Organic Chemistry Laboratory-First Term A.Y.

2016-2017

Extraction of Caffeine from Tea Leaves

Tana, Demariel G., Tigulo, Celina Ysabel G., & Yonzon, Angela Cathleen SP.*

Department of Biological Sciences, University of Santo Tomas, Manila, Philippines

Date Submitted: September 20, 2016

Abstract

This experiment deals with the extraction of caffeine from tealeaves. The sample that was
Lipton tea. The process involved repeated extraction process and purification via two methods,
sublimation and crystallization. To test the purity of the caffeine, it melting point must be first
determined. The percent yielded of caffeine was 1.08% while the weight of the extracted caffeine
was 0.1171 grams.

Keywords: extracted caffeine from tealeaves, sublimation and crystallization, melting point,
percent yield.

Introduction:

Caffeine, 1,3,7 trimethylxanthine, is an alkaloid stimulant commonly found in tea,

coffee and cola beverages. It usually tastes bitter and has a stimulating effect to the brain and
central nervous system, helping humans to be physiologically active. Several factors such as
variety of coffee bean or tealeaf, location of the plants growth and method of brewing may
affect the amount of caffeine in coffee or tea. [1] Belonging to the alkaloid class of compounds,
caffeine are nitrogenous basic compounds and can be considered to be constructed from the
purine ring system. [2]
Figure 1. Lewis Structures of purine and caffeine. Retrieved from: http://employees.oneonta.edu/knauerbr/chem226

Isolation of caffeine may be done through extraction wherein the sample is distributed
between two or more phases. [3] Extraction is a method used for separating an organic
compound from a mixture. In this technique, one or more compounds would be dissolved
selectively into a particular solvent. The extract would be the solution of the dissolved
compounds. [4] Although, tea leaves contain another component that may be co-extracted such
as tannins, the differential solubility of caffeine and tannins in dichloromethane (CH2Cl2) allows
the separation of the two during extraction.

To further purify a natural product and isolate it from undesired compounds, the
sublimation method may be used. In this process, the product will undergo a direct phase change
from solid to vapor without passing the liquid state. [5]

This experiment aims to isolate, purify and characterize caffeine from tea leaves, and
determine the percent yield of caffeine in the sample.

Results and Discussion

Table 1. Tabulation of experimental results

Brand of Tea Lipton Yellow Label

Weight of Tea Leaves 10.8469 grams
Volume of H2O used 150 mL
Color of aqueous tea extract Dark brown
Volume of dichloromethane used 60 mL
Volume of 6M NaOH used 20 mL
Amount of anhyrdrous Na2SO4 1 spatula
Color of dichloromethane extract colorless
 Weight of empty evaporating dish 115.4181 grams
Weight of evaporating dish and extracted caffeine 115.5352 grams
Weight of extracted caffeine 0.1171 grams
Yield of extracted caffeine 1.08
Color & appearance of extracted caffeine White solid

In the experiment, caffeine is extracted from Lipton Yellow Label tea leaves after
subjecting it to boiling, extraction, and sublimation. The compound, an alkaloid, is polar and is
soluble in boiling water at 666 mg/ml [6]. After cooling the tea extract, it was transferred to a
separatory funnel for extraction. In this, dichloromethane or methylene chloride (CH 2Cl2) was
added. CH2Cl2 is a volatile liquid, with a density of 1.33 g/cm3. This liquid is also polar with the
presence of two more electronegative chlorines against two hydrogens, creating a dipole moment
(Figure 2). Caffeine, although highly soluble in water at high temperatures, is more soluble in
CH2Cl2 at room temperature. The cooling of the tea extract before the extraction was done due to
this. Densities of liquids are at work in the extraction setup, with CH 2Cl2s 1.33g/cm3 higher than
waters density of 1.00g/cm3. Thus, caffeine will be dissolved in the lower CH 2Cl2 layer (Figure
4), leaving the upper water layer with less and less caffeine as the three 20 mL extractions are
finished.

Although caffeine is the substance of interest in

this experiment, tea leaves also contain a compound
called gallic acid, a phenolic acid. This compound is
better known for its antioxidant properties, with the
potential to initiate apoptosis in cells [7] and promote
cancer cell death [8]. In the extraction setup, both
caffeine and gallic acid are present in the lower layer Figure 2. Stereochemical drawing of CH2Cl2.

to be extracted. Due to this, a washing step involving

the addition of 6M NaOH solution is done. The
alkaline solution, when added to the CH 2Cl2 layer, will react with the gallic acid to form water,
carbon dioxide, and a gallic acid salt (Figure 3).
 Figure 3. Reaction between gallic acid and NaOH.

When the washing was conducted in the separatory funnel, bubbles readily evolved
(Figure 4), hinting the presence of carbon dioxide gas. The addition of the sodium ion increases
the polarity of gallic acid, increasing its solubility in water. In theory, the gallic acid in the form
of its salt must now be in the upper water layer, and the lower CH2Cl2 layer must contain the
caffeine to be extracted.

Figure 4. Actual extraction set up with labeled parts. Extraction of caffeine with CH2Cl2 (left) and washing with
NaOH, illustrating bubble formation (right).

