SWISS GERMAN UNIVERSITY

INORGANIC AND ORGANIC CHEMISTRY

LABORATORY REPORT
Subject : Inorganic and Organic Chemistry Laboratory
Lecturer : Dr. rer. nat. Filiana Santoso, Mr. Hery Susanto M.Si
Instructor : Mr. Tabligh Permana, Mr.Hery Sutanto M.Si, Ms. Sylvia Yusri, S.Si
Faculty/Class : Life Science/LS 2A
Date of Experiment : 6 May 2014
Date of Lab. Report : 13 May 2014
Semester : 2
Time of Experiment : 14.00 – 17.00 p.m

Experiment: Extraction of Caffeine from Tea

Name: Kristania Hadhiwaluyo

Chita Sakina Putrianti
Elias Harmanto

Campus BSD City Tel. +62 21 537 6221

Bumi Serpong Damai Fax. +62 21 537 6201
Tangerang 15321 – Indonesia [email protected]
www.sgu.ac.id
 I. Objectives
 To understand about the Extraction of Caffeine from Tea

II. Theoretical Background

Extraction is a method used for the separation of organic compound from a mixture of compound.
This technique selectively dissolves one or more compounds into an appropriate solvent. The
solution of these dissolved compounds is referred to as the extract. The process is extremely
important in a wide range of technical applications, for instance biotechnology, the pharmaceutical
and food industries as well as environmental protection. Extraction is a separating process which
has the advantage of low energy consumption, high efficiency, high selectivity and less expensive
alternative compared with competing separating methods such as distillation, evaporation and
membrane technology.

This experiment will be conducted to extract caffeine

sample from tea. Tea itself is a beverage that is
commonly consumed by many people since 2,000
years ago in China, and infusing the young leaves
basically produces it and leaf buds of the tea plant,
Camelia Sinesis in the boiling water. In terms of its
chemical composition, the chemical substances in tea
can be divided into two major groups: water
(moisture) (75-78% in fresh fleches) and dry matter (22-25% in fresh fleches). Inorganic matters
constitute 3.5-7.0% and organic matters constitute 93-96.5%. However only 30-50% of all
substances is water-soluble (extractive) and passes into tea infusion. In the case of this
experiment, the organic compound caffeine will be focused on.

Caffeine is a chemical name, 1,3,7 - trimethylxanthine, belongs to a

wide class of compounds known as alkaloids that is found in over 60
plant species. Caffeine is found in coffee (100 mg/cup), tea (30-75
mg/cup), chocolate (6-35 mg/oz), and cola (46 mg/12 oz). The
caffeine itself is belong to a family of naturally occurring compounds
known as xanthines which is considered as the oldest known
stimulants. Additionally, this organic compound is considered as the
most powerful xanthine in its ability to increase alertness, put off
sleep, to increase ones capacity for thinking, relaxes the blood
vessels, and increases urination. Due to its structure, caffeine is both soluble in polar and non-
polar solvent. The solubility of caffeine in water is 22mg/ml at 25°C, 180mg/ml at 80°C, and
670mg/ml at 100°C. In this experiment, the organic solvent dichloromethane (CH2Cl2) is used to
extract caffeine from aqueous extract of tea powder because caffeine is more soluble in
dichloromethane (140mg/ml) than it is in water (22mg/ml). The dichloromethane and caffeine
mixture can then be separated on the basis of the different densities of dichloromethane and
water because dichloromethane is much denser than water and insoluble in it. Residual water is
separated from dichloromethane by drain out the dichloromethane through separating funnel, thus
dichloromethane passed through the funnel while polar solvents such as water is still remains in
the funnel. But since, water and dichloromethane is slightly soluble in each other, so after
separating the solvents, residual water will remain the organic layer.

