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1. SUSB 012
Aspirin Purity by pH Titration
prepared by R. C. Kerber, M. J. Akhtar, and R. F. Schneider, SUNY at Stony Brook (Rev 3/00)
Purpose of this Exercise: To determine the purity of your synthesized aspirin sample by acid-base
titration, and to compare the results with those from pure salicylic acid, acetylsalicylic acid, and with
commercial aspirin tablets.
Background Information
Aspirin (originally a legally restricted brand name owned by Bayer for its brand of acetylsalicylic acid,
but now a generic term) has been in use as an analgesic (pain-killer) and antipyretic (fever-reducer) for
over a century. During most of that time, little was known about its mode of action in the body,
although this has become better understood in recent years. It has also been realized that, in addition to
its mild short-term analgesic effect, aspirin has some potent long-range benefits, including reducing the
probability of users' suffering heart attacks and colon cancer.
Chewing willow twigs was a traditional folk remedy in many parts of Europe for headache and other
minor pains. In the nineteenth century, chemists isolated salicylic acid from willow twigs and showed that
it was the effective ingredient. The name derives from the Latin name Salix, the genus of willow trees.
Pure salicylic acid, however, is very damaging to the stomach, and the acetyl derivative was prepared in
order to reduce this undesirable side effect. Acetylsalicylic acid has become the most extensively used
pharmaceutical product in the world.
On standing for prolonged periods of time in a humid atmosphere, aspirin tablets develop a vinegary
smell that you may have noticed. This is due to the hydrolysis of acetylsalicylic acid (ASA) to form
salicylic acid (SA). A hydrolysis is a reaction with water to break one or more bonds. In this case, the
acetyl group comes off as acetic acid, which causes the vinegary smell.
This is a reversal of the synthesis process you carried out previously in this course.
In this exercise, we will determine by acid-base titration the amounts of ASA and SA in your
synthesized sample of aspirin. [Incomplete reaction or inadequate washing of the product are likely to
have left the ASA contaminated with some SA.] The same titration process can be used to determine
ASA content in commercial aspirin tablets. Commercial tablets usually contain inert binders such as
starch, so it is not possible to determine the ratio of SA and ASA by titration alone unless the binder is
removed. We can, however, determine the overall percent of active ingredient.
We will make use of the effective molar mass of the synthesized samples to assay their content, but we
will also take note of the overall titration curve (see below) for confirmation of our conclusions. This
can be done for both the synthesized sample and the tablets.
2. Some data on SA and ASA relevant to this exercise are the following:
Compound Salicylic Acid (SA) Acetylsalicylic Acid (ASA)
Formula C7H6O3 C9H8O4
Molar Mass 138.12 180.15
Ka 1.08 x 10-3 2.72 x 10-5
pKa 2.99 4.57
Solubility (g/100 mL) 0.18 0.25
SA and ASA have significantly different molar masses. If we titrate the same weight of the two acids
with base, it will take more base to reach the endpoint with salicylic acid, since there will be more
mmoles of acid in the sample due to its lower molar mass. A mixture will require an intermediate
amount of base. We can use this fact to assay the sample.
It can also be seen from the data above that SA is a stronger acid. The Ka of a weak acid is the
equilibrium constant for the reaction in which the acid dissociates in water. A smaller value indicates
less dissociation and therefore a weaker acid. SA is about 40 times stronger than ASA, and we can
detect this if we look at titration curves of the two acids. A titration curve is a plot of the pH of a
solution of the acid as a function of the amount of base added. The stronger acid will produce a more
acidic solution (lower pH) in the lower region of the curve prior to complete neutralization. The figure
below illustrates calculated titration curves for 300 mg of pure SA and 300 mg of pure ASA with 0.1 M
NaOH. Remember that the pH at the point of half-neutralization is equal to the pKa of the acid.
3. 14
12
10
8
6
4
2
pH
0 5 10 15 20 25 30 35 40 45 50
mL of 0.1 M NaOH ADDED
3OO mg ASA
3OO mg SA
4. Procedures
CAUTION Sodium hydroxide solutions are very caustic and can cause prolonged and painful injuries
to skin or eyes. Avoid all contact with these solutions. If accidents occur, flood the affected area with
water for several minutes. Wear safety glasses at all times while in the laboratory.
