Extraction of Caffeine from Tea

Protocol written by Robert Booth

Montclair State University

Spring 2015 Semester

Introduction

Figure 1: Molecular Structure of Caffeine

Caffeine is an organic compound belonging to a class of molecules known as alkaloids.

Alkaloids are naturally occurring nitrogenous compounds found in plants, and some, like
caffeine, find uses in everyday life. Aside from finding a place in beverages such as soda, coffee,
and tea, there are also some medical uses of caffeine. Caffeine tablets are sold primarily in
pharmacies as over-the-counter (OTC) supplements for the treatment of headaches and
migraines. Furthermore, caffeine can be found in combination drugs such as Excedrin, which
contains caffeine, acetaminophen (Tylenol), and aspirin (all of which are organic compounds).

In this experiment, you will be extracting caffeine from tea leaves and isolating it from
unwanted impurities once it is coaxed out of the tea bags. You will be using a separatory funnel
to “force” the caffeine out of the water it is initially dissolved in. Dichloromethane is a common
organic solvent used for this purpose, since it is immiscible in water (does not mix
homogenously). The solubility of caffeine in water is 22 mg/mL at room temperature (RT), while
the solubility of caffeine in dichloromethane is 140 mg/mL at RT. Therefore, all of the caffeine
will travel from the water/aqueous layer to the dichloromethane/organic layer because caffeine is
more structurally similar to dichloromethane than it is to water. When you mix these two
solvents, you will create two “layers” in the separatory funnel that will make it easy to isolate the
caffeine-containing layer. After “washing” your sample with dichloromethane and removing it
from the funnel three times, you will isolate the caffeine from any unwanted impurities that also
mix with dichloromethane.
 Procedure

Figure 2: Crude Drawing of a Separatory Funnel (I’m a chemist, not an artist)

1) Obtain ~200 mL of tea in a beaker and pour into a separatory funnel. Before pouring the
tea into the separatory funnel, make sure the stopcock is in the “closed” position
(perpendicular to the direction of solvent flow through the funnel, as shown in Figure 2).
2) Obtain 20 mL of dichloromethane from your instructor (do not take any dichloromethane
yourself). Add the 20 mL of dichloromethane to your separatory funnel.
3) Place the stopper securely on top of the separatory funnel and gently rock the funnel for a
total of ~3 minutes in order to mix the organic and aqueous layers. Every 15-30 seconds,
remove the stopper from the funnel to relieve pressure.
4) Set up the separatory funnel on a ring stand. Obtain a clean beaker and decant the
dichloromethane/organic layer (see Figure 2) into the clean beaker by switching the
stopcock to the “open” position (parallel to solvent flow). DO NOT COLLECT THE
EMULSION LAYER; THIS SHOULD STAY IN THE FUNNEL.
 5) Repeat steps 2-4 two more times. You should perform three washes and decantations
with dichloromethane in total.
6) Using a metal scooper or spatula, transfer a small amount of anhydrous Na2SO4 to your

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dichloromethane beaker (Na2SO4 should cover approximately the bottom th inch of the
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beaker).
7) Swirl the beaker and let the mixture settle for ~10 minutes. It is important to give the
anhydrous salt enough time to absorb any excess water that may still be mixed in with
your dichloromethane and caffeine.
8) With the help of a glass stirring rod, decant the liquid in your dichloromethane beaker
into another clean beaker. You should use the stirring rod to help guide the stream of
dichloromethane into the new beaker, as well as to prevent any salt from escaping (you
do not want any Na2SO4 in the new beaker).
9) Add some Teflon boiling chips to your new beaker of decanted liquid. Set a hot plate to
~115 ˚C and drive off the dichloromethane through evaporation (DO THIS IN THE
FUME HOOD). After the dichloromethane evaporates, collect the remaining solid. This
solid is your extracted and purified caffeine, and should have a powdery appearance at
the bottom of the beaker. Save your caffeine samples for future analysis.

Discussion Questions

1) Why is it important to avoid collecting any of the emulsion layer during washing in the
separatory funnel (if one is present)?
2) What would happen to your calculated percent yield if you did not drive off all of the
dichloromethane through heating in the final step?
3) What would happen to your calculated percent yield if the water + tea mixture was heated
to 80 ˚C without your knowledge prior to collecting your ~200 mL portion in step #1?