EXTRACTION

Jyle Fraium L. Dino, ​Franc Ison P. Dy​, Micole Manolo I. Gabriel,

Demi Louise L. Go, Vheverli Whendel P. Go
Group 4 2A Medical Technology Organic Chemistry Laboratory

ABSTRACT
The experiment consisted of separating caffeine from five Lipton tea bags which weighed a total of 10 grams by
multiple extraction. By introducing 20 mL dichloromethane each time to the solution containing 4.40 grams of
anhydrous sodium carbonate and 100 mL distilled water, an organic layer was collected. With a total amount of 60 mL
dichloromethane placed, this procedure was repeated thrice. Subsequently, a spatula of anhydrous sodium sulfate was
added to the combined organic layer, which was then covered and left to evaporate in order to obtain the caffeine.
Based from the experiment, the caffeine acquired weighed a total of 0.05 grams. With this, 0.5% caffeine was
recovered from the multiple extraction.

I. INTRODUCTION
​Extraction is a technique used to separate a B. Procedure
desired substance from a mixture [1]. The 1. Preparing the Water Bath
process of transferring from one phase of a 4.4g of anhydrous sodium carbonate was
compound into another is stated by the weighed in a 400 mL tared beaker. 100 mL of
extraction theory. Solid-liquid extraction and distilled water was then added to the beaker.
liquid-liquid extraction are the two kinds of Afterwards, the beaker was heated in the hot
extraction. In liquid-liquid extraction or solvent plate.
extraction, there are two types: single and
multiple extraction.
Single extraction is the combination of an
organic solvent and water to form a bilayer. Most
organic solvents are immiscible in water and are
much less polar than water. They follow the rule
for solubility which states that like dissolves like.
After stirring the dichloromethane with the
solution, a heterogeneous solution can be
observed; the more dense solvent settles on the
lower layer while the less dense solvent settles
on the upper layer. In single extraction, the
whole aqueous solution is extracted [3].
Multiple extraction is a way to increase
extraction yield. It involves repeated extraction Figure 1. ​Weighing of 4.4g Anhydrous Sodium
processes and divided solvent is added to Carbonate
solution for every process. A better recovery will
be obtained by using two equal volumes of
solvent than the recovery that will be obtained by
using the summation of all volumes; thus making
multiple extraction more efficient than single
extraction. In addition, not all of the component
of the mixture is extracted when only a fraction
of the solvent is used [3].
The objectives of the experiment were:
1. To compare single and multiple
extractions of caffeine from dried tea
leaves
2. To calculate the percentage yield of
caffeine for both extraction procedures.
Figure 2. ​Heating the Water Bath
II. EXPERIMENTAL 2. Solid-Liquid Extraction
A. Test Compound/s or (Sample/s) used When the mixture in the beaker is boiling, add
Anhydrous Sodium Carbonate (Na​2​CO​3​), the 10g of tea (5 tea bags) in the boiling mixture
Anhydrous Sodium Sulfate (Na​2​SO​4​), then cover the flask with a watch glass. After
Dichloromethane (DCM), Distilled Water, Lipton
Black Tea Leaves
boiling for 10 minutes, the extract was cooled to
room temperature.
Figure 3. ​Solid-Liquid Extraction
3. Multiple Liquid-Liquid Extraction
​Odd numbered groups were assigned to do
single while the even numbered groups were
tasked to do multiple extraction. The tea extract
was put in the separatory funnel and 20 mL of
dichloromethane was added in the funnel. It
stood for 2 minutes or until two layers were
separated and clearly visible, the aqueous layer
(tannin) and the organic layer (caffeine). The
organic layer below was drained into a beaker
then covered with a watch glass. This process
was done three times.
Figure 4. ​Multiple Liquid-Liquid Extraction Set-up
4. Drying of Caffeine Extract
An evaporating dish was weighed using an
electronic gram balance. A half spatula of
anhydrous sodium sulfate was then placed in
evaporating dish. The organic layer was then
transferred into the evaporating dish with the
anhydrous sodium sulfate and dried until it
formed a residue.
Figure 5. ​Drying of The Caffeine Extract
5. Calculating the Percentage Recovery
The residue was weighed and the percentage
recovery was calculated by the weight of the
residue over the weight of the sample multiplied
by 100.
Figure 6. ​Weighing of Residue
III. RESULTS AND DISCUSSION
Extraction is a separation process that purifies
products or reaction, and as a result of the
miscibility of organic compounds with water,
layers are formed when the two immiscible
liquids come into contact with each other.
Density is used to determine the location of the
layer of an extraction solvent. The “like dissolves
like” rule is employed in extraction procedures as
organic compounds are more soluble in organic
solvents, which is why caffeine is soluble with
dichloromethane during the formation of the
organic layer and aqueous layer in the separatory
funnel in the experiment.
In the experiment, solid-liquid extraction was
initially done. The tea leaves sample was
immersed in the boiling mixture of anhydrous
sodium carbonate and distilled water in order to
extract water soluble components of the tea
leaves, which are the tannin and caffeine, as extraction is more efficient than single extraction
liquid extraction solvent. Anhydrous sodium as it shows a more efficient technique in
carbonate, a drying agent, helped recover pure recovering percentage recovery.
caffeine when the solvent evaporated at room
temperature as it removes traces of water from IV. REFERENCES
any organic solutions. The sodium carbonate also [1] ​Chemistry Dictionary. (n.d.). Retrieved
converted tannins into phenolic anions, which are October 6, 2018, from
not soluble in the dichloromethane but are https://www.chemicool.com/definition/extraction.
soluble in highly polar water [2]. Multiple html
liquid-liquid extraction was done next, with 20
mL of dichloromethane being added to the tea [2] Isolation of Caffeine from Tea Leaves. (n.d.).
extract in the separatory funnel every extraction. Retrieved October 11, 2018, from
The organic layer, which is the caffeine, and http://employees.oneonta.edu/knauerbr/chem22
aqueous layer, which is the tannin, can be 6/226expts/226_expt06_pro.pdf
distinguished as they differ in density. The
organic layer was then transferred in an [3] Theory of Liquid-Liquid Extraction. (n.d.).
evaporating dish with anhydrous sodium sulfate, Retrieved October 11, 2018, from
which will absorb the small amount of water that https://www.thevespiary.org/rhodium/Rhodium/c
is dissolved in the dichloromethane and small hemistry/extraction_theory.html
amounts of water from the aqueous layer that
may have gotten into the flask [2].

Table 1. ​Data of the weights used

A. Weight of tea leaves 10.00 g

B. Weight of evaporating dish + 128.02 g

caffeine

C. Weight of empty evaporating dish 127.97 g

D. Weight of caffeine 0.05 g

With the data shown above in Table 1, 0.05g of

caffeine was obtained from 10.00g of tea leaves
in multiple extraction. In single extraction
however, 0.03g of caffeine was collected by
Group 7.

Table 2. ​Data used in percentage recovery

Mass of caffeine 0.05 g

Mass of tea leaves used 10.00 g

Percentage recovery 0.50%

Percent by weight recovery of crude caffeine is

given by the formula and solution:
% ww = massmass of caf f eine
of tea leaves used
x 100
0.05g
= 10.00g x 100
= 0.50%
where 0.50% was yielded using the data shown
above in Table 2. In comparison to the yielded
recovery of 0.30% by Group 7, the group
obtained a higher percentage recovery of the
organic compound caffeine. Due to the extract
undergoing repeated separation in multiple
extraction, it can be concluded that multiple