MSc CHEMISTRY

GRADE:

PRACTICAL REPORT
SYNTHESIS OF ORGANIC AND INORGANIC COMPOUNDS

EXPERIMENT 1
SYNTHESIS OF ASPIRIN (ACETYL SALICYLIC ACID)

NAME : Greef Rose A. PRACTICUM DATE : 04-11-2023

STUDENT NUMBER : 22923010 COLLECTION DATE : 06-11-2023
GROUP : I RECEIVED BY :
ASISSTANT : Bilqis CORRECTED BY :

Yogyakarta, 04 November 2023

ASSESSMENT CRITERIA
Cover : (Maks.5)
Purpose : (Maks.5)
Introduction : (Maks.10)
Tools and materials : (Maks.5)
Method : (Maks.5) (_____________________________________)
Result and discussion : (Maks.55) Lecturer,
Conclusion : (Maks: 5)
References : (Maks.5)
Attachment : (Maks.5) (Prof. Allwar, Ph.D.)

TEACHING CHEMISTRY LABORATORY

FACULTY OF MATHEMATICS AND NATURAL SCIENCES
UNIVERSITAS ISLAM INDONESIA
YOGYAKARTA
2023
 EXPERIMENT 1
SYNTHESIS OF ASPIRIN (ACETYL SALICYLIC ACID)

I. Experimental Goal
To study the synthesis of ester compound.

II. Introduction
Aspirin is an effective analgesic (pain reliever), antipyretic (fever reducer) and anti-
inflammatory agent and is one of the most widely used non-prescription drugs. The use
of aspirin had its origin in the 18th century, when it was found that an extract from the
bark of willow trees was useful in reducing pain and fever. The active ingredient in
willow bark was later found to be salicylic acid. The structure of salicylic acid is shown
below. Although salicylic acid was effective at reducing pain and fever, it also had
some unpleasant side effects. It is irritating to the lining of the mouth, esophagus, and
stomach, and can cause hemorrhaging of the stomach lining. In 1899, the Bayer
Company in Germany patented a drug they called aspirin, which was a modification of
salicylic acid (Kristian, 2007).
Acetylation reaction is a reaction of acetyl group revenues (-COCH3) which is
applied into the phenol group. In this case, phenol acts as a nucleophilic group being
acetyl act as electrophiles. Aspirin has the molecular formula C9H8O4, which is also
known as acetyl salicylic acid, acentria, aspirin, and acetophen. The properties of
aspirin:
● Its shape is like a crystal needle, with a glossy white color, and is odorless.
● Its specific weight is 1,36 g / mL.
● It is stable in dry measurement but decomposes in boiling water.
● It has no smell, but in the wet air it is gradually hydrolyzed into acetic acid and
salicylic acid that causes odor of acetic acid.
● It can be used as an analgesic and antipyretic because it is not stable. Therefore,
aspirin is used in the form of solid consistency, eg. tablets, capsules, powders and
suppositories. In the form of oil, aspirin can cause itching and skin diseases. Aspirin is
mostly combined by acetophenetidum and caffeine known as apc. Aspirin is easily
hydrolyzed by the intense heat, when coupled with FeCI3 which will give the color
purple. The structure of aspirin are as follows:

Figure 1. Aspirin/Salicylic Acetic Acid

Esters are carboxylic acid derivatives with the -OR group from alcohol. Esters
can be made from an acid with an alcohol or from an anhydride of an acid with an
alcohol. A carboxylic acid ester is a compound that contains a -CO2R group with
R which can form alkyl or acyl. Alcohols with carboxylic acids and carboxylic acid
derivatives and carboxylic acid derivatives. This reaction is called the esterification
reaction (Fessenden and Fessenden, 1986).
The aspirin collected will then be purified by recrystallization. In this
purification method, the crude aspirin will be dissolved in a small amount of warm
ethanol. Water will then be added and the solution will be cooled slowly and then
chilled. The acetylsalicylic acid will recrystallize, and the solid impurities
(unreacted salicylic acid) should remain dissolved in the solution. The solid aspirin
will again be collected using vacuum filtration and tested for purity. This aspirin
should be more pure than the original aspirin. Recrystallization is a method of
purifying a crystal from its impurities. The mixture of compounds will be purified
by dissolving in a suitable solvent at a temperature close to its boiling point.
Impurities or other substances can be separated from the desired substance by
filtering until crystals form (Cahyono, 1991).
III. Equipment and Material
Equipment
a. Pumpkin heater of 100 mL
b. Water heater
c. Beaker of 100 mL
d. Glass stirrer
e. Thermometers 220°C
f. Glass Funnel

