INTRODUCTION

CAFFEINE:

Caffeine belongs to the family of heterocyclic compounds known as purines. It has the
systematic name 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; it is also known as 1,3,7-
trimethylxanthine, and 1,3,7-trimethyl-2,6-dioxopurine. Caffeine can be classified as
an alkaloid , a term used for substances produced as end products of
nitrogen metabolism in some plants. The chemical formula is C 8 H 10 N 4 O 2 . The chemical
is also known as coffeine, theine, mateine, guaranine, or methyltheobromine. Caffeine has
a molar mass of 194.19 grams (6.85 ounces). It is soluble in water and in many organic
solvents, and it appears in pure form as white crystals. Caffeine can be prepared by
extraction from natural sources or by synthesis from uric acid.

More than sixty plants, including those that give us coffee, tea, cola, and cacao, produce
caffeine from the purine xanthine. Whereas caffeine is a natural constituent in coffee, tea,
chocolate, and some cola drinks, it is added to consumer products such as soft drinks, diet
pills, and analgesics . The molecule was first isolated by the German chemist Friedrich
Ferdinand Runge in 1819

Caffeine is an alkaloid stimulant with a cyclic backbone structure analogous to the purine
structures of DNA, giving it the ability to affect biochemical pathways in the body 1. In
commercial application, caffeine supplements pharmaceuticals and certain beverages such
as coffee or tea. Standard tea bags contain 2.00 +/- 0.05 g of tea leaves along with
approximately 55 mg of caffeine[1]. Using the proper extraction methods, the caffeine
within a tea bag could potentially be isolated to yield a pure solid; the mass of this solid
would reflect the actual yield of caffeine in the tea. To do so, caffeine must be introduced to
a solvent that is both volatile and insoluble to water; a perfect example is methylene
chloride[2]. Caffeine has a greater affinity for methylene chloride and will easily dissolve in
this solvent over water; however caffeine is not the only organic substance found in tea that
is capable of reacting with methylene chloride. Along with caffeine, tea bags contain
organic substances called tannins, or gallic acid 1. Both caffeine and gallic acid are capable
of dissolving in water; however, caffeine has a stronger attraction to water due to the dipole-
dipole interaction that results from the greater polarity of caffeine and the hydrogen bonds
that form between caffeine and water1. Theoretically, the intermolecular forces of gallic acid
can be manipulated to induce a stronger dipole-ion interaction. If a common salt like
sodium carbonate was introduced to the solution, gallic acid could revert back into phenol
salt: a polar, inorganic molecule that is insoluble in methylene chloride [3].

In methylene chloride, caffeine will have a greater attraction for the organic solvent and the
hydrogen bonds between caffeine and water will be broken. Using a separatory apparatus,
two insoluble solutions can be separated, isolating caffeine and the new phenol anion from
one another. The denser methylene chloride layer can then be released from the funnel to
render a pure solution of caffeine and methylene chloride. To ensure that no water
interferes with the interaction of caffeine and methylene chloride, sodium sulfate could be
used to absorb any excess water that may have escaped from the tea solution 1. If heated,
the solvent would quickly evaporate due to low boiling point of methylene chloride 2. The
remaining solid would then be pure caffeine.

Milligrams of Caffeine

Beverage: Average per serving: Range: Per ounce:

Coffee (5 oz. cup) 80 40 - 170 16.00
Cola (12 oz. can) 45 30 - 60 3.75
Black Tea (one tea bag) 40 25 - 110 5.00
Oolong Tea (one tea bag) 30 12 - 55 3.75
Green Tea (one tea bag) 20 8 - 30 2.50
White Tea (one tea bag) 15 6 - 25 2.00
Decaf Tea (one tea bag) 2 1-4 0.50
Herbal Tea (one tea bag) 0 0 0.00
Effects of caffeine on body:

When purified, caffeine is an intensely bitter white powder. It is added to colas and other soft
drinks to impart a pleasing bitter note. However, caffeine is also an addictive stimulant. In
humans, it stimulates the central nervous system, heart rate, and respiration, has
psychotropic (mood altering) properties, and acts as a mild diuretic.

A normal dose of caffeine is generally considered to be 100 mg, which is roughly the
amount found in a cup of coffee.

However, more than half of all American adults consume more than 300 mg of caffeine
every day, which makes it America's most popular drug. Caffeine is generally consumed in
coffee, cola, chocolate, and tea, although it is also available over-the-counter as a stimulant.

Caffeine is believed to work by blocking adenosine receptors in the brain and other organs.
This reduces the ability of adenosine to bind to the receptors, which would slow down
cellular activity. The stimulated nerve cells release the hormone epinephrine (adrenaline),
which increases heart rate, blood pressure, and blood flow to muscles, decreases blood
flow to the skin and organs, and causes the liver to release glucose. Caffeine also increases
levels of the neurotransmitter dopamine.

