SYNTHESISOF ASPIRIN
INDEX
S.N PG.N
O CONTENT O
1. Introduction 4
2. Review of literature 6
3. Invention, Eects and Remedies 8
4. Materials required 9
5. Procedure 10
6. Analysis 12
7. Observation 15
8. Uses and Harmful e ects 17
9. Conclusion 18
10. Bibliography 22
INTRODUCTION
Aspirin is the common name for the compound acetylsalicylic acid, widely
used as a fever reducer and as a painkiller. Salicylic acid, whose name comes from
Salix, the willow family of plants, was derived from willow bark extracts. In folk
medicine, willow bark teas were used as headache remedies and other tonics.
Nowadays, salicylic acid is administered in the form of aspirin which is less
irritating to the stomach than salicylic acid. To prepare aspirin, salicylic acid is
reacted with an excess of acetic anhydride. A small amount of a strong acid is
used as a catalyst which speeds up the reaction. In this experiment, phosphoric
acid will be used as the catalyst. The excess acetic acid will be quenched with the
addition of water. The aspirin product is not very soluble in water so the aspirin
product will precipitate when water is added. The synthesis reaction of aspirin is
shown below:
REVIEW OF LITERATURE
Aspirin is the most widely sold over-the-counter drug. Since acetic acid
is very soluble in water, it is easily separated from the aspirin product. The
aspirin isolated in this step is the “crude product”. A “purified product” can
be obtained through recrystallization of the crude product in hot ethanol. In
this experiment, the crude product will be the desired product. The percent
yield of the crude product will be determined for this reaction. The purity of
the product will also be analyzed. The product will be analyzed by three
different methods: melting point, titration, and spectroscopic assay. The
melting point range of pure aspirin is 138-140 degree C and the melting
point range of the salicylic acid starting material is 158-161 degree C. If
impurities are present in your crude sample, the melting point range for your
product will be lower than the range of pure aspirin. Also, your melting point
range may be greater than 2 degrees. From the titration of your sample, the
moles of acetylsalicylic acid present can be determined assuming that there
is not a large percentage of an acid impurity present in your crude sample.
The spectroscopic analysis of aspirin will involve the complexing of iron
(III) to the deprotonated form of salicylic acid (salicylate ion) to give a purple
solution. Only the salicylate ion complexes to iron (III). Your aspirin product
as well as a commercial aspirin tablet will be compared to a standard 0.15%
ferric-salicylate solution. In the presence of moisture, aspirin may
decompose (hydrolysis) into salicylic acid and acetic acid. This reaction is the
reverse of the synthesis reaction. The maximum allowable amount of free
salicylic acid in an aspirin sample is 0.15% salicylic acid It has the ability to
reduce fever (antipyretic), to reduce pain (an analgesic), and to reduce
swelling, soreness, and redness (an anti-inflammatory agent). One of the
first recorded accounts for the discovery of aspirin appeared in England, in
1763, crediting the bark of willow trees with a beneficial effect in alleviating
distress due to fevers, aches, and pains.
Later, the compound salicylic acid (named for the Latin word for
willow, Salix) was isolated from willow bark. It proved to be the active
ingredient. By 1860, organic chemists were able to synthesize salicylic acid
from basic starting materials, this furthered the therapeutic use of the
substance, but there were problems. Salicylic acid proved to be irritating to
the membranes of the throat, mouth, and stomach. These problems are
directly associated with the high acidity of the compound, but a simple
remedy was discovered, namely, replacement of the acidic phenolic
hydrogen atom with an acetyl group
When interpreting the structures of the above organic compounds,
note the following characteristics of these molecules. Organic molecules are
complex compounds of carbon. Carbon always shares four pairs of electrons
in bonds with other molecular groups or atoms. When the structure of an
organic molecule is drawn using the condensed method, carbon rings are
represented with simple geometric shapes, such as a hexagon. Each corner
of the hexagon represents a carbon atom and the number of hydrogen
atoms required to share 4 pairs of Electrons with the carbon. If the “corner”
has no other marks, that means there is a carbon atom bonded to 2 other
carbon atoms (in the ring) plus 2 hydrogen atoms. The hydrogen atoms are
implied, not shown. If a carbon to carbon double bond (C =C) is present and
the carbons are attached in a ring, each of the two carbon atoms is bonded
to two others with 6 pairs of electrons, and only one hydrogen is attached to
each of these carbons give the full complement of four bonds. If a triple
bond is present then only one other atom may be attached. Check the
structures below to see that each carbon has four and only four bonds.
