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Synthesis of Aspirin

This document describes the synthesis of aspirin via the esterification reaction of salicylic acid and acetic anhydride, catalyzed by sulfuric acid. The synthesis yields aspirin and acetic acid. The document discusses choosing an appropriate solvent for recrystallization based on boiling point and solubility. It then outlines the experimental procedure for synthesizing aspirin, including a single and double solvent recrystallization followed by a hydroxamic acid test to verify the product.

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43 views

Synthesis of Aspirin

This document describes the synthesis of aspirin via the esterification reaction of salicylic acid and acetic anhydride, catalyzed by sulfuric acid. The synthesis yields aspirin and acetic acid. The document discusses choosing an appropriate solvent for recrystallization based on boiling point and solubility. It then outlines the experimental procedure for synthesizing aspirin, including a single and double solvent recrystallization followed by a hydroxamic acid test to verify the product.

Uploaded by

Patty
Copyright
© © All Rights Reserved
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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SYNTHESIS OF ASPIRIN

ABSTRACT
This experiment is to synthesize the common pain killer aspirin via an
esterification reaction between Salicylic Acid and Acetic Anhydride in the presence of
concentrated sulfuric acid acting as a catalyst.

INTRODUCTION

Aspirin is most widely sold over-the-counter drug. It has the ability to reduce
fever (an 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
show. If a carbon to carbon double bond (C =C) is present and the carbons are attached

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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 compliment 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.
A useful synthesis of acetylsalicylic 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 acetylsalicylic acid for Bayer. More than 50 million 5-grain tablets of aspirin
are consumed daily in the United States. In Part I of this experiment, you will prepare
aspirin by reaction of salicylic acid with acetic anhydride, using concentrated sulfuric
acid as a catalyst.

Limiting Reagent and % Yield: Synthesizing a compound in the laboratory usually


requires the student to compare the experimental yield of product with the amount that
is theoretically possible based on the amounts of materials used. The first step in this
process is to determine the molar ratio of the reactants actually used relative to the
stoichiometric molar ratio as defined in the balanced equation of the reaction. In most
laboratory courses one of the reagents has an insufficient number of moles to react with
the other reagent. This reagent is referred to the “limiting Reagent,” while the other
reagent is considered “in excess.” Thus, the limiting reagent is totally consumed in the
reaction and it dictates, on a molar equivalent basis, the theoretical amount of product
that can be expected from the reaction. The % yield of the experiment is then
determined from the ratio of the amount of product actually obtained to this theoretical
amount (mass or moles can be used for the calculation). C7H6O3 Salicylic Acid
C4H6O3 Acetic Anhydride C9H8O4 Acetyl Salicylic Acid C2H4O2 Acetic Acid Actual
Yield % Yield = × 100 Theoretical Yield.

RESULTS AND DISCUSSION


CHOOSING THE RECRYSTALLIZING SOLVENT

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BOILING POINT ROOM HIGH LOW
TEMPERATURE TEMPERATURE TEMPERATURE
HEXANE 69°C Insoluble Insoluble

WATER 100°C Insoluble Soluble Insoluble

METHANOL 65°C Soluble Soluble

ETHYL 76°C Soluble Soluble


ACETATE

Discussion of the results


Water is the most crystallizing solvent.
Hydroxamic Acid test result: Violet

C7H6O3 Salicylic acid 138.121 g/mol


C4H6O3 Acetic anhydride 102.09 g/mol
C9H8O4 + HC2H3O2

Theoretical Yield:
C7H6O3 + C4H6O3 ----------- C9H8O4 + C2H4O2
Theoretical Yield: 2.693g
Actual Yield: 0.728g
Percent Yield:
__Actual Yield__ = 0.727g_ x 100 = 27.03%
Theoretical Yield 2.6293g

EXPERIMENTAL

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First, 2 grams of salicylic acid, 4mL of acetic anhydride and 5 drops concentrated
sulfuric acid was placed in 125mL Erlenmeyer flask. It was heated in water bath about
80°C until the solid was dissolved. 20mL of ice water was added and was placed in an
ice bath and filtered using vacuum filtration. Second, the filtrate was discarded. The
residue is the crude aspirin.

SINGLE SOLVENT RECRYSTALLIZATION


First, the crude aspirin was placed in 100mL beaker and added 25mL solvent. It
was heated to boiling temperature of solvent and was filtered while hot with the use of
gravity filtration. The residue was discarded while the filtrate was placed in an ice bath
and was filtered by vacuum filtration. The filtrate which is the mother liquor was
discarded and residue which is the aspirin crystals undergo Hydroxamic acid test until it
reaches its melting point and IR Spectroscopy was made.

DOUBLE SOLVENT RECRYSTALLIZATION


First, the crude aspirin was placed in 100mL beaker and added 10mL solvent A.
Second, it was heated to boiling temperature of the solvent A. and was filtered while hot
using gravity filtration. The residue was discarded while the filtrate was added by
solvent B dropwise until cloudy. It was placed in an ice bath and was filtered by vacuum
filtration. The filtrate which is the mother liquor was discarded while the residue undergo
hydroxamic acid test until it reaches its melting point and IR Spectroscopy was made.

HYDROXAMIC TEST
First, 10 drops of test compound was placed in 100mL beaker. 5 drops of
Hydroxyl amine solution and 5 drops of 3M Sodium Hydroxide was added. Second, it
was placed in a boiling water bath for 1 minute and cooled. 10 drops of 3M Hyrochloric
acid and 2 drops of Iron (III) chloride was added. Observation was made while doing
and after doing the test.

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REFERENCES

[1] Solomons, G., Fryhle, C & Snyder, S (2014) Organic Chemistry: International
Student Version. John Wiley & Sons Singapore Pte. Ltd. 11th Edition.

[2] Table of acids with Ka and pKa values. Retrieved from:


http://clas.sa.ucsb.edu/staff/Resource%20Folder/Chem109ABC/Acid,%20Base%20Stre
ngth/Table%20of%20Acids%20w%20Kas%20and%20pKas.pdf (accessed on April 1,
2017)

[3] Haynes, W. M. (2014) CRC Handbook of Chemistry and Physics : A Ready-


reference Book of Chemical and Physical data, 95th edition, CRC Taylor and Francis.

[4] Dheri, J (2014). Solubility. Chapter 4.4. Retrieved from:


https://chem.libretexts.org/LibreTexts/Purdue/Purdue%3A_Chem_26505%3A_Organic_
Chemistry_I_(Lipton)/Chapter_4._Intermolecular_Forces_and_Physical_Properties/4.4_
Solubility (accessed on April 3, 2017)

[5] Boikess, R (2015). Chemical Principles for Organic Chemistry. Cengage Learning,
200 First Stamford Place, USA.

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