Extraction of Caffeine from Tea

Lab No. 4
Organic Chemistry Lab
CHEM1252L – Section 1
Date Performed: October 26, 2019
Due Date: October 10, 2019
Rocio Briceno
Mr. Kareem Daniels
Objectives
 Compare the melting point of the Caffeine recovered from the Tea.
 Determine the percentage recovery of the Caffeine.
 Observe the different separation techniques to extract Caffeine from Tea.

Material Safety Data Sheet

Sodium Methylene Sodium Sulfate Caffeine

Carbonate Chloride
Physical State Solid Liquid Solid, crystalline Crystalline
powdery dust Solid
Color White Colorless White White
Odor Odorless Mildly sweet odor, Odorless Odorless
chloroform-like
Hazard Causes serious Harmful is May cause eye Hazardous
(Caution) eye irritation and swallowed and irritation. Causes in case of
skin irritation enters airways. redness and pain. skin contact
and digestive Causes skin May cause skin (irritant), of
tract irritation. irritation. Causes irritation. May eye contact
serious eye cause an allergic (irritant), of
irritation. May cause reaction in certain ingestion,
respiratory irritation. individuals. May of
May cause cause inhalation.
drowsiness or gastrointestinal Severe
dizziness. Causes irritation with over-
damage to nausea, vomiting exposure
cardiovascular and diarrhea. May can result
system including be harmful if in death.
elevated swallowed. May
carboxyhemoglobin cause respiratory
levels. May cause tract irritation.
damage to blood and May be harmful if
liver through inhaled.
prolonged and
repeated exposures.
Suspected of causing
cancer.
Melting Point / 851 / 1,600 95 / 40 880 – 888 / 1,700 237.8 – 238
Boiling Point / 238
(oC)
Density (g/cm3) 2.54 1.33 2.66 1.23
Materials and Apparatus
Distilled water Hot plate apparatus Weighing apparatus
150ml Beaker Tea bag Pasteur pipet
Watch glass 5 Centrifuge tubes 1 Test tube
5 Centrifuge tube caps Erlenmeyer flask Micro spatula
1 Vial Melting point apparatus 1 Vial cap
Chemicals
Methylene Chloride Sodium Carbonate
Sodium Sulfate Caffeine
Method
1. 50 mL of water was poured into a 150 mL beaker. The beaker was covered with a watch
glass and the water was heated on a hot plate until it was near boiling. The mass of tea in
one tea bag was obtained using a weighing apparatus. The tea bag was immersed in the
water and the watch glass was replaced.

2. The beaker and contents was heated for about 15 minutes. The tea bag was assured to
being immersed in the water. If water evaporated then more water was added keep the
volume constant.

3. A Pasteur pipet was used to transfer the solution to five centrifuge tubes, dividing the
liquid equally. After the beaker was drained, a test tube was used to press the liquid out
of the bag and the expelled liquid was transferred to the centrifuge tubes. 5 mL of water
added to the beaker and squeezed out of the bag which was added to the tubes as well.

4. 0.1 g of sodium carbonate was added to each tube which was then capped and shaken
until the solid dissolved.

5. The extraction of caffeine occurred by cooling the tea, then adding 5 mL of methylene
chloride (dichloromethane) to each tube. The tubes were shaken gently and opened
occasionally to release pressure. The tubes were shaken for several minutes.

6. After the tubes were shaken, a layer at the interface of the water and methylene chloride
appeared which an emulsion was. Which appeared as a third layer between the top and
bottom layer. The tubes were centrifuged for several minutes which removed the layer of
emulsion. If the emulsion was still present then the tubes were centrifuged again.

7. The organic layers were removed from each tube and poured in a small Erlenmeyer flask.
New 3 mL portions of methylene chloride were added to the centrifuge tubes and the
extraction process, including centrifugation was repeated again.
 8. All the methylene chloride was collected in the Erlenmeyer flask. If any tea was present,
the methylene chloride was transferred to a new flask. A micro spatula was used to add
three to four scoops of sodium sulfate and the contents was swirled in the flask gently. If
the sodium sulfate clumped together, another scoop of sodium sulfate was added. The
flask set ten to fifteen minutes, swirling it occasionally.

