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[Chemical Engineering Laboratory 2]

Preparation of Aspirin and Oil and


Wintergreen
Candidates Name
Student ID

:
:

Yuga Raaj A/L J.Balar

SCM025537

Group Members Name :

Thivya A/P Maran

Viveta Priyaa A/P


Selvarajan
Divaan Raj A/L
Karunakaran
Shahrukh Ahmed
Lecturer/ Supervisor

Mohd Rezuwan

Date of Submission

3/10/2013

Title: Preparation of Aspirin and Oil of Wintergreen


Abstract
1) To determine the synthesize a sample of acetylsalicylic acid (aspirin)
2) To determine the synthesis of methyl salicylate
3) To calculate the percentage yield of the synthesis

Introduction
Esters are derived from organic acids. Esters usually have a pleasant smell,
fruitlike odors and fragrances of many fruits and flowers. Two compounds will
be produced in the experiment which is aspirin (acetylsalicylic acid) and oil of
wintergreen (methyl salicylate). Both of these compounds are from ester
group. An ester is a compound that is formed when carboxylic acid react with
an alcohol. These two groups have different functional group where
carboxylic acid will provide COOH group and alcohol provide OH group. The
reaction for this compound is call esterification

Aspirin is one of the generally most useful drugs known. It is both an


analgesic (painkiller) and an antipyretic (reduce fever). The second ester
product is called methyl salicylate, which is a compound of oil and
wintergreen. It is prepared by esterification process of carboxylic acid
(COOH) of salicylic acid with methanol. The reaction of these two is

Phenols are class of compounds in which the OH group is attached to the


phenyl ring. This type of group is present in both salicylic acid and methyl
salicylate but not in acetylsalicyclic acid. Most of the phenol form colour
complex. Therefore, a test is conducted to prove the presence of phenol by
adding 1% of FeCl3 solution because phenol form a colour complex.

Apparatus
125 mL of Erlenmeyer flask, 10 mL of graduated cylinder, small awtch glass,
thermometer, filter paper, wire gauze, 600 mL beaker, large test tube,
funnel.

Chemicals
Acetic anhydride, 1% FeCl3 solution, salicyclic acid, ice, absolute ethanol,
methyl alchhol and concentrated H2SO4

Procedure : Synthesis of Aspirin

Synthesis of Methyl Salicylate

Result
A)Synthesis of Aspirin
Mass of salicylic acid
Mass of dry recrystallized aspirin

2.96

6.9

Percent yield
Moles of salicylic acid used (mol wt of salicylic acid = 138 amu)

0.02
mol

Theoretical number of moles of aspirin

0.02
mol

Theoretical grams of aspirin (mol wt of aspirin = 180 amu)


Percent yield =

3.6

grams aspirin obtained


100
theoretical grams aspirin
82.22

yield
The colour of FeCl3 turns into brown when added to salicylic acid. When FeCl3
added into aspirin, the colour changes from colourless to purple/ violet. The
colour of the mixture turns into purple / violet when FeCl3 added to
recrystallized aspirin. The process recrystallization didnt remove any phenolic
impurities

B) Synthesis of Methyl Salicylate


The odor of the product that obtained from the reaction smells pleasant. The
smell can be compared as fragrances of fruit and flowers. The addition of
FeCl3 to the product provides a colour change from colourless to violet colour.

Discussion
Esters are chemical compound consisting of a carboxylate group attached to the
parent chain. They are derived by reacting a carboxylic group with hydroxyl
group. Esters are usually derived from an inorganic acid and organic acid. Overall
esters are formed by condensing an acid with an alcohol. Esters usually have a
pleasant smell, fruitlike odors and fragrances of many fruits and flowers.
The general formula for ester are typically written as RCO2R, where R and R are
the hydrocarbon part of an alcohol and carboxylic acid.

The general structure of an ester


These two groups have different functional group where carboxylic acid will
provide COOH group and alcohol provide OH group. The reaction for this
compound is call esterification. The mineral acid is used in esterification
process because to activate the oxygen atom which attached at the moment
with carboxylic acid. Ester can be prepared by reacting an alcohol and
carboxylic acid with help of a mineral acid. General physical property of an
ester is they will form a colour complex compound with pleasant smell. The test
of phenol can be tested by adding a drop of 1% FeCl3 solution to the
compound. The colour changing of the compound to violet proves the presence
of phenol. The functional group of carboxylic acid is COOH. The purpose of
recrystallization is to remove the impurities from the compound to get an exact
amount of yield.

