ISOLATION OF EUGENOL

IV. DISCUSSION
Isolation of eugenol from Eugenia aromatica, also known as
the clove, highly revolves around the use of steam distillation to
separate the different components of the clove from each other to
be able to isolate the eugenol oil present. Around 80-95% of the oil
found in cloves is eugenol, with eugenol having three main
functional groups in its structure: phenol, ether, and alkene, as seen
below.
(EUGENOL STRUCTURE)
Eugenol is not the only component in cloves, since it also contains
beta-caryophyllene, acetyl eugenol, and vanillin. (Hema, 2010) To
separate these oils from the solid cloves, the diluted clove leaves
were heated until boiling occurred. Boiling occurs when the
barometric pressure or the vapor pressure of the liquid is already
equal with the pressure of the gas above it. (Goldberg, 1988)
Meaning, using steam distillation, volatile components can be
separated from the other non-volatile components of a substance by
heating them to its boiling point to turn it into vapor. The steam
distillation setup brings the vapor upwards to lead it through the
condenser, where cold water is running around its sides, to turn the
vapor back into its liquid state. Eugenol, along with betacaryophyllene and acetyl eugenol, is easily vaporized, given their
boiling point is around 250-280 degrees Celsius, and the oil was
collected using separatory funnel to commence liquid-liquid
extraction for the separation of eugenol from the other components
of clove oil. The distillate is not completely pure, given that there
were oils included other than eugenol, so dichloromethane was
added to the distillate after standing to dissolve the organic layer,
creating two layers from the previous cloudy/turbid white distillate.
It was extracted twice, discarding the combined aqueous layers
since it only contained water and the organic layer contained the
three oils. After combining the obtained organic layers, it was then
extracted with 10% NaOH to separate eugenol from the other oils.
Eugenol, when added with an alkaline solution, is deprotonated to
give a phenoxide ion. (strc uture) Phenoxide ions are more soluble in
water than phenols in eugenol because of the non-bonding electrons
on the oxygen, which can be sites of bonding with water molecules.
Extraction is done thrice this time, to ensure total extraction of the
water-soluble eugenol from the other oils. Since the aqueous layer
contains the eugenol, the organic layer is then saved for later
characterization and as much as possible, it should not have even
trace amounts of eugenol in it and only caryophyllenes and
acetyleugenol should be present.
After being able to obtain the aqueous layer, it was washed again
once with dichloromethane to ensure organic anez deprotonated
The aqueous layer is acidified with concentrated HCl (to pH1) to
convert it back to its nonpolar form. Since it still ahs water,

dichloromethane is added to separate the water from the thenorganic eugenol, which composes the organic layer. Aqueous layers
combined were then discarded while the organic layer washed with
distilled H2O and NaCl was added to salt out
Salting out is done to further separate the remaining atmounf of
water remaining and it was dried over MgSo4 to remove the last
amounts of water to obtain a pure eugenol oil that is of the pale
yellow color.
Percent oil etc etc
Eugenol contains a carboncarbon double bond and an aromatic
hydroxyl group called a phenol. These functional groups provide the
basis for simple chemical tests used to characterize the clove oil.
Eugenols structure contain a phenol, which is then used for
characterization. Phenols (ArOH) (structure) react with the Fe3+ ion
in iron(III) chloride (FeCl3) to give complexes that are blue, green,
red, or purple, as shown in Equation 5. The color may last for only a
few seconds or for many hours, depending on the stability of the
complex. On the other hand, characterizing the saved organic layer
should have yielded a result where the organic layer is retained
(along with its characteristics) since it should not have had any
eugenol present in it. A small percentage of eugenol in it would
make a big difference, since the dark complex would somehow form
in the solution.
Goldberg, David E. (1988). 3,000 Solved Problems in Chemistry (1st
ed.). McGraw-Hill. section 17.43, p. 321
http://www.motherearthliving.com/plant-profile/eugenol.aspx
C. Leigh Broadhurst, Ph.D. and James A. Duke, Ph.D.
May/June 1997
www.sciencepub.net/researcher/.../01_4123research0212_1_4.pd
Hema R., 1S. Kumaravel, 2Sivasubramanian C.
GC-MS Study On The Potentials Of Syzygium aromaticum
1

Steam distillation is a co-distillation technique that uses live steam

to separate components of a mixture. It is effective at extracting
high boiling-point components of essential oils, where boiling points
are as high as 200C. Yet the oil vapors themselves are closer to
100C, thus helping to preserve the structural integrity of the
compounds. It allows distillation to be performed at temperatures
below the boiling points of the individual components. Indirect
steam distillation is a technique used for generating steam in situ,
where the water level is kept below the plant material.
Co-distillation is distillation of components of a mixture that are
immiscible with water. Steam vaporizes the high-boiling essential
oils and the hot vapors condense back into a liquid, along with

water, as they pass through a cooling system. Since the oils are
immiscible in water a two- phase distillate is produced, a water layer
and an oil layer. The oil is usually less dense and floats atop the
water. The aqueous layer can then be siphoned off using a
separatory funnel. If an emulsion develops, as is often the case in
small-scale distillation, the immiscibility of the hydrophobic oil
makes extraction and isolation of the product with a non-polar
organic solvent highly effective.