Mike Baldwin

Gabrielle Pros and Brandon Vernier

Chem 228L-1
15 October 2015
Identifying Eugenol in the Essential Oil of Cloves
Steam Distillation, Liquid-Liquid Extraction, IR Spectrometry
Purpose:
The primary objective of this lab was to identify the major component of clove oil by
infrared spectroscopy. The major component was isolated via steam distillation and liquid-liquid
extraction.
Background:
Cloves are a spice produced from the dried flowers of a tropical evergreen tree. While
cloves are delicious in foods, the essential oil is highly useful for medicinal usage. The essential
oil of a plant is a collection of organic compounds that commonly contain the scent and
characteristics of the plant. Many other essential oils are comprised of several major
components, but clove oil only has one major component. This component can be isolated
through the use of several procedures.
In order to attain the major component of the essential oil of cloves, three separate
techniques were used: steam distillation, liquid-liquid extraction, and infrared spectrometry.
Steam distillation is the process of extracting a desired oil from some starting material. The
starting material and water are heated until the water boils, generating steam. As the materials
heat they release the oil into the boiling water. The steam carries some of the oil into the air,
where it is condensed in a cooled tube and collected for further testing.
Liquid-liquid extraction is the process of adding two immiscible liquids to each other in
order to create an organic layer and an aqueous layer. The desire is to isolate some product into
one layer and discard of the other. The separatory funnel is used for such an extraction, while
allowing venting for the buildup of gas that occurs from the reactions of the liquids. The liquidliquid extraction of essential oils results in an organic layer and an aqueous layer, one with all
the polar molecules in the aqueous layer and all the non-polar compounds in the organic layer.
Infrared spectrometry is the process of viewing the stretching and bending of functional
groups under an infrared beam. IR spectrometry is not often used as a tool to build an unknown
compound, but to confirm the presence of functional groups in a compound. In this lab, the IR
spectrometry was used to choose one of six given compounds as the major component of clove
oil.
Chemical Hazards:

Baldwin 2
Dichloromethane

Severe eye and skin irritant. Hazardous to

inhale or ingest. May cause headaches if
inhaled. Long-term inhalation could lead to

Clove Oil

cancer.
Severe eye and skin irritant. Hazardous to

3.0 M HCl
1.0 M NaOH

inhale or ingest.
Severe skin and eye irritant.
Severe skin and eye irritant. Avoid inhalation.

Procedure:
Materials:
Ring Stand
Separatory Funnel with frosted glass tip
500 mL boiling flask
Sand bath
Rubber tubing
Clamps
West Condenser
Steam cone
Ground cloves
Glass stir rod
Procedure for Isolation of Clove Oil

Stemless funnel
50 mL beaker
250 mL Erlenmeyer flask
100 mL graduated cylinder
Boiling stick
3.0 M HCl
1.0 M NaOH
Blue litmus paper
Infrared spectrometer
10 mL graduated cylinder

1. The distillation apparatus was assembled as seen in Fig. 1.

2. After massing, the ground cloves and 50 mL of DI water were mixed in a 500 mL round
bottom

Fig. 1
Created by Marvene Cribbs

boiling flask.

Baldwin 3
3. The round bottom flask was placed into the apparatus depicted in Fig. 1. The flask was
then heated in the sand bath until boiling. The water from the separatory funnel was let
into the flask at a slow rate, ~45drops/minute. The oil was distilled for about an hour.
4. The collected distillate was then covered with multiple layers of parafilm and left in a
drawer for a week.
5. The distillate was poured into a 250 mL separatory funnel. The funnel was set up with a
ring stand and clamp such that the funnel drained into a 125 mL Erlenmeyer flask.
6. Two 20 mL aliquots of dichloromethane were used for the first two liquid-liquid exactions.
The aqueous layer was discarded, while the organic layer was put back into the
separatory funnel. (The bottom layer was organic).
7. Two 15 mL aliquots of 1M NaOH were used to extract two aqueous layers from the
organic layer acquired in step 6. The resulting solution was acidified by using ~9 mL of
3M HCl.
8. The acidified solution was put through liquid-liquid extraction using two 15 portions of
dichloromethane. The organic layer was saved.
9. Anhydrous Na2SO4 was added to the organic layer until it stopped clumping when
swirled.
10. The solution was then decanted into a previously massed 150 mL beaker and boiled via
steam cone, with a boiling stick. The solution was boiled until a small amount of clear
yellow liquid remained.
11. The beaker was massed with the liquid and then allowed to sit for a few minutes
uncovered. The beaker was massed and allowed to sit out again. This was repeated
until the mass was approximately constant.
12. IR spectroscopy was preformed on the yellow solution.
Discussion and Results:
Results:Calculations:
Experimental yield

