EXPERIMENT: 3

EXTRACTION TECHNIQUE: LIQUID-LIQUID EXTRACTION

Abstract

The aim of this experiment is to use one of the extraction techniques which is the liquid-
liquid extraction to separate benzoic acid from two organic compounds mixture of naphthalene
and benzoic acid. By bringing the solution to be in contact with another liquid, it is possible to
extract a desired solute from the liquid mixture. The percentage of recovery of the benzoic acid
obtained at the end of this experiment is 94.31%.

Introduction

Liquid-liquid extraction which is also known as partitioning is defined as a separation

process by transferring a solute from one solvent to another whereas the two solvents are
immiscible or partially miscible with each other. One of the most common method of liquid-liquid
extraction is applied by using a separatory funnel. Usually, one of the solvents is an aqueous
solvent while the other is an organic solvent. The liquid-liquid extraction consists of 2 steps which
is mixing followed by a step of phase separation. The 2 solvents are transferred to a separatory
funnel, and the compounds in the system will distribute between the two phases. Two layers are
form because the 2 solvents are immiscible and the solvent that has a higher density will be at the
bottom. Initially, the solute is only present in one of the solvents but after extraction it is present
in both the solvents.

One of the important separation methods used in research and chemical analysis is
undeniable the liquid-liquid extraction. There are many various applications of the liquid-liquid
extraction. It is often used in chemical and mining industries and in the downstream recovery of
fermentation products. For instance, fermentation products include antibiotics, amino acids, and
steroids. Besides, it is also applied in food industry such as by transferring the carotenoid pigments
from organic solvents to edible oils. Furthermore, the petroleum industry also uses it to separate
aromatic hydrocarbons from paraffin hydrocarbons of the same boiling range using solvents such
as liquified sulfur dioxide.

Objectives

1) To separate benzoic acid from two organic compounds mixture which are naphthalene and
benzoic acid.

Chemicals

Naphthalene, Benzoic acid, Dichloromethane, Aqueous sodium hydroxide, concentrated

hydrochloric acid and distilled water.

Apparatus

Beaker, graduated cylinder, thermometer, glass rod, retort stands with clamp, separatory funnel,
dropper, filter paper, pH paper, suction flask, vacuum filter, Buchner funnel and ice bath.

Methodology

1. 0.5g of benzoic acid and 0.5g of naphthalene are weighted and dissolved in 25 ml of
dichloromethane.
2. The mixture is transferred to a clean separatory funnel.
3. 25 ml of 10% aqueous sodium hydroxide is added into the separatory funnel.
4. The separatory funnel is then shaken gently to mix the mixture well and the gas inside is
released every three shakes.
5. The organic phase and aqueous phase are determined. These two phases are then extracted
thoroughly to separate them completely.
6. The aqueous phase is washed with 10ml of dichloromethane.
7. The aqueous layer is poured into a small beaker and it is cooled down to about 15°C.
 8. While stirring, ice-cooled concentrated hydrochloric acid is added drop by drop to the
aqueous layer by using a dropper until a pH of 1 is obtained.
9. The precipitate formed was filtrated by using vacuum filter into a Buchner funnel. The
filtrate was used to rinse the precipitate from the beaker into the funnel.
10. The product is dried and weighted to calculate the percentage of recovery based on the
amount of the initial mixture.

Precaution

1. Beware of handling hydrochloric acid.

2. Do not pour chemicals in the sink.

Results

Mass of filter paper Mass of filter paper Initial mass of benzoic Mass of benzoic
(g) with benzoic acid (g) acid (g) acid (g)
0.1250 0.6090 0.5132 0.4840

Calculation

Mass of benzoic acid = mass of filter papers with benzoic acid – mass of filter paper

=0.6090g - 0.1250g

=0.4840g

𝑀𝑎𝑠𝑠 𝑜𝑓 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑

Percentage of recovery benzoic acid = 𝐼𝑛𝑖𝑡𝑖𝑎𝑙 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑏𝑒𝑛𝑧𝑜𝑖𝑐 𝑎𝑐𝑖𝑑 x100%

0.484𝑔
=0.5132𝑔 x100%

=94.31%

Discussion
 In this experiment, benzoic acid was separated from the two organic compounds mixture
which are naphthalene and benzoic acid.