However in the tealeaves, caffeine does not exist as the only organic compound. Instead, the tea
leaves are mainly consist of cellulose, pigments, chlorophylls, and tannins. Tannin, also called
Tannic Acid, is any of a group of pale-yellow to light-brown amorphous substances in the form of
powder, flakes, or a spongy mass, widely distributed in
plants and used chiefly in tanning leather, dyeing fabric,
making ink, and in various medical applications. Tannin
solutions are acid and have an astringent taste. This
organic compound is responsible for the astringency,
colour, and some of the flavour in tea. The presence of
these other compounds finally may lead to the impurity of
the caffeine after it has been extracted from the tea
sample which may cause alteration in the method used in
extracting the tea sample, which will be shown later in the
report.

III. Equipment and Materials

 Equipment:
- Round bottom flask, 100 cm3, 1
- Magnetic stirrer, 1
- Hotplate
- Cod water bath
- Separation funnel, 100 cm3, 1
- Distillation unit
- Digital Balance
 - Glass rod, 1
- Glass beaker, 100 cm3
- Glass beaker, 250 cm3
- Oven
- Graduated cylinder, 50 cm3
- Bulb
- Graduated pipette, 25 cm3
 Materials:
- H2O(l), distilled water, 30 cm3
- H2O(s), ice block
- Tea Bag, 1
- Sodium carbonate (Na2CO3), 2 g
- Dichloromethane (CH2Cl2), 75 cm3

IV. Procedures
1. The mass of the tea bag was measured in a digital balance, and the value that was
obtained was recorded in the data table as follows

Mass (g)
Empty 100 cm3 round bottom flask + magnetic stirrer
100 cm3 round bottom flask + caffeine + magnetic stirrer
Tea bag

2. The mass of an empty 100 cm3 round bottom flask and magnetic stirrer was
measured and the data value was recorded in the data table.
3. The 100 cm3 glass beaker was filled with 30 cm3 H2O(l), distilled water
4. 2g of Sodium carbonate (Na2CO3), was measured and placed inside the 100 cm4
glass beaker
5. The tea bag was also placed inside the 100 cm4 glass beaker and then was heated
while being stirred with a glass rod, on a hot plate with a temperature of 290 0C for
20 minutes
6. The mixture obtained in the 5th step was placed in a water bath containing ice block
to cool its temperature until its temperature reached around 25 0C (the more or less
similar value to the room temperature).
7. 25 cm3 Dichloromethane (CH2Cl2) was taken with bulb and graduated pipette and
was placed inside a 50 cm3 graduated cylinder.
8. The cool tea extract was transferred into a separation funnel and 25 cm3
Dichloromethane (CH2Cl2) was added carefully into the solution by tilting the
separation funnel.
9. The separation funnel was held horizontally with two hands, the stopper was held
tightly with one hand (by inverting the funnel) and the cap of the separation funnel
was also held tightly using another hand to make sure there was no liquid that
would spilled.
10. The separation funnel was gently shaken up and down (counted as 1 shake) for 5
times. Built up pressure caused by gases accumulating inside was released by
opening the stopper.
11. The 10th time was repeated if there were some gas bubbles containing CO2 that can
be seen.
12. Two distinct layers were formed after a few minutes with the dichloromethane layer
at the bottom.
13. The lower layer was carefully drained into another 100 cm3 beaker glass.
Note: Procedures that might be done according to condition
- In the case of this experiment, the seventh up to the thirteenth may be
repeated for 2 or three times by reading the filtered lower layer back into
the separation funnel and by adding another 25 cm3 Dichloromethane
(CH2Cl2) until a clear solution form at the bottom layer was formed.
- If an emulsion (cloudy) layer between two clear layers was formed, another
25 cm3 Dichloromethane (CH2Cl2) may be added into the separation funnel
14. Distillation unit was set according to the figure as shown below
 15. The clear solution obtained from the separation funnel was poured into the empty,
100 cm3 round bottom flask that has already had a magnetic stirrer.
16. The 100 cm3 round bottom flask containing the solution was put into the distillation
unit until the Dichloromethane (CH2Cl2) solvent was gone leaving the caffeine in the
form of solid precipitate behind.
17. The 100 cm3 round bottom flask containing the sample were put into the oven to
evaporate all water molecules that are also present within the distilled sample.
18. The mass of 100 cm3 round bottom flask containing thin crust (after being put
inside the oven) and magnetic stirrer was measured and recorded in the data table.

