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I. Introduction
The group used Biguerlai (Laxative) brand for caffeine extraction which has an
actual mass of 10.1640g from the 5 tea bags that we obtained. Essentially, caffeine is a
purine with three functional groups: an amine, amide, and an alkene. The basic property
of caffeine comes from the lone pair of electrons found around the nitrogen (Postu,
2013). A vacuum filtration is usually faster than a simple gravity filtration (Vacuum
Filtration, 2007) that’s why we used Buchner funnel. The solution was also cooled
before the dichloromethane was added because dichloromethane has a boiling point of
40°C. If the cold water was not added to lower the temperature, the dichloromethane
would have evaporated and caffeine would not be properly extracted (Postu, 2013).
Calcium hydroxide is added to the extraction medium to ensure that the acidic
components in the tea leaves remain water soluble and that caffeine is the free base.
Calcium hydroxide is basic. Tannins are acidic compounds with a high molecular weight
that have an –OH directly bound to an aromatic ring. Because tannins are acidic and can
be converted to phenolic salts by deprotonation of the –OH group when a base is added,
it is possible to separate the tannins from caffeine (Finchsigmate, 2015). Calcium
hydroxide serves two main functions: to place caffeine in a more basic environment so
that it has a higher affinity for dichloromethane and to cause the tannins to form phenolic
salts in the aqueous solution. Adding something basic to caffeine will make it more
neutral, and the “like dissolves like” idea can be applied. In this situation, the sodium
carbonate acts as a nucleophile and the tannin is an electrophile.
Liquid-liquid extraction of Caffeine
Caffeine's polarity is not high and solubility is low in water. Compounds which
are poorly miscible in organic solvents but highly miscible in water can be extracted
into organic compounds either by (1) repetitive extraction with a separatory funnel or
(2) by using a liquid-Liquid extractor. Extraction methods differ depending upon
the density of the solvent being used. Solvents more dense than water will require
different glassware vs. solvents that are less dense than water (Finchsigmate, 2015). In
the liquid-liquid extraction, an extracting solvent was mixed with the aqueous extract.
This solvent was dichloromethane which is a volatile, clear and organic compound. It
has a density of 1.325 g/m. It had chloro functional groups that make it susceptible to
both substitution and elimination reactions (Oneota, 2003). Two layers could be seen
in the funnel. The upper layer was brown colored while the lower was supposedly
colorless but our tea has coloring which made the bottom clear yellowish in color.
Caffeine is more soluble in dichloromethane than in water that is why caffeine
transferred from water to dichloromethane. Since the dichloromethane solution was
denser, it can be easily drained from the funnel by carefully controlling the stop cock.
To thoroughly extract the caffeine, the procedures in liquid-liquid extraction was done
thrice using the same amount of solvent which is 30 ml.
Washing and Drying of Caffeine Extract
A drying agent was added to the organic layer because dichloromethane
dissolved not only the caffeine, but water as well. The drying agent, anhydrous Na2SO4
was added to remove excess water so that a pure sample of caffeine could be obtained
after the solvent evaporated at room temperature (Williamson & Masters, 2007).
Anhydrous Na2SO4has a high affinity for water, and then reverses back to the hydrous
form after it has absorbed the water. Na2SO4 is a preferred drying agent because the
pellets form clumps when excess water is present that make it simple to identify how
much drying agent is needed.
Distillation to Separate Organic Solvent from Caffeine
During distillation, dichloromethane is the most suitable extraction solvent for
extraction of volatile components because of their weakly polar characteristics (Ming,
Li, & He, 2008). In this experimental, dichloromethane was used as extraction solvent
for distillation, due to its property of low combustion, and higher boiling point (40°C).
Caffeine was the final product. Overall, a total of 0.0347 g was obtained from
a possible amount of 10.1640g tea. The total percent recovery was 0.3414 %. This
number reflects on how erroneous the procedure was performed. Many sources of error
may have occurred such as an incorrect calibration of the scales with which the samples
were measured and not “washing” the solution thoroughly enough to obtain as much
sample as possible. It was not possible to obtain 100% recovery because the reaction
never goes 100 % to completion and because of material loss through transfer during
the procedure.
