Jamie Mosher

Partners: Ashley P., Natasha N.

CHM 111 FA120
16 November 2016

Extraction of Caffeine from Tea

PURPOSE:
To extract caffeine from tea bags, isolate the substance in a process called liquid-
liquid extraction, investigate the physical properties of caffeine, and to find the
percentage of caffeine in a tea bag.

INTRODUCTION:
In chemistry, there is often an interest in knowing what substances are in different
foods and drinks. However, it can be difficult to isolate individual chemicals. In some
situations, a liquid-liquid extraction is necessary to fully separate a chemical from a
substance1. These situations are specific to isolating active chemicals from natural
products. A liquid-liquid extraction makes it possible to observe the physical properties
of substances based on their polarity found from their structure and chemical makeup.
In this lab, the main focus and chemical being explored is caffeine. Caffeines
molecular formula is C8H10N4O2 and has a molar mass of 194.194 g/mol. Additionally,
caffeine is a polar compound, and it has a combination of a pentagon and a hexagon
structure. Caffeine can be found in several beverages, including coffee, tea, energy
drinks, and soft drinks. Caffeine is also an alkaloid, meaning that it is a nitrogenous
organic compound that originated from a plant and has proven physiological effects on
humans2.
http://i.stack.imgur.com/EfNDt.png
 An obstacle that can make the separate of caffeine more difficult is the tannic
acid present in tea. Tannic acid (C76H52O46) is made up of large polar organic
compounds that can cause the caffeine extraction to be impure. To prevent the tannins
from being included in the extraction, sodium carbonate (Na 2CO3) is added during the
boiling process. The sodium carbonate reacts with the tannins in the tea, which ensures
that the tannins stayed in the water solution and the caffeine is only chemical being
extracted.
The solvent presented in the isolation process is an organic solvent called
dichloromethane (CH2Cl2). The caffeine is removed from the tea solution and absorbed
by the CH2Cl2. Dichloromethane is a polar compound with existing dipole-dipole forces
and London Forces. In the lab, the CH2Cl2 has a density of 1.325g/cm3, so it is denser
than water (H2O) which has a density of 1.000g/cm3. This means that the
dichloromethane is the bottom layer solvent in the extraction.
To assure that there is no residual aqueous solution in the solvent, sodium
sulfate (Na2SO4) is added. The sodium sulfate absorbs the water and forms a hydrate
called sodium sulfate decahydrate. Additionally, the solution is filtered through filter
paper into a round bottom flask to make certain that only dichloromethane and caffeine
are present in the solution.
When the rotorary evaporator is used, the round bottom flask is connected to the
evaporator. A rotorary evaporator works by having a heated water bath to keep the
solvent from freezing during the evaporation process and rotating the flask until all of
the solvent is removed. The solvent is then removed by a low pressure vacuum, which
left a residue of the white powder of caffeine in the flask. The boiling point is changed in
the process because the pressure is altered. In a low pressure situation, the boiling
point is lowered from its normal boiling point.
For this lab, there are a few calculations that need to be computed. First, the two
tea bags are weighed and the mass of each tea bag is determined. After isolating the
caffeine sample, the number of moles of caffeine has to be calculated. Finally, the
theoretical mass and the actual mass are computed to find the percent error of the
extracted caffeine.
 Mass of caffeine per tea bag = Mass of isolated caffeine / 2
Mass % of caffeine per one tea bag = Mass of crude caffeine per bag / mass of tea bag
Moles of isolated caffeine = Mass of isolated caffeine / Molar Mass of caffeine
% Error = ((mg of caffeine found / theoretical yield) / theoretical yield) x 100

EXPERIMENTAL:
Chemicals:
C8H10N4O2: Caffeine2
Molar mass: 194.194 g/mol
Physical state and appearance: solid, powder
Color: white
Melting point: 236.2 degrees C
Boiling point: 178 degrees C

Na2CO3: Sodium Carbonate3

Molar mass: 105.988 g/mol
Physical state and appearance: solid, powder
Color: white
Melting point: 856 degrees C
Boiling point: 1600 degrees C

Na2SO4: Sodium Sulfate4

Molar mass: 142.036 g/mol
Physical state and appearance: solid, powder
Color: white
Melting point: 888 degrees C
Boiling point: 1429 degrees C

CH2Cl2: Dichloromethane5
Molar mass: 84.927 g/mol
Physical state and appearance: liquid
Color: colorless
Melting point: -95 degrees C
Boiling point: 39.75 degrees C
Density: 1.325 g/cm3 at 25 degrees C