Naphthalene is an organic compound with chemical formula C10H8. It is an aromatic

hydrocarbon containing solely carbon and hydrogen atoms. Naphthalene is a non-polar,
polycyclic aromatic hydrocarbon. It is insoluble in water but soluble in organic solvent. It will
dissolve in dichloromethane to form two different immiscible liquid which is the polar aqueous
layer and non-polar organic layer.

The dichloromethane used is a colourless, volatile organochlorine compound. Since it is

immiscible with water and miscible with many organic compounds, so it is widely used as an
organic solvent. It has low boiling point of 39.6°C and density of 1.33g/ml.

Sodium hydroxide is an inorganic compound with the chemical formula of NaOH. It is an

ionic compound consisting of sodium cations Na+ and hydroxide anions OH−. It is a strong base
as it can dissociates completely into ions (Na+ and OH−) when it is in water. It has a pH of 13 and
it is slightly soluble in water. It is a white crystalline solid at room temperature.

Benzoic acid is an organic compound with chemical formula C6H5COOH. The benzoic
acid used is an aromatic monobasic carboxylic acid which is a white crystalline solid at room
temperature. It is soluble in organic solvent but only slightly soluble in water due to the nonpolar
aromatic ring of the benzoic acid. Benzoic acid is a weak acid which dissociates partially in an
aqueous solution or water. It can be deprotonated which is the removal of a proton (H+) by sodium
hydroxide because sodium hydroxide is a strong base. This reaction is called a
neutralization reaction by which an acid reacts with a base to form salt and water.

When NaOH solution is added into the mixture containing benzoic acid and naphthalene,
it will undergo neutralization reaction with the benzoic acid to form the carboxylate salt of sodium
benzoate. In this reaction, benzoic acid is deprotonated by NaOH to become the benzoate ion
(C6H5COO-) and it enters the aqueous layer. After neutralization, the sodium benzoate salt formed
stays in the aqueous layer, leaving the naphthalene in the organic layer as it has no affinity for the
aqueous layer, nor can it react with NaOH. Benzoic acid ionizes partially in water as it is a weak
acid. Hence, NaOH can separate the mixture of two organic compounds which are naphthalene
and benzoic acid.
 C6H5COOH (s) + NaOH (aq) ⇌ C6H5COO-Na+(aq) + H2O (l)

(Chemical equation for the neutralization reaction above)

The water has a density of 1.00g/mol while the dichloromethane has a density of 1.33 g/mol,
so it is easier to differentiate the two immiscible layers. The denser organic layer will be at the
bottom while the upper less dense portion is the aqueous layer.

The addition of cold concentrated HCl drop by drop while stirring can help to convert the
sodium benzoate back to its neutral form. This can help to disrupt any emulsions. During
acidification, white precipitate which is the benzoic acid was formed. After the acidification, the
solid form of benzoic acid can be collected using the Büchner funnel.

C6H5COO-Na+(aq) + HCl (aq) ⇌ C6H5COOH (s) + NaCl (aq)

(Chemical equation of the addition of concentrated HCl to the salt to obtain benzoic acid)

The total mass of the benzoic acid collected is 0.4840 g which is lower than the initial mass
which is 0.5132 g. The compound may be lost in the filtration step by using the Buchner funnel.
In this experiment, the percent recovery of benzoic acid is 94.31% and it was calculated by dividing
the mass of benzoic acid with the initial mass of benzoic acid. A few precaution steps were taken
in this experiment. Firstly, the gas was released after every three shakes of the separation funnel.
This is to prevent the increase of the pressure of gas in the separation funnel which is emitted from
the chemical reaction. Next, the vacuum filter was handled properly and two filter papers were
used instead of one to prevent the filter papers from puncturing. This is due to the fact that the
pressure exerted by the vacuum filter was very high. Furthermore, hydrochloric acid is handled
carefully as it is a hazardous liquid. Lastly, shaking is required when adding the sodium hydroxide
solution to prevent the emulsion layer from forming in the mixture which will affect the results
obtained.

Conclusion
 The objective of this experiment is to separate benzoic acid from two organic compounds
mixture which are benzoic acid and naphthalene. Initially, benzoic acid and naphthalene are both
at the organic layer. However, the sodium benzoate salt formed resides at the aqueous layer leaving
naphthalene at the organic layer as it cannot react with NaOH. The organic phase which has a
higher density will be at the bottom and it was then extracted to filter by using the Vacuum filter.
The benzoic acid crystals are collected in the end of this experiment with a mass of 0.4840 g which
is lower than the initial mass which is 0.5132 g and the percentage recovery is 94.31%.

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