After drying the substance through adding anhydrous Na2SO4, the product was sublimed
and weighed. The weight of the crude caffeine obtained from the experiment was 0.1171 grams,
leading to a percent yield of 1.08% (Table 1). This was computed by dividing the experimental
yield of crude caffeine by the total grams of tea leaves used, which is 10.8469 grams. Thus, the
experimental results show that a tea bag of Lipton Yellow Label black tea has approximately
23.42 milligrams of crude caffeine. Ideally, 8 fluid ounces of Lipton Yellow Label black tea
(approximately one tea bag) has 55 milligrams of caffeine. [9]

Sample Computations

weight extcd . caffeine=wt .of evap .dishextcd . caffeinewt . of evap . dish

weight extcd . caffeine=115.5352 g115 .4181 g weight extcd . caffeine=0.1171 g

weight exctd . caffeine

yield of caffeine= 100
weight of tealeaves

0.1171 g extcd . caffeine

yield of caffeine= 100
10.8469 g tealeaves

0.108 100

yield of caffeine=1.08

weight extcd . caffeine

caffeine per tea bag=
number of teabags

0.1171 g extcd . caffeine

caffeine per tea bag=
5tea bags

caffeine per tea bag=0.02342 g per bag 23.42 mg per bag

The lower yield of 23.42 milligrams compared to the ideal 55 milligrams can be
attributed to some errors in the duration of the experiment. In the infusion setup, the tea leaves
were brewed for five minutes until the extract was dark brown. A darker color could have been
achieved if the teas were infused for a longer period of time. A darker color signifies a stronger
caffeine extract, thus, a larger yield. An increase in the temperature controlled by the Bunsen
flame could also potentially increase caffeine yield, since the latters solubility in boiling water is
significantly high. Due to the experiments restrictions, the purity of the obtained crude caffeine
was not tested.

Experimental

Five Lipton tea bags were used in this experiment. The combined weights of the tea
leaves were recorded and returned in the bags and were secured with a staple wire. The teabags
were boiled in 100 mL water for 5 minutes. The side of the flask was cooled in running water for
2 minutes and an ice cube was mixed with the tea extract to cool it to room temperature. The tea
extract was transferred in a separatory funnel containing 20 mL of CH 2Cl2 (Dicholoromethane).
The stopcock of the separatory funnel was opened to release the pressure constantly. The lower
layer was drained into a clean flask and the extraction was repeated twice. The remained brown
layer was discarded and the separatory funnel was cleaned. The CH 2Cl2 layer was then returned
to the separatory funnel and 20 mL of 6M NaOH was added. The NaOH layer then was
discarded. The CH2Cl2 layer was drained into a clean, dry 125 mL Erlenmeyer flask containing
half spatula of anhydrous Na2SO4 and was swirled until the Na2SO4 settled. The mixture was
decanted in a preweighed evaporating dish. The evaporating dish was placed on top of a 250 mL
beaker to allow it to evaporate until the white residue was obtained. The white residue weighed
and the percent yield was calculated. The extracted caffeine was then transferred into an empty
preweighed vial.

References

[1] Snelling. (2003). Extraction of Caffeine from Tea Leaves. Retrieved September 18, 2016 from

http://www2.volstate.edu/CHEM/2010/Labs/Caffeine_Extraction.htm

[2] Isolation of Caffeine from Tea Leaves. Retrieved Septermber 19, 2016 from

http://employees.oneonta.edu/knauerbr/chem226/226expts/226_expt06_pro.pdf

[3] S.L. Weaver. (2014). Extraction: Isolation of Caffeine from Tea Leaves notes. Retrieved

Septermber 19, 2016 from http://www.xula.edu/chemistry/crs-

orgleclab/Organic_Lab_1_2230L_Web_Files/15_Caffeine_notes.pdf

[4] vlab.amrita.edu,. (2011). Extraction of Caffeine from Tea. Retrieved September 19, 2016,

from vlab.amrita.edu/?sub=3&brch=64&sim=169&cnt=6
[5] Knutson. (n.d.) Sublimation of Caffeine. Retrieved September 19, 2016 from

http://www.ou.edu/englhale/pronarmode.doc

[6] Sigma-Aldrich, Inc. (1999). Caffeine (anhydrous). Retrieved September 18, 2016 from
https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma-
Aldrich/Product_Information_Sheet/c0750pis.pdf.

[7] Inoue, M., Suzuki, R., Koide, T., Sakaguchi, N., Ogihara, Y. & Yabu, Y. (1994). Antioxidant,
gallic acid, induces apoptosis in HL-60RG cells. Biochemical and Biophysical Research
Communications, 204(2). pp. 898-904.

[8] Inoue, M., Suzuki, R., Sakaguchi, N., Li, Z., Takeda, T., Ogihara, Y., Jiang, B. Y. & Chen, Y.
(1995). Selective induction of cell death in cancer cells by gallic acid. Biological &
Pharmaceutical Bulletin, 18(11). pp. 1526-1530.

[9] Lipton (2016). Claims. Lipton, Americas favorite tea. Retrieved September 18, 2016 from
http://smartlabel.liptontea.com/product/2706333/other/claims.

Trimble, J. (n.d.). Isolation of caffeine from tea leaves. Retrieved September 18, 2016 from
http://www.odinity.com/isolation-of-caffeine-tea/.