to a pure acetanilide product. The melting point is a way to determine the
identity or purity of a compound in this case. In the case of this experiment, the melting
point range of the ure products has decreased showing the removal of impurities that
cause a different melting point.
Experimental error - Loss of product may occur by determining the pure products
melting point. Loss of product may occur during transfer of pure product from flask to
container.
Amount of purified acetanilide recovered : 0.8775 g
Percentage Recovery: 43.875 %
Melting point of crude acetanilide: 1140c
Melting point of purified acetanilide: 1130c

Post-lab Questions 1. Water was selected a the usable solvent because acetanilide is soluble in water. The
was dissolved the desired compound acetanilide being purified at low temperature is
small quantities. The water will not react with the acetanilide, and remove any soluble
impurities. The water is also easy removed from the recrystallized pure compound when
dried.
2. The removal of soluble impurities takes place during the reflux method. Insoluble
impurities are removed during hot filtration. Using water to recrystallize the acetanilide
would for example remove the soluble sugar during the reflux step and the charcoal
through hot filtration. The charcoal would act as an absorbent and be removing during
filtration. A vacuum filtration could also be performed for the removal of soluble
impurities.
3. Vacuum filtration can be performed over gravity filtration because the vacuum
filtration allows for a dryer product to be obtained in the least amount of time. The
vacuum filtration is prefered in this experiment because we are looking to obtain the
crude solid sample, and not the liquid filtrate.
4. It is important to pack a melting point tube tightly because it tests for the melting point
range of a compound which can help identify a compound or asses its purity. A small
amount of time is required to transfer the heat throughout the capillary tube therefore it
is important to make sure there is enough material to relate to the compounds density.
It is important to heat the melting tube slowly and steadily because you do not want to
melt the product too quickly. It would be difficult to determine the melting point range
and could result in a higher melting point than average.
5. When too large of a sample to packed into a capillary tube and measured for its
melting point it may result in a different melting point range that may be too high or have
to large of a range.
Conclusion: In conclusion 0.8775 g of the purift acetalinde product was recovred with a
percent recovery of 43.875 %. The melting range point of the pure product decreased
giving observation to the formation of a purer product than originated. This
recrystallization process was successful in obtaining a more purified compound as a
result demonstrated by the lowered melting point.