Part 1. Indicator Titration
1. Be sure to read SUPL-006 carefully before coming to lab. Part 1 of this exercise will be done in
pairs, but each student must do a phenolphthalein titration of his/her synthesized aspirin..
2. Accurately (on the analytical balance) weigh out ~0.2 g samples of SA, ASA, and each of your
synthesized aspirin samples. You don't have to do all the weighings at once, but label containers clearly
so you won't get confused.
3. Dissolve each sample in 10 mL of 95% ethanol stirring vigorously. When the sample is completely
dissolved, add 90 mL of distilled water, and stir the solution again.
4. Add two or three drops of phenolphthalein indicator to each solution and titrate with the
standardized sodium hydroxide solution provided. (The concentration is about 0.05 M. Record the
precise value in your notebook and on the data sheet.) Determine the endpoint carefully by looking for
formation of a persistent light pink color. Repeat as necessary to assure an accurate and reproducible
result.
5. Calculate the effective molar mass (EMM) of each sample, using the data sheet as a guide. The
EMM is the mass of sample in mg which produces one mmole of H+ ions upon titration. For a pure
compound with one acid group per molecule, this should be the actual molar mass of the compound.
For a mixture, this will be a weighted average of the molar masses of the acid components.
6. If the sample consists only of ASA and SA, then the percent composition can be derived from the
EMM according to the relationships:
%SA = 100 ( 180.15 - EMM ) / ( 180.15 - 138.12 ) = 2.379 ( 180.15 - EMM )
%ASA = 100 ( EMM - 138.12 ) / ( 180.15 - 138.12 ) = 2.379 ( EMM - 138.12 )
Calculate the % composition of your sample.
Note that the relationship between percent composition and EMM applies to mixtures containing only
SA and ASA! If the measured EMM is greater than 180.15 or less than 138.12, the above
formulas do not apply. Simply report that the EMM was out of the possible range and assume
the sample consists of 100% SA or ASA, whichever is appropriate.
If your EMM for pure SA or pure ASA differs from the expected value by more than 10%, you should
repeat that titration before proceeding to the next part.
5. Part 2. pH Titration.
Part 2 will be done individually sharing pH meters. Please work efficiently and cooperatively. Before
beginning this part, using data from Part 1, calculate how much of your synthesized aspirin will be
required to consume 25 ± 3 mL of the sodium hydroxide.
7. Weigh another sample of your synthesized aspirin in accordance with the calculation above on the
analytical balance. Dissolve the sample in 10 mL of 95% ethanol. When the sample is completely
dissolved, add 90 mL of distilled water as in Part 1. Be sure that the solution is homogeneous, and that
it is at room temperature.
(a) Calculate the volume of NaOH which will be required to titrate the actual weight of
your sample and enter it in your notebook and on the data sheet.
(b) Using the pH meter, determine the pH of the solution.
(c) Add about 2 mL of NaOH solution from your buret, read the buret, and again
determine the pH. Record in your notebook a table showing buret reading, total
volume of base added, and pH.
(d) Repeatedly measure the pH after adding incremental amounts of standard NaOH solution
from your buret. Two mL increments will be adequate at first, but decrease the size of the increments
as you approach the endpoint. You should be able to calculate from your work in Part I the volume of
NaOH solution required to reach the endpoint. As you approach it, the pH begins to change more
quickly. You should then reduce the amount of NaOH solution added between pH readings. In the
vicinity of the endpoint (within ±1 mL), you should take readings after every drop. A
suggested format for data collection is on the back of Data Sheet 1. This will insure that you plot pH
against the actual volume delivered.
(e) After the endpoint has been passed by about 1 mL, continue adding base, up to an
additional 10 mL, in one mL, and then, two mL increments, taking pH readings in order to define the
upper portion of the titration curve.
(f) Plot the data on graph paper, using Fig. 1 as a guide, and turn in your graph with the data
sheet. Indicate the endpoint on your graph explicitly. Write on your graph the EMM calculated from
your endpoint, and the percent composition of your sample.