Oxygen, on the other hand, will bond covalently to only two atoms, and
hydrogen bonds to only one.
INVENTION:
A useful synthesis of acetyl salicylic acid was developed in 1893,
patented in 1899, marketed under the trade name of “aspirin” by the Bayer
Company in Germany. The name aspirin was invented by the
chemist, Felix Hofmann, who originally synthesized this for Bayer. More than
50 million 5-grains tablets of aspirin are consumed daily in the United States.
Aspirin still has its side effects .Note that the carboxylic acid functional group
remains intact.
EFFECTS ON HUMAN BODY : Even consumption or injection of
normal doses of aspirin may result in hemorrhaging of the stomach wall.
REMEDIES : The acid irritation can be reduced through the use of
buffering agents, like antacid, in the form of magnesium hydroxide,
magnesium carbonate and aluminum glycinate when mixed with aspirin
(bufferin).
MATERIALS REQUIRED:
For PREPARATION For ANALYSIS
01. Salicylic acid
02. Burnt clamp
03. Burette
04. Acetic anhydride
05. Stand with iron ring
06. Distilled water
07. 85% phosphoric acid
08. wire gauze
09. Ice bath
10. 50 mL flask
11. Beaker of tap water
12. Filter paper
13. Buchner funnel
14. Aspirator
PROCEDURE:
01. Use a centigram balance to weigh a 50 mL Erlenmeyer flask. Place
about 2 g of salicylic acid in the flask and weigh again. In the fume
hood, the instructor will transfer 5.0 mL of acetic anhydride from a
burette into the flask. Add 5 drops of 85% phosphoric acid (catalyst)
to the flask.
02. Clamp the flask in a beaker of tap water supported on a ring stand
over a burner flame. Stir if needed to dissolve the salicylic acid.
Heat the water to boiling, and shut off the flame. Keep the flask in
the hot water bath for 10 more minutes.
03. While the flask is still in the water bath, slowly add 2 mL of distilled
water to the flask to decompose any excess acetic anhydride.
04. A er a minute, remove the flask from the water bath and add 20 mL
of distilled water. Let the flask cool to room temperature. As the
solution cools, crystals of aspirin will appear. Cool the solution
further by placing the reaction flask in an ice bath. Chill 5-10 mL of
distilled water in a separate container.
05. Weigh a watch glass and filter paper on the centigram balance.
06. Set up a Buchner funnel on a vacuum flask connected to a water
aspirator. Place the filter paper in the funnel and moisten with
distilled water from a squirt bottle. Turn on the aspirator and
transfer the aspirin slurry into the funnel. Wash the crystals with 5
mL of the cold DI water.
07. Transfer the filter paper and aspirin to a pre-weighed watch glass
and allow it to air dry in your locker until the next lab period.
08. It is safe to discard the filtrate down the sink with water.
09. Set the flask aside to cool, observing it carefully.
10. When crystals start to form, cool the flask by surrounding it with
cold water. The crystallization process will then go to completion
11. Collect the crystals by vacuum filtration. Allow the crystals to dry.
Save your sample of the aspirin for a melting point determination and
further analysis.
ANALYSIS OF PREPARED ASPIRIN:
● MELTINGPOINT :
1. Weigh the dry product to obtain the yield of the reaction.
2. Calculate the theoretical yield and percent yield of the reaction.
3. Pack a few crystals of your aspirin product in a melting point
capillary tube. Allow the temperature of the melting point
apparatus to increase 1 degree C per minute starting from 120
degree C.
