Isolation of Caffeine from Tea Leaves, Coffee and Soda

Drinks
Lai-chi V. Arrieta
University of San Carlos
laichimeah@gmail.com
I. Introduction
Caffeine is a member of nitro group of compounds called. Alkaloids are mostly
found on plants. These compounds are bitter and are physiologically active in the human
body. Caffeine also causes an increase in respiration and heart rate, as well as nervousness
and insomnia. Though caffeine has demonstrated to have physical dependence, it is also
capable of improving alertness, learning capacity, and exercise performance
Extraction is a technique used to isolate one compound from another. There are
three types of extractions: liquid-liquid extractions, liquid-solid extractions and acid-base
extractions. Extractions are performed in a separatory funnel. Polar and nonpolar compounds
will separate and form layers inside the separatory funnel. Polar compounds are found in the
aqueous layer while nonpolar compounds are found in the organic layer. 'Like dissolves like'
is the general phrase used as a reminder that compounds of similar polarity are miscible.
Multiple extractions with small amounts of volume are always more efficient than
one single extraction with large volume. Using multiple portions of a solvent maximizes the
extractive power of the solvent.
The experiment called to employ the Extraction Method using liquid-liquid
extractions to isolate caffeine from rea leaves. Modern day tea has caffeine only a minor
constituent of its composition. Caffeine is water soluble but so are some tannins and gallic
acid which is formed in the process of boiling tea leaves. The latter two components can be
converted to their calcium salts which are insoluble in water. The caffeine can then be
extracted from the water by methylene chloride in almost pure form.

In the case of this experiment, tea is the beverage where caffeine is to be extracted
from. Tea has been consumed as a beverage for almost 2,000 years in China. Tea leaves can
contain 3.5% caffeine – which is more than a coffee bean. Tea leaves have more caffeine
 than coffee beans but more beans are used to make a cup of coffee so typically, there is more
caffeine in a cup of coffee than a cup of tea.

A Buchner funnel was used in the experiment during the filtration of the tea leaves
and calcium carbonate. The funnel has a vacuum in the flask underneath the filter paper. This
would allow the atmospheric pressure on the sample to force the liquid in the sample to pass
through the filter paper resulting in a much faster filtration.

II. Methodology
The preparation and seeping of the tea in water was the first step in the procedure.
Ten grams of tea, along with 4.8 grams of calcium carbonate was added to 100 mL of distilled
water. Some of the components may dissolve in the water but generally, most of the
components will not dissolve. All of these were heated until boiling to give the tea more time
to release its flavor and caffeine in its leaves. Allow the
mixture to cool down before filtration.
Using a buchner funnel, liquid from the tea mixture
was filtered. In the filtering process, it was made sure that
no solids of any kind passed through the filter. Solids and
other compounds may differ the results.
The cooled filtered liquid is then poured in a 250-
mL separatory funnel. 20 mL of dichloromethane is also
Buchner Funnel Set Up
added to the same separatory funnel. While
holding the cap and the other end of the funnel tightly and properly, the mixture
was gently swirled and mixed in the funnel. The stopcock is opened time to
time in the middle of the swirling action to vent out pressure and air building
up inside the funnel.
The resulting mixture will have two layers present. The bottom layer
would be the organic layer or the layer that contains the caffeine and the upper
layer would be the aqueous layer. The bottom layer is collected by letting it
pass through the stopcock, ensuring only the bottom layer was extracted. The
Separating Funnel DCM and upper layer is then added with another 20 mL of dichloromethane. The
Water
 procedure is repeated until three times or until caffeine or a bottom layer is formed at every
addition of dichloromethane.
Emulsion of the two layers may appear in the middle of shaking and mixing of the
two layers. Emulsion happens due to the anions formed from the tannins in the mixture. The
emulsion is a combination of water and the organic layer. If the emulsion is not removed,
then a part of your organic layer – the caffeine – will not be extracted. Emulsion can be
removed by aggravating it with a stirring rod or to leave the mixture
untouched and let the layers separate by themselves.
After repeating a bunch of times, the collected bottom layer
had to through crystallization. The collected layer is heated under a
stream of steam or the collected layer is heated using a hot water
bath. The bottom layer should evaporate until only 5 mL of the
mixture is left. In the remaining mixture, 10 drops of petroleum ether
is added. The sides and bottom of the flask are scratched to aid in the
crystallization of caffeine. Crystals should form at the bottom of
Melting Point Determination
the flask. Set Up

The crystals formed on the flask should be weighed to

determine the percentage yield of caffeine from the tea leaves.
The crystals also had to go through the melting point test to determine the purity of
caffeine extracted from the tea leaves. Caffeine melts at 235-238°C.
III. Presentation of Results

Table 1 shows the difference of color of the mixtures before the addition of
dichloromethane and after the extraction of the dichloromethane and caffeine in the bottom
layer. The original mixture was dark brown in color but the extracted liquid from the separatory
funnel had a light green color.

