EXTRACTION

Erika C. Rabara, Harvey Mher M. Rarang, Maika L. Regala, Chelejan Mhare U. Regino, Erik
Kristian Victor B. Sabio, Mica Gienela A. Sanchez, Arianne Nicole Denise T. Yoro
Group 8
2D Medical Technology
Organic Chemistry Laboratory

ABSTRACT
The extraction of caffeine in tea leaves is the aim of the experiment. A 10g of tea leaves is
extracted using simple extraction technique. Caffeine is more soluble to dichloromethane
(DCM) so it is used to separate the non-caffeine components of the tea extract. Anhydrous
sodium carbonate is used to convert impurities into insoluble salts and anhydrous sodium
sulfate to absorb impurities to keep the extract pure. The DCM solution is dried and the
caffeine weighed 1g that gave 10% recovery.

INTRODUCTION

Theophylline and Theobromine are both

related to caffeine and all three belong to a

In this experiment, caffeine is

extracted from tea leaves using the
process of extraction. Extraction is a very
common laboratory procedure used when
isolating or purifying a product. Organic
chemistry employs solid-liquid, liquidliquid, and acid-base extractions. The
theory of extraction lies in the concept of
immiscibility between two phases to
separate a solute from the other phase.
[1]

class of
Xanthines.

In this experiment, caffeine is the

substance to be extracted. Caffeine is an
alkaloid, a class of naturally occurring
compounds
containing
nitrogen
and
having the properties of an organic amine
base. That is why in its pure form, caffeine
is an intensely bitter and white powder. It
is odourless and is composed of long
hexagonal prisms. It has the IUPAC name
of 1,3,7-Trimethylpurine-2,6-dione and a
chemical formula of C8H10N4O2.[2]

Caffeine extraction from tea

leaves
involves
an
acid/base
liquid/liquid extraction. The reaction
involves a homogenous mixture of an
organic and aqueous layer. The ideal
solvent in the extraction should have a
low boiling point, not react with the
solute or other solvents, not be toxic
or highly flammable, not miscible with
water, be inexpensive, and should
readily dissolve caffeine at room
temperature. A common liquid/liquid
solvent pair for the extraction of
caffeine is water-dichloromethane.
Because water is present in the
pairing, it possible to separate
inorganic compounds from organic
compounds due to the fact that
organic substances are immiscible in
water. When mixing the liquid pairs,
the density of the both solvents
predict which solvent is the top and
which the bottom layer is. Caffeine,

Fig. 1 Chemical Structure of Caffeine

other

In this experiment, there are some

compounds
in
the
extract.

organic

compounds

Fig.
2
Chemical
Structure
Theobromine and Theophylline

called

of

which was present in the organic

layer, was located below the aqueous
layer. The product that is collected
after extraction still has many
impurities. Sublimation is one way to
purify the sample, because caffeine
has the ability to pass directly from
the solid to vapor and reverse to form
a solid all without undergoing the
liquid phase. Caffeine has the ability to
undergo sublimation under different
conditions than the impurities, and
can thus be isolated. A series of
techniques were used to extract pure
caffeine from tea leaves. The percent
error and percent recovery were
calculated to assess how much pure
caffeine was obtained, and to account
for errors that may have occurred that
led to a loss of product. [3]
In this experiment, the group
should be able to attain the following
objectives: extract caffeine from dried tea
leaves, know the amount of caffeine
present in 10 g of tea leaves, compare
single and multiple extractions, and
calculate the percentage yield for both
extraction procedures.

EXPERIMENTAL
A. Compounds tested (or Samples
Used)
In this experiment, separatory
funnel was used to contain the layer of
organic solvent and the tea extract. The
dried tea leaves are from black tea.
Dichloromethane (DCM) was used
as the organic solvent. Both Sodium
carbonate and Sodium sulfate were also
used as a converter of impurities into
insoluble salts and absorbent of water and
other soluble salts that remained in the
organic layer, respectively.

