CHE2623 Experiment 1

CHE2623 Experiment 1
May 12, 2024
Monitoring the liquid-liquid extraction separation of a mixture using TLC.
Christell Stoltz
Student no: 67952259
Lab partner: Audrey Choshi (45123446)
1
1 Objective
The aim of this experiment was to isolate a mixture of organic compounds
by extracting them using liquid-liquid extraction. After each extraction the
organic layer was spotted onto a TLC plate to monitor the extraction until
only one compound is present.
2 Introduction
Liquid-liquid extraction is a separation method used in this experiment to
transfer organic compounds dissolved in an organic solvent to an aqueous
solvent. The to solvents are immiscible and form two layers. The organic
compounds can be transferred between the two solvents by taking their sol-
ubility properties into account. Most organic compounds are neutral and
insoluble in aqueous solvents, by adding a acid or a base the organic com-
pound becomes ionic, known as an organic salt. If the pH of the aqueous
solvent is neutralised the organic salts will revert to their non-ionic forms
and precipitate out of the solvent.
Thin layer chromatography (TLC) can be used to monitor the extrac-
tion of the organic compounds during liquid-liquid extraction. The organic
solvent is spotted onto the end of a plate containing a stationary phase (usu-
ally silica) before the beginning extraction and then after each subsequent
extraction. The end of the plate is then put into a mobile phase (this exper-
iment used Chloroform). The different compounds present in each spot will
migrate up the stationary phase at different rates. These differential rates
are due to the affinity that each compound has to the stationary and mobile
phase. Compounds can be identified by comparing their Rf values [5].
3 Reaction Mechanism
Figure 1: The reaction mechanism of Benzoic acid with Sodium Hydroxide

to form Sodium benzoate.
1
Figure 2: The reaction mechanism of p-Nitroaniline with Hydrochloric acid.
4 Experimental Method
1g Naphthalene, 0.5g p-Nitroaniline and 0.5g Benzoic acid was weighed and
dissolved in 45mL Dichloromethane (Solution M). A TLC plate was prepared
and solution M was spotted onto the plate. Solution M was transferred to
a separating funnel and 20mL Hydrochloric acid was added. The separating
funnel was shaken and then left for the layers to fully seperate. The bottom
the layers were drained seperately and the procedure was repeated again with
20mL Sodium Hydroxide. The organic layer was then spotted onto the TLC
plate and the process repeated using Sodium Hydroxide.
The organic layer was then dried using Sodium sulphate anhydrous and
evaporated until crystals formed. The acidic and basic aqueous layers were
neutralised separately and the precipitates were filtered and dried.
The TLC plate was developed in Chloroform and viewed under UV-light.
5 Results
Figure 3: The melting points (MP) in °C obtained from the crys-

tals/precipitates of each layer separated.
2
Figure 4: The melting points (MP) in °F obtained from sources [3], [4], [2]
and converted to °C
According to the melting points obtained the addition of an acid resulted

in the extraction of p-Nitroanaline and the addition of a base extracted Ben-
zoic acid. Napthalene was not extracted and remained in the organic layer.
Figure 5: The TLC plate marked after being viewed under UV-light. M
corresponds to the complete mixture of compounds. 1 corresponds to the
mixture after bing extracted with an acid. 2 was incorrectly dotted and
should be disregarded. 3 corresponds to the mixture after extraction with a
base.
3
Figure 6: The Rf calculated.
Distance travelled by compound

Rf = (1)
Distance travelled bymobile phase
The Rf values of compounds is not easy to compare with known values, the
Rf values depend heavily on the choice of solvent and the solvent front line.
[1].
Figure 7: The percentage yield obtained form the isolated compounds.
M ass recovered(g)
% yield = × 100 (2)
M ass dissolved(g)
6 Discussion
The melting point for p-Nitroaniline (Fig.4) corresponds to the melting point
of the compound extracted with an acid (Fig.3). The average melting point
differs from the given melting point by 11°C, which indicated a small amount
of impurities still present.
The melting point for Benzoic acid (Fig.4) corresponds to the melting
point of the compound extracted with a base (Fig.3). The average melting
point differs from the given melting point by 3.1°C, which indicates that if
there are impurities present that they can be considered as negligable.
4
The melting point for Naphthalene (Fig.4) corresponds with the melting
point of the compound that was left in the organic solvent after extraction
with an acid and a base (Fig.3). The average melting point differs from the
given melting point by 8.9°C, which indicates a small amount of impurities
present in the isolated product.
The Rf value for M which corresponds with the mixture of compounds
is 0.36 (Fig.6). The compounds did not separate during the development of
the TLC plate, this can be due to an insufficient solvent being used during
the development. The experiment can be rerun using a different solvent
to develop the TLC plate. [1]. The same collusion can be reached for
spot 1 where two compounds should still be present. Spot 3 shows that
2 compounds were present, which can be due to contamination during the
spotting procedure. The TLC plate overall was executed unsuccessfully.
The percentage yield for Naphthalene and p-Nitroaniline was 78.94% and
85.36% respectively, the extraction and precipitation of p-Nitroaniline was
successful and the loss yield can be accounted for during the transfer of
the crystals from the filter paper and from the round bottom flask to a
pre-weighed watch-glass, during future attempts the filter paper can be pre-
weighed and then weighed with the crystals to obtain the mass of the crystals.
Similarly the round bottom flask can be pre-weighed and then weighed with
the dried crystals to prevent loss of yield due to transfer. The percentage
yield of Benzoic acid was 58.72%, this is a relatively low yield and can also be
due to loss during transfer, some other factors that could have impacted the
yield include an incomplete extraction due to the low concentration base or
the neutralization set during precipitation could have been overshot leaving
some Benzoic acid to still be dissolved in the aqueous solution.
7 Conclusion
The objective of this experiment to isolate compounds was reached, even
though Benzoic acid had a low yield it was mostly pure. The purety and
yield of Naphthalene and p-Nitroaniline was high. The monitoring of the
extractions through TLC was not as effective and adjustments can be made
as discussed.
5
References
[1] C Hall. “Thin Layer Chromatography: A Complete Guide to TLC”. In:
CHEMISTRY HALL (2020).
[2] PubChem Compound Summary for CID 243, Benzoic Acid. https://
pubchem.ncbi.nlm.nih.gov/compound/Benzoic-Acid.
[3] PubChem Compound Summary for CID 7475, 4-Nitroaniline. https :
//pubchem.ncbi.nlm.nih.gov/compound/4-Nitroaniline.
[4] PubChem Compound Summary for CID 931, Naphthalene. https://
pubchem.ncbi.nlm.nih.gov/compound/Naphthalene.
[5] Joseph Sherma and Bernard Fried. Handbook of thin-layer chromatog-
raphy. CRC press, 2003.

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CHE2623 Experiment 1

May 12, 2024

Monitoring the liquid-liquid extraction separation of a mixture using TLC.

Lab partner: Audrey Choshi (45123446)

Figure 1: The reaction mechanism of Benzoic acid with Sodium Hydroxide

Figure 3: The melting points (MP) in °C obtained from the crys-

According to the melting points obtained the addition of an acid resulted

Distance travelled by compound

Figure 7: The percentage yield obtained form the isolated compounds.

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