TABLE 1. Color of Extracted Liquid Before and After DCM

Before DCM After DCM (extracted)

Color
Dark Brown Light Green
 Table 2 shows the melting point of the crystals formed in the beaker and the actual melting
point of caffeine. The melting point of the extracted liquid had a more lower melting temperature
than actual caffeine.

TABLE 2. Melting Point of Crystals and Actual Caffeine

Crystals Melting Started (°C) Completely Melted (°C)

Collected 220 232
Actual Caffeine -- 235-238

IV. Discussion of Results

Tea leaves consists mostly of cellulose and varying amounts of caffeine, tannins
and chlorophyll. The experiment needs to extract the water-soluble materials in the tea
leaves into the hot water. Caffeine is soluble in water (22mg/mL) but it is more soluble in
dichloromethane (140 mg/mL) thus caffeine is readily soluble in dichloromethane once it
is added to the mixture. However, the tannins in the tea leaves are slightly soluble in
dichloromethane thus, before extraction and filtration, the tea leaves are soaked in and
boiled in hot water along with calcium carbonate. Calcium carbonate converts the tannins
into their anions which are not soluble in dichloromethane but are soluble in highly
polarized water. The assurance of extracting only dissolved caffeine in dichloromethane is
ensured.

The extracted liquid from the separatory funnel had a slight hue of green which
indicates that some of the chlorophyll from the tea leaves had not separated and have mixed
in with the dichloromethane. This would be an impurity in the resulting crystals after the
crystallization. The crystals also had a slight green hue. Dichloromethane also dissolved
some water molecules, which in turn is an impurity to the sample. A drying agent should
have been added before crystallization to ensure no water molecule is in the organic layer
to be crystallized. Impurities also greatly impacts the melting point of the crystals which
can be seen in the results in Table 2. Pure caffeine has a melting point of 235-238°C while
 the experimental crystals has only a melting point of 232°C. Impurities in the sample
widens the range and lowers the temperature needed to melt the entirety of the crystals.
Melting point of the crystals can be greatly influenced by not only the purity of the
sample but also the size of the crystals formed, the amount of the material in the tube, the
density of its packing in the tube and the rate of heating. The crystals have a closer chance
of attaining its true meting point when it is finely powdered due to higher surface area
contact with heat. Excess sample in the capillary tube will need more heat to melt and result
in a larger melting range. Tight compaction of the crystals in the tube will result in bubble
formation that interferes in seeing if every crystal has melted. If the melted crystals have
any discoloration (blackening, etc.) then the sample had undergone decomposition before
liquefaction which complicates melting point observation.
Unfortunately, during the experiment, the beaker used to store the extracted liquid
needed to be crystallized had not been weighed. Also, during the experiment, the extracted
liquid had to sit out for a whole week. When the experiment resumed, all liquid had
evaporated and crystals had formed even before the addition of petroleum ether. Mishaps
like this during an experiment leads to faulty results and incomplete data. Regrettably, there
is no data for the weight of the crystals formed after the liquid had evaporated. Yield of the
crystals cannot be computed and be compared to the general yield of caffeine in tea
experiments.

V. Conclusion
The goal of the experiment was to isolate caffeine from the tea leaves, calculate and
maximize yield of extracted caffeine and to test its purity by its melting point. Caffeine can
be isolated from beverages with high caffeine content in them when steps of the experiment
are done accurately and properly. Every step of the experiment is essential to yield pure
caffeine, especially during the extraction and crystallization process. Multiple extractions
in smaller volumes of solvent is better than one-time extractions in larger volumes of
solvent in terms of yield. Yield of caffeine could have been maximized by doing multiple
extractions to ensure maximum withdrawals of caffeine from the mixture. Without letting
the extracted liquid to evaporate into dryness, petroleum ether should have been added to
ensure that crystallization happened before evaporation started.
VI. References
• (n.d.). Retrieved from http://www.pitt.edu/~ceder/lab2/extraction.html.
• Caffeine content for coffee, tea, soda and more. (2017, April 14). Retrieved from https://www.mayoclinic.org/healthy-
lifestyle/nutrition-and-healthy-eating/in-depth/caffeine/art-20049372.
• Libretexts. (2019, June 23). 4: Extraction. Retrieved from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book:_Organic_Chemistry_Lab_Techniques_(Nichols)/4:
_Extraction.
• Libretexts. (2019, August 18). 4.4: Extraction Theory. Retrieved from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book:_Organic_Chemistry_Lab_Techniques_(Nichols)/4:
_Extraction/4.4:_Extraction_Theory.
• Libretexts. (2019, June 5). 3: Extraction of Caffeine (Experiment). Retrieved from
https://chem.libretexts.org/Bookshelves/Ancillary_Materials/Laboratory_Experiments/Wet_Lab_Experiments/Organic
_Chemistry_Labs/Experiments/3:_Extraction_of_Caffeine_(Experiment).
• Objective: (n.d.). Retrieved from http://vlab.amrita.edu/?sub=3&brch=64&sim=169&cnt=1.