B. Procedure
A 4.4 anhydrous sodium carbonate
is placed on a 500-ml beaker along with a
100-ml distilled water. It is heated in a
very high temperature until the anhydrous

sodium carbonate is totally dissolved. Five

packets of 2.00g teabags were measured
using triple beam balance to obtain a
10.0g and then put in the aqueous
solution and covered with a watch glass in
a lower temperature until it has boiled for
approximately 10 minutes.
The teabags were removed after
boiling and the remaining extracts in the
teabags were squeezed using a spatula to
the side of the beaker. If teabags were
ruptured and the solid residue came out of
the teabag, the collected mixture must be
filtered using a filtered paper. It is then
cooled by placing the bottom of the
beaker in a running water.
The separatory funnel was then
filled with 60 ml of dichloromethane
(DCM) making sure that the stopcock is
closed to avoid spillage. The cooled
extract was then transferred into the
separatory funnel using a stirring rod to
guide the flow of the liquid. The
separatory funnel was then sealed and
inverted upside-down followed by the
opening of the stopcock for the removal of
the pressure caused by the build-up of
gases inside the funnel. It is then swirled
thrice to mix the liquid and is stood for 2
minutes until the separation between two
layers is visible.
The
weight
of
an
empty
evaporating dish was weighed using a
triple beam balance for the collection of
caffeine. A half spatula of anhydrous
sodium sulfate is placed in an Erlenmeyer
flask in order to collect the organic layer
of the extract.
After these two liquid are obtained,
the organic layer is then transferred to the
Erlenmeyer flask containing the anhydrous
sodium sulfate by opening the stopcock
and being alert on the speed of flow of the
organic layer into the flask. The lid on top
of the separatory funnel is opened to
avoid accumulation of bubbles in the
extract. The organic layer is drained and
the aqueous layer was left and disposed.

The solution collected in the

Erlenmeyer flask was decanted into the
pre-weighed evaporating dish. It is then
dried in the fume hood until a white
residue is left. The obtained dish with the
residue was weighed using a triple beam
balance. The weight of the caffeine is
represented by the difference of the
weight of the evaporating dish before and
after the experiment. The percentage
yield was then calculated by dividing the
mass of caffeine over the tea sample,
multiplied by 100%

RESULTS AND DISCUSSION

The obtained values of the different

weight of the materials and samples were
gathered for the calculations needed in
the experiment.
Weight of Black Tea Leaves
10.0g
Weight of Evaporating dish
123.50g
+ caffeine
Weight of Evaporating dish
122.50g
Weight of Caffeine
1.0g
Table 1: Weight of the containers and
samples used in the experiment
Table 1 shows the calculation of the
weight of the caffeine. All the listed
weights were measured on the same triple
beam balance to maintain accuracy and
consistency on the recording of the
measurements. The weight if the caffeine
is calculated by subtracting the weight of
the empty evaporating dish to the weight
of the evaporating dish containing
caffeine.
Using the formula:
Weight of caffeine
100%
% yield = Weight of tea leaves used
% yield =

1.0 grams
10.0 grams

= 10%

x 100%

A percentage yield of 10% was

calculated by dividing the mass of the
caffeine over the mass of tea sample then
multiplied by 100%. The interpretation is
that for every 100g of tea bags, there was
10.0 grams of caffeine present in the
black tea.
The anhydrous sodium carbonate
and sodium sulfate ensured the purity of
the caffeine sample because they covert
impurities into insoluble salts and absorbs
impurities, respectively.
Single extraction process is used in
this
experiment
that
used
dichloromethane as an organic solvent on
the sample once. However, it is considered
less efficient and accurate compared to
multiple extraction because there is a
lower yield obtained compared to those
who did multiple extraction.
There are a lot of agents that
cause error in the experiment. The
mechanical fault and especially the triple
beam balance problem can alter the
results of the weight of the caffeine
obtained. Another one is the inability of
obtaining the entire dichloromethane layer
because it is needed to prevent aqueous
layer from coming with the sodium sulfate
that can reduce the yield of caffeine.

REFERENCES
[1] www.coursehero.com Acadia CHEM
CHEM 331
[2]
https://myorganicchemistry.wikispaces.co
m/Caffeine
[3]
http://edspace.american.edu/ap7794a/wp
content/uploads/sites/159/2015/03/Isolati
on-of-Caffeine-from-Tea-Leaves-via-AcidBase-Liquid-Liquid-Extraction.pdf