Caffeine Isolated from Tea Bags

Organic Chemistry Labs477 Views984 Words

Abstract:

The purpose of this experiment was to determine the yield, percent recovery and melting point of
caffeine isolated from tea bag. During the experiment, a tea bag was heated in boiling water for about
15 minutes. The resulting mixture was collected for the extraction of caffeine. Caffeine was isolated
from the mixture using methylene chloride. This is because caffeine is more soluble in methylene
chloride than in water. Sodium carbonate was also added to the mixture. This was done to form a
sodium salt derivative of tannin compounds contained in tea. Tannins are a class of compounds that
have certain properties in common.1

Tannins have a phenolic group and also hydrolyzes to form an acid. Because of their phenolic groups and
acid formation after hydrolysis, they can react with sodium carbonate to form a salt. The salt is soluble
in aqueous solution; therefore, it does not separate into the organic layer. The organic layer separates
to the bottom because methylene chloride is denser than water. A micro pipet was used to transfer the
organic layer to a flask. It was dried using sodium sulfate. The resulting dry mixture was evaporated by
heating. Because of low boiling of methylene chloride, it vaporizes at 400C and impure caffeine crystals
were collected. Caffeine do not vaporizes at this temperature because it has a boiling point of 1780C
and a melting point of 2380C. The impure caffeine had a melting point range of 223.6-229.30C. This
suggested that it contained impurity. Sublimation was used to extract pure caffeine from the impure.
The tea bag yielded 0.031g of crude caffeine, which is about 1.3% of the mass of tea in one tea bag. 13%
of pure caffeine was recovered after sublimation. The sublimed caffeine had a melting point range of
231.2-234.60C.





REPORTS & DISCUSSION

Compound Melting point Yield % Recovery
Pure caffeine 235.3-238.5
Crude caffeine 223.6-229.3 0.031g
Sublimed caffeine 231.2-234.6 0.004g 13%


Caffeine is a common substance and is found in coffee, tea, soft drinks and chocolates. It can be isolated
from natural sources like tea leaves, cola nuts and cacao beans. Caffeine is an alkaloid, and more
specifically, a member of the methlxanthines.2 Caffeine has been found to act as receptor antagonists
by inhibiting the effect of adenosine.3 Adenosine is a modulator that regulates sleep and other neural
phenomena in human.3 This inhibitory effect of caffeine makes it a central nervous system stimulant.
High doses of caffeine in human adult can be fatal. The acute lethal dose of caffeine in human adult has
been estimated to be 10g/person.4 To isolate caffeine from tea, extraction is used to separate the
caffeine from other components of tea. Extraction is a separation technique based on the differences in
the solubility of substances in two immiscible solvents.5

For the purpose of this experiment, methylene chloride was used as the solvent because caffeine is
more soluble in methylene chloride than in water. Caffeine was extracted by adding 3ml of methylene
chloride to the tea solution. 0.5g of sodium carbonate was also added to the mixture. Sodium carbonate
was added in order to convert tannins and gallic acid to sodium salts which are soluble in water. When
the extraction was carried out, an emulsion was formed. An emulsion is dispersion of liquid in another
liquid. The emulsion was broken into two layers by centrifugation. The organic layer which is denser
than water settled on the bottom of the tube, while the aqueous layer was on top. The high density of
the organic layer is because of the two chlorine atoms bonded to an alkyl group in methylene chloride.
The organic layer was separated from the aqueous layer and dried by adding sodium sulfate. Drying is
complete when the sodium sulfate clumps together. When this had occurred, the organic layer is
separated from the hydrated sulfate using a Pasteur pipet.

The dry organic layer was then evaporated by heating in water bath. After the methylene chloride had
evaporated, solid caffeine was collected which had some greenish stains on the solid crystals. The
melting point of the crude crystal was found to be between 223.60C-229.30C. This suggested that the
crystals contained impurity. The crude crystal weighed 31mg. This mass was calculated by subtracting
the mass of the flask from the mass of the flask when it contained crude caffeine crystal. The crude
crystal was purified by sublimation under reduced pressure. The pure crystal recovered was whitish and
had a powdery texture. The percent recovery was calculated by dividing 0.004g which is the amount
recovered by 0.031g, amount of impure crystal and multiplying the result by 100. The melting point of
the recovered crystal lied between 231.20C-234.60C. This range differed from the pure range of
235.30C-238.50C. The literature melting of caffeine is 2360C. The difference in melting point was as a
result of operator error and the crystal absorbing moisture from the ice cooled tube used in the set up
and from surrounding air.

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Q2: Both calcium carbonate and sodium carbonate was added in the two experiment to form a salt
derivative of the tannin compounds.

Q3: This was because it contained chlorophyll

Q4: Some possible explanations are the caffeine might still contain impurity as a result of equipment
error, and also the caffeine may have absorbed moisture condensing on the cold test tube from the
surrounding air. This causes it to become wet.

Q5: More heat would be required to sublime the crystals which can cause it to decompose.





REFERENCES:

(1) Pavia, D.; Lampman, G et al. Organic Lab.Tech. 3rd ed.; Cengage: Belmont, 2011, 77.

(2) Isolation of caffeine from tea, http://www.oxford.net/~mavarod/portal/school/caffeine.html
(accessed 10/26/2013)

(3) Role and Reg. of adenosine, http://www.cscb.northwestern.edu/jcpdfs/dunwiddie01.pdf. (accessed
10/25/2013)

(4) Nawrot, P.; Eastwood, J, e tal. Food Additives And Contaminant[online], 2003, Vol. 20, 2.
http://ehis.ebscohost.com.db20.linccweb.org/ehost/pdfviewer/pdfviewer?vid=3&sid=4415681e-3b1b-
4d6a-bda9-f720bd9c776d%40sessionmgr10&hid=16 (accessed 10/25/2013)

(5) Extraction, http://chemistry.csudh.edu/faculty/noel/CHE317L/Extraction%20Experiment.htm
(accessed 10/26/2013)

ACIDIC TANNINSALKALOIDSEMULSIONSEXTRACTIONSSUBLIMATION
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