9. A 25ml round bottom flask was weighed and the methylene chloride was transferred to
the flask. It was then placed in a water bath.

10. The mass of the caffeine recovered. Some of the caffeine was added in a small vial and
the melting points of the caffeine was determined by using the melting point apparatus.

Results
Method
The tea bag was immersed in the water.
0.1g of Sodium carbonate was added to each
tube and shaken well
5ml of methylene chloride was added to the
already containing tea centrifuge tubes. The
tubes were shaken well.
3 to 4 scoops of Sodium Sulfate were added
to the methylene chloride.
The methylene chloride was placed in a water
bath.
Observation
The smaller particles containing color and
flavor can pass through the bag.
The teabag itself acts as the partially
permeable membrane. The addition of heat
from the hot water to the tea bag causes its
molecules to move much faster than at room
temperature.
The acidic components in the tea leaves and
water remains soluble and caffeine is the free
base.
After the tubes were shaken, a layer at the
interface of the water and methylene chloride
appeared which an emulsion was. Which
appeared as a third layer between the top and
bottom layer.
The anhydrous sodium sulfate absorbed the
small amount of water that was dissolved in
the dichloromethane and small amounts of
water from the aqueous layer that may have
gotten into the flask by accident (Drying
agent).
The methylene chloride became a white
crystal-like solid surrounding the beaker.
 Caffeine Caffeine in Weight Weight Recovered Percentage Percentage
in 50ml 55mg of Tea of of Caffeine Recovery Error
of tea by Beaker Beaker
Manufacturer and
caffeine
1.691 fl. 8 fl. oz 50.392g 50.503g 0.11g 946.64% 99.89%
Oz =
11.625mg
= 0.012g
Recovered caffeine: Weight of Beaker and caffeine – Weight of Beaker
Percentage Recovery: Recovered Mass of caffeine / Actual mass of caffeine * 100
Percentage Error: (Recovered Caffeine – Actual mass of Caffeine / Actual mass of Caffeine) *
100
Experimental melting point of purified caffeine was 222oC.
Actual melting point of purified caffeine is 237.8oC.
Discussion
Caffeine, 1,3,7 - trimethylxanthine, belongs to a wide class of compounds known as alkaloids.
These are plant derived compounds with complex structure containing nitrogen, and usually have
roles in physiological activity. The melting point of Caffeine is 238°C. Caffeine is a chemical
found in coffee, tea, cola and more. Caffeine is most commonly used to improve mental
alertness, but it has many other uses (Amrita U, 2013). Caffeine is used by mouth or rectally in
combination with painkillers (such as aspirin and acetaminophen). Caffeine works by stimulating
the central nervous system (CNS), heart, muscles, and the centers that control blood pressure.
Caffeine can raise blood pressure, but might not have this effect in people who use it all the time.
Caffeine can also act like a “water pill” that increases urine flow. The technique used to separate
an organic compound from a mixture of compounds is called Extraction (Dullo. A, 2013). Where
the lab experiment included centrifugation and drying agents. In order to extract caffeine from
tea, several methods are used. First, a solid/liquid extraction must take place in order to get the
solid natural product into the liquid solvent. This can be done by simply brewing a cup of tea. In
order to isolate the desired reaction compounds from the natural product, liquid/liquid
extractions are used. Neutral and acid/base are two forms of liquid/liquid extractions Caffeine
extraction from tea involves an acid/base liquid/liquid extraction. The reaction involves a
homogenous mixture of an organic and aqueous layer. (J. Magdalan, 2017). Extraction process
selectively dissolves one or more of the mixture compounds into a suitable solvent. The solution
of these dissolved compounds is referred to as the Extract. A common liquid/liquid solvent pair
for the extraction of caffeine is water-dichloromethane. Here the organic solvent
dichloromethane is used to extract caffeine from an aqueous extract of tea because caffeine is
