Experiment 1:

Isolation of Caffeine from a Tea Bag

Objective/s:

To learn the isolation of a natural product utilizing acid base extraction

technique. To extract caffeine from tea powder using polar - nonpolar solvent
extraction technique.

Introduction:

The taste of caffeine is a bitter taste. The characteristic of caffeine is

white crystalline xanthine alkaloid. It can be found in various quantity in the
seeds, leaves and fruits of certain plants. Caffeine in the plant can acts as a
natural pesticide that paralyzes and kills certain insects feeding on the plants.
The molecular formula of Caffeine is C8H10N4O2. The molecular weight of
caffeine is 194.1906 g/mol. The molecular structure of caffeine can be shown
as below.
Material:

Tea bag (BOH)

100mL beaker

50mL beaker

Small separatory funnel

Measuring cylinder

Analytical balance

Filter funnel

Round bottomed flask

Rotary evaporator

Chemical:

Sodium carbonate

dichloromethane

Anhydrous sodium sulphate

Water
Procedure:

1. 50ml of water was added into 100ml beaker to make the tea solution.
2. The hot tea solution then was transferred into a small conical flask and
was added with 0.5 of sodium carbonate.
3. Since the tea bag was used, the filter process was skipped. If the tea
leaves were used in this experiment, the filter process are necessarily.
The solution then was transferred into the separatory funnel.
4. 15ml of dichloromethane was added into the separatory funnel and the
extraction process was done.
5. Then, the lower layer of dichloromethane was collected and another
10ml was added into the separatory funnel. Then this process was
repeated to ensure all of the caffeine was collected.
6. The collected dichloromethane then was dried by using anhydrous
sodium sulphate.
7. The dried dichloromethane solution then was transferred into a pre-
weight round bottom flask and was evaporate off using rotary-
evaporator.
Results and Calculations:

Tea brand BOH

Mass of tea leaves / g 2.00

Mass of empty round bottomed flask / g 42.0052

Mass of round bottomed flask + caffeine / g 42.0798

Mass of caffeine / g 0.0746

Percentage of caffeine in a packet of tea.

𝑚𝑎𝑠𝑠 𝑜𝑓 𝑐𝑎𝑓𝑓𝑒𝑖𝑛𝑒,𝑔
= 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑡𝑒𝑎 𝑙𝑒𝑎𝑣𝑒𝑠,𝑔 × 100

0.0746
= × 100
2.00

= 3.73 %

Theoretically, BOH tea is said to be 3% of caffeine by weight. That tells, in this

experiment, when 2g of tea was used, the caffeine that should obtained is

Theoretical mass of caffeine

3
= 100 × 2.00𝑔

=0.0600g

The percentage error can be done by using bellow formula

|𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑣𝑎𝑙𝑢𝑒−𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑣𝑎𝑙𝑢𝑒|

% error= × 100
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑣𝑎𝑙𝑢𝑒

|3%−3.73%|
= × 100
3%

=24.33%
Discussion:

In this experiment, BOH brand tea bag was used. The mass of the tea
leaves obtained from a packet of tea is 2.00g. The acid base extraction method
was done in this experiment which mixing a tea with hot water to make a tea
solution. Sodium carbonate was mixed into the solution because sodium
carbonate acts as a base. The base converts the tannins into their sodium salts
and 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.

The solution then was transferred into the separatory funnel and was
added dichloromethane which is a polar organic solvent and good in dissolving
most organic molecules like caffeine. Dichloromethane is immiscible with
water and denser than water which form a separate layer at the bottom of the
solution. Then the mixture was shaken to confirm that the caffeine will migrate
from the tea into the extractant. The lower layer in the separatory funnel then
was collected and added with anhydrous sodium sulphate to dry the solution.

The extract was then evaporated using a rotary evaporator. After the
evaporating process, the caffeine will leave on the wall of round bottom flask.
The empty flask was pre-weighed before the evaporation process. The weight
of the caffeine can be obtained by subtract the mass of round bottom flask and
caffeine with the empty round bottom flask. The amount of the caffeine
obtained from the experiment was 0.0.746 g. Since the BOH company claimed
that their tea only has 0.0600g of caffeine. Here is clearly shows that there was
an error in the experiment and the percentage error was 24.33%.

One of the errors detected is, when weighing the mass of the round
bottomed flask, it has to be held a bit because it is not stable. The real mass
of the bottomed flask might be an error because there is interruption during the
weighing process. Furthermore, the round bottom flask after using the rotary
evaporator is quite warm. This also causing the reading of the analytical
balance was not stable and make the mass of the round bottom flask with
caffeine are slightly heavy then the actual reading. To overcome the error in
the future, it is a good idea to carefully and calmly conduct the experiment.

From the experiment, the caffeine obtained was 3.73% which is quite
different from the theoretical percentage. Caffeine can be an agent for elevate
alertness. It also helps in relaxing smooth muscles and stimulates cardiac
muscle. Caffeine also can stimulate dieresis and appears to be useful in the
treatment of certain headache. The excessive amount of caffeine also could
be dangerous and may raise blood pressure or cause incontinence.

Conclusion

As a conclusion, the isolation of a natural product utilizing acid base

extraction technique and extraction of caffeine from tea powder using polar -
nonpolar solvent extraction technique was learned. The results in this
experiment is 3.73% and the percentage error is 24.33%
Question:

1. Outline a separation scheme for isolation caffeine from tea. Use a

flowchart similar in format to that shown in Technique 2.

2. Why was the sodium carbonate added in the experiment?

- Sodium carbonate act as base in this experiment which converts the
tannins into their sodium salts and being ionic solution. These salts
are not soluble in dichloromethane so being remain in the aqueous
layer during extraction and produce 2 separate layers. This allows
purer caffeine to be extracted.

3. The crude caffeine isolated from tea has a green tinge. Why?
- Because there are certain components in the tea leaves are cannot
been extracted and absorbed by dichloromethane even the pigment
and chlorophyll were absorbed.
4. What are some possible explanations for why the melting point of your
isolated caffeine may be lower than the literature value(236oC)?
- This is because the caffeine is in this experiment had impurities
and probably also had traces of others chemical that was used to
separate it.

5. What would happen to the caffeine if the sublimation step were

performed at atmospheric pressure?
- Some of the caffeine might be decomposed and would use
additional heat. If this were used, the quality of the caffeine might
be low.
References

1. Nawrot, P & Jordan, S & Eastwood, J & Rotstein, J & Hugenholtz, A &
Feeley, Mark. (2003). Effect of caffeine on human health. Food
additives and contaminants. 20. 1-30.
10.1080/0265203021000007840.

2. https://www.medicalnewstoday.com/articles/271707.php
3. https://en.wikipedia.org/wiki/caffeine/
4. https://www.webmd.com/vitamins/ai/ingredientmono-979/caffeine
5. http://science.answers.com/Q/What_would_happen_to_sublimation_of
_caffeine_was_performed_at_atmospheric_pressure
Pre-laboratory preparations