Material
a. Dry salicylic acid
b. Concentrated sulfuric acid
c. Distilled Water
d. Acetic acid anhydride
e. Pure alcohol
f. Iron (III) chloride

IV. METHOD
1. Pour in 5 grams of salicylic acid into a 100 mL flask, 7,5 g of acetic acid anhydride
and 5 drops of concentrated sulfuric acid.
2. Shake the mixture until it perfectly dissolve.
3. Then heat over a water heater (the temperature inside the flask is maintained at 50-
60 ° C) while stirring for 15 minutes

Isolation
1. Let it cool while still stirring, and add 150 mL of water
2. Then strain it with the aid of suction.

Purification
1. The purification is done by recrystallization.
 2. The solvent used is a mixture of 15 mL of 96% alcohol and 37,5 mL of distilled
water. 3. Put in the crystal in a solvent and heat it until all crystals dissolve, then cool
it gradually.
4. The mixture will result in gorgeous needle-like crystals.
5. The crystal is then tested with a reagent of iron (III) chloride.

V. RESULT AND DISCUSSION

Principle of aspirin synthesis by esterification reaction. Aspirin can be made by
reacting salicylic acid with acetic acid in the presence of an acid catalyst. The phenol
group on the salicylic acid forms an ester with the carboxyl group on the acetic acid.
However, this reaction is slow and has a relatively low yield. If acetic anhydride is used
instead of acetic acid, the reaction is much faster and has a higher yield (since acetic
anhydride is much more reactive than acetic acid). The reaction is shown on the
following page.
 The mechanism that occurs is that acetic anhydride attacks H+ and experiences
resonance. Acetic acid anhydride attacks the phenol group of salicylic acid H+ apart
from OH- and binds to the O atom in acetic acid anhydride. Acetic anhydride breaks
down into acetic acid and acetyl salicylic acid (aspirin) H+ will be released from
aspirin. The total reaction that occurs is as follows:
 The treatment function and the phenomenon that occurs is that the solution is
cloudy and there is a white precipitate when mixing 5 grams of salicylic acid + 7 ml of
anhydrous acetic acid + 5 drops of concentrated sulfuric acid. After that, a heating
process is carried out to make the mixture dissolve homogeneously at a temperature of
50 - 60 degrees Celsius to maintain evaporation. Heating aims to remove impurities
contained in the solution so as to produce aspirin with a high level of purity. This
heating also aims to speed up the solubility of salicylic acid. After heating, the solution
turns cloudy white and a little precipitate appears, the solution is cooled and distilled
water is added. Then filtered using filter paper and a Buchner filter to speed up
filtration. The filtered residue is purified to dissolve hot distilled water which aims to
dissolve salicylic acid as a raw material for the formation of aspirin.However, after the
heating process was completed for 15 minutes, the solution did not dissolve completely.
then add the white mixed distilled water. filtered to produce impure filtrate and crystals.
then recrystallization was carried out with a suitable solvent, namely 15 ml of ethanol
p.a. and 38 ml of distilled water. then heated until dissolved. After that it is cooled to
accelerate the formation of crystals. White needle-like crystals will be obtained. then
filtered. The crystals obtained were oven-dried at 60 degrees Celsius to dry the filter
paper.
The filter paper was weighed before and after use to obtain crystals, namely
6.1212 grams. Finally, the % yield of aspirin crystals was calculated, namely 98.47%.
In this experiment, the salicylic acid is the limiting reactant and the acetic anhydride is
in excess. After the reaction heating period is over, the excess unreacted acetic
anhydride will be destroyed by the addition of water to the mixture: water reacts with
acetic anhydride to form 2 molecules of acetic acid, according to the reaction shown
below. When the esterification reaction is complete, water will be added to the mixture.
This will cause the precipitation of the acetylsalicylic acid and will react with any.
 remaining acetic anhydride. The solid aspirin will be collected using vacuum filtration.
Any other reaction ingredients that are soluble (this includes acetic acid, phosphoric
acid, and water) will pass through the filter paper. The collected aspirin will be tested
for its purity using FeCl3 (aq). Iron (III) ion reacts with phenols to form a purple
complex. Salicylic acid contains a phenol group, but acetylsalicylic acid does not.
Therefore, if you add FeCl3 to an aspirin sample and you see a purple color, it means
that there is still some salicylic acid present and the sample is impure.
The crystals obtained after qualitative testing produced a purple color. This
proves that there is still salicylic acid in the product or has been hydrolyzed. The
possibility that causes this is: the synthesis is not perfect because there are parts that
are not dissolved in the synthesis process.