Preparation of Aspirin

The experiment explains that salicylic acid react with acetic anhydride to
produce ester. When certain amount of salicylic acid is react with acetic
anhydride, the reaction do not take place because without presence of mineral
acid. In this experiment, the mineral was used is concentrated sulfuric acid.
When the oxygen is activated by H2SO4, the hydrogen atom break from
hydroxyl group. From acetic anhydride, the CH3CO bond is break to join
hydrogen atom from salicylic acid forming acetic acid. The remaining
compound will bond to produce acetyl salicylic acid or commonly known as
aspirin (C3H8O4).
The mixture is cooled in an ice bath to complete crystallization; the mixture
turns into cloudy with white precipitates. The addition of distilled water
important in isolation and purification because aspirin is insoluble in water.
Purification is required to remove the acetic acid product and sulfuric acid as
well as unreacted salicylic acid and acetic anhydride. Isolation was completed
through filtration using filter paper to obtain crystals. The phenol test was
carried out by adding 1% of FeCl3 for salicylic acid and obtained aspirin. The
salicylic acid change colour from colourless to dark purple where aspirin
doesnt change in colour due to no phenol compound in aspirin.
The second part of the experiment was recrystallization. This is also called the
second part of purification process. 20 mL of absolute ethanol was added to the
crystals and 50mL of warm distilled water added. The mixture turns to cloudy.
Ethanol was used to dissolve aspirin with other impurities such as salicylic acid
and others. Then the solution cool slowly which left the impurities behind. The
mixture later was cooled in ice baths which help aspirin in recrystallization.
After aspirin had filtered and dried, the mass was recorded to calculate the
theoretical and the percent of yield.

Preparation of Methyl salicylate

This experiment illustrates that salicylic acid react with methanol to produce
ester. When certain amount of salicylic acid is react methanol, the reaction do
not take place because without presence of mineral acid. In this experiment, the
mineral acid was used is concentrated sulfuric acid. The role of mineral acid to
activate the oxygen atom from salicylic acid. When the oxygen is activated, it
will remove hydrogen atom from hydroxyl group of salicylic acid. From methyl
alcohol, the hydroxyl group breaks to bond with the hydrogen from salicylic acid
to form water molecule (H2O). The remaining will bonded to form ester known as
methyl salicylate. The compound is placed at water bath to help the reaction
occurs at perfect temperature which is 70 C. The purpose of adding 1% of FeCl3
solution is to confirm the presence of phenol. This test can be proven by the
changing colour from colourless to violet and a pleasant smell.

Questions
1) Aspirin insoluble in cold water compare to the rest of compound such as
concentrated sulfuric acid (H2SO4). H2SO4 an acid which soluble in cold
water. Therefore, the purpose of washing aspirin using cold water to
remove the impurities from the compound.
2) a) Pure aspirin turn into purple colour complex because the phenol group
is present.
b) Oil of wintergreen turn into purple colour complex because its exhibit
properties of ester
and presence of phenol group.

3) a)

b) (CH3CO) 2O +

CH3CH2OH

Ethanol + Acetic anhydride

c)

C3H7OH (aq)

CH3CO2CH2CH3 + CH3COOH
Ethyl acetate

+ Ethanoic acid

+ C2H5CO2H (aq) C2H5CO2C3H7 (aq)

Propanic acid +

propanol

+ H2O

propyl propanate + water

4) a) Ethyl acetate
1. Esterification
CH3CH2OH + CH3COOH H+
Acetic acid + ethanol

CH3COOHCH2CH3
ethyl acetate

+
+

H2O
water

2. Dehydrogenation of ethanol

b) Methyl acetate
CH3CH2OH + CH3OH H+
Acetic acid + methanol

CH3COOCH3
+ H2O
methyl acetate + water

5) The yield of aspirin is greater than 100% because the aspirin the aspirin
sample is not dry and retain a large amount of water. The excessive
product mass also contributes to the remaining product.
Conclusion
Aspirin was obtained from the reaction between salicylic acid and acetic
anhydride. Concentrated sulfuric acid was used as a catalyst. When the addition
of ice, acetic acid was formed and thus eliminated. Recrystallization process
helped in removing other impurities such as salicylic acid.
Other than that, the preparation of methyl salicylate also obtained from the
reaction of salicylic acid which is carboxylic acid and methyl alcohol. The phenol
test was conducted to ensure the existence of phenol that represents the
presence of ester compound. 1% of FeCl3 was used in the phenol test
Reference
1) Rainsford, K.D. (2004). Aspirin and related Drugs, USA: Taylor & Francis Inc. no
page (e book)
2) Whitten K.W.R.E. Davis, M.L. Peck, G.G. Stanley (2007). Chemistry, 8th ed. USA,
page 947
3) Karen C. Timberlake (2009), Chemistry: an Introduction to General and Organic
Chemistry. No page ( www.boundless.com )