H2O: Water6
Molar mass: 18.015 g/mol
Physical state and appearance: liquid
Color: clear, colorless
Melting point: 0 degrees C
Boiling point: 100 degrees C
Density: 1.000 g/cm3 at 25 degrees C

Health Hazards:
Caffeine, sodium sulfate, and sodium carbonate can cause slight skin irritation, and
dichloromethane can cause severe redness and irritation to eyes.
Eye Contact:
Contact lenses should not be worn. In case of contact to eyes, immediately flush eyes
with plenty of warm water for at least 15 minutes. Seek medical attention immediately.
Skin Contact:
In case of contact, flush affected skin areas with plenty of water for at least 15 minutes,
remove all contaminated clothing, and apply moisturizer to affected areas. Get medical
attention immediately. Wash all clothing before reuse.
Personal Protection:
A local exhaustion ventilation system should be present when handling all chemicals,
especially dichloromethane. Safety goggles, gloves, and lab coat must be worn while
handling chemicals.
Physical Hazards:
Dichloromethane must remain under fume hood at all times. Dichloromethane is
combustible at times and gives off irritating and toxic fumes. Caffeine can be
combustible at high temperatures.
Storage and disposal:
Keep caffeine stored and away from heat or sources of ignition. Sodium carbonate is
hygroscopic, so it should be stored in a closed container and away from moisture. Keep
dichloromethane away from metals and foods. Dispose all wastes and excess
chemicals into in appropriate waste containers under fume hoods. Do not rinse down
drain.

Equipment:

Balance
50 mL Erlenmeyer flask, 250 mL Erlenmeyer flask, 50 mL round bottom flask
Hot plate
Stand and ring clamp
Separatory funnel
Graduated cylinder
Filter paper and funnel
Rotorary evaporator
Small curved spatula
Vial

Procedure:
A sample of 6.000 0.02 g of sodium carbonate, two tea bags which weighed at
4.9675g, and 50 mL of deionized water were measured and added to a 125 mL
Erlenmeyer flask. Next, the flask was placed onto a hot plate for about 30 minutes in
order to boil the solution and release caffeine from tea leaves. The liquid in the flask
was then poured into a separatory funnel and 6.000 0.02 mL of dichloromethane
solvent was added into the mixture before placing a stopper at the top of the separatory
funnel. The dichloromethane and the tea liquid separated into two distinct layers with
the dichloromethane as the bottom layer. The mixture was swirled in the separatory
funnel and pressure was released using the stopcock. This process was repeated three
times before replacing the separatory funnel to the stand. After the two liquids created
the immiscible layers, the dichloromethane was removed from the separatory funnel
and placed into a 50 mL Erlenmeyer flask. The process of adding dichloromethane,
swirling mixture, releasing pressure, and extracting the dichloromethane was repeated
two additional times. After removing the dichloromethane from the separatory funnel,
3.000 0.02 g of sodium sulfate was added to the liquid. Then, the sample was filtered
through a funnel and placed into a round bottom flask. The round bottom flask was then
attached to a rotorary evaporator that evaporated the solvent from the caffeine.

https://www.learnnext.com/nextgurukul/wiki/concept/CBSE/IX/Science/Methods-of-Separation-of-Mixtures.htm

The heavy liquid in the image represents the dichloromethane

because it is denser than the lighter liquid that represents the
water solution.

DATA AND CALCULATIONS:

Refer to the equations mentioned in the introduction of the lab report. The mass
of each tea bag was found by taking the weight of two tea bags, 4.9765g, and dividing
that number by two. The mass of caffeine per tea bag was found by taking the total
mass of the crude caffeine sample and dividing it by two because there were two tea
bags. The mass percent of caffeine per one tea bag was found by taking the mass of
crude caffeine per tea bag and dividing it by the mass of one tea bag, and then
multiplying that number by 100. The percent error of caffeine isolated was found by
dividing the actual yield by the theoretical yield and multiplying that number by 100.

