ORGANIC CHEMISTRY I

LABORATORY
220L-Tue 1-4pm

Extraction of Caffeine from Tea

Kathleen Swanson
11/01/2013
Introduction:

Chemical Extractions have been a part of human lives for centuries. While this procedure is
used by many laypersons to brew coffee, tea it is also a process commonly employed by
chemists and biochemists in order to target and separate desired products used for making
medications like quinine, morphine and menthol, perfumes. Extractions can be either solid-
liquid, or liquid-liquid, depending upon the desired compound. In both types, a liquid solvent
is used to isolate the compound. Scientists often perform extractions of organic material,
utilizing an inorganic solvent in order to better separate the organic compound from the
typical byproducts and starting materials. In these types of liquid-liquid extractions it is
important to choose an appropriate solvent that will not dissolve in water, have a low boiling
point so it can be easily removed; it should not react with the solute or other solvent. Ideally,
a well-chosen organic solvent when mixed with the mixture containing the liquid compound,
will create two immiscible layers; one containing the extraneous materials in the aqueous
layer, and the compound to be extracted in the organic layer.

This laboratory exercise, caffeine is first extracted in a solid-liquid extraction from tea leaves
into boiling water (a polar, inorganic solvent). Then the caffeine in the water is extracted using
dichloromethane (an organic solvent) in a liquid-liquid extraction procedure (carried out in a
separatory funnel). Caffeine, a naturally occurring stimulant belonging to a class of
compounds known as alkaloids (based on the amine, Purine). It is found in many beverages
and often addicting, especially for those that consume caffeine daily to promote attentiveness
and increase energy levels. While caffeine is a naturally white, slightly bitter, crystalline solid,
when extracted from tea leaves, the water turns a brownish color demonstrating that other
impurities are present in the solid-liquid extraction. When the caffeine dissolves in the organic
dichloromethane, extracted from the confounding impurities the mixture is clear in
appearance, leaving behind the brown in the aqueous solution. The solubility of caffeine in
water is 2.2 mg/mL at 25°C, 180 mg/mL at 80°C, and 670 mg/mL at 100°C. It is quite soluble in
dichloromethane, the solvent used in this experiment to extract the caffeine from water.
 In addition to caffeine, tea leaves also contain a number of colored compounds, a small
amount of decomposed chlorophyll, and tannins, a weakly acidic phenol with a Pk of 10.0.
Tannins are slightly soluble in dichloromethane, the solvent used in the liquid-liquid phase of
the extraction, so to eliminate and neutralize these weak acids, sodium carbonate (NaCO 3) is
added to convert the phenols to their salts (phenol anions) by deprotonation of the –OH
group, which remain in the H2O. The basic property of alkaloids comes from the lone pair of
electrons found on at least one of the nitrogen. When phenol is converted to phenolic salts
(by adding NaCO3) creates a more basic environment decreasing the solubility of caffeine in
water by causing it to take on its neutral form (C8H10N4O2), making it only somewhat polar. In
this way the basic N in caffeine can be used to increase or decrease its water solubility. In
contrast to the basic alkaline conditions, acidic conditions will form the conjugate acid salt
(C8H9N4O2 + H3O+) giving caffeine increased water solubility as a cation. This cation form would
make it very difficult to draw the caffeine from the aqueous layer into the organic layer.

Compounds Used:

Phenol (tannins) Caffeine Magnesium Sulfate Sodium Carbonate

 MW Density Vol. Mass mol Hazard
Compound
(g/mol) (g/mL) (mL) (g)
skin contact or eye
Caffeine 3.35 mL 4g
194.2 g/mol 1.23 g/mL 0.0206 contact (irritant),
(C8H10N4O2) (calculated) (2 tea bags)
ingestion, of inhalation.
eye and skin, and
respiratory tract
74 mL irritation; Harmful if
Dichloromethane 98.42 g
84.92 g/mol 1.33 g/mL (7x 10mL + 1.159 swallowed; May be
CH2Cl2 (calculated)
2x 2mL) harmful if inhaled; May
cause central nervous
system effects.
skin contact (irritant),
Sodium Carbonate 0.79 mL
105.99 g/mol 2.532 g/mL 2g 0.0189 ingestion, of inhalation
(NaCO3) (calculated)
(lung irritant)
Ingestion; Slightly
non
Magnesium hazardous in case of skin
120.38 g/mol Not available - specified -
Sulfate (MgSO4) contact or eye contact
amount
(irritant), of inhalation.
skin contact (corrosive,
Phenol non
irritant), of eye contact
(C6H5OH) 94.11 g/mol 1.057 g/mL specified
(irritant), of ingestion, of
*from tannins/tea amount
inhalation
Water 35 mL 35 g
18.02 g/mol 1.00 g/mL 1.94 none
(H2O) (15 +20 mL) (calculated)
Table 1: Table of Physical Properties

Beverage (8 oz.) Caffeine (mg)

coffee 50 – 200 mg

decaffeinated coffee 1 – 5 mg

tea 30 to 75 mg

soft drink 20 – 50 mg

Table 2: common beverages and caffeine content

Experimental:

The solid/liquid phase was conducted first, using a beaker with (15mL) boiling water to extract
the caffeine from 2 tea bags. Additional quantities of water, totaling 20 mL of water, were
added to maintain the initial volume of water while evaporation occurred during boiling. As
previously discussed, 2 grams of sodium carbonate (NaCO3) was added to the boiling water to
help ensure the Caffeine would remain a free base when mixed with water and other
compounds in the tea leaves. NaCO3 neutralizes the slightly acidic ph. of the tannins
(containing phenol, a weak acid). After allowing the concentrated solution to cool to room
temperature, an ice bath was used to further cool the mixture in preparation for the
liquid/liquid extraction procedure.