more soluble in dichloromethane. Because water is present in the pairing, it is possible to
separate inorganic compounds from organic compounds due to the fact that organic substances
are immiscible in water. When mixing the liquid pairs, the density of both solvents predict which
solvent is the top and which is the bottom layer (D.S Murray, 1995). Caffeine, which was
present in the organic layer, was located below the aqueous layer. The product that is collected
after extraction still has many impurities. Essentially, caffeine is a purine with three functional
groups: an amine, amide, and an alkene. The basic property of caffeine comes from the lone pair
of electrons found around the nitrogen. It is an achiral molecule and does not have any
stereoisomers. Caffeine is also a polar molecule; this is evident because of the London dispersion
forces, dipole dipole interactions, and hydrogen bonding present when it is in water. It also has a
very hydrophobic region. The nitrogen present in caffeine controls solubility. The percent error
and percent recovery were calculated to assess how much pure caffeine was obtained, and to
account for errors that may have occurred that led to a loss of product. It is an organic molecule
that has the properties of an organic amine base. During the solid/liquid extraction the solid
insoluble material such as cellulose is separated from caffeine and tannins, which are water
soluble. In order to isolate caffeine a difference in solubility must occur to separate the tannins
into the aqueous layer. However, the tannins that are slightly soluble in 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. Sodium carbonate serves
two main functions: to place caffeine in a more basic environment so that it has a higher affinity
for dichloromethane and to cause the tannins to form phenolic salts in the aqueous solution. In
this situation, the sodium carbonate acts as a nucleophile and the tannin is an electrophile.
Nucleophile attacks electrophile. It is basically an acid/base reaction. The aqueous layer
contained dissolved tannin salts and chlorophyll. Dipole dipole interactions, london dispersion
forces, hydrogen bonding, and ionic bonding with the salts took place. When dichloromethane
was added to extract caffeine from the aqueous solution, two immiscible layers formed: an
organic and aqueous layer. In this instance, caffeine is usually a polar substance, but it becomes
significantly less polar when it is in a basic solution. Therefore, it is soluble in dichloromethane
and suspends in the organic layer. Dichloromethane is an alkyl halide and is denser than water,
so it is located at the bottom. It had chloro functional groups that make it susceptible to both
substitution and elimination reactions. Emulsions are small droplets of the organic layer that are
suspended in the aqueous that are a result of vigorous shaking of the centrifuge tubes. There are
numerous ways to remove emulsions. Emulsions may break after a sufficient amount of time.
The aqueous layer can also be made more ionic, and centrifugation works very well especially on
a microscale level. A drying agent was added to the organic layer because dichloromethane
dissolved not only the caffeine, but water as well. The drying agent, sodium sulfate was added to
remove excess water so that a pure sample of caffeine could be obtained after the solvent
evaporated at room temperature. Sodium sulfate has a high affinity for water, and then reverses
back to the hydrous form after it has absorbed the water. Sodium sulfate is a preferred drying
agent because it clumps when excess water is present that make it simple to identify how much
drying agent is needed. When clumping had come to a stop which was very rapid, effective, and
ideal for microscale experiments. In order to remove the dichloromethane, the beaker could be
placed in a hot water bath so that the solvent would evaporate and leave a pure sample. Liquid-
liquid extractions were used to transfer a solute from one solvent to another and isolate desired
product (P. Andra, 2013).

