PURIFICATION OF ACETANILIDE BY RECRYSTALLIZATION

Irish Jane B. Patron, Margaret Corinne U. Ramos, Gabrielli Ann B. Saavedra,

Juan Miguel C. Santos, Rea Cristine B. Tapel and Kyra Zara N. Tieng
Group 7 2G Pharmacy Organic Chemistry Laboratory
ABSTRACT
Recrystallization is a widely-used technique to purify a solid mixture. The desired product is isolated from its
impurities by differences in solubility at different temperatures. In this experiment, pure acetanilide was put and
dissolved into three test tubes, each containing different solvents which are water, ethanol and hexane. After, it was
placed in a warm water bath (37oC 40oC) for 1-5 minutes and was cooled down as crystals form out.
Mixing aniline with acetic anhydride produced crude acetanilide. The recrystallizing solvent was added and it dissolved
the crude acetanilide in a water bath. Crystals formed after cooling the solution in an ice bath. Thus, pure acetanilide
was the product obtained after removing the impurities from the solution.

INTRODUCTION
Recrystallization is a purification process used
to remove impurities from organic compounds
that are solid at room temperature. This process
is based on the premise that the solubility of a
compound
in
a
solvent
increases
with
temperature. Conversely, the solubility of the
compound decreases as the solution cools, and
crystals form. [1]

in boiling solvent; (3) solvent's boiling point must

be lower than the compound's melting point; (4)
an abundant quantity of crystals must be
recoverable from the cool solvent [2]

Figure 2. Structural Formula of Aniline

Figure 1. Layer by layer, additional molecules attach

to this crystal, forming a growing crystal lattice.

Very pure compounds can be produced by

recrystallization. As a heated solution of the
desired compound cools, a small, pure seed
crystal of the compound forms in the solution.
The molecules in the crystal have a greater
affinity for other molecules of the same kind than
they do for any impurities present in the solution.
In effect, the process of crystal formation
removes one kind of molecule from the solution.
[1]
Selecting an appropriate recrystallizing solvent
to use is probably the most difficult step of
recrystallization. The primary consideration when
choosing a recrystallizing solvent is the extent to
which the compound and impurities are soluble in
the solvent at high and low temperatures. The
criteria for selecting the right recrystallizing
solvent are as follow: (1) the compound being
purified must be insoluble in solvent at room
temperature; (2) the compound must be soluble

Aniline is the starting material in the dye

manufacturing industry. It forms aniline colors
when combined with other substances,
particularly chlorine or chlorates. Aromatic
amines are weaker bases reacting with strong
acids to form amides. Anilide is an amide derived
from aniline by substitution of an acyl group for
the hydrogen of NH2. Acetanilide is from acetic
acid and aniline. Aniline is converted into
sulfanilic acid, which is the parent compound of
the sulfa drugs. Aniline is also important in the
manufacture of rubber-processing chemicals,
explosives, plastics, antioxidants and varnishes.
[3]

Figure 3. Structural Formula of Acetic anhydride

Acetic Anhydride is a clear, colorless liquid with

a very pungent, penetrating, vinegar-like odor
that combines with water to form acetic acid. It is
soluble in ether, chloroform and benzene. It
reacts with alcohols. Acetic anhydride is prepared
commercially in either of two ways. Acetaldehyde