A separatory funnel was used for the liquid/liquid phase of the extraction. It is important to
adequately grease the stop cock and joints of the funnel. 10mL of dichloromethane was added
to the funnel along with the mixture containing water and the caffeine and other extracted
contents from the tea bags. The funnel was shaken gently back and forth, three times, at
which point the building vapor pressure was expelled by inverting the funnel and opening the
stopcock. (a significant decrease in the boiling point of compounds is inversely proportionate
to vapor pressure). Shaking allows the caffeine the opportunity to leave the aqueous layer,
extracted into the organic, dichloromethane layer found at the bottom of the funnel due to its
density +.33 g/mol, that of water. After allowing the layers time to separate, the funnel was
slowly drained of the dichloromethane layer only (containing caffeine). The organic layer was
clear, and the inorganic layer a dark brown color. Vigorous shaking caused extreme amounts
of emulsions to be formed, as evidenced by a third, lighter brown layer wedged between the
aqueous and the organic layers. In order to the process of adding 10mL of solvent (CH2Cl2) was
repeated 7 times, as opposed to 2. Which each addition of 10mL solvent, the organic layer
was subsequently drained in an effort to extract the highest yield of caffeine possible. Each
extraction was added to a larger beaker. While the original lab called for 2 x 10mL extractions
with dichloromethane, Extractions are most effective when repeated several times with small
volumes of solvent rather than once with a large volume.
 After the liquid-liquid extraction the combine extracts contain very minute amounts of water,
so in order to thoroughly dry the mixture of all aqueous solvent, anhydrous magnesium
sulfate was added to the extracts until the powder persistently floated (as opposed to
clumping and sinking which denotes the presence of water in the sample). Using
gravity/vacuum filtration, the sample was washed two times, each with 2mL portions of
dichloromethane and allowed to evaporate to dry. Once completely dry of aqueous and
organic solvent the remnants, crude caffeine were transferred to weigh paper and the mass of
the extracted caffeine recorded.

Mass: filter paper + flask + crude caffeine 29.54g

Mass: filter paper + flask 29.47g

Mass of Crude Caffeine: 0.07g

** 1 tea bag contains 30-75 mg caffeine; average of 52.5 mg was used for actual value

2 𝑥 52.5 𝑚𝑔 (𝑚𝑒𝑎𝑛) = 105 𝑚𝑔 = 0.105 𝑔 𝑐𝑎𝑓𝑓𝑒𝑖𝑛𝑒 (𝑎𝑣𝑎𝑖𝑙𝑎𝑏𝑙𝑒 𝑓𝑜𝑟 𝑒𝑥𝑡𝑟𝑎𝑐𝑡𝑖𝑜𝑛)

.07𝑔
% 𝑦𝑖𝑒𝑙𝑑 𝑐𝑎𝑓𝑓𝑒𝑖𝑛𝑒 = 𝑥 100 = 66.66%
.105 𝑔

Discussion:

It was estimated based upon mean reported values, which the two tea bags used provided a
potential 0.105 g of caffeine available for extraction. The total volume of water was held at 15
mL throughout the extraction of caffeine from the tea bags. Considering a rate of 670 mg/mL
at boiling (100 °C), it is assumed that all of the 0.105 grams were extracted into the water.
Based upon these values, the percent yield was calculated to be 66.66% with 0.07 grams of
crude caffeine obtained. There were several factors in addition to standard human error that
are believed to have had an impact on the crude caffeine yields following extraction. During
the liquid/liquid phase of extraction, the separatory funnel was inadvertently shaken very
vigorously causing a thick layer of emulsion to form between the aqueous and organic layers.
In an attempt to recover as much available caffeine as possible, the original protocol of 2 x 10
mL of dichloromethane was increased to 7 x 10mL of dichloromethane, extracting the organic
layer each time. At completion of the 7th trial, there was still a heavy layer of emulsions,
indicating that there was still a large amount of caffeine that would not be available for
recovery.

The percent yield was performed based upon the total weight of one tea bag (2 g) multiplied
by the two tea bags used, however tea leaves are composed of many other compounds other
than caffeine (tannins, colored compounds and small amounts of chlorophyll). Consideration
of the 4 grams of tea leaves as the total mass of caffeine available for extraction is a
misrepresentation of the true amount; however information regarding the mass or
percentages of other compounds contained in a single tea bag were not available for use in
percent yield calculations.

In addition to the above, many protocols for caffeine extraction by this Macroscale method
indicate the crude caffeine residue should be left a number of days to ensure the sample is
completely dry. This laboratory called for recording of mass within the single lab period,
making it impossible to obtain a mass of a dry sample of crude caffeine. It is believed that
some of the recorded mass (0.07 g) consists of small amounts of undetected CH 2Cl2, remaining
in the sample.

This lab exercise successfully demonstrated both types of extractions, and allowed for visual
demonstration of organic methods for separation of two liquids in a mixture. In addition to
learning a fundamental concept needed in many types of chemical laboratories across vast
numbers of industries, this exercise offered many opportunities for application of several
concepts (of densities, polarities, boiling points, acid/base interactions, etc.) in the context of
a multiplayer, multifaceted framework. It is clear that not only are extraction techniques some
of the longest held chemical procedures known to scientists and non-scientists alike, but also
the true necessity and potential possibilities for extraction procedures.
Resources:

Macroscale and Microscale Organic Experiments, Williamson, K.L., 2nd Edition. D.C. Health and
Company

UC Davis Chem Wiki,

http://chemwiki.ucdavis.edu/Organic_Chemistry/Phenols/Phenols/Acidity_of_Phenols