Extraction

C.P. Espinola, E. Galamiton, K.D. Geronimo, A.C. Greas, J.N. Guce, O. Icamen
Group 3, 2FPH, Faculty of Pharmacy, University of Santo Tomas, Espaa, Manila

ABSTRACT
Extraction is a technique that uses two immiscible phases to disperse the substance from one phase into the other. The concept of immiscibility is one of
the factors of theory in extraction. There are two kinds of extraction, the single and multiple extractions. In this experiment, caffeine was extracted from
tea leaves by means of the multiple extraction procedure. Ten grams of tea bag was boiled in a solution of 4.4 grams of anhydrous sodium carbonate
and 100 milliliters of distilled water, at that juncture was placed in a separatory funnel with 60 milliliters of dichloromethane. Through the use of
Erlenmeyer flask containing half a spatula of anhydrous sodium sulfate, the extract was sapped, then and there transported into an evaporating dish and
subsequently evaporated to dryness. The extract collected was weighed and found to be 1.05 grams. The percentage yield was calculated by dividing
the mass of crude caffeine by the mass of the tea leaves used. The percentage yield was 10.5%. The outcomes in this multiple extractions experiment
were compared with the results gained from single extractions in terms of their efficacy.

I.

Introduction
Extractions are a way to separate a desired
substance when it is mixed with others. The mixture
is brought into contact with a solvent in which the
substance of interest is soluble, but the other
substances present are insoluble. It makes use of
two immiscible phases to separate the substance
from one phase into the other. Typical lab
extractions are of organic compounds out of an
aqueous phase and into an organic phase. The
distribution of a solute between two phases is an
equilibrium condition described by partition theory.1
The technique used to separate an organic
compound from a mixture of compounds is called
extraction. Extraction process selectively dissolves
one or more of the mixture compounds into a
suitable solvent. The solution of these dissolved
compounds is referred to as the Extract. Here the
organic solvent dichloromethane is used to extract
caffeine from an aqueous extract of tea leaves
because caffeine is more soluble in dichloromethane
(140 mg/ml) than it is in water (22 mg/ml).2
Single extraction is commonly used on the small
scale in chemical labs.3 It is normal to use a
separating funnel. Multiple extraction is known as an
elegant way to increase the extraction yield.
Different solvents dissolve different components of a
material extracted.4

II.

Methodology
1. The Experimental Set-up

Figure 2.1 Experimental Set-up

2. Dissolution and Heating
The anhydrous sodium carbonate weighing 4.4
grams was added to 100 mL of distilled water in a
250 mL beaker. After which, it was heated in a
water bath until the solid dissolved.

The boiled tea solution was transported into a

separatory funnel, the aforementioned in put in an
extraction set-up. Subsequently, 20 mL of
dichloromethane was added to the aqueous
solution thrice each time in a separatory funnel.

Figure 2.2 Heating of anhydrous sodium carbonate

Succeeding, 10 grams of tea leaves in a tea bag
was placed into the beaker and then mixture was
heated for 10 minutes on a low flame.
Figure 2.5 Addition of boiled tea solution to
dichloromethane

For
the
caffeine
to
dissolve
into
the
dichloromethane, physical exacerbation was
required. The separatory funnel was rotated on the
palm, permitting the substances to swirl, and
intermittently opening the cap to allow air to drip.

Figure 2.3 Heating of tea bags

3. Involving of Dichloromethane
The tea bag was pressed against the side of the
beaker with a glass rod in to collect the excess
liquids within.

Figure 2.6 Swirling of the separatory funnel

4. Collecting the Organic Solution

Figure 2.4 Pressing of tea bags

After 10 sets of rotations, the separatory funnel

was set back onto the iron ring and left to stand
for 2 minutes until the separation between the
two layers was clearly visible. The organic
solution was drained into the Erlenmeyer flask
underneath it and the aqueous solution was
disposed of.

5.

Weighing of the Residue and Calculating

Percentage Yield
The evaporating dish containing the residue was
now weighed using a triple beam balance. The
records that showed up were then deducted by
the mass of the evaporating dish alone (it was
assessed previously using a triple beam
balance), to calculate for the weight of pure
caffeine: 1.05 grams. At that point, quantity was
divided by the weight of the tea leaves and then
the quotient was multiplied by hundred, resulting
in the percentage yield of 10.5%.

Figure 2.7 Collecting of organic solution

Subsequent, the extract (organic solution) was
decanted on to an evaporating dish. The dish was
subsequently covered with a piece of paper or
parafilm which was pierced with holes, then placed
on a fume hood to vaporize to dryness.

