Experiment 1 - Isolation of Caffeine From Tea

Name: Kate Alyssa Caton Date Completed: November 26,
2010
Partners: Xharisz Yuka Mae Dulin Date Submitted: December 3, 2010
Prem Patrick Parcon
EXPERIMENT 1
Isolation of Caffeine from Tea
Objectives:
 To gain experience in using extraction as a method of separation.
 To assemble and use a simple distillation setup in the separation of volatile substances from non-
volatile materials.
 To determine the boiling point of a liquid sample.
 To isolate caffeine from tea and gain experience in chemical laboratory manipulation of plant
materials.
Results:
Discussion of Results: PARAPHRASE, BITCH.
Tea leafs contain from 2 to 5% caffeine, along with cellulose, tannins, flavonoid pigments and
chlorophylls (see structures of caffeine and tannins on next page). The caffeine can be extracted from tea
using hot water. However, the tannins, pigments and chlorophylls will also be extracted into the water.
The caffeine can then be extracted from the water using methylene chloride (dichloromethane). Since the
tannins are acidic, base is added to the aqueous extract in order to ionize the tannins and insure that they
remain in the aqueous layer. Along with the caffeine, the chlorophylls (which are present only in small
quantities) will also go into the organic layer. Thus, the caffeine that you obtain after evaporating the
methylene chloride will not be totally pure. Either sublimation or crystallization can be used to further
purify the caffeine. However, we will not do that in this experiment (the caffeine is already close to pure).
The idea in this experiment is to extract the water soluble materials in the tea
leaves into hot water. [The solubility of caffeine in water is 22 mg/ml at 25oC, 180 mg/ml
at 80oC, and 670 mg/ml at 100oC.] The hot solution is allowed to cool and the caffeine is
then extracted from the water with dichloromethane (methylene chloride), which is an
organic solvent that is insoluble in water. Since caffeine is more soluble in
dichloromethane (140 mg/ml) than it is in water (22 mg/ml), it readily dissolves in the
dichloromethane. However, the tannins are slightly soluble in the dichloromethane. But
we want to separate the caffeine from the tannins by having the caffeine dissolve in the
dichloromethane and the tannins remain in the water. We can do this by taking
advantage of the fact that phenols are acidic enough to be converted to their salts
(deprotonation of the -OH group) by reaction with sodium carbonate. So, we will add
sodium carbonate to the water and the tannins will be converted to phenolic anions,
which are not soluble in the dichloromethane but are soluble in highly polar water.
There is one practical disadvantage in converting the tannins to their salts – they become
anionic surfactants. Detergents and soap are surfactants. It is the purpose of surfactants
to cause materials that do not dissolve in water (like oil, grease and dichloromethane) to
form an emulsion with water. We want to be able to separate the aqueous phase from
the dichloromethane phase, so the last thing we want is an emulsion of the two.
Principle of the experiment:
The technique used to separate an organic compound from a mixture of compounds is called Extraction. Extraction process selectively
dissolves one or more of the mixture compounds into an appropriate solvent. The solution of these dissolved compounds is referred as
the Extract. Caffeine is a naturally occurring alkaloid (a class of naturally occurring compounds containing nitrogen and having the
properties of an organic amine base) found in coffee, tea, Cocoa, Guarana (Paullinia cupana) and kola nuts.
Caffeine belongs to a family of naturally occurring compounds known as xanthines. Caffeine is chemically 1,3,7-trimethylxanthine
(C8H10N4O2). Caffeine acts as a stimulant. It stimulates the heart, respiration, the central nervous system, and is a vasodilator (relaxes the
blood vessels) as well as a diuretic (increases urination). It is a beverage produced by steeping in freshly boiled water the young leaves and
leaf buds of the tea plant, Camellia sinensis. Two principal varieties of tea are used, the small-leaved China plant (C. sinensis) and the large-
leaved Assam plant (C. assamica). The leaves may be fermented or left unfermented. Fermented teas are referred to as black tea,
unfermented teas as green tea, and partially fermented teas as oolong tea. Tea leaves consist mostly of cellulose (a water-insoluble
polymer of glucose), caffeine, tannins (phenolic compounds, compounds that have an -OH directly bonded to an aromatic ring) and a small
amount of chlorophyll. The solubility of caffeine in water is 22 mg/ml at 25 ·C, 180 mg/ml at 80·C, and 670 mg/ml at 100·C. Here the organic
solvent dichloromethane is used to extract caffeine from aqueous extract of tea leaves because caffeine is more soluble in dichloromethane
(140 mg/ml) than it is in water (22 mg/ml). However, the tannins that are slightly soluble in the dichloromethane can be eliminated by
converting it to their salts (phenolic anions by adding sodium carbonate) (tannins are phenolic compounds of high molecular weight and
being acidic in nature can be converted to salts by deprotonation of the -OH group) which remain in the water.
Conclusion:
Question & Answers:
A. Discuss briefly the role of the following in the isolation of caffeine:

i. sodium carbonate
Sodium carbonate also a base, and it is added in the first extraction to make sure that the caffeine
remains in the free base form (that is, to prevent it from reacting with any acids that may be present).
If you do not use a base the tannins will also be extracted into the solvent (i.e. methylene chloride) used
in the subsequent extraction . The base converts the tannins into their sodium salts - being ionic these
salts are not soluble in solvents like methylene chloride so remain in the aqueous layer during
extraction. This allows purer caffeine to be extracted.
ii. sodium sulfate
Sodium sulfate serves as a drying agent in most reactions to absorb all excess water from the solution.
A. Give at least three characteristics of chloroform that make it a good extracting solvent for
caffeine.
Chloroform was chosen as the solvent because Caffeine is very soluble in this substance.
Thus, when the separatory funnel is used, the Caffeine in the tea dissolves into the
Chloroform and the rest of the tea can be discarded. This is done three times so that the
amount of Caffeine left in the discarded tea is minimized. This is followed by two
washings with Sodium Hydroxide and one with water. It is believed that the Sodium
Hydroxide weakens the attraction Chloroform has on Caffeine, allowing the Caffeine to be
isolated more easily later on.
B. How efficient is the extraction of tea leaves containing 1.0 g of caffeine with two 30-mL portions
of chloroform over that of a single step extraction (K 25ºC = 8.36)?
C. What are emulsions? Why do they form during extractions? How are they minimized?
D. Why is it necessary to remove a stopper from a separatory funnel when liquid is being drained
from it through a stopcock.

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Name: Kate Alyssa Caton Date Completed: November 26,

Discussion of Results: PARAPHRASE, BITCH.

Principle of the experiment:

Question & Answers:

A. Discuss briefly the role of the following in the isolation of caffeine:

ii. sodium sulfate

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