Experiment 2 Chem 33.1

Araniador, Glaicyl Dame Ann B.
2016
Date Performed: January 28,
Bronzal, Lucile A.
Date Submitted: February 4, 2016
Mameloco, Neri May G.

EXPERIMENT NO. 2
ISOLATION OF CAFFEINE FROM TEA
I.
INTRODUCTION
Tea is one of the most widely used caffeinated drinks in the world. The caffeine
(C8H10N4O2) found in tea is known to be bitter in taste, white, crystalline
methylxanthine, and a member of an alkaloid compounds. Alkaloids are basic nitrogen
containing compounds commonly found on plants.
Figure 1.1 Structure of the Caffeine

Alkaloids, such as caffeine are often physiologically active in humans and are
known to be central nervous system stimulants. It has the ability to increase alertness,
put off sleep and can increase a persons capacity for thinking. Some examples of this
are morphine, heroin, cocaine, quinine and nicotine.
Tea leaves in which caffeine can be found, also contains tannins which are acids
from plants, undecomposed chlorophyll, cellulose, and pigments. To extract the caffeine
from tea leaves, it should be present as the free base. In order to do so, the acidic
substances found in plants that are mentioned above must be water-soluble.
In order to determine the amount of caffeine from tea, series of techniques were
performed. The major component of tea is cellulose which is virtually insoluble in water
while caffeine is water soluble. Using hot water these components will be separated
from tea leaves. Other compounds such as tannins will also be extracted using this
solid/liquid extraction. To isolate the caffeine from these other compounds, liquid/liquid
extraction will be used. This procedure involves the use of two immiscible solvents of
different polarities, typically water and an organic solvent known as dichloromethane.
They are placed in a separatory funnel and shaken to ensure mixing. The solvents were
chosen so that the compound of interest, which is the caffeine, will dissolve into one
solvent while the other compounds dissolve in dichloromethane. Since the two solvents
are immiscible, two layers will form and will allow an easy separation. After the layer
containing the caffeine has been separated, it is washed with 10% NaOH to help
remove any acids or polyphenols that were extracted along with the caffeine. The
solvent is then dried by adding Na 2SO4 to remove trace amounts water. The dried
solvent is then removed by distillation and the crude caffeine is isolated. The crude
caffeine can be further purified using recrystallization.
II.
RESULTS AND DISCUSSION

Table 1.1 Mass Obtained From Green Tea, Watch Glass, Watch Glass with Caffeine
Product and Recovered Caffeine
Weight
Weight
Weight
Weight
of
of
of
of
Green tea (5 bags)

Watch Glass with Caffeine Product
Watch Glass
Recovered Caffeine
10.39 g
37.5496 g
37.4753 g
0.0743 g
The various weights of the watch glass and green tea are obtained in order to
calculate the final mount of caffeine product in grams. The final amount of caffeine
extracted is then used to calculate percent recovery.
The predetermined masses provided by the Lipton Green Tea manufacturers are
accepted as the experimental measurements of both tea and caffeine. In the
experiment using 5 tea bags, 10.39 g is the actual weight obtain. A watch glass is
weighed in advance with a total mass of 37.4753 g. The weighed watch glass together
with caffeine product is 37.5496 g. The difference of the initial weight and the final
product yield a weight of 0.0743 g.
By calculation, the mass of the extracted caffeine from 5 tea bags is only 0.72%
of the theoretical yield but in consideration of all the factors responsible for error. The
error in yield results from a number of unavoidable experimental flaws. This data may
be inaccurate because during the extraction of caffeine, emulsions may have happen.
This takes place when an organic compound of one liquid in a second liquid and the
first compound will not mix like in the case of water and oil. Because of this, a random
amount of caffeine is separated depending on how gentle students shake the mixture.
Caffeine is more soluble in an organic solvent, which is why dichloromethane is
used instead of water to extract the organic solvent and separate it from water soluble
compounds. Sodium Hydroxide is used to prevent the extraction of acidic compounds
called tannins from the tea leaves.
III.
CONCLUSION AND RECOMMENDATIONS

