Pre-Lab Report

Name: Artoza, Aizel Subject: Organic Chemistry (Lab)

Group No. 1 Course Code/Section: CHE 0211.1/2
Group Members: Date Submitted: November 27, 2020
1. Acosta, Deanne Rosselini
2. Ariola, Aizel
3. Artoza, Christian Jelo
4. Ayran, Jhonee

Title of the Experiment:

Purification of Paracetamol
Experiment No. 3

Introduction:
Paracetamol or acetaminophen is a widely known drug used as a fever reducer and pain
reliever. It is one of the most popular over-the- counter drugs. It is a non-steroidal anti-
inflammatory drug (NSAID), analgesic drug and antipyretic drug, which means it is part of the
drugs that reduces pain, decreases fever, prevents blood clots, and in higher doses decreases
inflammation. It reduces pain by blocking the COX-2 and inhibiting endocannabinoid reuptake
almost exclusively within the brain, but not much in the rest of the body. In addition, most of the
pain reliever drugs or NSAIDs had unwanted gastrointestinal side effects, which can cause liver
and kidney failure, thus having an excessive intake of paracetamol can cause lethal effect in the
body, or worst death.

Paracetamol(acetaminophen) is a synthetic drug, it is synthesized in the laboratory, just like other

medicinal drugs, which means having side effects in the long run is inevitable, for synthetic
compounds always have an isomer. Upon synthesizing, purification is applied, to remove
unwanted impurities in the organic compound. A compound can be purified by sublimation,
distillation, crystallization, and recrystallization.

In this experiment, the researchers will focus on the purification of paracetamol(acetaminophen)

by recrystallization. Recrystallization is a process of purifying a compound in a solvent. In which
as the temperature increases the amount of solute that can dissolve in a solvent increases, thus as
the solution cools, the solvent becomes saturated with the solute and the solute crystals, which are
the reform solids.

Objectives:
At the end of the experiment the students should:

● Be able to purify the sample

● Be able to describe and understand the process of recrystallization
● Be able to calculate the percent recovery of the sample

Apparatus:

GRAVITY FILTRATION
SET UP

SUCTION FILTRATION
APPARATUS
Reagent/s:
Structural Molecular Boiling Melting
Name Solubility Appearance
Formula Weight Point Point
(in water)
Odorless
white
Acetamino- 1.4 g/100 ml crystalline
phen 151.16 g/mol 420 °C 169.0 °C (20°C) solid..
(C8H9NO2)

Clear,
Acetone 58.08 g/mol 55.75 °C -94.8 °C Miscible colorless
(C3H6O)

Benzoic 0.29 g/L Odorless

Acid 122.12 g/mol 249.2 °C 122.4 °C at 20 °C white
(C7H6O2) crystalline
solid.

Phthalic White solid

Acid 166.13 g/mol 289 °C 230 °C 0.54 g / 100
(C8H6O4) Decomposes mL at 14 °C
Procedure:
Purification of Benzoic Acid by Recrystallization

As a precautionary
measure, wear safety
goggles and gloves
before preparing the
reagents to be used in
the experiment.
add 10 mL of distilled
water into the flask
Weigh 260 mg of
cointaining benzoic
impure benzoid acid
acid. Then, In a
and put it in an
separate flask, put
Erlenmeyer flask.
another 10 mL of
distilled water.

When the solution and To set up the gravity

the water starts to boil,
immediately remove the
filtration apparatus in
the hot plate. Then,
pour all the benzoic acid
in the filtration setup.
Be careful in handling
the flasks for it may be
too hot.
filtration apparatus, Use
another Erlenmeyer flask
and put 10 mL of water. Put the two
Then, put a funnel on top erlenmeyer flasks into
of the flask. Using a filter the hot plate and heat
paper, make a cone and it.
place it in the funnel.
Afterwards, put it in the
hot plate.

Remove the funnel on

Pour 5 mL of water into
the filtration setup to
redissolve the benzoic
acid. Once all the water
gets through the filter
paper, rinse the filter
with the remaining 5
mL hot water.
the flask. Then, set After cooling the
aside the flask and let it solution, place the flask
cool slowly to room in an ice-water bath for
temperature as it further cooling. Then,
recrystallizes. The pour 10 mL of distilled
solution should not be water into a separate
moved for any agitation flask and cool it also in
may disrupt the an ice-water bath.
process.