V. Observation (Data)

Table 1: Mass of different materials used in the experiment

Mass (g)
Empty 100 cm3 round bottom flask + magnetic stirrer 49.1246
100 cm3 round bottom flask + caffeine + magnetic stirrer 49.1598
Tea bag 1.79

Table 2: Observation on Changes that happen during the extraction process

Process Changes
The tea bag used in this experiment was boiled with
Heating (boiling the tea water and sodium carbonate, after 5 to 10 minutes
with water & sodium the color of the solution starts to change in to a
carbonate (Na2CO3)) brown color, which its intensity increases through
time and odors could be smelled.

After the solvent, dichloromethane was added into

the solution two layers was formed, the bottom layer
was dichloromethane that was contained of caffeine
while the upper layer containing the other solution
that was not soluble in dichloromethane.
Extraction using However when the 25 cm3 Dichloromethane (CH2Cl2)
separation funnel was firstly added into the solution, emulsion a cloudy
layer between two clear layers was formed. Although
the simplest way to get rid of the formed emulsion is
by swirling the contents of the funnel or by stirring
the contents using a glass rod another 25 cm3
Dichloromethane (CH2Cl2) was added.
 White crust in the form of precipitate was formed
and present in the bottom surface of the round
bottom flask. This crust-like precipitate contains the
caffeine (the targeted product), however it is seen in
the figure below that the caffeine that should be
white in color has a greenish color which indicates a
presence of another organic substance, namely
called tannin.

Distillation and End Result

VI. Discussion

Mass of Caffeine
Mass of 100 cm3 round bottom flask, extracted caffeine, and magnetic stirrer - Mass of
empty 100 cm3 round bottom flask and magnetic stirrer
49.1598 - 49.1246 = 0.0352 g

ANALYSIS
Obtaining pure organic sample from a mixture of various different compound inside a
substance require the method that can separate that certain pure organic sample from the
other components. The method that is used to separate an organic compound from a
mixture of various kind of compound is called extraction. A good application of this method
is the extraction of caffeine, which separates caffeine from the other substances found in
tea leaves. Basically tea is the dried and prepared leaves of a shrub, Camellia sinensis,
from which a somewhat bitter, aromatic beverage is prepared by infusion in hot water. This
common yet nutritive beverage contains different kinds of substances that can be
categorized into two major groups: water (moisture) (75-78% in fresh fleches) and dry
matter (22-25% in fresh fleches). Inorganic matters constitute 3.5-7.0% and organic
matters constitute 93-96.5%. However the composition that makes up the commercially
sold tea, found in the market only made up of 30-50% of all substances that is water-
soluble (extractive).

In the case of this experiment, the substance that is going to be separate from the various
different substances present in the tea is caffeine. Caffeine is a natural organic substance
that is found inside the tea and it will be extracted by following the mechanism as follow:

The first step of the mechanism was solid-liquid extraction in which insoluble material
(material inside the tea that is insoluble in water) or non-polar components are separated
from the soluble material or polar components. This process was done by boiling the tea
bag with water along with 2g of Sodium carbonate (Na2CO3). Firstly, the boiling process
dissolved the caffeine in the tealeaves into the water so it would be separated from other
insoluble substances such as cellulose, the primary leaf component. These insoluble
substances were then become easily removed because it is virtually insoluble in water.
Secondly the 2 g of the Sodium carbonate (Na2CO3) was also added in this boiling process,
because if the boiled or brewed tea is directly inserted to the separation funnel with the
add of the solvent, dichloromethane (CH2Cl2) other organic compounds such as tannins will
also be extracted therefore by acting like a base that convert organic compounds such as
tannins into their sodium salts so during the extraction process using the separation funnel
they will be substances which are not soluble in solvents in the aqueous layer during
extraction and will only be soluble in the water. As a result, this enables caffeine to be
isolated from the tea bag.

