Isolation and Characterization of Eugenol From Cloves

DE LA SALLE UNIVERSITY-DASMARIAS
COLLEGE OF SCIENCE AND COMPUTER STUDIES

PHYSICAL SCIENCES DEPARTMENT
EXPERIMENT NO. 2
ISOLATION AND CHARACTERIZATION OF EUGENOL FROM CLOVES
SUBMITTED BY: GROUP 1
SUBMITTED TO:
MENDOZA, Mari Angelique V.

PANDILI, Jahzel Bless M.
Mr. Ricardo S. Causaren
SAPRID, Jamae A.
July 27, 2015
ZOLETA, Eunice Anne Q.
ISOLATION AND CHARACTERIZATION OF EUGENOL FROM CLOVES

ABSTRACT
Eugenol is an example of phenylpropanoid, which is a natural product, that is

present as major component of clove oil. In this experiment, eugenol was
isolated from cloves. Two methods of isolation were performed in this
activity. The first method was the steam distillation of clove oil. The
temperature of volatilization of eugenol was 98C in this experiment, lower
than its actual boiling point which is 254C. A total of 25mL distillate was
collected. The second method used was the hexane extraction to further
isolate eugenol from its other components, eugenol acetate and
caryophyllene. The isolated eugenol underwent two qualitative tests, Bayers
and Ferric chloride test. In reaction to KMnO 4, the extract exhibited a purple
turned to brown color. In reaction to FeCl 3, the extract exhibited a yellow
turned to orange color.
INTRODUCTION
Eugenol is a member of phenylpropanoid class which is synthesized

from amino acid phenylalanine in many aromatic plants. It is a colorless to
pale yellow oily liquid extracted from certain essential oils especially from
clove oil. It is made up of C=C (double bond, alkene) and an aromatic
hydroxyl group, phenol.
Research shows that it offers health benefits to the human body as
well. Cloves or eugenol is commonly used by dentists because it is antiseptic
and anti-inflammatory. They often apply it to the gums to kill germs and
relieve the pain of dental surgery such as tooth extractions, fillings, and root
canals.
In this experiment the students will perform steam distillation a
classic method of separation process for temperature sensitive materials like
natural aromatic compounds like cloves, where oil can be isolated with lower
temperature than the actual boiling point of the two components. Moreover,
Chemically Active Extraction was done, wherein acidic property will be
isolated from minor constituents.
MATERIALS AND METHODS

MATERIALS
Distilling flask (250ml)
Condenser
Erlenmeyer flask (250ml)
Filtration funnel
Graduated cylinder (50m) Watch glass
Separatory funnel (250ml) Red litmus paper
Test tubes
Ice bath
Clamps
Filter paper
Rubber tubing
Iron ring
Adaptor
Spatula
REAGENTS
Ground cloves
Distilled water
Hexane
NaOH (10% w/v)
HCl (6.00 M)
Anhydrous Na2SO4
NaCl
1% FeCl3
Bayers Reagent
First, 5.00g of ground cloves were weighed on a watch glass and transferred
onto a 250mL distilling flask. Then, 75 mL of distilled water was added and mixed. The
distillation apparatus was assembled for steam distillation and stirred motor below the
heating Bunsen burner. Water supply was added into the distillation apparatus and
every now and then the temperature was recorded. A total of 25ml distillate was
collected from the distillation process; the temperature was recorded every 5mL of
collected liquid.
In the second part of the experiment, the collected distillate was transferred into a
250mL Erlenmeyer flask and cooled in an ice bath. Then, it was transferred into a 250mL separatory funnel.
After that, 25mL of C6H14 (Hexane) was added to the extract where occasional
shaking and venting was made to release the pressure. After a few minutes, 2 layers
were formed. The aqueous layer was drained and discarded.
Then, 25mL of NaOH was added, with the same procedure done to the Hexane
only that the organic layer was discarded and the aqueous solution was kept. The same
procedure was repeated after the solution was cooled in an ice bath and acidified with 6
M HCl.
After that, the aqueous layer was drained and discarded. A small amount of
Anhydrous Na2SO4 was added and swirled to the hexane extract. Then, after swirling a
couple of minutes, the hexane extract was filtered into a clean flask. Lastly, 10 drops of
the final extract was placed into two separate test tubes and was tested with Bayers
Test and Ferric Chloride test.
RESULTS AND DISCUSSION
A. Yield of Eugenol
Mass of Ground Clove:

Color Reaction of Eugenol with 1% FeCl3
Color Reaction of Eugenol with Bayers Reagent
5.00 mg
Yellow to Orange
Purple to Brown
B. Distillation Curve
Temperature in Degrees Celsius

120
100
80
Temerature C
Temperature in
Degrees Celsius
60
40
20
0
0
10 15 20 25
Volume (mL)
The temperature of volatilization of eugenol is almost but not higher

than 100C. The actual boiling point of eugenol is 254C, making the
temperature of volatilization much lower than its boiling point. With the use
of steam distillation distilling eugenol at a very high temperature can be
avoided as its temperature of volatilization is 98C in this experiment.
The hexane extract turned from yellow to orange when added with
ferric chloride. This shows that phenol is present as the ferric chloride test is
used to determine the presence of phenols in compound when change in
color happens.
Consequently, the extract turned from purple to brown when added
with Bayers reagent. This proves that alkyne structures, double bonds or
aromatic hydrocarbons are present as Bayers test is used to these.
Hexane was used as the solvent because of its organic and non-polar
characteristic.
In addition, to isolate eugenol, sodium hydroxide was introduced to
convert eugenol to form a sodium salt. When the sodium salt was dissolved
in the aqueous layer, eugenol was separated from the organic layer. For the
aqueous layer, hydrochloric acid was introduced to protonate sodium salt to
form eugenol. A cloudy solution was formed during the addition of
hydrochloric acid. This is because the eugenol formed from the acidification
did not dissolve in the aqueous layer. Finally, eugenol was extracted and the
organic solvent was removed.
A small amount of magnesium sulfate anhydrous, dries and removes
all the water in the organic layer.
CONCLUSION
Eugenol and other neutral products from cloves were successfully

isolated from cloves through the use of steam distillation and solvent
extraction. The experiment also shows that Eugenol has an aromatic
compound because of the reaction it made when mixed with Ferric chloride.
The solution was also positive in the Bayers test which shows that it has a
double or triple bond in the solution.
REFERENCES:
(1)
Lynn, A. (2013). Isolation and Characterization of Eugenol From
Cloves. Scribd. Retrieved July 25, 2015, 12:21pm from
http://www.scribd.com/doc/124637481/Isolation-andCharacterization-of-Eugenol-From-Cloves#scribd
(2)
Rivera, M. (2012). Isolation and Characterization of Eugenol
From Cloves. Scribd. Retrieved July 25, 2015, 12:54pm from
http://www.scribd.com/doc/116032778/isolation-andcharacterization-of-eugenol-from-cloves#scribd
(3)
Bayers reagent. Wikipedia The Free Encyclopedia. Retrieved July
25, 2015 1:10pm from
https://en.wikipedia.org/wiki/Baeyer%27s_reagent

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DE LA SALLE UNIVERSITY-DASMARIAS

COLLEGE OF SCIENCE AND COMPUTER STUDIES

SUBMITTED BY: GROUP 1

MENDOZA, Mari Angelique V.

Mr. Ricardo S. Causaren

July 27, 2015

ZOLETA, Eunice Anne Q.

ISOLATION AND CHARACTERIZATION OF EUGENOL FROM CLOVES

Eugenol is an example of phenylpropanoid, which is a natural product, that is

Eugenol is a member of phenylpropanoid class which is synthesized

MATERIALS AND METHODS

RESULTS AND DISCUSSION

Mass of Ground Clove:

Temperature in Degrees Celsius

The temperature of volatilization of eugenol is almost but not higher

Eugenol and other neutral products from cloves were successfully

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