EXTRACTION AND PURIFICATION OF CAFFEINE

J.V. DE GUZMAN
DEPARTMENT OF CHEMICAL ENGINEERING, COLLEGE OF ENGINEERING
UNIVERSITY OF THE PHILIPPINES, DILIMAN QUEZON CITY, PHILIPPINES
DATE PERFORMED: FEBRUARY 4, 2015
INSTRUCTORS NAME: ALLAN KENNETH REGUNTON

REASONS WHY CAFFEINE WAS NOT EXTRACTED FROM

COFFEE:
Given that coffee contains many organic compounds, caffeine must
have reacted with these organic compounds most likely, organic acids, when
it is shake vigorously. As such, no caffeine was extracted even after the
addition of sodium hydroxide since it is already not in its free base form.
Another factor is that, some coffee aqueous layer had slipped down on the
receiving flask during first extraction with dichloromethane and the present
compounds in this portion of aqueous layer may have hindered the
separation of organic and aqueous layer during addition of sodium
hydroxide.

ANSWERS TO QUESTIONS
1. What is the purpose of washing the organic layer with 6 M
NaOH?
Caffeine is a naturally occurring alkaloid found in coffee beans
and tea leaves. It contains basic nitrogen and exhibits properties of
organic amine bases. As such, sodium hydroxide which is a strong base
was used to wash the organic layer in order to make sure that caffeine
remains in the base form and prevents it from reacting or being
neutralize with organic acids also present in coffee. If acid-base
neutralization occurs, caffeine will not be isolated from the coffee or
tea.
2. Compare the solid products obtained after extraction and after
purification. Account for the difference between the two solids.
After extraction, the product obtained called crude caffeine is
brownish white in appearance implying the presence of impurities.
These impurities are usually organic compounds found in coffee or tea
such as chlorophyll. It also has a distinct grass-like smell. After the
crude product was sublimed, the purified caffeine becomes a whiter
crystalline solid showing that impurities are removed.
3. What are the other applications of solvent extraction?
Solvent extraction is a liquid-liquid extraction technique in which

the original mixture containing the solute of interest is allowed in

contact with a solvent that is partially or totally immiscible with the
original solution. It is used as an extraction technique to obtain solutes
from complex solutions like caffeine isolation from coffee and tea but
other applications holds significance in petroleum, pharmaceutical and
metallurgic industries. This includes metal extraction from metal-ore
leach solution like copper, tantalum, hafnium, thorium and uranium.
For petroleum industry, solvent extraction is used to produce paraffin
and naphthalene from the crude petroleum distillate; aromatic
hydrocarbons from gasoline, kerosene fractions and catalytic
reformates; wax and asphalt from heavy crude residuum. In
pharmaceutical, it is used to extract penicillin from its fermentation
broth and bacitracin from soya bean fermented meal. It is also used to
remove high boiling organics from waste water.
4. What are the different phase changes that occur during
purification using sublimation?
The solid caffeine found in the crude product was change into a
gaseous phase through sublimation while the impurities were left in
the solid state. When the gaseous caffeine touches the filter paper
having a lower temperature, they were deposited their as a solid, pure
caffeine. As such, the phase changes that occur during purification are
sublimation then deposition of caffeine.
5. Give two advantages of sublimation over recrystallization as a
purification technique.
a. Minimized loss of product-Sublimation is preferred as a micro scale
purification technique over recrystallization since product loss is
minimized. The product to be purified is simply kept on a beaker
placed in a hot oil bath to sublime and thus material is less likely to
be loss in the process unlike in the recrystallization technique where
the material can be loss during transferring and filtration process. It
also doesnt depend on the solubility of the desired compound with
the solvent such that loss of material during dissolution is also
prevented. As such, sublimation gives a higher percent recovery of
product of interest.
b. Traces of solvents are less likely found in the product-Since
sublimation doesnt involve the use of solvents unlike
recrystallization, products are less likely to be contaminated with
adhering mother liquor and solvent traces that can be occluded and
trapped in the formed crystals or precipitates. Thus, sublimation
provides a purer yield compared to recrystallization.
6. Give at least two limitations of sublimation as a purification
technique.
a. Substance to be purified must be less than 100 mg (microscale
level only) - Since sublimation usually involves high temperature
phase change; it only applies as a purification technique at a micro

scale level since above 100 mg, higher temperature is needed in

order to sublime and purify the entire sample making it
inconvenient to use. At a macro scale level, recrystallization is much
preferred as a purification technique.
b. Substance to be purified must possess the appropriate propertiesSublimation as a purification technique mostly depends on the
vapor pressures of the substance constituents- not only the
compound of interest but also of the impurities present in the crude
product. As such, the properties of both the desired compound and
the impurities must agree with each other: the compound of interest
must have a relatively high vapor pressure than the impurities or
vice-versa. Sublimation is problematic to use as a purification
technique when the impurities and the desired compound have the
same vapor pressure.
REFERENCES:
Portland Community College. Extraction of Caffeine from Tea Leaves.
[Online].
2014.
http://spot.pcc.edu/~chandy/241/CaffeineExtractionCH2CCl2.pdf
(accessed February 9, 2015)
Ali, N. Applications of Solvent Extraction: A Summary. Universiti Teknologi
Malaysia [Online]. 1991. http://eprints.utm.my/4501/ (accessed
February 9, 2015)
University of Toronto Scarborough. Sublimation Theory. Chemistry Online
UTSC.
[Online].
2014.
http://webapps.utsc.utoronto.ca/chemistryonline/sublimation.php
(accessed February 15, 2015)
Pedersen, S and Myers, A. Understanding the Principles of Organic Chemistry:
A Laboratory Course. Chapter 7: Isolation and Purification of Organic
Compounds. Brooks/Cole: California, 2010 pp 110-111.