Caffeine is quickly and completely removed from the brain. Its effects are short-lived and it
tends not to negatively affect concentration or higher brain functions. However, continued
exposure to caffeine leads to developing a tolerance to it. Tolerance causes the body to
become sensitized to to adenosine, so withdrawal causes blood pressure to drop, which can
result in a headache and other symptoms. Too much caffeine can result in caffeine
intoxication, which is characterized by nervousness, excitement, increased urination,
insomnia, flushed face, cold hands/feet, intestinal complaints, and sometimes
hallucinations. Some people experience the symptoms of caffeine intoxication after
ingesting as little as 250 mg per day. The lethal ingested dose, for an adult person, is
estimated to be 13-19 grams. While generally considered safe for people, caffeine can be
very toxic to household pets, such as dogs, horses, or parrots. Caffeine intake has been
demonstrated to reduce the risk of type II diabetes mellitus. In addition to use as a stimulant
and flavoring agent, caffeine is included in many over-the-counter headache remedies.
Extraction:

To start, a 150 mL beaker containing 50 mL deionized water and 2 boiling stones was
prepared to dissolve 2.0 grams of sodium carbonate to react with the gallic acid in tea. The
beaker was allowed to heat until the water started to boil, at which point the temperature
was lowered and 2 tea bags were placed into the water. The solution was heated for 10 to
12 minutes to achieve the highest concentration of tea. At the same time, the insoluble
cellulose components of tea separated from the solution rendering the tea concentrate,
caffeine, and the new phenol anion product. The final saturated solution was poured into a
100 mL beaker while the fluids trapped within the tea bags were simultaneously rinsed with
an additional 10 mL of deionized water. Once cooled, the solution was transferred into a
125 mL separatory apparatus, a glass funnel used to separate unmixable solutions. From
the top of the funnel, methylene chloride was poured into the solution in increments of 5
mL. Following every addition of methylene chloride, the funnel was inverted to release the
built-up pressure from the reaction. The reaction rendered brown top layer of tea and a
clear bottom layer of dense methylene chloride. The bottom layer was released from the
stopcock and collected into a 100 mL beaker leaving behind a thin layer of methylene
chloride to prevent contamination.

Methylene chloride was added 2 more times to assure that all of the caffeine was reacted
with. Sodium sulfate was added to the extraction to absorb any water that escaped from
the tea and the remaining fluid was decanted and rinsed into a pre-weighed 50 mL beaker
with boiling stones using an additional 2.0 mL of methylene chloride. When boiled, the
volatile methylene chloride evaporated, rendering pure, solid caffeine. The crude
caffeine can be further purified using recrystallization or
sublimation.

Vacuum Sublimation:
While caffeine can be purified by recrystallization, we will take advantage of its
unique phase diagram to purify it by reduced pressure sublimation.

The vast majority of compounds when heated progress from solid to

liquid and finally to gas. The caffeine phase diagram shows that if
we heat solid caffeine at atmospheric pressure, it will follow this
pattern and will melt before boiling (blue line). Unfortunately, this
requires enough heat that some of the caffeine decomposes, and
some of it reacts with other compounds to create undesired by
products. Both of these processes reduce the yield of caffeine.
However, if we reduce the pressure enough, we can see that
caffeine will actual sublime (green line). This happens at much
reduced temperature and so avoids both of the problems associated
with atmosphere pressure heating.
You will purify your crude caffeine using a simple vacuum
sublimation apparatus similar to the one in the figure below. It
consists of a 50 mL or 100 mL filter flask which has a cold finger
(test tube filled with ice) inserted through a rubber stopper:
 Data Summary:

Experiment 1: Isolation of Caffeine from Tea Leaves

Density of H2O g/mL

0.997

Density of CH2Cl2 g/mL

1.32

units

Weight of Tea Bags 4.00 g

Weight of 50 mL beaker and boiling stones

27.56 g
 Weight of 50 mL beaker, boiling stones, and caffeine
27.58 g

Weight of Caffeine 0.02 g

Theoretical Yield of Caffeine

0.11 g

Actual Yield of Caffeine 0.02 g

Percent Yield
18.18 %

Results:
The predetermined masses provided by the Lipton Tea manufacturers are accepted as the
experimental measurements of both tea and caffeine. The approximate weight of an
individual Lipton tea bag is 2.00 0.05 g, containing 55 mg of caffeine per bag. In an
experiment using 2 tea bags, 110 mg is the expected yield of caffeine to obtain. A 50 mL
beaker, along with 2 boiling stones, was weighed in advance with a total mass of 27.56 g
during the extraction process. To extract caffeine, the heated tea solution, along with 5 mL
of methylene chloride, was poured into an isolated separatory funnel and inverted to mix the
solution completely. Due to the reaction, pressure built up inside the funnel, requiring the
stopcock to be opened to release excess gas following each inversion. Once settled, the
solution separated into 2 layers: the polar, brown tea solution on the top and the nonpolar,
clear methylene chloride on the bottom. The tea separated above the methylene chloride
because while the density of water is 0.997 g/mL, the density of methylene chloride is 1.32
g/mL. Between the two layers sat small bubbles or possible emulsions that restricted the
amount of methylene chloride that could be extracted. Despite this, the methylene chloride/
caffeine layer was effectively drained into the pre-weighed 50 mL beaker and the process
was repeated 2 additional times to ensure that all of the caffeine was reacted with. In doing
so, the volatile methylene chloride began to evaporate into the surroundings due to the
increased room temperature. The remaining solution was heated briefly until the volatile
solvent evaporated, leaving behind solid caffeine. When weighed, the beaker, stones, and
caffeine rendered a total mass of 27.58 g. The difference in mass between the initial weight
of the beaker and the final product was then the actual yield of caffeine, 0.02 g. In
comparison to the theoretical mass, the experiment provided 18.18% yield of caffeine.

The solid caffeine product was run through an Infrared Spectrometer that uses bond
energies to identify chemical compounds. The spectrometer produced a graph based on
measurements of photon energy within a frequency range between 400 and 4000 Hz.
Individual spikes on the graph indicate the unique bond energies of certain functional
groups. For example, the photon energy spike visible around the 3000 Hz frequency
represents amine and amide group apparent in caffeine. The other important spike appears
around 1600 Hz and 1750 Hz. This spike represents the alkene portion of the caffeine
molecule. Using these individual spikes in photon energy, the infrared spectrometer
predicts the composition of the compound present. The spectrometer predicted the
probability that the sample produced was caffeine to be 869 out of 1000. This value has no
relation to the purity of caffeine.

Conclusion:

As is expected, the percent yield of caffeine was not 100%; however, achieving this goal is
impossible. The mass of caffeine from 2 Lipton tea bags was only 18.18% of the theoretical
yield but in consideration of all the factors responsible for error, 18.18% is an acceptable
value. The error in yield results from a number of unavoidable experimental flaws. The first
flaw originates from the reaction between gallic acid and sodium carbonate. Although the
conversion of gallic acid is necessary for the reaction of caffeine and methylene chloride to
occur, the phenol anion byproduct of this reaction is responsible for necessary error [1].
When phenolic acids are reverted back into salts, anionic surfactants are produced 4. These
surfactants are responsible for emulsifying water insoluble materials like methylene
chloride. As a result, large soapy bubbles called emulsions are produced by the polar and
nonpolar solutions. During the extraction phase of this experiment, these bubbles restricted
the amount of caffeine released from the separatory funnel resulting in a lesser yield.
Another source of lesser yield originated from techniques used to prevent the contamination
of the methylene chloride solution. While extracting the caffeine, a small layer of methylene
chloride needed to be left behind to avoid tainting the final product [2]. By discarding part of
the methylene chloride solution, a portion of the caffeine was left behind that affected the
overall yield of the product. The final source of error originates from unpreventable
environmental conditions. As a result of the hot plates used prior to the caffeine extraction
phase, the temperature of the laboratory was increased. Methylene chloride does not
usually evaporate at room temperature but being out in the open at an increased
temperature triggered the solution to react early on leaving less methylene chloride to react
with the caffeine. This would result in a lesser amount of caffeine extracted from the
solution and a lesser yield.

Bibliography:

http://www.odinity.com/isolation-of-caffeine-tea/
Isolation of Caffeine from Tea Leaves
By: Julia Trimble

http://www2.volstate.edu/CHEM/2010/Labs/Caffeine_Extraction.htm

sublimation:

1) Assemble the vacuum sublimation apparatus and place it on the hot plate.
2) Start heating at a setting of "4". The sublimation should be complete in 10-15
minutes.
3) After the sublimation is complete, remove the hot plate and allow the filter flask to
cool to room temperature. Leave the vacuum line attached while cooling.
4) After cooling, remove the vacuum line from the apparatus (DO NOT turn off the water
first). Then carefully remove the cold finger from the apparatus and scrape its
contents into a beaker.

Caffeine
 INTRODUCTION

ACKNOWLEDGEMENT

INTRODUCTION
 INTRODUCTION
CAFFEINE CONTENTS IN VARIOUS
BEVERAGES
EFFECTS OF CAFFEINE
EXTRACTION
VACUUM SUBLIMATION
DATA SUMMARY
RESULTS
CONCLUSION
BIBLIOGRAPHY