Lab Report

Caffeine Extraction

Due September 19th, 2018

Members

Noppasorn Swangswai 5960167

Supanut Sritong-in 5961070
Pakjira Chartpumrujee 5961165
Sumeta Vongpiphopmongkol 5961062
Summary/abstract

This experiment was conducted in order to extract the caffeine and characterized the
caffeine crude. The problem with this experiment is that shaking too intense can slows down
the separation of the dichloromethane layer. The main method that we use is separating the
caffeine from tea. In conclusion, we were able to determined the caffeine crude and the Rf
value from this experiment through caffeine isolation and TLC process.

Introduction

Tea is a very famous drinks around the world that helps prevent people from getting
sleepy. In addition, all teas contain caffeine that affects the length of time that people sleep.
The caffeine that found in tea varies according to the type of tea leaves. Such as white,
green, and black tea caffeine are ranged from 14 to 61 milligrams per servings (Nina K., Oct
3, 2017). In contrast, the amount of caffeine in coffee bean varies in different types as well.
Such as espresso coffee beans contain about 63 milligrams and instant coffee contains
roughly about 30-90 milligrams (Bjarnadottir, June 3,2017). However, in the labs of
extraction caffeine, teas are easier for the experiment because tea contains non-caffeine
chemicals less than coffee.
TLC or thin layer chromatography is one of the common methods that are used for
doing the caffeine extraction lab. The purpose of this lab to be able to extract the caffeine
from the tea and identify caffeine crude. In the extraction lab, we use dichloromethane and
anhydrous sodium sulfate to extract caffeine from the tea solution. Then, the caffeine powder
are put in the hirsch funnel to separate the extra water from the caffeine. When we get the
caffeine powder and determined the melting point of the caffeine powder.

Objective

- to extract the caffeine from tea

- to characterize caffeine crude.

Material

- Tea bags
- TLC silica gel
- Seperatory funnel
- Water
- Beaker
- Rotary evaporator
- UV lamb
- Vacuum filtration set
- Dropper
- Erlenmeyer flask
- Filter paper
- Filter funnel
- Chemicals
- Dichloromethane
- Sodium sulfate

Method

1. Transfer the tea extract from the Erlenmeyer flask to a separatory funnel that is
supported by a ring on a ring stand.
2. Add 15 milliliters of dichloromethane to the separatory funnel. Use the stopper to
close the funnel and grab the neck of the funnel with one hand. Hold the stopper onto
the neck of the funnel with your other hand and grasp the stopcock in such a way
that you can turn the plug in the barrel to open and close the stopcock. While holding
the stopper tightly, into the neck of the funnel, invert the funnel so the liquid is no
longer in contact with the stopcock. While pointing the stem of the funnel away from
everybody, open the stopcock to release any pressure that may have built up inside
the funnel, close the stopcock and agitate the material in the funnel without shaking it
vigorously – you want the contents to mix, but you do not want to generate an
emulsion. Point the stem of the funnel upward, and making sure no liquid is in contact
with the stopcock, open it, again, to release any pressure that is building up. Close
the stopcock and agitate again as before and reclamp the separatory funnel to the
ring stand.
3. Allow the contents of the separatory funnel to settle. There should be two distinct
mostly clear layers. If there is an emulsion (cloudy) layer between two clear layers it
is sometimes possible to break the emulsion by swirling the contents of the funnel or
stirring the contents using a glass rod. If the emulsion persists seek your instructors
help.
4. Carefully drain the lower (dichloromethane) layer into a 25 ml Erlenmeyer flask. Try
to not include any of the aqueous (upper) layer. If there is a lot of emulsion, include it
in the Erlenmeyer flask.
5. Repeat steps 5 through 7 using a second 5 ml portion of dichloromethane.
6. Add 0.5 g of anhydrous sodium sulfate to combine dichloromethane extracts in the
25 ml Erlenmeyer flask and swirl the contents of the flask. The anhydrous sodium
sulfate will absorb the small amount of water that is dissolved in the dichloromethane
and small amount of water from the aqueous layer that may have gotten into the flask
by accident. [If you collected a substantial amount of emulsion in the Erlenmeyer
flask, the sodium sulfate should help “breaking” the emulsion. You may need to
separate the aqueous material from the dichloromethane solution at this point.]
7. Set up the Hirsch funnel from the microkit. Be sure to clamp the filter flask to a ring
stand and to place a piece of filter paper in the funnel. Connect a rubber hose from
the side-arm on the flask to the side-arm of the aspirator. Turn on the aspirator. Pour
the crystals and mother liquor from the beaker into the Hirsch funnel. If some crystals
stick to the beaker, you can scrape them out with a spatula or wash them out with the
mother liquor in the filter flask if you used a clean flask. Allow air to be drawn through
the crystals for 10 minutes. Place the powder in an unstoppered vial in your drawer.
 8. Then, brings the filter flask that contains the mother liquor and puts it into the
distillation machine to separate dichloromethane from the caffeine. As a result, the
power form of caffeine is form.
9. After that, use TLC method to identify the Rf value of the caffeine by dissolve the
caffeine powder into dichloromethane and paste it on the silica gel sheet. There will
be a reference caffeine paste on the silica gel sheet as well.
10. Then put the silica gel sheet into dichloromethane can let the TLC runs. From this
you will be able to determine if your caffeine is pure or not and the Rf value of your
caffeine powder.
11. Next, determine their melting point. The melting point reported in the melting point
machine is 238℃, so you can heat the Thiele tube rapidly at least up to 200℃. Do
not exceed the 260℃ limit of the thermometer. Hand your sample of caffeine in along
with your report sheet.