III.

Results and Discussion

Data gathered from the experiment are:

Weight in grams
Tea leaves

10 g

Evaporating dish
and Caffeine

87.35g

Empty
Evaporating dish

86.30g

Caffeine

1.05g

Percentage recovery:

Figure 2.8 Transferring of organic solution

% Yield =

1.05
10

100

100

= 10.5 % yield
A percentage yield of 10.5% is obtained after
computing the ratio of weight of crude caffeine and
weight of tea leaves multiplied by 100%. Therefore,
in every 10 grams of tea leaves it contains 1.05
grams of caffeine.
Figure 2.9 Preparation to be evaporated

Caffeine is an active ingredient of teas and coffees.

It is an alkaloid, which properties come from the lone
pair of nitrogen. The Nitrogen present in caffeine can
be used to control its water solubility. When

extracting caffeine the temperature should be high,

caffeine is water soluble at 670 mg/ml at 100oC.

b) Formation of Emulsions
Emulsions are small droplets of the organic layer
that are suspended in the aqueous that are
result of vigorous shaking of separatory funnel.

1. Addition of Anhydrous Sodium Carbonate

It ensures that the acidic components of the tea
leaves remains water soluble. It also ensures that
the caffeine is a free base. Sodium Carbonate
places caffeine in a more basic environment so
that it has higher affinity for dichloromethane and
to cause the tannins to form phenolic salts to
ensure purity of the extract.
a) Cooling of Solution

Thorough mixing is the best technique to avoid

emulsions and it is also important because the
two solutions must be in contact with each other
to allow the solute to be extracted into the
second layer.
IV.

The students therefore conclude that multiple

extractions are more efficient than simple extraction
because the addition of dichloromethane is divided
thereby increasing the percentage recovery of the
caffeine to the tea leaves. The percentage recovery
of the caffeine as shown in the result is 10.5%. This
indicates how much of the pure product was
recovered from the crude product. It was impossible
to obtain 100% recovery of the caffeine because of
the procedures that was done on the tea leaves.

The solution was cooled before the addition of

dichloromethane because it has a boiling point
of 40oC. If the solution was not cooled,
dichloromethane would evaporated and the
caffeine would not be properly extracted.
2. Addition of Dichloromethane
It forms two immiscible layers. The upper layer,
which is the aqueous layer consists of mostly
water and other constituents. The bottom layer,
the organic layer which has greater density
consists of dichloromethane and caffeine.
3. Addition of Anhydrous Sodium Sulfate
It ensures the pureness of the caffeine extract by
removing the excess water in the solution before
the solvent evaporated at room temperature. It is
also added to dry out the dichloromethane
because it dissolves not only in caffeine but also in
water.
4. Swirling and Inverting
These methods are used to mix the two layers to
provide maximum surface contact between the
two immiscible layers so that substances can be
pulled or extracted from one to another. This will
result to a very effective extraction.
a) Popping off of Separatory Funnel Caps
These are due to built up vapors. Vapor
pressure is created while mixing the two layers
since extraction solvents have a very high vapor
pressure which results to low boiling point.

Conclusion

V.

References
From book:
[5] Bathan, G.I., Bayquen, A.V., Crisostomo, A.B.C.,
Cruz, C.T., De Guia, R.M., Farrow, F.L., Pea, G.T.,
Sarile, A.S. & Torres, P.C. (2014). Laboratory
Manual in Organic Chemistry. Manila: C&E
Publishing, Inc. p.27-28
From internet:
[1] [No author mentioned] Definition of Extraction
http://www.chemicool.com/definition/extraction.html
[2] [No author mentioned] Extraction of Caffeine
from Tea
vlab.amrita.edu/?sub=3&brch=64&sim=169&cnt=1
[3] [No author mentioned] Liquid-liquid Extraction
https://en.wikipedia.org/wiki/Liquid%E2%80%93liqui
d_extraction#Batchwise_single_stage_extractions
[4] [No author mentioned] Multiple Extraction
http://www.funqa.com/chemistry/2501-1-Chemistry4.html
[6] Postu, A. Isolation of Caffeine from Tea Leaves
via Acid-Base Liquid-Liquid Extraction,
http://edspace.american.edu/ap7794a/wpcontent/uploads/sites/159/2015/03/Isolation-ofCaffeine-from-Tea-Leaves-via-Acid-Base-LiquidLiquid-Extraction.pdf