[Chemical Engineering Laboratory I]

SEGi University

ANALYSIS OF ASPIRIN
Candidates Name: Kee Tze San
Student ID: SUKD1601886
Group Number: 2
Group Members Name:
1. Chow Yee Lin SUKD1502359
2. Tan Xin Ren SUKD1500882
3. Tan Jee Yuen SUKD1600614
Lecturer/ Supervisor: Ms. Nazlina bt Zulbaldi
Date of Experiment: 10.10.2016
Date of Submission: 17.10.2016
1.0 Abstract

The objective of this experiment is to analyze the purity of aspirin by acid-base titration.
The purity of aspirin or acetylsalicylic acid can be analyzed by using acid-base titration. This can
be done by weighing 0.5g of the aspirin prepared in the previous experiment into a clean
Erlenmeyer flask. 25ml of alcohol is then added into the flask to dissolve the aspirin and two
drop of phenolphthalein is added into the flask as an indicator to the color change happened
during the titration. 0.1M of NaOH was then used to titrate the sample to a faint pink end point.
The volume of base used is then recorded. The volume of base used is the volume required to
neutralize all acids in the sample of aspirin prepared. This includes impurities and acetylsalicylic
acid present in the sample. An addition of 15ml of base is added to the titrated solution, this
volume of NaOH is added to the Erlenmeyer flask from the burette. The mixture is heated in
water bath for 15 minutes at the temperature 90C to 95C. Add two more drops of
phenolphthalein if the solution is not pink visible anymore. For back-titration, HCl was used to
titrate the excess base until the pink colors disappear. The initial and final volume of HCl used
for back-titration is then recorded.

2.0 Theory/Introduction

In the previous experiment, weve learned how to prepare aspirin. The aspirin prepared is
most likely not 100% pure. Even most commercial aspirin tablets are not 100% pure
acetylsalicylic acid. This is because most aspirin tablet is bind by a type of chemically inert
binder to hold it in a form of tablet. One of the chemical properties of aspirin is that it is slightly
soluble in water because of the anhydride group present in chemical compound. Therefore, when
exposed to humid air or moisture, it will hydrolyze and decomposed slowly in the surrounding.
The product formed from the decomposition of aspirin is ethanoic acid. Ethanoic acid is
responsible for the pungent smell present in vinegar.

OH OH
H+ catalyst O
O O
+ H2O
OH
+ OH
O

O
 In this experiment, the purity of aspirin prepared will be determined by percentage. Back
titration would be utilized to analyze the purity of the aspirin prepared.

Normally, titration is used to determine the concentration of an unknown acid or base.

First, titration is carried out to determine the amount of base required to neutralize all acid
material present in the aspirin. The solution is then added with excess base to further hydrolyze
the solution. The hydrolyzed solution is then back titrate using acid. By using this technique, the
amount of reactants not reacted in the excess can be determine. Hence, the number of milimoles
of reagent reacted can be calculated by using this formula:

Milimoles reagent reacted = total milimoles milimoles back-titrated

At low temperature, aspirin can be neutralized with base:

OO-
HO O

O O + OH- + H2O
O

If no impurities are found in the compound, a normal acid-base titration can be used to
determine the purity of the aspirin. However, if impurities are present, the base will neutralize
both the acid present in the acetylsalicylic acid and the acid present in the impurities. Thus, the
volume of the base required to neutralize the solution can be used to determine the number of
milimoles present in the acid.

Total milimoles acid = milliliters NaOH x molarity NaOH

At high temperature, aspirin can be neutralized with excess base:

OO-

O
+ OH-
+ CH3CO2-

HO OO-
O
 To determine the amount of acetylsalicylic acid present in the aspirin prepared, excess
base is added to the titrated solution and placed in hot water bath to speed up the reaction. This
process is known as saponification of esters. In high temperature and with the present of excess
base, the ester will undergo hydrolysis forming alcohol and carboxylic acid. The excess based
not reacted in the hydrolysis will be determined by a back-titration with acid HCl. With all the
data collected, we can now determine the mass of acetylsalicylic acid present in the aspirin we
prepared.

3.0 Apparatus and Material

Apparatus
1. 250ml Erlenmeyer Flask (3)
2. 50ml burettes (2)
3. 600ml beaker
4. Burette clamp
5. Water bath
Materials
1. Aspirin
2. Phenolphthalein
3. 95% ethyl alcohol
4. 0.1M HCl
5. 0.1M NaOH

4.0 Procedures

1. 5.0g of the aspirin prepared in the previous experiment was weigh into a clean, dry 250ml
Erlenmeyer flask.
2. 25ml of ethyl alcohol was added to the flask and the flask was swirled to dissolve the aspirin.
Two drops of phenolphthalein were added.
3. The sample with 0.1M of NaOH was titrated to a faint pink end point. The volume of NaOH
used was recorded. This volume of base corresponds to that which is required to neutralize
all acids present in the sample, impurities as well as the acetylsalicylic acid.
4. 15ml of the volume of base required in the previous titration was added. About this volume
of NaOH was added to the Erlenmeyer flask from the burette.
5. The mixture was heated in a water bath at temperature 90C to 95C for 15 minutes to
hydrolyze the aspirin. The flask was swirled occasionally.
6. The flask was cooled to room temperature by running it with cold tap water. Two more drops
of phenolphthalein should be added if the solution is not pink.
7. The initial volume of HCl was recorded and the excess base was titrated using HCl until the
pink color disappears. The volume of HCl used was recorded.