Part 3. Analysis of commercial aspirin tablet
8. A commercial aspirin tablet usually contains 325 mg (0.325 g) of acetylsalicylic acid. This is an
appropriate amount to titrate. If your tablet is a different size, adjust the amounts by using, for
example four 80 mg tablets. Weigh a tablet (or tablets, as appropriate) and crush it completely,
dissolve it in 10 mL of 95% ethanol by stirring vigorously. Because of the binders in normal aspirin
6. tables, this solution may not turn clear . When the tablet appears to be dissolved, add 90 mL of
distilled water, and titrate the resulting solution either with phenolphthalein indicator or with the pH
meter, as in Part 2. Assuming that all of the acid in the tablet is acetylsalicylic acid, calculate the
amount present. If you obtained a titration curve, is the curve consistent with that of pure
acetylsalicylic acid?
NOTE:
In choosing tablets to bring in for this exercise, you should investigate the composition of the tablets
carefully. There are some elements of common sense that need to be considered.
1.) The tablets must contain aspirin. Tablets with aspirin substitutes such as acetaminophen, ibuprofen
or naproxen will not give meaningful results in this exercise. Such tablets are sold under a wide
variety of trade names. You must read the label.
2.) Buffered aspirin tablets will not give meaningful results. Why?
You are encouraged to prepare a table in your notebook like the one on the back of the datasheet for
collection of the pH titration data before coming to class.
7.
8. SUSB-012 Data Sheet
_____________________________________________________________________________
Name Section Date
______________________________________
Partner's Name
Part 1 Run 1 Run2 Run 3
Pure ASA Pure SA Synth. Asp.
Conc. of NaOH solution _________M
Mass of vial + sample _________mg _________mg _________mg
Mass of vial - sample _________mg _________mg _________mg
Mass of sample _________mg _________mg _________mg
Final buret reading _________mL _________mL _________mL
Initial buret reading _________mL _________mL _________mL
Volume of NaOH used _________mL _________mL _________mL
mmoles of NaOH used _________mmol _________mmol _______mmol
mmoles acid _________mmol _________mmol _______mmol
EMM = mg/mmol _________ _________ _________
% Salicylic Acid _________%
% Acetylsalicylic Acid _________%
Part 2: Please attach your titration curve(s) to this data sheet.
Weight of your sample ___________ mg Calculated Volume of NaOH ___________ mL
Part 3
Mass of aspirin tablet: __________g
Vol. of NaOH solution: __________mL
Mmoles of NaOH used: __________mmol
Mmoles of ASA present: __________mmol
Mass of ASA present: __________g
% ASA by weight __________%
9. Buret
Reading
Net Volume
Added*
pH Buret
Reading
Net Volume
Added*
pH
10. * The net volume added is the buret reading minus the initial buret reading.
11. SUSB-012 Pre-Laboratory Assignment
_____________________________________________________________________________
Name Section Date
1. A student, Iva Heddake, weighs an aspirin tablet and finds that it weighs 385 mg. She crushes it,
dissolves it, and titrates it with 0.0500 M. NaOH solution. The volume required to reach the endpoint
is 29.97 mL. How much ASA is in the tablet, and what is its % by weight of the tablet? [You can't use
the EMM formula for this problem. Why not?]
2. Another student, Peter Principle, boils the water in which he is attempting to dissolve his aspirin
tablet, which weighs 392 mg, for several minutes. His titration with 0.050 M. NaOH solution requires
44.37 mL. What is the apparent % ASA in the tablet? [Again, don't attempt to use the EMM
formula.] Is there a problem here? If so, what is likely to have happened?
3. Titration of a 324 mg sample of Joe Bftsplk's synthesized aspirin with 0.100 M. NaOH solution
required 20.30 mL. What is the EMM of the sample, and what is the % ASA?
4. A buffered aspirin sample containing 325 mg of aspirin and 360 mg of calcium carbonate is dissolved
in 100 mL of water and the solution is permitted to stand for an extended period. What reaction(s) is
(are) likely to occur? How much 0.05 M NaOH will be required to titrate the resulting solution to a
phenophthalein end point? Why?