In general, a total of 0.0743 g of caffeine was obtained from a 10.39 g of green
tea (5 bags). The total percent of caffeine recovered was 0.72 %. This percentage does
not only reflect on how the procedure was executed but it also signifies a relevant
amount of product lost throughout the process. A loss of product could have occurred
due to emulsions and due to not carefully washing with dichloromethane to extract as
a large amount caffeine as possible. The solutions were often transferred to different
containers during the experiment, which provide factors to lose a part of the product. It
is also possible that the caffeine is not concentrated enough because excessive amount
of water was added. It is impossible to recover everything because the reaction never
goes 100% to completion and due to the material loss during the transfer in the
experiment.
Moreover, some of the reagents used are very hazardous in case of skin contact,
eye contact, ingestion and inhalation. Therefore, proper precautionary measures should
be observed when handling those hazardous reagents and should wear suitable
protective clothing. It is also essential to make sure that the lock of the separatory
funnel is well secured in order to avoid leakage. Students must also shake the solution
gently in order to avoid formation of tiny bubbles at the boundary of the two layers. In
extracting the caffeine one must be careful not to contaminate with the other
components of tea.
IV.
REFERENCES/ BIBLIOGRAPHY
BK Rev. (2003) Isolation of Caffeine from Tea Leaves. Retrieve February 2, 2016, from
http://employees.oneonta.edu/knauerbr/chem226/226expts/226_expt06_pro.pdf
Snelling C.R., (2003) Extraction of Caffeine From Tea Leaves. Retrieved February 2,
2016, from http://www2.volstate.edu/CHEM/2010/Labs/Caffeine_Extraction.htm
Trimble J. (n.d.), Isolation of Caffeine from Tea Leaves. Retrieved February 2, 2016, from
http://www.odinity.com/isolation-of-caffeine-tea/
University of Pittsburgh at Bradford, Chemistry Lab 023, (n.d.). Caffeine extraction
From Tea. Retrieved February 2, 2016, from www.upb.pitt.edu
Bedel B. (2012). Background: Extraction of Caffeine from Tea Leaves. Retrieved
February 2, 2016 from https://mynotebook.labarchives.com/share/Sample:%20Organic
%20Chemistry%20Lab/NTkuOHwzOTI1LzQ2L1RyZWVOb2RlLzMzOTEyNzcwMjZ8MTUxLjg
Chem 33.1 Laboratory Manual
Chem 33.1 Course Syllabus
V.
ANSWERS TO QUESTIONS/ CALCULATIONS

1. Discuss the role/s of the following in the isolation of caffeine:
a. Dichloromethane
Caffeine is more soluble in an organic solvent. Therefore, dichloromethane
is used to extract organic solvents present in the tea solution and separate
caffeine from glucose, tannins, and other water soluble compounds.
b. NaOH aqueous solution
Sodium Hydroxide is use to prevent the extraction of acidic compounds
called tannins from the tea leaves.
c. Ca(OH)2
Calcium hydroxide is use to precipitate out the tannic acid as calcium
tannate in tea leaves. If sodium hydroxide is used, no precipitate will form
because sodium tannate is a water soluble compound. If tannate salt is not
precipitated, the caffeine product will be contaminated.
2. Explain why salt was added to the water before the liquid-liquid extraction of
caffeine. What is happening, why and how?
Salt is added to water before the liquid-liquid extraction because at different
salt concentrations it will cause different degrees of phase separation. When added
to water, the Na+ ion of NaCl is attracted to oxygen while the Cl- ion is attracted to
hydrogen. This cause sodium chloride to split in water and the NaCl dissolves
separately into Na+ and Cl- atoms. A hydration shell is formed which prevents Na +
and Cl- to form ionic bonds. This process is use to isolate compounds of interest.
3. How efficient is the extraction of tea leaves containing 1.0 g of caffeine with 3 20mL portions of dichloromethane over that of the single step extraction?
Dichloromethane is effective in dissolving other components present in tea

leaves so that caffeine will be completely extracted.
4. What are emulsions and why do they form during extractions? How are they
minimized and removed?
Emulsion is a mixture of two heterogeneous chemicals that will not dissolve in
one another and will not form a layer. Existence of tiny droplets that are mix
together are observed instead of two (2) desired layers. However, emulsions can be
minimized by letting the solution settle for few more minutes. It can also be
removed in the process of pumping or seeding. In pumping, two heterogeneous
substances are sent through a centrifugal pump that divides the tiny droplets in
order to form two desired layers.
5. Why is it necessary to remove the stopper from the separatory funnel when liquid is
being drained from it through the stopcock?
It is necessary to remove the stopper from the separatory funnel when liquid is
being drained because a vacuum is created inside the funnel if the stopper is not
removed. Eventually, vacuum will build up and air will percolate into the funnel that
may disturb the layers that were formed. Removing the stopper gives equal
pressure inside and outside the funnel that makes the solution flow nice and
smooth.
Weight of Caffeine=Weight of Watch GlassCaffeine ProductWeight of Watch Glass

= 37.5496 g - 37.4753 g
= 0.0743 g
Mass % =
weight
weight of recovered caffeine
tea
( )
g
( 0.0743
10.39 g )
= 0.72 %
x 100
x 100

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Araniador, Glaicyl Dame Ann B.

Date Performed: January 28,

Date Submitted: February 4, 2016

Mameloco, Neri May G.

Figure 1.1 Structure of the Caffeine

RESULTS AND DISCUSSION

Green tea (5 bags)

CONCLUSION AND RECOMMENDATIONS

ANSWERS TO QUESTIONS/ CALCULATIONS

Dichloromethane is effective in dissolving other components present in tea

Weight of Caffeine=Weight of Watch GlassCaffeine ProductWeight of Watch Glass

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