5.0 Results

Molarity of NaOH =___ 0.1 _____M

Molarity of HCl =_____0.1_______M

Mass of aspirin =_____0.5_______g

Volume of NaOH required to neutralize all acid material

Final reading =____ 57______ml

Initial reading =____ _ 20______ml

Volume of NaOH =______37______ml

Milimoles of NaOH =______3.7_______

Volume of NaOH used in hydrolysis

Final reading =______89______ml

Initial reading =_____ 37______ml

Volume of NaOH =______52 _____ml

Milimoles of NaOH =______5.2______ml

Volume of HCl in back titration

Final reading =______57______ml

Initial reading =______ 0______ml

Volume of HCl =______57______ml

Milimoles of HCl =______5.7_______

Milimoles of acetylsalicylic acid =_____-0.5______

Grams of acetylsalicylic acid in sample =_____-0.09_____

Purity of aspirin (%) =_____-18_______

5.1 Sample calculation

Calculation of milimoles of acetylsalicylic acid

Milimoles of acetylsalicylic acid=

milimoles of NaOH used in hydrolysis - milimoles of HCl used in back titration

5.2 - 5.7 = -0.5

Calculation of grams of acetylsalicylic acid in sample

Grams of acetylsalicylic acid in sample

molecular weight of acetylsalicylic acid x moles of acetylsalicylic acid
=
1000

180 x -0.5
=
1000

= -0.09

Calculation of purity of acetylsalicylic acid

 grams of acetylsalicylic acid
Purity= x 100%
mass of aspirin

-0.09
= x100%
0.5

= -18%

6.0 Discussion

The aim of this experiment is to investigate the purity of the aspirin made during the
previous experiment. The techniques used to determine the purity of the aspirin made were
titration and back-titration. The purpose of doing titration is to neutralize all acid present in the
aspirin and the back titration is used to determine the milimoles of acetylsalicylic acid present in
the aspirin. At the end of the experiment, weve noticed that the percentage purity of the aspirin
we made was -18%. The obtained is definitely not the ideal result. The reason and error behind
the result obtained will be further discussed as below.

Figure 1: Before titration: solution is colorless

 Figure 2: After titration: colorless to light pink

The mlimoles used to titrate the acid present in aspirin was 3.7 milimoles whereas the
milimoles used in the hydrolysis process were 5.2 milimoles. On the other hand, the milimoles
used in HCl for back-titration was 5.7 milimoles. By the end of the titration and back-titration,
the solution should experience a color change of from pink to colorless.

Figure 3: Before back-titration: 2 drops of phenolphthalein were added to increase the intensity
of pink.
 Figure 4: After back-titration: solution turns from pink to colorless

From the experiment, the purity level of the aspirin falls into the negative percentage
range. The aspirin prepared might not be prepared in a proper way as we did not recrystallize the
sample of aspirin weve prepared in the previous experiment. Thus, causing some impurities
present in the aspirin sample. The back-titration technique used in this experiment involves the
titration of excess base with acid. Base used in this experiment was NaOH and the acid used was
the common acid HCl. The amount of milimoles reacted from the hydrolyzed excess base with
the acid will give us the number of milimoles of acetylsalicylic acid present in the solution.

The outcome of this experiment was far from ideal because of the errors made during this
experiment. There are high chances that the molarity prepared for the titration and back-titration
is incorrect. Before any titration is carried out, we always have to make sure the molarity of the
bases is correct. The failure to obtained 100% purity of acetylsalicylic acid is also due to the
impurities present in the aspirin we prepared. Therefore, we need to carry out recrystallization
when preparing aspirin. Lastly the data obtained was inaccurate because there is no duplication
of data. Thus, we should repeat the experiment for at least 3 times to obtain a better average of
the results.
7.0 Conclusion
In conclusion, the experiment was not successful because the results obtained deviates far
from the ideal results we expected. Percentage purity of the aspirin sample is -18%. The negative
value portrays the molarity of base used in titration is not the correct molarity or either there is
too much of impurities present in the sample. However, we have carried out the titration and
back-titration successfully. The color changes in the solution indicates there is an reaction
occurred with the base and acid used for titration.

8.0 References

1. Chemguide.co.uk. (2016). acid anhydrides and water, alcohols or phenol. [online] Available
at: http://www.chemguide.co.uk/organicprops/anhydrides/oxygen.html [Accessed 16 Oct.
2016].
2. Aspirin - Should it be The Ideal Medicine?. (2016). Chemical Properties. [online] Available
at: http://aspirinpositivenegativeeffects.weebly.com/chemical-properties.html [Accessed 16
Oct. 2016].
3. Determination of Aspirin using Back Titration. (2016). 1st ed. [ebook] Available at:
http://www.lasalle.edu/~prushan/BackTitration-lab4.pdf [Accessed 13 Oct. 2016].
4. Chemguide.co.uk. (2016). hydrolysis of esters. [online] Available at:
http://www.chemguide.co.uk/organicprops/esters/hydrolysis.html [Accessed 16 Oct. 2016].