Exercise no.

SUBLIMATION OF CRUDE CAFFEINE

Valerie Mae L. Areño September 9, 2019

Monday 7-10AM September 16,

2019

OBJECTIVES

1. Use sublimation method to purify an organic compound.

2. Determine the percent recovery of the purified caffeine.

INTRODUCTION

Sublimation is a process used to isolate a natural product from other undesired compounds, and
then purify it by a direct phase change of that product from a solid to a vapor. Most substances
under normal conditions of atmospheric pressure will change phases with an increase in
temperature from a solid, to a liquid, and to a gas, while other compounds such as, iodine and
carbon dioxide will undergo sublimation at this temperature and pressure of a system, we can
induce this sort of change in a crude caffeine. Crude caffeine is extracted from coffee/tea, and
it contains many impurities that may have been separated with it, such as, tannic acids
(carboxylic acid that contains constituents). Unlike pure caffeine that has a lower boiling point
than the rest of the impurities that makes it crude.

DISCUSSION

Preparing a petri dish with a crude caffeine (0.30 g) inside it, and cover with a filter paper.
Placing it in a hotplate with a temperature of 250-350 ̊C with a beaker the contains cold iced
water on top of the petri dish. As it is placed in the hotplate, observe the crude caffeine
evaporating through the air and is sticking to the filter paper. Turn off the hotplate if there
won’t be any crude caffeine left at the bottom of the petri dish. Remove the cover slowly so
that there won’t be any particles from the filter paper that would be flown on the air or any
areas of the glassware. And notice the crystal like white color, which was the sublimed caffeine.
QUESTIONS

1. Which of the three compounds would most likely be amenable to purification by

sublimation: polyethylene, menthol, or benzoic acid?
2. A solid compound has a vapor pressure of 65 mmHg at its melting point of 112 ̊C. Give
a procedure for purifying this compound by sublimation.
3. Hexachloroethane has a vapor pressure of 780 mmHg at its melting point of 186 ̊C.
Describe how the solid would behave while carrying out melting-point determination
at atmospheric pressure (760 mmHg) in a capillary tube open at the top.

ANSWERS

1. The purification of solid substances at low vapor pressure takes place by sublimation
process, then the solid compounds with more melting point and low vapor pressure can
be purified easily by sublimation than liquids. Benzoic acid is liquid at a room
temperature, so it can purify by recrystallization procedure but menthol and
polyethylene are in solid state at room temperature. So menthol and polyethylene have
high melting point at a room temperature. So, the purification of the polymers by
sublimation is most amenable. Hence, the purification of polyethylene by sublimation
is the most amendable.

2. The vapor pressure of a solid compound is the pressure characteristic at any given
temperature of a vapor in equilibrium with its liquid or solid form. Vapor pressure is a
measure of the ability of a compound to bond with itself; compound molecules that
bond well with each other will have a low vapor pressure (less tendency to escape to
the vapor phase), while poorly bonding compounds will have a high vapor pressure.
Certain solid substances like Naphthalene or camphor when heated pass directly from
solid to the vapor state without melting. The vapors when cooled give back the solid
substance. This process is known as sublimation. This process is very helpful in
separating a volatile solid from a non-volatile solid. The powdered substance is taken
in a China dish and covered with a perforated filter paper and an inverted funnel. The
dish is carefully heated on a sand bath. The vapors passing through the holes in the
paper condense on the inner sides of the funnel. The non-volatile impurities remain in
 the dish. Need for purification of organic compounds. The organic compounds obtained
from natural sources are not pure. They contain a number of other compounds which
occur with them. Similarly, the organic compounds prepared in the laboratory are also
not pure. They are found to contain other products formed during the reaction. In order
to investigate the structure and properties of an organic compound, it should be in the
purest form. Hence purification of organic compounds become essential. Various
methods used for purification and separation of organic compounds
are: Crystallization; Fractional Crystallization; Sublimation; Distillation; Extraction
with solvents; Chromatography

3. The solid would behave while carrying out melting-point determination at atmospheric
pressure (760 mmHg) in a capillary tube open at the top would sublime before it melts.

RESULTS AND OBSERVATION

1. Weight of the crude caffeine = 0.30 g

2. Weight of paper + sublimed caffeine = 1.28 g

Weight of paper = 0.68 g
Weight of sublimed caffeine = 0.60 g

3. % Recovery
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑐𝑟𝑢𝑑𝑒 𝑐𝑎𝑓𝑓𝑒𝑖𝑛𝑒
= × 100%
𝑚𝑎𝑠𝑠 𝑜𝑓 𝑠𝑢𝑏𝑙𝑖𝑚𝑒𝑑 𝑐𝑎𝑓𝑓𝑒𝑖𝑛𝑒
0.30 𝑔
= × 100%
0.69 𝑔

= 44.12 %

4. Color of caffeine = Crystalline white

CONCLUSION

Sublimation is a process which must be completed in a very specific order. In addition to its
three main steps of the set-up, sublimation, and retrieval, many small factors may determine
how much product has been obtained, and how well it has been purified. In this type of
experiment, the powdered caffeine evaporated due to the heat of the hotplate and stocked on
the filter paper which is in the cover with the help of the cold water stacked on it. By this
method, cold apparatus is a vacuum or magnet to crude caffeines.

REFERENCES

 Palleros, D. R. “Extraction and Isolation of Caffeine from Tea Leaves,” Experimental

Organic Chemistry, 2000. Wiley: New York.
 11thh Standard Class. Organic Inorganic Physical Chemistry Higher Secondary
College Notes. https://www.brainkart.com/article/Methods-for-the-purification-of-
liquids-Distillation_2800/
 Johnson A.. Sublimation of Caffeine. Ravindu Nanayakkara. Section 40. October
2017. https://www.coursehero.com/file/26545141/Sublimation-of-Caffeine-Lab-
Reportdocx/