Use the Lipton brand of tea because it has no coloring and you can really see
the clear layer. Moreover, properly read the instructions because the group threw the
caffeine which will be used for the next laboratory experiment.
V. Answers to Questions/Calculations
1.) Discuss the role/s of the following in the isolation of caffeine:
a. Dichloromethane
Dichloromethane is used to extract caffeine from aqueous extract of tea
powder because caffeine is more soluble in dichloromethane (140mg/ml) than
it is in water (22mg/ml).The DCM- caffeine mixture can then be separated on
the basis of the different densities of dichloromethane and water because DCM
is much denser than water and insoluble in it (Amrita Edu, 2011).
3.) How efficient is the extraction of tea leaves containing 1.0 g of caffeine with 3 20-
mL portions of dichloromethane over that of a single step extraction?
It is efficient in order to obtain purity of the product – the recovered
caffeine residue.
4.) What are emulsions and why do they form during extractions? How are they
minimized and removed?
An emulsion is a mixture of two immiscible liquids. Chemically, they
are colloids where both phases are liquids. They are typically milky in appearance
and the suspended material may be colloidal in nature. When tannins are converted
to their salts, they become an ionic surfactant. These causes the materials that don’t
dissolve in water to form an emulsion with water. This emulsion can be minimized
reducing the energy input through slow and careful shaking and swirling of the
separatory funnel.
5.) Why is it necessary to remove the stopper from the separatory funnel when liquid
is being drained from it through the stopcock?
It is necessary to remove the stopper from a separatory funnel in order
for the liquid to continually flow out. Removing the stopper would release the
pressure so the liquid will flow continuously. When stopper is not removed, the
liquid will not drain out no matter how you manipulate the stopcock.
B. Distillation
Mass of Watch Glass 36.8642g
Mass of Watch Glass 36.8989g
with Caffeine Crystals
Mass of Caffeine 0.0347g
% Recovery 0.3414%
% recovery=(Mass of Caffeine/Mass of Tea) x 100%=(0.00347 g/ 10.1640 g) x 100% =0.3414 %
VI. References
Amrita Edu. (2011). Retrieved from Extraction of Caffeine from Tea: vlab.amrita.edu
Finchsigmate, K. (2015, September 29). Liquid-Liquid Extraction. Retrieved from
Libretexts.org:
http://chem.libretexts.org/Core/Analytical_Chemistry/Lab_Techniques/Liquid
-Liquid_Extraction
Gallardo-Williams, M. (2013). Extraction. Advanced Instructional Systems, Inc.
Ming, Z., Li, E., & He, H. (2008). Determination of volatile chemical constitutes in tea
by simultaneous distillation extraction, vacuum hydrodistillation and thermal
desorption. In Chromatographia (pp. 603-610).
Murray, D., & Hansen, P. (1995). In Chemistry.
Oneota, J. (2003). Isolation of Caffeine from Tea Leaves. Retrieved from
http://employees.oneonta.edu/
Postu, A. (2013, October 3). Isolation of Caffeine from Tea Leaves via Acid-Base
Liquid-Liquid Extraction. Retrieved from http://edspace.american.edu/:
http://edspace.american.edu/ap7794a/wp-
content/uploads/sites/159/2015/03/Isolation-of-Caffeine-from-Tea-Leaves-
via-Acid-Base-Liquid-Liquid-Extraction.pdf
Tea Fact Sheet. (2015). Retrieved from Tea Association of USA:
http://www.teausa.com/14655/tea-fact-sheet
The Columbia Electronic Encyclopedia. (2012). Columbia University Press.
Trimble, J. (2014). Isolation of Caffeine from Tea Leaves. Retrieved from Odinity:
http://www.odinity.com/isolation-of-caffeine-tea/
Vacuum Filtration. (2007, September 8). Retrieved from
http://www.chem.ucla.edu/~bacher/General/30BL/tips/vacuum.html
Williamson, K., & Masters, C. (2007). Macroscale and Microscale Organic
Experiments.