INORGANIC AND ORGANIC

CHEMISTRY
(R E P O R T)

MUHAMMAD HAIQAL ASSYIDDIQ BIN

RASHID

P1716458

Class: DCHE/FT/1B/07

Date of Experiment: 6 November 2017

Date of Submission: 20 November 2017

 Contents Page

Synopsis --------------------------------------------------------------------------------------- Page 2

Introduction ----------------------------------------------------------------------------------- Page 2

1) What is Aspirin?

2) Uses of Aspirin

3) Methods for development of Aspirin

Theory ----------------------------------------------------------------------------------------- Page 3

1) Functional Group

2) Synthesis of Aspirin

3) Esterification Process

4) Acetic Anhydride

5) Recrystallisation of Aspirin

Procedure ------------------------------------------------------------------------------------ Page 4

1) Preparation of Aspirin

2) Recrystallization of Aspirin

3) Apparatus and Product ----------------------------------------------------------------------------------- Page 5

Results and Calculations ----------------------------------------------------------------- Page 6

Discussion ------------------------------------------------------------------------------------Page 7
1) Comments on results

2) Personal reflection

Conclusion ----------------------------------------------------------------------------------- Page 8

References ---------------------------------------------------------------------------------- Page 9

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 Synopsis

This report is about how the synthetisation of aspirin, a simple organic compound, is
conducted, how the skills of recrystallisation and the technique of melting point
determination were being reinforced throughout the experiment. This experiment was
determined by adding acetic anhydride to salicylic acid with an addition of a few drops
(3 – 4) of sulphuric acid in a flask to allow recrystallisation to aspirin by going through
the process of heating using a digital water bath and suction filtration using a set up
made up of Buchner funnel, filter papers and a filtration flask. Next, the flask containing
the substances are being cooled in an ice bath then dried in an oven and a desiccator.
The percentage yield, melting point and the appearance of the aspirin were written
down to determine the purity of the aspirin obtained. The percentage yield obtained
during this experiment is 131.8% and the melting point of the aspirin is 60⁰C – 91.5⁰C.
The appearance of the aspirin was supposed to be shiny, white and needle-like, but
our aspirin crystals was only white but not shiny.

Introduction

1) What is Aspirin and who created it?

Aspirin, otherwise called, acetylsalicylic corrosive (C9H8O4), is a painkiller created by

Felix Hoffman. The “headache” medicine appeared in the late 1890s when scientist
Felix Hoffmann at Bayer, Germany, utilized it to mitigate his father's ailment. Starting
in 1899, Bayer dispersed a powder with this fixing to doctors to provide for patients.
2) How does aspirin work and what are the uses?

Aspirin can be consumed to reduce fever and ease moderate pain from conditions
like migraines, toothaches, muscle throbs, swelling, arthritis and common cold.
Aspirin is a nonsteroidal anti-inflammatory drug (NSAID). It obstructs a specific
natural substance in our body to diminish inflammations. Moreover, taking low doses
of aspirin can avert blood clots and prompt lower danger of encountering stroke and
heart attack.
3) Methods of Development of Aspirin

The methods that were being carried out during the synthesis of aspirin are
esterification, melting point determination, suction filtration and recrystallization.

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 Theory
Functional Groups
Aspirin contains three groups:
 ester (R-O-CO-R')
 carboxylic acid (R-COOH)
 aromatic (benzene ring)

Synthesis of Aspirin (acetylsalicylic acid)

This is a rapid reaction between salicylic acid and acetic anhydride in the presence
of an acid catalyst to produce aspirin (acetylsalicylic acid) and acetic acid (ethanoic
acid).
Common catalyst used in this reaction is sulphuric acid or phosphoric acid.

Esterification Process

In an esterification reaction, salicylic acid can react with acetic (ethanoic) acid but the
reaction is very slow, taking days to reach equilibrium, and the yield is low:

For this reason, the commercial preparation of aspirin relies on the faster reaction
between salicylic acid and the more reactive acetic anhydride which produces a
greater yield of aspirin.

