Wednesday, March 3, 2022 Ahmed Medhat Mohamed

Making Phthalimide
The main use of phthalimide is a precursor for anthranilic acid which can be used
to make azo dyes and saccharin which an artificial sweetener. It’s an organic
compound with a formula of C8H5NO2 which is the imide derivative of phthalic
anhydride. It is a sublimely white solid that is slightly soluble in water but more so
upon addition of base.

- Physical properties: - First-aid measures

Eye Contact Rinse immediately with
Appearance Off-white solid
plenty of water, also
Odor Slight under the eyelids, for at
least 15 minutes. Get
Melting Point/Range 233 - 235 °C medical attention
Skin Contact Wash off immediately
with plenty of water for
Boiling Point/Range 366 °C
at least 15 minutes. Get
medical attention
immediately if
Flash Point 165 °C
symptoms occur.
Autoignition 500 °C Inhalation Remove to fresh air.
Temperature Get medical attention
immediately if
Molecular Weight 147.13 symptoms occur
Ingestion Clean mouth with water
and drink afterwards
Solubility in water <0.1 g/100 ml plenty of water. Get
(19.5 °C) medical attention if
symptoms occur

- Chemical and glass wares

1. Chemicals:
10g Phthalic anhydride, 3.6g Urea, Ethanol
2. Glass wares:
250mL beaker, glass rod, funnel,
- Preparation:
Phthalimide can be prepared by heating phthalic anhydride with alcoholic ammonia. Also, it may be prepared
by treating the phthalic anhydride with ammonium carbonate or urea.
In this paper we will discuss the urea method.
As the melting point of both ingredients (Phthalic anhydride = 131.6 °C, Urea = 133 °C) are almost the same,
they can react with each other without any solvents. So, in 250mL beaker 4.5g Phthalic anhydride will mixed
and fused with 2g Urea until the mix reach the melting point of urea 133 °C. This rection should be take place
in an oil bath but I don’t have one so I have to ignore it. In the solid state not much reacting occurs, but once
the mix reaches the melting point of urea that’s when the reaction starts taking place.
Wednesday, March 3, 2022 Ahmed Medhat Mohamed

When it comes to the reaction mechanism, first the urea reacts with the phthalic anhydride to produce
phthalimide, CO2 gas and ammonia. The produced ammonia is able to react with another molecule of phthalic
anhydride to form another phthalimide molecule. After several minutes of reaching the melting point, the
mix will froth up and this will be the end point of the reaction.

1. First molecule formation 2. Second molecule formation

The beaker will set to cool down at room temperature then washed with some water to remove any unreacted
urea as the phthalimide is insoluble in water (<0.1 g/100 ml). This mixture is the filtered and the ppt will be
the crude phthalimide which is need to be purify. Crude phthalimide can be purified by recyclization in
alcohol or acetone but because its solubility is slightly lower in alcohol, I will use it.
The recrystallization process is done by addition of ethanol to the crude phthalimide on heating at 70 °C
until the sample completely dissolved. Then, the beaker is setting to cool down until the crystals grow up and
filtered of. These solid crystals are the nearly pure phthalimide and the final yield should be about 9.8g.
To make sure that the product is pure phthalimide, thin layer chromatography (TLC) and instrumental
analysis can be achieved.
- Instrumental Analysis:
1. IR Spectroscopy:
IR spectroscopy used to identify the functional group in the compound using IR radiation which cause
vibrational transitions of the molecule. When it comes to phthalimide, it has two function groups. The
first one is the carbonyl group which produce a very sharp peak at 1680-1800 cm-1. The second one is
the secondary amine which form sharp peak at 3300 cm-1.
Wednesday, March 3, 2022 Ahmed Medhat Mohamed

2. Mass spectroscopy:
Mass spectroscopy used to determine the Mwt and molecular formula of the compound by fragmentation
of it with an electron beam. From the Mwt of these fragments, the Mwt and formula were detected.

3. H1NMR:
Nuclear magnetic resonance detects the structure of the chemical compound using radio frequency
radiation which cause nuclear spin for the protons. The sharp peak at 7-8 ppm is due to the nuclear spin
of the protons on the aromatic ring of phthalimide. The peak at 11-12 ppm is due to the nuclear spin of
the proton on the secondary amine group.