VI. CONCLUSION
The synthesis of aspirin was obtained by an esterification reaction by reacting
concentrated anhydrous salicylic acid and acetic acid with a concentrated sulfuric acid
catalyst and recrystallization for purification with a % yield of 98.47% and the FeCl3
test produced a purple color.
REFERENCE

Baysinger, G. 2004. CRC Handbook of Chemistry and Physics 85th ed. America:
CRC Press.

Cahyono. 1991. Segi Praktisi dan Metode Pemisahan Senyawa Organik. Semarang:
FMIPA Universitas Diponegoro.

Fessenden, R. J., dan Fessenden, J. S. 1986. Kimia Organik Jilid 2. Jakarta:

Erlangga.

Kristian, R. 2007. Asam Salisilat dan Phenol. Banten: Teknik Kimia Universitas
Ageng Tirtayasa
 Work Scheme

5 grams of salicylic acid into a 100

mL flask, 7,5 g of acetic acid
anhydride and 5 drops of
concentrated sulfuric acid

Shake the mixture until it perfectly dissolve.

heat over a water heater (the

temperature inside the flask
is maintained at 50-60 ° C)
while stirring for 15 minutes

Let it cool while still stirring, and add 150 mL of

water

Then strain it with the aid of

suction.

1. 2.
Filtrate
Purification Crystal

Recrystallization with the

solvent used is a mixture of
15 mL of 96% alcohol and
37,5 mL of distilled water

Put in the crystal in a solvent and heat it

until all crystals dissolve, then cool it
gradually.

The mixture will result in gorgeous

needle-like crystals.

The crystal is then

tested with a reagent
of iron (III) chloride

% Rendemen
 Data Analysis

Is known :
Weight of empty filter paper: 0.6145 grams
Weight of filter paper + aspirin crystals: 6.7357 grams
Weight of pure aspirin crystals: 6.1212 grams

Calculating the moles of salicylic acid and anhydrous acetic acid:

moles of salicylic acid = mass : Mr = 5.0016 grams : 138 grams/mol = 0.0367 mol

mass of anhydrous acetic acid = p.V = 1.08 gram/cm3. 7.5 ml = 7.875 grams
moles of anhydrous acetic acid = mass : Mr = 7.875 grams : 102, gram/mol = 0.0772 mol

at first 0,0362 0,0772 - -

reaction 0,0362 0,0362 0,0362 0,0362

balanced 0 0,0409 0,0362 0,0362

weight of aspirin = mol.Mr = 0.0367 mol.180.157 gram/mol = 6.5216 gram

% yield = (weight obtained: theoretical weight). 100% = (6.1212: 6.216). 100% = 98.47%
 LABORATORIUM KIMIA PENDIDIKAN
FAKULTAS MIPA UNIVERSITAS ISLAM INDONESIA
Jl. Kaliurang km.14,5 Jogjakarta
Nama/ NIM Greef Rose Aulia/22923010 Tanggal 04 November 2023
Kelas/ Shift A/1 Judul SYNTHESIS OF ASPIRIN (ACETYL
SALICYLIC ACID)
Kelompok 1

LAPORAN SEMENTARA PRAKTIKUM KIMIA

PROGRAM STUDI S2 KIMIA FAKULTAS MIPA UII

Treatment Observation Result

5.0016 grams of salicylic acid + 7 mL of acid The solution is cloudy and contains sediment
acetic anhydrous + 5 drops of concentrated
sulfuric acid, stir until homogeneous
Heat and stir for 15 minutes, keeping the The mixture has not completely dissolved.
temperature in a 100 mL beaker in the range
between 50-60 C.
Add 75 mL of distilled water The mixture is white.

Filtered with a Buchner filter and pump White precipitate and clear filtrate were
vacuum obtained.

Recrystallization using a solvent mixture of White crystals are obtained.

15 mL ethanol PA and 38 mL distilled water
Heated. Heated on the stove Dissolved precipitation.

Cool in a bath containing ice cubes Crystals are formed.

Filtered with a Buchner filter and vacuum White needle-shaped crystals are obtained.
pump
Considered:
Weight of empty filter paper 0,6145 gram
Filter paper weight + aspirin crystals 6,7357 gram
Weight of pure aspirin crystals 6,1212 gram
% Aspirin crystal yield 98,47%
Tested with FeCl3 solution The result is purple

Dibuat oleh Diperiksa Disetujui Nilai

Praktikan, Asisten, Dosen Pengampu,

Greef Rose Aulia Bilqis Prof. Allwar, Ph.D