VELOSO, Ella Beatrice R. Expt.

3 – Extraction of Caffeine from Tea

CH 22.2 C January 22, 2018

Objectives

1. To be able to extract caffeine from tea by means of hydrolysis of tannins, gravity

filtration, solid-liquid extraction, liquid-liquid extraction, and distillation.
2. To determine the percent recovery and melting point of pure benzoic acid.
3. To ensure the purity of the extract by eliminating dichloromethane through distillation.

Introduction

Extractions can be either solid-liquid, or liquid-liquid, depending upon the desired compound. In both
types, a liquid solvent is used to isolate the compound. Scientists often perform extractions of organic
material, utilizing an inorganic solvent in order to better separate the organic compound from the
typical byproducts and starting materials. In these types of liquid-liquid extractions it is important to
choose an appropriate solvent that will not dissolve in water, have a low boiling point so it can be easily
removed; it should not react with the solute or other solvent. Ideally, a well-chosen organic solvent
when mixed with the mixture containing the liquid compound, will create two immiscible layers; one
containing the extraneous materials in the aqueous layer, and the compound to be extracted in the
organic layer.

This laboratory exercise, caffeine is first extracted in a solid-liquid extraction from tea leaves into boiling
water (a polar, inorganic solvent). Then the caffeine in the water is extracted using dichloromethane (an
organic solvent) in a liquid-liquid extraction procedure (carried out in a separatory funnel)

xtraction is a common technique used in organic chemistry to separate or isolate a desired compound
from a mixture. Extraction process selectively dissolves one or more of the mixture compounds into an
appropriate solvent.

Solid-liquid extraction is often used to isolate a natural product from its biological source, such as the
leaves or bark of a tree. For example, the anti-cancer drug paclitaxel (Taxol®) can be isolated from the
bark of the Pacific yew tree by solid-liquid extraction with methanol. Liquid-liquid extraction is the most
common extraction technique, and involves partitioning a solute between two immiscible liquid phases,
usually an aqueous phase and an organic solvent phase. In this case, we particularly used the liquid-
liquid extraction also known as solvent extraction and partitioning.

Prelab Questions

1. Explain the difference between solid-liquid and liquid-liquid extraction.

a. Two common types of extraction are the solid-liquid and liquid-liquid extraction. Liquid-
Liquid extractions involves using a liquid solvent to remove a component from the
mixture and are normally done to remove vitamins from aqueous solutions. Solid-Liquid
 extraction allows soluble components to be removed from solids using a solvent and are
commonly used to obtain oil from oil seeds
2. What are the components of tea? Which ones are removed during solid-liquid extraction?
Liquid-liquid extraction?
a. The main component of tea leaves is cellulose, the material that makes up the principal
structure of all plants. Cellulose is a polymer of glucose (Figure 2). It also contains
caffeine, proteins and amino acids, polyphenols or tannins, pigments, and small
amounts of saponins.
i. Caffeine, hydrolyzed tannins, residual pigments, small amounts of glucose, free
amino acids, some proteins, and saponins go to the aqueous filtrate
ii. Caffeine is then extracted from the rest of the components in the aqueous
filtrate based on the difference in polarity among the various components.
iii. One of the main components of tea leaves are cellulose which is normally
removed through solid-liquid extractions. Other components are caffeine,
proteins, amino acids, tannins and pigments which are removed using the liquid
extraction technique
3. Caffeine is a polar compound that can dissociate in water and in organic solvents, it has a
partition coefficient of 10 between dichloromethane and water. This is why the dissociation
constant is expected to be greater than one. KD is the dissociation constant defined as the
ration of compound in the organic phase to the amount of compound in the aqueous phase.
Since most organic compounds are soluble in organic solvents than in water, the numerator
would be larger than the denominator making it greater than 1.
a. KD is known to be a dissociation constant, a specific type of equilibrium constant that
measures the propensity of a larger object to dissociate reversible into smaller
compounds.
b. KD is the dissociation constant defined as the ration of compound in the organic phase
to the amount of compound in the aqueous phase. Since most organic compounds are
more soluble in organic solvents than water. The numerator would be larger than the
denominator leading to a KD greater than 1.
4. There are numerous steps in extracting with solvents and it is most advisable to use small
amounts rather than larger ones. Smaller amounts in multiple quantities will not need a higher
concentration unlike larger amounts. Higher concentrations would make the solution
exothermic and cause pressure build up.
a. When you extract, the residue will have the same concentration of material as the
extract itself. If you extract again, the concentration will be lower, in the extract as well
as in the residue. So with multiple extractions the amount of material left in the residue
will be lower, ergo the extraction will be more complete.
5. When heating tea in an aqueous base, frothing is expected to occur because of the other
substances that are extracted other than caffeine. This is why tea is steeped in sodium
carbonate instead of water, to prevent tannins to combine with the caffeine
a. When you boil tea leaves tannins dissolve in the water as well as the caffeine. 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
b. We can do this by takingadvantage 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 addsodium 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.
6. When heating tea in an aqueous base, frothing is expected to occur because of the other
substances that are extracted other than caffeine
a. Frothing is expected when heating the tea in aqueous base because, aside from caffeine
being extracted, other substances are also extracted which may cause the tea to froth
7. Distillation of dichloromethane and not evaporation. Evaporation is not advisable with
compounds such as dichloromethane because of its toxicity, being highly carcinogenic, the
process of evaporation would bring risks of inhalation and distillation is a much faster and
efficient way