4. Measure the melting point range of the aspirin product. The
melting point range is the temperature when you first notice the
aspirin crystals melting up until the temperature when no crystals
remain.
● PURITY:
1. Label three test tubes; place a few crystals of salicylic acid into test
tube 1, a small sample of your aspirin into test tube 2, and a small
sample of crushed commercial aspirin into 3. Add 5 mL of deionized
water to each test tube and swirl to dissolve the crystals.
2. Add 10 drops of 1% ferric chloride to each test tube.
3. Compare and record your observations.
● TITRATION
1. Accurately weigh between 0.10-0.15 g of the aspirin product into a
125 mL Erlenmeyer flask. Add 15 mL of 95 % ethanol and swirl to
dissolve. Add 2 drops of phenolphthalein indicator to the flask.
2. Record the exact concentration of the standard 0.1 M NaOH solution.
Fill a burette with the standard NaOH solution and record the initial
volume. Titrate the sample until a faint pink end point is reached.
3. The pink color should last for at least 30 seconds a er swirling.
4. Repeat the titration with 0.10-0.15 g of a crushed aspirin tablet. You
may need to use a mortar and pestle to crush the tablet.
OBSERVATION
➢If phenol is present in a sample, the resulting color means the product
is impure. The purple color indicates the presence of a phenol group.
The intensity of the color qualitatively tells how much impurity is
present.
➢Determine the moles of aspirin from the titration and calculate the
percent purity of the crude aspirin product from the titration analysis.
➢Plot a Beer’s Law graph of the standard 0.15% salicylic acid solution (C)
on excel with Absorbance (y-axis) vs. % salicylic acid
(x-axis). To make a Beer’s Law plot,
enter % Salicylic Acid into one
column on the excel
spreadsheet (0 and 0.15) and
absorbanceinto the next
column (0 and the absorbance
reading). Highlight the data
and select insert, and scatter (w/
only markers). Right click a
data point and select the add trend line. Now set the y-intercept to 0
and check the display equation box. To add titles to the plot, select
layout, axis titles, and then chart titles.
USES OF ASPIRIN:
➢ Aspirin inhibits the synthesis of a chemical known as prostaglandins
which simulate inflammation in the tissue and cause pain.
➢ These drugs are effective in relieving skeletal pain such as that due to
arthritis.
➢ These drugs are also used to reduce fever (antipyretic).
➢ These drugs are also used for preventing platelet coagulation because
of its anti-blood clotting action.
➢ Aspirin finds use in prevention of heart attacks.
HARMFUL EFFECTS:
➢ Abdominal or stomach pain, cramping, or burning.
➢ It causes a decrease in frequency or amount of urine which would be
bloody or cloudy urine or dark urine.
➢ Chest pain or discomfort.
➢ Constipation , diarrhea.
➢ Difficult breathing as well Fast breathing.
➢ Fainting, fever, general tiredness and weakness.
Health Risks Associated with Acetylsalicylic Acid
● Exposure pathways – Skin or eye contact, ingestion, and inhalation.
● Symptoms – Irritation in eyes, upper respiratory system, skin,
increased blood clotting time, vomiting, and nausea.
● Aspirin, or acetylsalicylic acid (ASA), is widely used as a pain relief for
mild aches and pains and to alleviate fever. It is also an anti-
inflammatory drug that can be used as a blood thinner.
● Aspirin is not typically recommended for children aged under 16
years, since it can raise the likelihood of Reye’s syndrome, which can
arise with an infection, such as a cough, flu, or chickenpox. It may lead
to permanent damage to the brain or death.
DISCUSSION
Aspirin crystals were formed.
Weight of crystals formed a er drying: 0.450 g
BIBLIOGRAPHY
To make this project I had reference from the following
sources:
● NCERT Textbook
● LAB MANUAL
● https://en.wikipedia.org
● https://byjus.com
● https://laney.edu
● Sources from various blogs
