Name: Sanglad, Chariezza Lei J.

Date Performed: June 20, 2017

Group No:5 Date Submitted: June 27, 2017

Experiment no:1

SYNTHESIS OF ASPIRIN
Objectives:
1. To be able to synthesize aspirin using salicylic acid and acetic anhydride as starting
material.
2. To be able to measure the synthesized Aspirin’s percent yield.

Procedure:
Pre-weigh 50-ml Erlenmeyer flask
+2.0 g salicylic acid, weigh again
Pour 5.0 mL acetic anhydride in flask
+ 5 drops conc. Sulfuric acid
put flask in the beaker of H2O (see figure 1)
H2O to 75°C and maintain temperature 15 min(stir occasionally)
+2 mL H2O to flask
When liquid stop giving vapours, remove flask
+16-20 mL H2O
Cool flask (crystals of aspirin should begin to appear)
Put flask in ice bath
Collect aspirin by filtering through Buchner funnel (figure 2)
Pour 5 mL ice cold deionized water over crystals, repeat 2 times
Draw air to funnel
Transfer collected crystals to pre-weighed watch glass
Data and Results
Table1. Preparation of Aspirin

Mass of 50-mL Erlenmeyer flask(g) 94.3508

Mass of flask and salicylic acid (g) 96.4386
Mass of salicylic acid (g) 2.0879
Volume of acetic anhydride (mL) 5.0
Mass of watch glass (g) 33.3983
Mass of watch glass and aspirin (g) 35.7141
mass of filter paper (g) 0.7664
Mass of filter paper and watch glass (g) 34.1646
Mass of aspirin (actual yield) (g) 2.3158
Theoretical yield (g) 2.7234
% yield of aspirin 85.01%
Discussion:
The first part of the experiment was the preparation of Acetylsalicylic Acid (Aspirin). A
white, milky mixture was obtained when salicylic acid, acetic anhydride and for the reaction to
take place, an inorganic acid such as sulfuric acid is used as a catalyst. The mechanism of the
reaction is:

Aspirin is synthesized through the reaction of salicylic acid with acetyl anhydride which
causes a chemical reaction that turns salicylic acid's hydroxyl group into an acetyl group, (R—
OH → R—OCOCH3).
The reaction above shows that the oxygen in salicylic acid attacks one of the carbons in
acetic anhydride. Also, the mechanism shows how acetic acid was separated from the
acetylsalicylic acid.
The mass of salicylic acid used was 2.0879 g and volume of acetic anhydride was 5.0
mL. The theoretical yield of aspirin was 2.7234 g.
Heating of the mixture was done and a clear liquid was obtained. Heating was employed
so that salicylic acid would melt and react with acetic anhydride. Then water was added after
heating. This is to prevent the reaction of acetic anhydride with water at the start of the
experiment, if this had happened, then there will be no aspirin could have formed. With this,
acetic anhydride was decomposed after the formation of aspirin. After the adding 10mL ice-cold
water, cooling to room temperature and placing in an ice bath, the liquid became whitish/cloudy
with white precipitates. The addition of cold water is very important in purification and isolation
of the crystals from the liquid since aspirin is insoluble in cold water. To eliminate any salicylic
acid and acetic anhydride that did not react, as well as the acetic acid product and sulfuric acid,
purification is needed. In this part, purification is not yet complete (it was continued on the
recrystallization part). Isolation was done through suction filtration, white, sugar-like crystals
were obtained.
Cold water is used to recrystallize only aspirin, thus, leaving all the impurities behind.
Since aspirin is an ester, it should not be recrystallized from hot water since esters hydrolyses in
hot water. After cooling in an ice bath (which further facilitates recrystallization and
purification), the mixture was then suction filtered.
The weight of the recovered sample was 2.3158g. The calculations for percent yield was
shown after this discussion. The percent yield was 85.01%, meaning there was a slight error.
Perhaps, the sample was not weighed properly or it was weighed when still wet or this could be
due to handling problems in suction filtration or drying.
For the dehydration of the ASA crystals, the only thing that can be improved is to wait
longer before weighing it on a scale. It is not easy to tell whether or not the product is completely
dry, but it is safer to leave it alone for a slightly longer amount of time just in case.
Calculations:

Moles of a molecule = (Mass of substance) / (Molar mass)

Acetic Anhydride (C4H6O3): 102.09 g/mol,
Density is 1.082 g/mL, therefore 5.0mL contains 5.0mL x 1.082g/mL =5.41 g acetic anhydride
Therefore there are 5.41 g / 102.09 g/mol = 0.05299 moles
Salicylic Acid (C7H6O3): 138.12 g/mol, thus there are 2.0879 g / 138.12 g/mol = 0.01512 moles

The balanced equation is

C4H6O3 + C4H6O3 → C9H8O4 + C2H4O2

which can also be written as

C6H4OHCOOH + (CH3CO)2O → C9H8O4 + CH3COOH
to show the molecular structure of aspirin more clearly.

Equal amounts of acetic anhydride and salicylic acid are required for this reaction, therefore
salicylic acid is the limiting reagent.
Therefore only 0.01512 moles of aspirin will be produced.

The molecular mass of aspirin is 180.16 g/mol

Moles of a molecule = (Mass of substance) / (Molar mass)

Therefore,
Mass of a substance = (Moles of a substance) * (Molar mass)

180.16 g/mol x 0.01512 mol = 2.7234 g aspirin

The percentage yield for this synthesis of aspirin may be calculated as follows:
Theoretical yield = 2.7234 g
Actual yield =2.3158 g
Actual yield
Percentage yield = x 100%
𝑀𝑎𝑥𝑖𝑚𝑢𝑚 𝑌𝑖𝑒𝑙𝑑

2.3158
= x 100%
2.7234
=85.01%