Acetic Anhydride

In this experiment, we used acetic anhydride instead of acetic acid. Acetic anhydride is an
anhydride of acetic acid and ‘anhydride’ just means that the acid is ‘dehydrated’ or in other
words “in the absence of water”

Acetic anhydride was used instead of acetic acid because acetic anhydride can react faster
with salicylic acid.

Recrystallization of Aspirin

Recrystallisation is a purifying technique to purify chemicals.

Major steps:

1. Solute is being dissolved in solvent

2. The solution is being cooled in open air
3. The crystals of the solute are being obtained using vacuum filtration
4. The crystals are being dried

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 Procedure
1. Preparation of Aspirin

1.1. 2.4g of salicylic acid was approximately weighed into a dry 100 ml conical flask
and the actual weight was recorded which is 2.4665g.
1.2. In the fume hood, using a bottle top dispenser, 12 ml of acetic anhydride was
added to the flask containing salicylic acid.
1.3. 3 drops of concentrated sulphuric acid was added to the mixture and the flask
was swirled to mix the contents.
1.4. The mixture was heated in a water bath for 10 to 15 minutes to complete the
reaction.
1.5. The flask was removed from the water bath and while it is still hot, about 1 ml
of distilled water was added from a dropper to decompose the excess acetic
anhydride.
1.6. 40 ml of cold water was added, and the mixture was stirred with a stirring rod
to induce crystallisation.
1.7. The crude product was collected by suction filtration using a Buchner funnel
and a vacuum pump which then was washed with a little cold water.

2. Recrystallisation of Aspirin

2.1. The crude product was dissolved in approximately 5 ml of ethanol in a 100ml

conical flask. The mixture was warmed on a hot plate.
2.2. Approximately 30 ml of hot distilled water was added to the solution.
2.3. At this point, the solution was warmed until the solid had already dissolved in
the solution completely.
2.4. The solution was left to cool.
2.5. A clean, dry watch glass together with 2 filter papers were being weighed. The
weight is 35.2189g.
2.6. The weighed filter papers were used to obtain the recrystallized product by
suction filtration.
2.7. The aspirin crystals and filter paper were transferred onto the weighed watch
glass. They were dried in the oven (100⁰C) for 5 minutes.
2.8. The crystals, filter paper and watch glass were placed in the desiccator for 5
minutes.
2.9. The dried crystals together with the filter paper and watch glass were weighed
again. The weight is 39.4583g. The weight of the dried, recrystallized aspirin
was then 4.2394g.
2.10. The expected yield of aspirin was calculated from the amount of salicylic
acid that was used. The percentage yield of the dried, recrystallized aspirin is
131.8%.

3. Melting Point Determination of Aspirin

3.1. The melting point of Aspirin was determined using EZ- Melt.
4. The Aspirin was discarded in the ‘Aspirin Waste’ container.

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 Apparatus and Product

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 Results and Calculations

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 Discussion
Firstly, my group member and I added about 12ml of acetic anhydride instead of 6ml. We
continued with the procedures as per normal because we were not told to modify certain
procedures. Unfortunately, we obtained a very low melting point of 60⁰C – 91.5⁰C. This was
mainly because we did not wash the crystals with excess water therefore there were still traces
of acetic anhydride. Therefore, the large amount of impurities has caused our melting point of
aspirin to be very low and hence unacceptable for the use in hot weather countries.

Time Constraint

I personally feel that my experiment would have gone by smoothly if hadn’t for the excess
addition of the acetic anhydride. The amount of salicylic acid added was constant and the
catalyst, sulphuric acid, just helped to speed up the reaction. Hence the only thing that vary
was the volume of acetic anhydride. This eventually produce too much impurities in my aspirin.

Secondly, me and my partner admitted that we were running out of time because we panicked
when we realised we did not achieve a colourless solution in the beginning. We had to add
more acetic anhydride and undergo the water bath process again. Hence, we did not have
enough time to leave our crystals in the oven for 15 minutes. We left our aspirin crystals for 5
minutes in the oven and 5 minutes in the desiccator. We then realised that the weight of our
dried aspirin crystals was heavier than the expected weight of the aspirin crystals. This was
because our crystals were still wet and did not dry fully causing in the large value of
Percentage Yield (%).