Results

As the result of the experiment, from the extraction that we put into capillary tube
which is caffeine crudes and pure caffeine. Then, we test by put it into boiling point test. In
addition, from considering boiling point of both pure caffeine and caffeine crudes, we have
seen that pure substance is melting to the liquid quicker than our crudes. Due to the
outcome, the temperature of pure caffeine is 220​°C​ and the temperature of caffeine crudes
is 226​°C​.

Discussion

Emulsion is a dispersion of liquid droplet in another liquid which not mixed together.
This emulsion can occur when we shaking the mixture in separatory funnel too vigorous. In
order to avoid it, we need to shaking slowly and carefully. The simple method to destroy it is
to add small amount of saturated aqueous sodium chloride to the solution or use
centrifugation technique (Spectrosci, n.d.). In drying agent, it is an chemical used to remove
the water from organic compound in solution. In the experiment, there might have some
water left in dichloromethane during an extraction. Then, the drying agent was used to
remove the remain water in the solution. Sodium sulfate was used as drying agent because
it’s has a very high water capacity and mainly use for every wet solution. After we pour
sodium sulfate, it’s react and absorb the water readily. (Chem, 2016). Moreover, we can
identify that the caffeine that we is from tea leaves by using thin-layer chromatography
method and boiling/melting point test. By using TLC method, we need compared the
similarity and difference of two sample by test it’s polarity. If it is the same compound, the
spot will be at the same place. Moreover, we can check the purity by observe the spot. If it
leave more than one spot, we can consider that it’s not pure as it’s has many component.
Furthermore, we can use boiling/melting point test to test its purity. The crude can be used to
determine by compare the melting point and boiling point with the the pure
caffeine(Chemguide, 2016). There were some error taking place during the experiment. In
the step that we had to agitate the mixture of dichloromethane and tea extract, sometime we
shaked it too hard so the mixture were not completely separate. The bubble layer(H2O)
occurred and when we release the dichloromethane layer there might had some bubble
layer drop too. To avoid this, when we run the experiment, we need to be claim and carefully
shake the separatory funnel. The molecular formula of caffeine is ​C8H10N4O2, which is
polar molecule. It is polar molecule because it’s contain four different element that has
different electronegativity. Beside, the geometry shape of the caffeine also allow it to be
polarity.(Caffeine the molecule, n.d.). As it’s polarity, the intermolecular that can exits are
dipole-dipole force and dispersion force. Nevertheless, the strongest ​ intermolecular forces
present in caffeine is ​dipole-dipole force because the attraction between positive and
negative charges while dispersion force is temporary attractive force that cause by motion of
electron(Chem, n.d.). According to Cormier, Hudson and Siegel, the Rf value of caffeine is
about 0.35 (A consumer experiment, n.d).

Calculations
Unless otherwise stated, all calculations are to be shown. Calculations are to be well
labeled, logically comprehensible and clearly show how the result was obtained.

Rf value = sample distance / solvent distance

= 1.5 / 5
= 0.3

Conclusion
In conclusion, the caffeine crude can be characterized by boiling the caffeine powder. Not
only the caffeine crude, but the Rf values can also be determined from the caffeine through
TLC method as well.
References

Nina K. (2017). How Much Caffeine Is Contained in a Tea Bag? Retrieved from
https://www.livestrong.com/article/281148-how-much-caffeine-is-contained-in-a-tea-b
ag/
Adda Bjarnadottir (2017). How Much Caffeine in a Cup of Coffee? A Detailed Guide.
Retrieved from​ ​https://www.healthline.com/nutrition/how-much-caffeine-in-coffee
Nick London (2014). Apparently tea contains more caffeine than coffee. Retrieved
from ​https://www.theguardian.com/notesandqueries/query/0,5753,-25502,00.html
TeaClass (2008). The Truth About Caffeine. Retrieved from
https://www.teaclass.com/lesson_0112.html
UCLA Chemistry and Biochemistry (2005). Gas Chromatography Theory, Drying
agents. Retrieved from
http://www.chem.ucla.edu/~bacher/Specialtopics/Drying%20Agents2.html
PURDUE science (Unknown). London Dispersion Forces. Retrieved from
https://www.chem.purdue.edu/gchelp/liquids/disperse.html
Erin Hutton (2017). Configuration. Retrieved from
https://caffeinethemolecule.weebly.com/configuration.html
Spectro Scientific (Unknown). Emulsion Breaking Techniques
for Oil in Water Solvent Extractions. Retrieved from
https://www.spectrosci.com/product/infracal-2-atr-sp-oil-in-water-analyzer/?fileID=8a
808189505a61330150a5b2df8f454c
Chemguide(2016).Thin layer chromatography. Retrieved from
https://www.chemguide.co.uk/analysis/chromatography/thinlayer.html