RECRYSTALLIZATION

Sharika Mae B. Espineli, Kamilah L. Fernando, Chester Bill C. Galapon

Jeana May C. Galinato and Jairish Keith Garcia
Group 4 2F Medical Technology Organic Chemistry Laboratory

ABSTRACT
Recrystallization is a common laboratory technique or method that is used to purify organic substances based on
solubility. In this experiment, crude acetanilide was produced by the acetylation of aniline and acetic anhydride. The
crude acetanilide was dissolved in the solvent using a heated water bath and immediately filtered. The filtrate was
cooled in an ice bath to hasten crystallization. Acetanilide underwent another crystallization process using the chosen
recrystallizing solvent which is water and filtered again to get the pure acetanilide. The data obtained was used to
compute for the percentage recovery of the pure acetanilide which is 29.17%.

INTRODUCTION A. Compound tested (or Samples used)

Organic compounds that are solid at room The samples used in the experiment were pure
temperature are usually purified by acetanilide, aniline and acetic anhydride.
crystallization. [9] Recrystallization is a method Different solvents were also used in selecting the
in which two crystallization processes were recrystallizing solvent such as water, hexane and
performed. It is referred to as the second ethanol.
crystallization. It depends on the difference of
solubility in a hot and in a cold solvent. [7]

Recrystallization of solids is a valuable

technique to master because it is one of the
methods used for purification of solids. Other
techniques for purifying solids include
sublimation, extraction, and chromatography.
Nevertheless, even when one of these alternative
methods of purification has been used, the solid
material thus isolated may still be recrystallized
to achieve the highest possible state of purity.
[10]

To understand the recrystallization process, Figure 1. Structural Formula of Aniline

solubility behaviour must first be considered. It is Aniline is a colourless to brown, oily liquid with
often stated that “like dissolves like”. More an aromatic amine-like odour. It is stable,
correctly, it should be stated that, “compounds incompatible with oxidizing agents, bases, acids,
having similar structural features will be soluble iron and iron salts, zinc, aluminium. It is also
in one another”. Some obvious structural light sensitive and combustible. [3]
features that may affect solubility include polarity
and the ability to hydrogen bond. For known
compounds, it is useful to consider the structure
of the compound when choosing a
recrystallization solvent. Usually, however, the
structure of a compound may not be known so
the solvent must be chosen by carrying out
solubility tests. [8]

The objectives of the experiment are (1) to

synthesize acetanilide by the acetylation of
aniline, and (2) to purify crude acetanilide
product by recrystallization.

EXPERIMENTAL
Figure 2. Structural Formula of Acetic 20 mL of the recrystallizing solvent was poured
Anhydride into the crude acetanilide and heated after to
dissolve all of the solids formed. The solution was
Acetic anhydride is a colourless liquid with a filtered immediately while still hot using a fluted
strong, pungent, vinegar-like odour. It is filter paper. The filtrate collected was allowed to
flammable and is also incompatible with strong cool in an ice bath to hasten crystallization. The
oxidizing agents, water, strong bases, and collected crystals were washed with distilled
alcohols. [2] water and were allowed to dry. The dried crystals
identified as pure acetanilide was weighed after.

Figure 3. Structural Formula of Acetanilide

Acetanilide is a grey or white powder or flakes.

It is stable and it is combustible. It is
incompatible with strong oxidizing agents,
caustics and alkalis. [1]

B. Procedure
1. Determining the Recrystallizing Solvent [4]
At the start of the experiment, a recrystallizing Figure 4. Recrystallization Set-up
solvent must be chosen. A pinch amount of pure
acetanilide was transferred into 3 separate test
tubes containing 3 mL distilled water, 3 mL
RESULTS AND DISCUSSION
ethanol and 3 mL hexane each. Each of the test
tube was tested for the solubility of the pure Recrystallization only works when a proper and
acetanilide in varying temperatures. First, the suitable recrystallizing solvent is used. The solute
solubility of the pure acetanilide in different must be relatively insoluble in the solvent at
solvents was observed at room temperature. room temperature, the solute should be much
Then, each test tube was heated in a water bath more soluble in the solvent at high temperature
(37-40˚C) for 1-5 minutes to check for the and insoluble upon cooling of the mixture. The
solubility of the pure acetanilide in higher impurities present should be soluble in the
temperature. After heating, the solution was solvent at room temperature and insoluble in the
allowed to cool down to again check for the solvent at high temperature.
solubility of the pure acetanilide.
A table was created to show the obtained data
2. Production of Crude Acetanilide during the first part of the experiment which is
choosing the suitable recrystallizing solvent.
In an Erlenmeyer flask, 2 mL of aniline and 20
mL of distilled water was mixed and 3 mL of Table 1. Solubility of pure acetanilide in various
acetic anhydride was slowly added after. The solvents
Erlenmeyer flask containing the solution was then
cooled in an ice bath to hasten the crystallization At room During Upon
process. The solution was filtered through a wet temperature heating cooling
filter paper. The residue collected was the crude Water Insoluble Soluble Insoluble
acetanilide. The crude acetanilide was dried and Ethanol Soluble Soluble Soluble
weighed after. [4] Hexane Insoluble Insoluble Insoluble
3. Recrystallization Process
 On table 1, it shows that there were three
solvents tested namely, water, ethanol and
hexane. Ethanol and hexane didn’t show the REFERENCES
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