Our aspirin crystals were still in clumps and were less in the powdered form. Our crystals were
not shiny, and this clearly shows that our crystals were not dried fully.

Drying

During the drying process, our crystals should be dried in an oven and a desiccator for around
15-20 minutes and 5-10 minutes respectively. However, my aspirin crystals were left in the
oven and desiccator for 5 minutes each. This means that my crystals were still wet, and it was
difficult to carry out the melting point determination process.

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Melting Point Determination

There are a few steps to carry out before determining the melting point of the aspirin crystal.
We must insert a small amount of crystals into a capillary tube. To carry out this step, we need
a hollow plastic tube with a diameter bigger than the capillary tube. The capillary tube is being
dabbed onto the aspirin crystals and to ensure that the crystals settle at the bottom of the
capillary tube, we must drop it through the capillary tube about 3 times.

However, since my crystals were wet, I had a hard time to let the crystals settle to the bottom
of the capillary tube because when the crystals are wet, the crystals exist in clumps and it is
very difficult for the crystals to travel down the capillary tube even after a few drops through
the large plastic tube.

Recrystallisation of Aspirin

I added 12ml of acetic anhydride to the salicylic acid and this means that I must wash the
crystals more than the rest of my classmates. This is because I could smell vinegar which is
scientifically known as acetic anhydride. I should have washed the crystals further so that the
acetic acid will be washed away. Then, I can start dissolving the crystals in the solvent and
heat up the solution. Next, the solution can be left overnight for the crystals to form. However,
due to time constraint, we forced the crystals to form by cooling the solution in an ice bath.
Hence, by washing the crystals in excess water, it will further improve my results and my
melting point of my aspirin crystals will be higher because there are lesser impurities.

Hence, in future, I will try my best to take note of all the mistakes I have made in this experiment
and will not repeat them. I will learn to manage my time well and stay composed when in
difficult situations.

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 Conclusion
The percentage yield obtained is 131.8% which is very unacceptable. Furthermore, my
aspirin crystals have a melting point of 60⁰C – 91.5⁰C, whereas the actual melting point is
135⁰C. This shows that my aspirin crystals are very impure and hence, this shows that the
recrystallisation process was unsuccessful to a certain extent.

The major learning point of the experiment was to learn how to carry out the process of
esterification to produce and product called Aspirin. We also learn how to carry out the
recrystallisation of aspirin. Furthermore, I mastered the skill to fold a 32-folds filter paper. I
also learn how to improve my skill during suction filtration using a Buchner funnel and a
vacuum pump so that the purity of the aspirin crystals can be improved. Lastly, I also learn
how to determine the melting point of the aspirin crystals using a EZ-Melt apparatus.

Hence, I would like to recommend some ways to further improve our results in future. Firstly,
make sure that the recrystallisation should be left overnight and not being forced using an
ice bath. This might force out the formation of impurities instead of the product. Also, I learn
that we should not use acetic acid to react with salicylic acid because it is a very slow
process. In addition, we should always remember to add distilled water to decompose
excess acetic anhydride because this will produce a less harmful substance which is acetic
acid also known as “vinegar”.

Lastly, I conclude that all objectives in this experiment is fulfilled.

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 References
Cnncom. 2017. Cnncom. [Online]. [16 November 2017]. Available from:
http://www.cnn.com/2010/HEALTH/12/22/aspirin.history/index.html

Googlecomsg. 2017. Googlecomsg. [Online]. [26 November 2017]. Available from:

https://www.google.com.sg/url?sa=i

Janice stubbings. 2017. Ausetutecomau. [Online]. [16 November 2017]. Available from:
http://www.ausetute.com.au/aspirin.html

Webmdcom. 2017. WebMD. [Online]. [16 November 2017]. Available from:

https://www.webmd.com/drugs/2/drug-1082-3/aspirin-oral/aspirin-oral/details

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