RECRYSTALLIZATION

Bianca C. Acuña, Pamela G. Agbayani, Gian S. Alkuino,

Justin G. Ang and Nadine T. Carag
Group 1 2A Medical Technology Organic Chemistry Laboratory

ABSTRACT
The goal of the experiment was to purify crude acetanilide by the method of recrystallization. Recrystallization is a
technique used in order to purify organic samples through the differences of solubility on different temperatures.
Acetylation of aniline was done in order to get the crude acetanilide, it had a yellowish flake-like appearances and
weighed 2.27g. The percentage yield from crude acetanilide was 76.69%. The crude acetanilide was placed in a hot
water bath and cooled in an Erlenmeyer flask with filter paper placed in an ice bath. During the process of cooling, the
compound crystallized and was collected and dried, producing the pure acetanilide. The pure acetanilide was colorless
to white and also had flake-like appearances.

I. INTRODUCTION impurities did not dissolve in the hot solution and

Organic compounds that have been were removed by filtration before the solution is
synthesized in laboratories or extracted from cooled, the crystals formed should be purer than
natural products are still in an impure form, thus the solid mixture [1].
there is a need for purification. The method to be By the end of the experiment, the students
employed in purifying compounds is based on must attain the following objectives: synthesize
their physical and chemical properties. If the acetanilide by the acetylation of aniline, and
product is a solid, sublimation and crystallization purify crude acetanilide product by
can be used to purify the compound. However, in recrystallization.
sublimation, the solids can only be purified if it
can pass directly into the vapor phase without II. EXPERIMENTAL
going through the liquid phase. Therefore, solids A. Test Compound/s used
not having this property can be purified through 1. 2 mL Aniline
recrystallization. In this method, the organic solid Molecular Formula: C6H7N
is purified based on the difference in solubility at Molecular Weight: 93.129 g/mol
different temperatures. Density: 1.02g/mL
Recrystallization involves the dissolution of the 2. 3 mL Acetic Anhydride
solid to be crystallized in an appropriate solvent Molecular Formula: C4H6O3
at an elevated temperature and the subsequent Molecular Weight: 102.089 g/mol
reformation of the crystals upon cooling so that Density: 1.08 g/mL
the impurities remain in the solution [1]. 3. 20 mL Distilled Water
Prior to the recrystallization process, it is Molecular Formula: dH2O
important to choose the proper recrystallizing Molecular Weight: 18.015 g/mol
solvent. The substance to be crystallized should Density: 1.00 g/mL
possess the ideal solubility behavior in the
solvent. The solute must be relatively insoluble at B. Procedure
room temperature and soluble in the solvent at Recrystallization is an important method in
higher temperature. At the same time, the purifying non-volatile organic solvents. It is a
impurities present must either be soluble at room process based on the principle that with
temperature or insoluble in the solvent at a increased temperature, the solubility of solids
higher temperature [2]. increases as well. In short, the amount of solute
After the recrystallization process, if the dissolved in a solvent increases as temperature
impurities present in the mixture have dissolved increases. To purify crude acetanilide, only dry
and remain dissolved even after the solution is glassware was used in the performing the
cooled, the crystals formed should ideally provide experiment as acetic anhydride is a very reactive
pure material. On the other hand, if the compound. Before the experiment was
performed, the limiting reagent was first
identified as well as the theoretical yield of the
acetanilide using the formula:
In synthesizing acetanilide by the acetylation of
aniline, 2 mL of aniline and 2 mL of distilled
water were mixed in an Erlenmeyer flask. Once
the two liquids were mixed, 3 mL of acetic
anhydride was slowly introduced to the mixture
using a serological pipette. Here, the acetylation
of aniline takes place where a nucleophilic
substitution occurred as acetic anhydride and