Analysis Questions

1. Look up the melting point of caffeine and comment on the purity of your sample of
caffeine.
The actual meting point of caffeine is 237.8oC. The experimental melting point achieved
of caffeine was 222oC. Therefore, proved that our caffeine was not pure and in fact, had a
whole bunch of impurities or simply a loss of product throughout the procedure due to
the melting point being far from that of the actual melting point of caffeine.
2. What observation(s) will allow you to answer question 1 in the Questions section?

A pure organic compound usually melts over a range of two degrees or less. If the
melting point of a pure compound is within a degree of the value found a lab handbook it
is presumed to be pure. A sample is impure if it has a melting point range that is lower
and/or wider than that the literature value. More impurities increase this effect. In the
 organic lab, unless something is wrong with the procedure or the equipment, a substance
generally cannot be observed to melt at a higher temperature than its melting point!
Experimental melting points should be always reported as a range, for example, 42-44°.

3. What is the difference between a phenol and an alcohol?

Alcohol is also known as ethanol. It is any organic compound in which
the hydroxyl functional group (–OH) is bound to a carbon. Alcohols are aliphatic
hydrocarbons i.e. the carbon compounds are linked to each other in a straight chain.
Phenol is an aromatic hydrocarbon and a white crystalline solid which is flammable and
has a strong odor. Its molecular formula is C6H5OH. Phenol, is characterized by a (−OH)
hydroxyl group attached to a carbon atom that is part of an aromatic ring. Phenols are
aromatic hydrocarbons i.e. the carbon compounds are connected to each other in ring
structure way with conjugated pi electrons. Alcohol is used in alcoholic beverages like
wine, whisky and beer. It is utilized to produce methylated spirit (meth) which is used as
a combustible material in certain stoves and lamps, especially the ones made for
camping. It is also used to get rid of ink from non-porous surfaces for e.g. metals and
plastics. Methylated spirit is used as a cleaning agent, especially for glass cleaning
purposes. Rubbing alcohol can also be used in cleaning certain instruments and vessels
present in the first aid kit, and it efficiently cleans minor wounds, cuts and scrapes.
Alcohol is also used as a fuel which is much more efficient than natural fossil fuels like
petrol. Phenol is used as an antiseptic. It is also an active ingredient in some oral
analgesics like Chlora-septic spray, Carmex and TCP. These analgesics are utilized to
temporarily treat pharyngitis. Phenol is industrial component in paint strippers used in
the aviation industry for the eradication of epoxy and other chemically resistant coatings.
Phenol derivatives are also used in forming cosmetics like sunscreens, hair colorings,
and skin lightening ointments.

4. Provide the structure of gallic acid and write a balanced equation for the reaction of

gallic acid and sodium carbonate.

 2CH76O5 + Na2CO3 → 2C7H5O5Na + CO2 + H2O

Conclusion

The weight of the caffeine extract was 0.11 g. The calculated percent recovery was 946.64 %.
This was the amount of caffeine extracted from the crude caffeine in the tea bags. This
demonstrates that there was a significant amount of product lost throughout the procedure. It is
also important to consider that the reaction cannot go to completion. A loss of product could
have occurred due to emulsions and due to not thoroughly “washing” with dichloromethane to
extract as much caffeine as possible. There was a lot of transfer throughout the procedure, which
presented many opportunities to loose product. It is also possible that the concentration of
caffeine was not height enough because too much water was added. A systematic error with the
scales was observed due to a lack of calibration, this could have affected the measurement of the
final product. Another source of error could be the theoretical amount of caffeine in the tea bags,
if it was more or less due to random error, the percent recovery would be calculated differently.
The overall percent error was about 99.89 %. This number could be skewed due to measurement
errors of the crude product. In order to reduce sources of error in the future, two trials could be
done. It is also possible to use a different source of caffeine, and to ensure all techniques are
performed properly.
 References

 University A. Extraction of Caffeine from Tea. 2013. http://amrita.vlab.co.in/?

sub=3&brch=64&sim=169&cnt=1 (accessed October 10, 2019).
 Dullo, A. Efficacy of green tea extract rich in catechin polyphenols and caffeine in
increasing 24- h energy expenditure and fat oxidation in humans. [Online] 2008. 1040-
1044. www.ajcn.org (accessed October 10, 2019).
 J. Magdalan. Caffeine. WebMD. https://www.webmd.com/vitamins/ai/ingredientmono-
979/caffeine (accessed October 10, 2019).
 Murray D.S. Extraction of Caffeine from Tea. VALUE @ Amrita.
https://vlab.amrita.edu/?sub=3&brch=64&sim=169&cnt=6 (accessed October 10, 2019).
 Postu A. Isolation of Caffeine from Tea leaves via Acid-Base, Liquid-Liquid Extraction.
https://edspace.american.edu/ap7794a/wp-content/uploads/sites/159/2015/03/Isolation-
of-Caffeine-from-Tea-Leaves-via-Acid-Base-Liquid-Liquid-Extraction.pdf (accessed
October 10, 2019).