Prithvi Dev Awasthi

09/29/2016

Acetaminophen
Objective
The objective of this lab was to synthesis amide (acetaminophen) from
amine (p-Aminophenol) and acid anhydride (Acetic Anhydride) by heating the
mixture and vacuum filtration process and find the melting and boiling point
of the crude and pure acetaminophen
Experiment Scheme
Initially, 1.53 gm of p-Aminophenol was placed in 50 ml Erlenmeyer
flask and 4.5 ml of water and 1.7 ml of acetic acid was added and magnetic
stir was placed in the flask for dissolving the solute in the solvent better. The
mixture was heated at 100 degree Celsius for 10 minutes. Thermometer was
placed intact to check the temperature of the solution while being heated.
After 10 minutes, the flask was removed from the heated plated allowed to
cool down to room temperature. Ice bath was prepared and the flask was
kept in the ice bath for 15 more minutes. After the crystal was formed, it was
dried using vacuum filtration in a Buchner funnel.
The flask was risen with ice water and the mixture of 50% water and
50% methanol by volume was poured in it and heated up to boiling point.
While doing that, crude acetaminophen was transferred into another flask
and weighed. Small sample was taken out for testing the melting point.
Then, 2gm of Sodium dithionite and crude acetaminophen was placed in 50

Prithvi Dev Awasthi

09/29/2016

ml Erlenmeyer flask. Small portions of hot solvent was added to the flask
until the solid dissolved completely. After dissolving, it was set down to cool
in the room temperature and then placed in the ice bath for 10 more
minutes. Then the crystals were collected in the Buchner funnel and dried for
5 to 10 minutes using vacuum filtration. Finally, the pure acetaminophen was
weighed and small sample was taken to check the melting point.
Percent yield can be calculated by dividing the actual yield by
theoretical yield. The actual yield was calculated by weighting the final
product and the theoretical yield was calculated by using the amount of paminophenol and acetic anhydride and their respective molecular weight.
The boiling point was determined by using a Mel-temp. Small amount
of the sample that was kept aside was placed in the melting-point tube and
placed in the machine. The melting and boiling points were observed by eyes
by looking the material through lens.
Name

Formul

MW

Amou

Mole

Sta

Densi

M.P

B.P

The

(g/mo

nt (g)

te

ty

o.

(g/cm

(oC)

(oC

Yiel

3
)
1.13

185

)
-

d
-

Toxic; Skin irritation

138

Sore throat

2.1

Liver damage

l)
p-

C6H7NO

aminophenol
Acetic

1.5

3
C4H6O3

anhydride
Acetaminophe

109.1

102.0

151.1
6

7
1.7

9
C8H9NO2

0.013

0.017

1.08

189
-73

9
-

Health Hazard

1.263

152
-

140
-

Prithvi Dev Awasthi

09/29/2016
172
Acetic acid

CH3COO

60.05

1.05

Sodium

H
Na2S2O4

174.1

2.19

Dithionite
Methanol

CH3OH

0
32.04

0.792

Eye irritation

52

Nausea, Vomiting

64.

Blindness if taken

97.

pure methanol

Data
Table 1

Equation 1: Formation of acetaminophen and acetic acid from p-aminophenol and acetic
anhydride

Theoretical yield of acetaminophen

1.5 g of p-aminophenol * 1mol/ 109.13g = 0.014 mol p-aminophenol
1.7 ml acetic anhydride * (1.1gm/mol) * (1mol/102.09g) = 0.018 mol acetic
anhydride
p-aminophenol has fewer number of moles so it is the limiting reagent and as
the proportion of the reactants is 1:1, the reaction is:
0.014 mol acetaminophen * (151.16gm/mol) = 2.1 gm of acetaminophen
Amount yield (In grams)

Prithvi Dev Awasthi

09/29/2016

Crude acetaminophen = 1.60 gm

Pure acetaminophen =

1.55 gm
Percent Yield
Crude acetaminophen

Pure acetaminophen

1.6/2.1*100% = 75.47%

1.55/2.1*100% = 73.11%

Melting point
Crude = 148o C 177o C

Pure = 152o C 172o C

Discussion
This experiment used a technique where an amide was synthesized
from an amine and an acid anhydride. The reaction is known as an
acetylation reaction, where an acetyl group is substituted for an active
hydrogen. After the mixture was made, it was heated so the reaction would
complete. Heating the mixture is necessary because it helps the solid paminophenol to dissolve in the mixture completely. After heating, when the
mixture was dissolved completely, it was cooled down so that the formed
acetaminophen could crystallize. The crystal and the solution were put
through a process of vacuum filtration for drying by using a Buchner funnel.
This process is necessary for removing the excess liquids that might be
present in the crystals. After the crystals were dried and removed in a flask,
the color appeared to be cream-white. This color appear because of the
oxidation of p-aminophenol.

Then the crystals were weighed and then

combined with sodium dithionite which helps in reducing the double bonds
that are present in the substance for changing colored substance to colorless
substance.

The

mixture

was

again

recrystallized

for

purifying

the

acetaminophen further. During this crystallization, hot solvent was added to

the mixture until it dissolved. Then it was set aside for cooling. As it cooled,
crystals of pure acetaminophen were formed leaving the impurities in the
solution.

The initial reaction may not have been carried out completely where
there might have been a loss of so product. It is also possible that some of
the product was lost during the filtration process from the Buchner funnel. If
the product had not crystallized properly when it was poured for filtration, it
is also possible that it might have passed through the filter paper with the
solution. Some product was also lost during the recrystallizing process. It
points towards that all the dissolved product cannot be recovered properly.
Just enough hot solvent needs to be added so that most of the product
crystallize and not remain the water.
Another source of error might be while measuring the melting point.
The observed melting point of pure acetaminophen was 152 -172 degree
Celsius which is a very wide range. It is hard to observe when exactly it
starts to melt. It is more likely to melt closer to 160 degree Celsius.
The experiment was successful because some amount of pure
acetaminophen was synthesized and gathered.
Questions
Q1: During the crystallization of acetaminophen, why was the mixture cooled
in the ice bath?
A: During the crystallization of acetaminophen, the mixture was cooled in an
ice-bath to give more complete crystallization of p-aminophenol. An icewater bath may also help to prevent the crystals from dissolving as room
temperature was high.

Q4: If 1.30 g of p-aminophenol is allowed to react with excess acetic

anhydride, what is the theoretical yield of acetaminophen in moles? In
grams? Show your work!
A: 1.30g p-aminophenol * 1mol / 109.13g = .0119mol p-aminophenol
.0119mol p-aminophenol = .0119mol acetaminophen (theoretical yield in
moles)
.0119mol acetaminophen * 151.16 g / mol = 1.80 g acetaminophen
(theoretical yield in grams)

References
1. Pavia, D.L.; Lampman, G.M.; Kriz, G.S.; Engel, R. Acetaminophen. In
organic chemistry lab manual, Third edition; Radke,K., Stolzenberg,G.
Eds.; Cengage learning: Manson, OH, 2009; 11-13
2. Budavari, S. The Merck index: an encyclopedia of chemicals, drugs, and biologicals;
Merck: Rahway, NJ, U.S.A., 1989.
3. Lehman, J. W. The Students lab Companion, 2nd ed.; Pearson