aniline reacted with one another. The products
formed from this reaction were acetanilide and
acetic acid which were the residue and filtrate
respectively.
Figure 1. Acetylation of Aniline.
This was then placed in a cool ice bath to
hasten the crystallization process. During the
process, changes in the mixture were noted.
After cooling in the ice bath, the mixture was
filtered using a wet and fluted filter paper,
separating the acetic acid from the crude
acetanilide. This setup was then left to air dry in
the locker for one day where it was covered and
wrapped with bond paper and masking tape.
Figure 2. Filtration of the cooled mixture.
Once the crude acetanilide has been dried, the
crystals obtained was then weighed. To compute
for the percentage yield of the crude acetanilide,
the following formula was used:
𝑤 𝑔 𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
% 𝑦𝑖𝑒𝑙𝑑 𝑐𝑟𝑢𝑑𝑒 𝑎𝑐𝑒𝑡𝑎𝑛𝑖𝑙𝑖𝑑𝑒 = × 100
𝑤 𝑔 𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
2.27𝑔
= × 100
2.96𝑔
= 76.69%
Figure 3. Crude Acetanilide.
After this, 20 mL of water, the recrystallizing
solvent, was poured unto the crude acetanilide.
This was then heated in a water bath until all the
solids were dissolved. After heating, the solution
appeared to be yellowish in color which did not
require the use of activated charcoal. As the
solution was still hot, it was then filtered
immediately using a fluted filter paper. Once the
solution had been completely filtered, the filtrate
was cooled by immersing the receiver in tap
water. After this, the crystals were then collected
and washed with ice-cold distilled water. The
appearance and color of the pure acetanilide
were then noted and recorded.
Figure 4. Pure Acetanilide
III. RESULTS AND DISCUSSION
In the experiment, aniline was placed inside
the Erlenmeyer flask with distilled water and was
added with acetic anhydride. Then the
Erlenmeyer flask was placed inside the ice bath
to quicken the process of crystallization. The
crude acetanilide formed inside the Erlenmeyer
flask was filtered through a pre-weighed fluted
filter paper. Filtration was used to eliminate
unwanted substances from the sample. The crude
acetanilide was dried and the weight of it with
the filter paper of 3.80g was subtracted to the
weight of fluted paper of 1.53g resulting in the
weight of crude acetanilide being 2.27g.
The color of the crude acetanilide is yellowish
and had a flake-like appearance. From the grams
collected in the filter paper, the percentage yield
of crude acetanilide was 76.69%.
Table 1. Recrystallization
The pure acetanilide could still have impurities
and this can be due to errors like sample being
kept in high temperature for a long period of
time, incomplete filtering of the crude acetanilide
before it was heated and pure acetanilide after it
was heated. Also, not all of the crude acetanilide
was turned into pure acetanilide, some stayed in
the evaporating dish while others stuck to the
stirring rod.
REFERENCES
[1] Recrystallization. (n.d.). Retrieved from
http://www.chem.utoronto.ca/coursenotes/C
HM249/Recrystallization.pdf 11/02/18
[2] Wired Chemist. (n.d.). Retrieved from
http://www.wiredchemist.com/chemistry/inst
ructional/laboratory-tutorials/recrystallization
11/02/18

Weight of crude acetanilide with filter 3.80g

paper

Weight of filter paper 1.53g

Weight of crude acetanilide 2.27g

Percentage yield of crude acetanilide 76.69%

Table 2. Color and Appearance of Crude and

Pure acetanilide

Observations Crude Pure

acetanilide acetanilide

Color Yellowish White/Colorless

Appearance Flake-like Flake-like

The filtered crude acetanilide was transferred

to an evaporating dish and poured 20 ml of the
recrystallizing solvent which is water into it. The
evaporating dish was placed in a hot water bath
in order to dissolve the crude acetanilide. The
solution was stirred until all the crude acetanilide
had dissolved. The hot solution was again filtered
into an Erlenmeyer in an ice bath in order to
induce crystallization. The pure acetanilide
crystals were collected and dried. The color of the
pure acetanilide was colorless to white and also
had flake-like appearances. It also had impurities
due to having yellowish colors.