Mass of caffeine per tea bag = 0.062g C8H10N4O2 / 2 tea bags = 0.031g C8H10N4O2
Mass % of caffeine per one tea bag = (0.031g C 8H10N4O2 / 2.488g) x 100 = 1.246%
% Error of caffeine isolated = (.031g actual yield / .055g theoretical yield) x 100 = 56.4%
RESULTS AND DISCUSSION:
The polar bonds in the caffeine structure are the C=O bonds and the NC bonds.
There are 25 sigma bonds and 4 pi bonds in the caffeine structure.

https://userscontent2.emaze.com/images/293dcfd0-6804-4575-b1ed-
13c8c24b6427/99e699b1-ce8c-4422-ae41-5fea63ee05d8.png

The caffeine was extracted from the tea solution to the dichloromethane liquid when the
pressure was released from the separatory funnel and the immiscible layer between the
two liquids formed. Caffeine, water, and dichloromethane all have London Forces and
dipole-dipole forces, but water also has hydrogen bonding. The oxygen atoms in
caffeine cause the negatively charged side of the compound while the CH 3 compounds
are positively charged. The chlorine atoms in dichloromethane make up the negatively
charged side of the compound. Because of the positive and negative charges of the
polar compounds, the caffeine was drawn into the dichloromethane. The caffeine was
soluble in two different liquids because water is polar as well, but when presented the
solvent, the caffeine was more drawn to the dichloromethane.

O1:
Hybridization: sp2
Shape: bent
Angle: 120 degrees

N1:
Hybridization: sp3
Shape: trigonal pyramidal
Angle: 107 degrees

N2:
Hybridization: sp2
Shape: bent
Angle: 120 degrees

CA:
Hybridization: sp2
Shape: trigonal planar
Angle: 120 degrees

CB:
Hybridization: sp3
Shape: tetrahedral
Angle: 109.5 degrees

The crude caffeine product from the lab was white and a fine powder, which is much
different that the appearance from the tea bags it came from. The tea bags were dark
brown, and there was a larger amount of contents in the tea bags than the contents in
the crude caffeine product. The caffeine could be purified further through the process of
sublimation. Sublimation is the process where a solid changes phases directly to a gas,
skipping the liquid phase of caffeine. The melting point of pure caffeine is 236.2 degrees
Celsius.

In this lab, the boiling of the tea in the water was not a chemical change because all of
the tea contents could easily be taken out of the water. Since the boiling point of water
is less than the boiling point of caffeine, the contents of the tea bag would be left after
boiling out all of the water. The brewing of the tea is a chemical change. When the
sodium carbonate was added to the tea mixture to neutralize the tannic acid, that was a
chemical change because the sodium carbonate had to react with the tannins in the tea
liquid so that they would stay in the water solution and not interfere with the caffeine and
dichloromethane solution. When mixing the aqueous tea solution with the
dichloromethane, this was a not chemical change. The two liquids could be easily
separated because they were immiscible, and the caffeine that was into the
dichloromethane could be boiled to remove the dichloromethane from the caffeine. The
boiling point for dichloromethane is much lower than the boiling point of caffeine. So,
this would be a not chemical change because it would not be hard to undo this change
and the caffeine did not change its chemical composition during this process. The
removal of the dichloromethane solvent with the rotorary evaporator was a physical
change because there was only evaporation occurring in this process. The solvent and
the crude caffeine could easily be recombined. Finally, the sublimation process of the
crude caffeine to pure caffeine would also be a physical change because there is not a
reaction occurring when changing the phases of the caffeine. The pure caffeine could
be cooled in order to become a crude caffeine again.

The mass percent of caffeine per one tea bag in this lab was 1.246%, and the percent
error was 56.4%. The procedure could be improved by repeating the addition of
dichloromethane to the separatory funnel more times because this would help remove
more of the caffeine from the aqueous solution.

CONCLUSION:
The extraction and isolation of the caffeine from tea process included boiling the
solution, adding dichloromethane to the solution, removing the dichloromethane with the
caffeine contents in the liquid, and evaporating the solvent out of the solution to have a
result of only crude caffeine powder. The caffeine ended up in the solvent
dichloromethane. The mass percent in one tea bag was 1.246% and the percent error
of isolated caffeine was 56.4%.
REFERENCES:
1. Liquid-Liquid Extraction using Separatory Funnel -
https://elearning.delta.edu/d2l/le/content/2871213/viewContent/1277959/View -
Oct 30, 2016
2. MSDS (C8H10N4O) -
https://pubchem.ncbi.nlm.nih.gov/compound/caffeine#section=Taste - Oct 30,
2016
3. MSDS (Na2CO3) -
https://pubchem.ncbi.nlm.nih.gov/compound/sodium_carbonate - Oct 30, 2016
4. MSDS (Na2SO4) - https://pubchem.ncbi.nlm.nih.gov/compound/sodium_sulfate -
Oct 30, 2016
5. MSDS (CH2Cl2) - https://pubchem.ncbi.nlm.nih.gov/compound/dichloromethane -
Oct 30, 2016
6. MSDS (H2O) - https://pubchem.ncbi.nlm.nih.gov/compound/water - Oct 30, 2016