Organic Chemistry

Du Preez, BJ, Mnr

18387918

8/4/2017
 The extraction of eugenol from cloves using steam distillation

du Preez, Brannigan 18387918 BScAgric Oenology (Specialised)

Organic Chemistry de Beers - Room 2017

Friday, 8 August 2017

Introduction

Aromatic compounds present in leaves and flowers have been widely used since ancient times for their
health benefits in addition to their pleasant odour. Various compounds have been extracted from spices, herbs,
flowers and fruit, owning to the aforementioned properties. An example of this are cloves, which are the dried
flower buds of Syzygium aromaticum (L.) Merr. et Perry, a tree of the family Myrtaceae.

Cloves derive from the Maluku Islands in Indonesia and are often used for their antioxidative and antibacterial
properties, with its use commonly observed to fight oral bacteria. In addition, sesquiterpenes, which are often
found naturally in both plants and insects, are also found in cloves and are known for its potential anti-
carcinogenic properties.

Eugenol, with the molecular formula C10 H12 O2 , is one of the main aromatic constituents in cloves and are a
reported to possess antioxidant properties. As a natural antioxidant, eugenol is commonly obtained from cloves -
in its pure form through a process known as steam distillation, which is followed by a subsequent solvent-
based extraction.

Hence, in this practical, steam distillation will be performed on cloves, following which the product, eugenol,
will be isolated by means of solvent-based extraction. Thereafter, its purity will be determined by means of thin-
layer chromatography (TLC).

Aim

The aim of the investigation is to separate eugenol from cloves by means of distillation and liquid extraction.

Method

The experimental procedure is explained as per the attached pre-lab report under the FLOW DIAGRAM
heading.
Observations

Distillation:

During the process of distillation of cloves, the distillate was obtained faster at higher temperatures, provided no
contamination of the distillate occurred. The distillate obtained was a clear substance.

Extraction:

A substantial amount of product was obtained when the white solution (containing the protonated eugenol) was
extracted (more than once) with dichloromethane. Upon drying the solution, while a substantial amount of
magnesium aided in drying the solution, upon settling, the two layers in the separation funnel were not too
distinctive. This was due to a possibly excessive addition of anhydrous magnesium sulphate.

Following the removal of dichloromethane from the rotary evaporator, a yellow substance formed in the
collecting round-bottom flask This was the product, eugenol. A rather low yield was obtained, equivalent to
0.11 ml. This yield was obtained by pre-weighing the 250 ml volumetric flask (61.175 g) before the rotary
evaporator contained the product (which additively weighed 61.164 g)

TLC:

The obtained eugenol was washed with approximately 5 ml of dichloromethane, and a spot thereof placed on the
chromatography paper. Following its visualisation though the UV-lamp, the compound contained a single spot
which travelled up close to the solvent front, indicating a pure mixture.

Experimental results

Based on the observations made, the amount of eugenol obtained was calculated as the quotient of the actual and
theoretical yield recovered (expressed in %). Since the actual mass of cloves was exactly 30 g, and the amount
of eugenol obtained was 0.11 ml, eugenol recovery percentage was calculated as 0.11 30 100% = 0.37%,
which is quite a low yield.

With regards to the TLC plate, the retention factor ( ) calculated as the quotient of the distance travelled by the
solute and the distance travelled by the solvent (to the solvent front), was calculated as 5.1 5.65 = 0.90.

Assuming the stationary phase was normal-phase silica gel, the high -value indicates that eugenol is non-
polar, theoretically speaking (even though the presence of an acidic hydrogen on the phenolic region of eugenol
indicates that it is indeed, a polar molecule.)

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Spectral assignments

6 4 3 1

10 2

4-allyl-2-methoxyphenol

The product was obtained as a yellow, aromatic solution (0.11 ml, 0.37 %)

- IR: (1 ) : 1033 (C-O stretch); 3075 (2 carbon); 3518 (O-H peak); 1463 1510 1463 (aromatic
C=C bond); 1612 (C=C bond)
- H-NMR: (300 MHz, 3 ) (ppm): 7.2 (s, 1H, C-OH), 3.88 (s, 1H, O-CH3)
- C-NMR
- m/z

Discussion

Distillations are rather fast at higher temperatures as was discovered during the experiment, provide no
contamination of the distillate. Fundamental knowledge is required to distinguish between organic and aqueous
solvent layers the fact that such a low product was obtained is attributed to the fact that the aqueous layer
containing the eugenol was discarded. In addition, excessive amounts of magnesium sulphate as the drying
agent made product extraction difficult. Finally it is evident as to what a remarkable technique TLC truly is, as it
showed that a pure, albeit small, amount of eugenol was obtained.

References

Anon., 2016. UV/Vis Spectroscopy. In: Chemistry 264 Practical Manual. Cape Town: Stellenbosch University,
pp. 19-22.

Harris, D. C., 2010. Quantitative Chemical Analysis. s.l.:Clancy Marshall.

Skoog, D., West, D. and Holler, F. (1996). Fundamentals of analytical chemistry. Fort Worth: Saunders College
Pub.

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