BACHELOR OF SCIENCE IN APPLIED CHEMISTRY

ORGANIC CHEMISTRY II
CHM556

EXPERIMENT 1
TITLE: ISOLATION OF CAFFEINE FROM A TEA BAG

PREPARED FOR:
ASSOC PROF ZURINA BINTI MAHMUD

DATE OF EXPERIMENT:
15 SEPTEMBER 2014

DATE OF SUBMISSION:
22 SEPTEMBER 2014

NAME MATRIC NO GROUP
NURUL FATIN IZZATY BINTI MD ZAKI
NUR AINA SYAZLIN BINTI AZMI (PARTNER)
SHARIFAH SHAHIDA BINTI HAMDAN @ AMIR (PARTNER)
2013724473
2013578315
2013380273
ASB3Cg
ASB3Cg
ASB3Cg
OBJECTIVE
To extract caffeine from a tea bag and determine its percentage.

INTRODUCTION
Caffeine is a white crystalline xanthine alkaloid that is a psychoactive stimulant drug.
Caffeine was discovered by a German chemist, Friedrich Ferdinand Runge, in 1819.
He coined the term ''kaffein'', a chemical compound in coffee, which in English
became ''caffeine''. Beverages containing caffeine, such as coffee, tea, soft drinks,
and energy drinks.

In the experiment, Caffeine will be extracted from a sample of tea bag. A
concentrated tea solution was prepared. A tea solution will be extracted by using
extraction technique which using methylene chloride. Then, the sample will be dried
to remove water by using anhydrous sodium sulphate. Finally, The sample will be
evaporated in the water bath to remove methylene chloride that remained. The
caffeine will be collected and weighted.


Figure 1: structure of caffeine


APPARATUS
Beaker, conical flask, separating funnel, hot plat, cotton wool, test tube, retord stand.

CHEMICAL
Water, tea bag, sodium carbonate, methyl chloride, anhydrous sodium sulphate.

PROCEDURE
50 mL of water was boiled in the 100 mL beaker. A tea bag was added to make tea
solution.
The hot tea was transfer into a 100 mL conical flask. Then, 0.5 g of sodium carbonate
was added to the tea solution. The tea solution was transfer to a separating funnel
while filtrated with using cotton wool. 15mL of methylene chloride was added to the
separating funnel and extraction started. Lower layer was drained, 10 mL of fresh
methylene chloride was added and extraction was started. This step was repeated 2
times. The lower layer was drained and fultered it by added anhydrous sodium
sulphate. A precipitate with clear brown solution formed. The solution was transfer
to the beaker. Finally, the methylene chloride was evaporated in the water bath.

RESULTS AND CALCULATIONS
Mass of tea bag 2.1066 g
Mass of beaker 49.6560 g
Mass beaker + caffeine 49.6713 g
Mass of caffeine 0.0153 g

Percentage of caffeine = mass of caffeine / mass of tea bag
= 0.0153/ 2.1066
=0.73%


OBSERVATIONS
Two layer was observed in the separating funnel. A dark brown solution at the top
layer and clear brown solution at lower layer. After the lower layer was drained, the
colour was become a little bit clear when anhydrous sodium sulphate was added. The
solution was evaporated in the water bath . The white powder was remain in the
flask.


QUESTIONS
1. Outline a separation scheme for isolating caffeine from tea.
Make concentrated tea solution
1. extract with 20 ml methylene chloride
2. Separate layers
Aqueous layer Organic layer
1. Extract with 20 ml methylene chloride
2. Separate layers
Aqueous layer Organic layer
1. Extract with 20 ml methylene chloride.
2. Separate layers.


Aqueous layer Organic layer
Discard down drain
1. Combine organic layer
2. Separate layer
Organic layer Aqueous layer
1. Dry over sodium sulphate
2. Decant into beaker Discard down drain
Organic layer
Rinse down drain 1. Use water bath to evaporate methylene chloride.
Residue Pure caffeine
Rinse down drain weight the mass of caffeine


2.Why was the sodium carbonate added in experiment?
Sodium carbonate is added to the tea because the tannins are acidic and sodium
carbonate is a base, so when sodium carbonate is added to the tea solution,, the
acids will converted to the sodium salts which are highly soluble in water

3.The crude caffeine isolated from tea has a green tinge. Why?
Because chlorophyll and other water soluble compounds still in the caffeine.

3.What are some possible explanations for why the melting point of your isolated
caffeine was lower than the literature value (236C)?
Caffeine used in this experiment was not pure and probably there were impurities in
the caffeine that were affecting the melting point. This depresses melting point.
There is also the possibility of melting point apparatus with AR grade compound did
not calibrate in the melting range.

5.What would happen to the caffeine if the sublimation step performed at
atmospheric pressure?
The caffeine would decompose, producing less yield and more heat required for
sublimation. Furthermore, increasing the pressure would decrease the amount of
heat required, while producing a "purer" sample.

DISCUSSION
During preparation of tea solution, it is important to push down the tea bag slowly in
order to have good contact between tea leave and the water without tear the tea
bag. When transfer the tea solution exert a gentle pressure to the tea bag to press
out much liquid as possible. During extraction process, after make a gentle shake to
the separating funnel. When releasing the pressure try to make it far from you under
the fume hood. In the separating funnel, caffeine will stay at lower layer due to its
density. Anhydrous sodium sulphate was added into the mixture to remove water
remain because it is a drying agent. Finally, the solution was evaporated in the water
bath to remove the methylene chloride due to its lower boiling point which is 396 C.
From the observation, the white powder formed can be determine as a caffeine
because the physical properties of the caffeine from the reference is same which is
white solid. The percentage of caffeine present in the tea bag is 0.73%. From the
article, percentage of caffeine in a tea bag is between 3% to 5%. The percentage of
the caffeine in the experiment was too small regarding to the poor separation
between caffeine and water in the separating funnel. In addition, the separating
funnel that we used in the experiments is leaking. A few drops of solution in the
beaker keep dropping before the separation started. From the result and observation
obtained, we can prove that the product obtained is a caffeine.

RECOMMENDATION
1. Should give some times to let the solution in the separating funnel separate
well.
2. Should shake the separating funnel vigorously to ensure intimate mixing
3. Add extra methylene chloride as it can extract caffeine from an aqueous
solution because caffeine is more soluble in methylene chloride (140 mg/ml)
than it is in water (22 mg/ml).
4. Should push down the tea bag slowly in order to have good contact between
tea leave and the water without tear the tea bag.
5. Let the solution to become a concentration solution as all the caffeine will
removes out from the tea bag.

CONCLUSION

The mass of caffeine is 0.0153 g. The percentage of caffeine in the tea bag is 0.73%.


REFERENCES
1. Extraction of caffeine from tea,
http://amrita.vlab.co.in/?sub=3&brch=64&sim=169&cnt=1
2. Introduction of Organic Laboratory Technique, A Small Scale Approach, 3rd
Edition by Engel Kriz, Lapman and Pavia.