EXERCISE 1
ISOLATION OF ALKALOIDS FROM TEA
A. DATA
Table 1. Extraction of alkaloids from tea leaves.
SAMPLE DESCRIPTON
Tea during boiling in water Water-soluble components in the tealeaves
or coffee beans are being transferred from a
solid phase, the leaves or beans, into a liquid
phase, the hot water.
Mixture after boiling Dark in color homogenous mixture
Mixture after cooling Becomes a little lighter homogenous mixture
Mixture after addition of sodium Conversion of tannin to water soluble salts,
carbonate to ensure that the caffeine and organic acids
are deprotonated. Thus, caffeine will be free
to dissolve in dichloromethane while the
carboxylate salts will not
Mixture during first extraction - caffeine is extracted in the first extraction,
- Aqueous layer (top layer) nearly the rest of it in the 2nd, and 3rd
- Organic layer (bottom layer) extraction of the organic layer
Mixture during second extraction - Aqueous layer (top layer) is much darker
- Aqueous layer (top layer) than the transparent/clear Organic layer
- Organic layer (bottom layer) (bottom layer), that was being separated
Mixture during third extraction from the separatory funnel.
- Aqueous layer (top layer) -The separation was good and clear with
- Organic layer (bottom layer) some bubbles in between.
Combined organic layer Cloudy, some brown spots, therefore some
impurities.
Mixture after addition of anhydrous The solution become clearer, and flakes of
sodium sulfate sodium sulfate (sedimented) can be seen
swirling around in the flask like a snow globe
Decantate before heating Complete separation of the liquid and the
sedimented particles of sodium sulfate
Residue (isolated alkaloid) White in color, cotton liked recrystallized
caffeine
B. POST-EXERCISE QUESTIONS
1. Briefly discuss the roles of (1) sodium carbonate, and (b) anhydrous sodium
sulfate
in the isolation of the alkaloid.
(1) The role of sodium carbonate in the isolation of caffeine is to act as a base. When tea
leaves are boiled, tannins dissolve in the water as well as the caffeine. If a base was not
used, the tannins will also be extracted into the solvent used in the succeeding extraction.
Sodium carbonate converted the tannins into their sodium salts, which made them
insoluble in the solvent; therefore, they remain in the aqueous layer during extraction. This
also allowed purer caffeine to be extracted.
(2) The role of sodium sulfate is to serve as a drying agent which will remove any water that
may be present before the evaporation of the solvent. Anhydrous sodium sulfate was
added to absorb possibly leaked water and to break the emulsion caused by turning tannins
to surfactants.
2. Give at least three characteristics of dichloromethane that makes it a good
extracting solvent for the alkaloid.
Caffeine can be extracted from tea by its ability to be better dissolved in dichloromethane than
water.
(1) Non-polar: immiscible with the solution to be extracted
(2) Not flammable
(3) Good solubility of the target compound
(4) Poor solubility of impurities: Major impurities ( e.g., from a reaction) should not be
soluble in the extracting solvent
(5) Volatility of the extraction solvent: sufficiently volatile so that it can be
removed easily from the extracted material by
distillation
* Dichloromethane is used as solvent in liquid-liquid extraction because caffeine has
higher solubility in Dichloromethane as compared to other solvents. After separation
of organic layer from the separating funnel it is then kept for evaporation to
evaporate the dichloromethane present in it
3. What are emulsions? Why do they form during extractions? How is the formation
of an emulsion minimized? How are emulsions removed?
(1) An emulsion is mixture of two liquids that would not normally mix. A mixture of two
immiscible liquids. Contains tiny particles of one liquid suspended in another.
Chemically, they are colloids where both phases are liquids.
(2) An emulsion happens when small droplets of one solution (the dispersed solution,
which is often oil based) are dispersed throughout another (the continuous solution,
which is often water based).
(3) The simplest way to prevent the formation of an emulsion is to gently swirl instead
of shaking the separatory funnel. By swirling the separatory funnel, the agitation
that can cause the emulsion to form is reduced, but the surface area of contact
between the two phases is maintained to allow for extraction to occur.
(4) Emulsions are thermodynamically unstable systems and
rapidly separate into separate layers of oil and water. This is due to different
densities between the oil and aqueous phases and the unfavorable contact between
oil and water molecules. Emulsions can be disrupted or removed by the addition of
brine or salt water, which increases the ionic strength of the aqueous layer and
facilitates separation of the two phases by forcing the surfactant-like molecule to
separate into one phase or the other-this technique is known as salting out.
4. Why is it necessary to remove a stopper from a separatory funnel when the liquid
is being drained from it through a stopcock?
The stopper must be removed in order to release the liquid from the funnel. If the stopper is
not removed, the vacuum that forms above the liquid will prevent the solution
from draining properly.