After cooling the solution

for 15 mins, use the vacuum
Leave the vacuum on filtration apparatus to
for atleast 10 mins so collect the crystals. To
the crystals dry out. collect it, wet the filter While the solution is
Then, carefully scrape cooling, set up the
paper using the cooled
the crystals and weigh vacuum filtration
water and pour the solution
it. apparatus.
into the Buchner funnel.
Rinse the flask with water
and pour it again in the
funnel
Recrystallization of Phthalic Acid
As a precautionary
measure, wear laboratory
googles and gloves before
doing the experiment.
Put the impure phthalic
acid into a beaker and
place it in a hot plate. Then,
add water. Let the sample
dissolve in minimal boiling
water.
Collect the crystals and
weigh.
After dissolving, remove
the beaker in the hot plate
and cool the solution
slowly. Be careful in
handling the beaker for it
may be too hot.
Separate the solution of
impurities from the purified
solid crystals by vacuum
filtration.
Post-Lab Report
Name: Ariola, Aizel Subject: Organic Chemistry (Lab)
Group No. 1 Course Code/Section: CHE 0211.1/2
Group Members: Date Submitted: November 27, 2020
1. Acosta, Deanne Rosselini
2. Ariola, Aizel
3. Artoza, Christian Jelo
4. Ayran, Jhonee

Title of the Experiment:

Purification of Paracetamol
Experiment No. 3

Results and Observations:

Table 1. Observations in the Recrystallization of Benzoic Acid

Observation
Impure Benzoic Acid Black and powdery
Purified Sample White and Flaky
Solution of Impurity Gray

Table 2. Observations in the Recrystallization of Phthalic Acid

Observation
Impure Phthalic Acid White with a hint of pink and flaky
Purified Sample White and had larger flakes
Solution of Impurity Pinkish

Table 3. Calculations in the Recrystallization of Benzoic Acid

Values Obtained
Solubility at 100 degrees Celsius 56.3 grams/1 L of water
Solubility at 0 degrees Celsius 1.7 grams/1 L of water
Impure Sample 260 milligrams
Actual Yield 110 milligrams
Percent Recovery 42%
Percent Error 58%
Table 4. Calculations in the Recrystallization of Phthalic Acid

Values Obtained
Solubility at 100 degrees Celsius 18 g/100 mL of water
Solubility at 14 degrees Celsius 0.54 g/100 mL of water

Calculation:
Percent Recovery and Percent Error of Benzoic Acid
𝐴𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑃𝑢𝑟𝑖𝑓𝑖𝑒𝑑 𝑐𝑜𝑚𝑝𝑜𝑢𝑛𝑑
Percent Recovery = 𝑥 100%
𝐴𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑂𝑟𝑖𝑔𝑖𝑛𝑎𝑙 𝑐𝑜𝑚𝑝𝑜𝑢𝑛𝑑

110 𝑚𝑖𝑙𝑙𝑖𝑔𝑟𝑎𝑚𝑠 𝑜𝑓 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑

= 𝑥 100 % = 42%
260 𝑚𝑖𝑙𝑙𝑖𝑔𝑟𝑎𝑚𝑠 𝑜𝑓 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑

𝐴𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑂𝑟𝑖𝑔𝑖𝑛𝑎𝑙 𝑐𝑜𝑚𝑝𝑜𝑢𝑛𝑑−𝐴𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑃𝑢𝑟𝑖𝑓𝑖𝑒𝑑 𝑐𝑜𝑚𝑝𝑜𝑢𝑛𝑑

Percent Error = 𝑥 100%
𝐴𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑂𝑟𝑖𝑔𝑖𝑛𝑎𝑙 𝑐𝑜𝑚𝑝𝑜𝑢𝑛𝑑

(260−110)𝑚𝑔 𝑜𝑓𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑

= 𝑥 100 % = 58 %
260 𝑚𝑔 𝑜𝑓 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑

Discussion of Results
In this experiment, two kinds of impure samples were recrystallized in order to get its pure
form. Specifically, the goal was to get the pure benzoic acid and the pure phthalic acid. The first
impure sample was the benzoic acid containing a few carbon boiling chips. The impure benzoic
acid looks black and white due to the carbon boiling chips that were mixed in the sample, which
are naturally black in color. Hence, when the benzoic acid and carbon were separated through
filtration, the observed solution of impurity was color black or grayish because it contains the
carbon boiling chips that was removed in the benzoic acid. The purified sample on the other hand
is color white because the benzoic acid is already in its pure form and it is the natural color of it.
Before purification through recrystallization, the benzoic acid is in powder form, but after
recrystallization is applied, benzoic acid formed into a white flaky crystal, which indicates that the
sample is now pure. In addition, based on the weighed sample, the percent recovery of benzoic
acid obtained is low (42%), which yields to a high percentage error (58%). This is due to some of
the mishandling errors of the researchers during the procedure, and some of the compound residue
may be left in the container after the transfer, and some may be transferred in the environment. In
addition to that, the solubility of benzoic acid in water at 14 and 100 degrees Celsius are 0.54 g/100
mL and 18 g/100 mL, respectively. Therefore, some of the benzoic acid had dissolved in water
which also caused the percent recovery to be low

The second impure sample was the phthalic acid contaminated with red food dye. The
impure sample of phthalic acid looked white with a hint of pink. The phthalic acid is naturally
white in color, yet it was contaminated with red dye which made the sample looked pinkish in
color. Then, when the phthalic acid and red dye were separated through filtration process, the
solution of impurity looked pinkish in color because it already contains the red dye that was
separated in the phthalic acid. Thus, the researchers were able to get the pure form of phthalic acid
which is naturally white. Also, at the beginning of the experiment, phthalic acid is in pinkish flaky
form, but after recrystallization, it produced a larger white flakes crystals, which indicates that the
sample is now pure, for the impurities are already separated during the recrystallization process
which enables the pure sample to crystallize together.

Answers to Questions:
1. What is recrystallization?
Recrystallization is a lab procedure for purifying solids. This procedure is causing a solid
to go into solution, and afterward continuously allowing the disintegrated solid to crystallize

2. State the characteristics of a good recrystallization solvent.

a. The solvent should not dissolve the substance we’re trying to purify
b. Solvent should not dissolve impurities at room temperature.
c. There should be no reaction between recrystallization solvent and the substance we’re
purifying
d. The solvent should not be volatile
e. The solvent should not be expensive

3. What is the use of the seed crystal?

Seed crystal can accelerate the growth of crystals if the growth process is slow.
4. Why is a solution cooled to effect recrystallization?
Decreasing the temperature causes the solubiltity of impurities in the solution and the
substance to decrease. As the solution cools, the solvent can no longer hold the all the solute
molecules and they begin to form solid crystals. It is important to slowly cool the the solution
because a rush crystal formation will trap the impurities within the lattice.

5. What is the advantage of using vacuum filtration using Buchner funnel over the simple
filtration?
The advantage of using vacuum filtration using Buchner funnel is that it is much faster to
collect the desired solid, because the solvent or solution and air is forced through filter paper
by the application of reduced pressure

Summary

The goal of the experiment is to apply recrystallization to purify a sample of benzoic acid
(C6H5CO2H), a colorless solid mainly consumed for the production of phenol (C6H6O); and a
sample of phthalic acid (C8H6O4), an aromatic dicarboxylic acid that is used mainly in the form of
the anhydride to produce other chemicals such as dyes, perfumes, and many other useful products.

Recrystallization is a purification technique that is based on the principle that the solubility of most
solids increases with increased temperature. Hence, it is a technique that works best when the
quantity of impurities is small and the solubility curve of the desired solute rises rapidly with
temperature. In the experiment, the technique was applied to a sample of impure benzoic acid and
that of impure phthalic acid with water being the solvent for both of the samples. After the
purification process, each of the two solutions containing one of the two samples were then
introduced to the suction filtration apparatus to separate the crystallized form of the compound,
the product of the experiment, that is contained in it.

The results of the experiment were the products of the processes, namely: the crystallized form of
the two compounds, benzoic acid and phthalic acid.
It is known that a certified pure sample of benzoic acid is a white (or colorless) solid, so the sample
of benzoic acid the researchers had initially was impure as it appears black in color. Similarly, a
certified pure sample of phthalic acid appears as a white (or colorless) solid but the initial sample
was known to be contaminated with red food dye, thus the initial sample was impure. Therefore,
since each of the two products appear the same as its pure form, the products that were obtained
from the process were pure samples of benzoic acid and phthalic acid. Hence, the main objective
of the experiment was accomplished.

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