Mass of beakeroilmass of beaker =mass of oil

66.257 g66.139 g=0.118 g
Theoretical yield

( 85 ) Mass of cloves=theoretical yield

( 0.85 ) 5.00 g=4.25 g

Percent yield

experimental yield
100= Yield
theoretical yield

Baldwin 4
0.118 g
100=2.8
4.25 g
Discussion:
In this lab, cloves had their essential oil extracted using steam distillation. The distillate
was a milky white opaque liquid. The distillate was then put through liquid-liquid extraction
several times over. The initial extraction used CH2Cl2 to separate the extra water from the steam
distillation from the desired organic compounds. The next extraction used 1.0 M NaOH to
deprotonate the major component and isolate it to the aqueous layer. HCl was used to
reprotonate the compound, and CH2Cl2 was used again to isolate the major compound into an
organic layer. The boiling off of any CH2Cl2 yielded a small amount of clear yellow liquid. This
was assumed to be almost purely the major component of clove oil.
The primary component of clove oil was then analyzed using infrared spectroscopy.
The resulting spectrum can be seen in Graph 1. The peaks at 3520.5 cm-1 are consistent with
that of an OH group. The presence of only one strong broad peak at approximately 3500 cm-1,
and no complimentary peak around 1750 cm-1, is indicative of an alcohol group rather than a
carboxyl group. Two sets of strong twin peaks at 1265-1231 cm-1 and 1265-1231 cm-1 are
indicative of two C-O bonds. This indicates the isolated molecule has an alcohol group, two C-O
bonds, and no C=O bonds.
The beaker and essential oil were massed to ascertain the percent yield. The dry beaker
was massed and the difference was taken to find how much of the oil was left. The theoretical
yield was predicted by taking 85% of the mass of cloves. This was based off of the prelab that
stated clove oil had one component that comprised 85% of its essential oil. The actual yield was
significantly lower, only 2.8%. This is most likely due to the early stopping of the distillation. Due
to time constraints, only 50 mL of distillate was obtained, leaving a majority of the clove and
water solution undistilled.
There are several sources of error in this lab that could have affected the yield and the
spectrometry. The first and greatest source of error stems from the time constraints of lab only
allowing 50 mL of solution to be distilled. The distillate was left in a drawer for a week, although
covered in parafilm, which invites the possibility of loss of liquid due to evaporation. The lowered
volume and insufficient time would significantly lower the yield, explaining the 82% difference in
theoretical and actual yield. The boiling step is also a source of error because the solution could
be boiled for too long or too short time. If the solution was boiled for too long, the product may
begin to evaporate and boil off with the dichloromethane. If the solution is not boiled for a

Baldwin 5
sufficient amount of time, the remaining dichloromethane could potentially interfere with the IR
spectrometry.
Questions:
1. The common name of the primary component of clove oil is eugenol. This was found
online at pubchem.ncbi.nlm.nih.gov, by referencing the IUPAC name 4-Allyl-2methoxyphenol.
2.
a. The alcohol group on the eugenol is what allows the major component of clove oil to
be separated from the minor. This was accomplished through the deprotonation via
NaOH. The deprotonation allowed the eugenol to become water soluble, while the
minor components remained in the organic layer. After the separation using the
NaOH, the eugenol was reprotonated via the HCl. The presence of an alcohol group
on one of the carbons in eugenol is consistent with the theory of deprotonation and
reprotonation.
b.
i.
ii.