Afterwards, the second step of this mechanism would be the extraction process where
caffeine is separated from other organic compound in the tea by selectively dissolves the
mixture into an appropriate solvent that can help separating the targeted organic
compound, in this case caffeine. The extract is the solution where caffeine dissolved in,
and it is obtained in the separation funnel. In the case of this experiment, dichloromethane
(CH2Cl2) was chosen as the solvent to separate the caffeine from aqueous extract of tea
(tea that has been brewed) because caffeine is more soluble in dichloromethane (with its
solubility value of 140 mg/ml) than in water (22
mg/ml). When dichloromethane (CH2Cl2) was added
into the separation funnel, it was seen that two
distinct layers would be formed as shown in the
figure. By following the basis of different densities of
dichloromethane (CH2Cl2) and water caffeine mixture
can be separated by draining out the
dichloromethane (CH2Cl2) solvent through the funnel
and therefore extracted from the tea sample. In this
case, since dichloromethane is a non-polar
substance, which is much denser than water and
therefore insoluble in it, the dichloromethane
(CH2Cl2) solvent containing the caffeine will be
located on the bottom layer present in the separation
funnel.

Lastly, the pure caffeine sample that is extracted from the tea can be obtained by
distillation and oven. Actually after the extraction process, the lower layer containing
dichloromethane (CH2Cl2) solvent and caffeine also contain some water molecules as water
and dichloromethane is slightly soluble in each other. Therefore to obtain the pure caffeine
sample, firstly, the lower layer was put into the distillation unit as distillation is a commonly
used method for purifying liquids and separating mixtures of liquids into their individual
components therefore separating the caffeine and water from the organic solvent,
dichloromethane (CH2Cl2), which is not needed as the product of the extraction process.
But since some residual water still present with the caffeine sample, the caffeine sample
obtained after the distillation process has finished was further placed in the oven to remove
those residual water therefore allowing us to obtained the caffeine sample, in this case of
this experiment 0.0352 g of caffeine was extracted from 1.79 g of tea bag.

Unfortunately there were some errors from our experiment as it was seen in the figure that
after the extraction process it was proven that the process did not give us the pure sample
of caffeine, however there is other organic compound named tannin that was also
 extracted thereby leaving some green-
colored compound in the caffeine
sample. This indicates that there were
not enough amount of sodium
carbonate (Na2CO3) that was added
during the boiling process which
causes the solution to be not basic
enough therefore not all tannins were
converted into its salt form which
makes them to be still soluble in the solvent, dichloromethane (CH2Cl2) and thereby
extracted when the organic layer (bottom layer present in the separation funnel) that
supposed to be contained of the solvent and caffeine, also contained the tannin. Besides,
there is also a possibility that not all caffeine was extracted through the separation funnel.
In conducting this experiment, we only add 75 cm3 of dichloromethane (CH2Cl2) into the
funnel, however maybe more of dichloromethane (CH2Cl2) should be added into the funnel
to ensure all caffeine were extracted.

VII. Conclusion

Based of our experiment, the amount of caffeine contained in tea that was successfully
extracted was 0.0352 grams from 1.79 grams tea, or only 1.96% out of 100%. There
should be more caffeine that can be obtained from this experiment but we concluded that
there were some errors occurred during the experiment like not all caffeine itself was
dissolved completely in dichloromethane and the impurity of the caffeine sample as there is
other substance like tannin that is also extracted during the extraction process. As a result
ann optimum result was not obtained after the distillation process.
VIII. References

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