NaOH +C10 H 12 O2 C10 H 11 O2 Na+ H 2 O

HCl+C10 H 11 O 2 Na C10 H 12 O2+ NaCl

3.
a.
b.

The reason the major component increases during steam distillation is that both

Fig. 2
water and heat are

provided to the minor compound. Water and

heat are the two components necessary for hydrolysis, and the minor compound

4.

hydrolyzes into eugenol and acetic acid.

C12 H 14 O3 + H 2 O+ Heat C10 H 12 O2+C 2 H 4 O2
i.
Eugenol and the cloves are a very green part of this experiment, as both exist in nature
and do not harm the environment. In comparison, dichloromethane is very
environmentally hazardous. In water, it is mildly toxic, while in the air it can be inhaled by
organic creatures. In organic beings dichloromethane deprives the body of oxygen and
is a known carcinogen.

5.

Baldwin 6
a. A possible effect of stopping the steam distillation too early is that there is not enough
of the major component to analyze. The lesser amount of distillate also leads to a
lower percent yield. This is not as large of a concern, as it occurred in the lab and an
IR spectroscopy was successfully run.
b. If the boiling flask contains residual amounts of sodium hydroxide, some of the
eugenol will be deprotonated too early and become water-soluble. If this occurs,
some or all of the product will be dissolved in the aqueous layer that gets thrown out
in the first liquid-liquid extraction. The lowered amount of product could impact the
analysis by not having enough of the eugenol to put through the IR spectroscopy.
c. If the dichloromethane is not boiled off for long enough it will affect the IR
spectroscopy because of the extra molecules. There will be some peaks over
emphasized and other peaks will be underemphasized.

6.
a.
Fig. 3

b. Caryophyllene is the common name of the compound according to The Merck Index.
Conclusion:
In this lab the major component of the essential oil of clove was isolated and identified.
Through steam distillation and liquid-liquid extraction the compound of was isolated. The
isolated product was then put through IR spectrometry. The resulting peaks indicated the
presence of an alcohol group, two carbon oxygen single bonds, and no carbon oxygen double

Baldwin 7
bonds. The compound found to have fit these criteria was 4-Allyl-2-methoxyphenol, more
commonly known as eugenol. Eugenol fits the criteria not only because of its matching
functional groups to the spectrometry, but also because its alcohol group would respond
appropriately to the deprotonation and reprotonation during the liquid-liquid extraction.
Furthermore, eugenols alcohol group allows it a location to easily add an acetic acid group via
hydrolysis. Though a low yield was obtained, the lab was a success as the major component of
clove oil was isolated and identified.

Improvements:
There are two major improvements to be made to this lab. The first is the availability of
more time, so that the distillation can fully run and more of the eugenol can be extracted. The
second improvement would be to use a more environmentally friendly solvent than
dichloromethane to extract the eugenol. Ethyl acetate is a solvent that is immiscible with water
and has fewer environmental impacts than dichloromethane.
References:
National Pollutant Inventory. Ethyl acetate. http://www.npi.gov.au/resource/ethyl-acetate
(accessed October 14, 2015).
PubChem. Eugenol. https://pubchem.ncbi.nlm.nih.gov/compound/3314#section=Top (accessed
October 13, 2015).
PubChem. Dichloromethane. https://pubchem.ncbi.nlm.nih.gov/compound/dichloromethane
(accessed October 7, 2015).
PubChem. HCl. https://pubchem.ncbi.nlm.nih.gov/compound/hydrochloric_acid (accessed
October 7, 2015).
PubChem. NaOH. https://pubchem.ncbi.nlm.nih.gov/compound/sodium_hydroxide (accessed
October 7, 2015).
Sigma Aldrich. Euganol Acetate. http://www.sigmaaldrich.com/catalog/product/aldrich/w246905?
lang=en&region=US (accessed October 13, 2015).
Wikipedia. Caryophyllene. https://en.wikipedia.org/wiki/Caryophyllene (accessed October 13,
2015).