Organic Chemistry Laboratory

Rejepbayev, Berdigylych
ID: 22101511
Date: 09/11/22

Lab Report
EXPERIMENT 4: STEAM DISTILLATION
§1 Purpose
We will extract a mixture of essential oils (eugenol and its acetyl derivative) from cloves by
using some chemical methods based on their characteristics and physical properties. In this
experiment, steam distillation, extraction, neutralization, and evaporation will be conducted
to obtain oil from the cloves. These techniques basically use the difference in chemical
structure and boiling point of different chemicals.

§2 Introduction
Steam distillation is widely used in industry to extract essential oils from fruits, roots, and
other parts of plants and trees. This technique is similar to simple distillation, but, in this
method, two immiscible liquids (generally, water and essential oil) are separated from each
other. The difference between the polarity of molecules prevents them from forming a
solution so each molecule acts alone (Fieser & Williamson, 1992). Due to this, the vapor
pressure of this kind of mixture is usually bigger than a similar mixture of liquid that forms a
solution (Williamson & Masters, 2011). In the latter case, solvent molecules dilute the solutes
and keep them in solution; therefore, their boiling points are between the boiling points of
individual components. However, in the former case, the boiling point mixture is below the
boiling points of pure components (Fieser & Williamson, 1992). Boiling takes place if the total
of the two partial pressures equals the external pressure. These two immiscible liquids
independently apply pressure against the common external pressure.
We can formulate the required amount of water (low molecular weight favors using it) to
distillate 1 g of a given compound.
By Dalton’s law, we have:

And boiling point does not change during the distillation if adequate amounts of both liquids
are present to keep the vapor saturated (Williamson & Masters, 2011). So, we know pwater =
760 – psubstance

The advantages of using steam distillation are high selectivity because water-insoluble liquids
are volatile but the impurities are not. Another benefit of using this technique is to avoid the
decomposition of some high-boiling point organic liquids because we can obtain them at
lower temperatures (Williamson & Masters, 2011).
Eugenol has a boiling point of 255 °C, however as it is insoluble in water, it will form an
azeotrope and steam distilled at a temperature just below that of water (Fieser & Williamson,
1992). Since eugenol is a phenol, it will dissolve in aqueous alkali to produce the phenolate
anion, which serves as the motivator for separating it from its acetyl derivative.

§3 Observations
Part A: Steam distillation of the cloves
5.008 g of cloves are boiled to perform steam distillation. The first drops were observed after
heating for 4 minutes and 10 seconds. The temperature was measured as 69 oC when the first
drops were seen and this temperature stayed constant throughout the first run. We poured
obtained drops into the graduated cylinder after some time for several times. The table time
versus obtained volume is given below.
Time 8 min 30 11 min 15 min 21 min 30 min 40 min
sec 30 sec 10 sec 30 sec
Volume of 5.5 8.0 10.0 11.5 12.0 15.0
liquid, ml

The decrease in the rate of drops is seen because we slowed the heat to prevent the diffusion
of foam and other impurities into our distillate because our water is near to finish. We
observed the temperature as 69 oC but we found out that it should be near 90 oC the reason for
our incorrect measurement is thermometer was not accurate (it has problems with mercury
inside (some of it is located at the top)). For the 2 nd run, we changed the thermometer, and
this time our temperature measured as 90oC. The below is time versus volume table for the
second run:
Time 6th minute 11th minute 16th minute 20th minute
Volume First drops 6 ml 12 ml 15 ml

From the first experiment, we obtained 30 ml of an unclear (white milky) solution of oils.
Part B: Extraction of Eugenol from the cloves.
We placed 30 ml of blurry (cloudy) white solution (obtained in 1 st part) in a 100 ml
separatory funnel. Then 10 ml of DCM was added to the separatory funnel. During that, we
see phase separation (some foam was formed between two phases) and a blurry layer located
at the top, and a clear solution located below it. Some of my teammates argued that there are
three (clear one between two whites) phases, but I think the photo is taken before the
equilibrium formed.
Figure 1: During phase separation; after phase separation
We shake the separatory funnel vigorously and heard the escape of some gas. Then after
waiting for a time, we took the below part. This procedure was repeated 3 times to extract as
much oil as we could.

Figure 2: The obtained solutions

We added a white powder of crystalline 2g of Na 2SO4 to the clear organic phase. This
compound went to the bottom of the flask where it formed a white-colorless precipitate. Then
we poured the liquid phase into a graduated cylinder. And by this, we obtained 21 ml of the
organic phase. Then, we took exactly 1/5 of that solution which was used in rotatory
evaporation. Our tared round bottom flask has a mass of 51.1173 g and the initial pressure of
evaporation is 520 mbar. This pressure starts to change after the evaporation started, and
also, we decreased the pressure monotonically to ca. 40 mbar during the process to speed up
the evaporation of DCM. The working principle of rotatory evaporation is decreasing the
boiling point of volatile solvents by decreasing external pressure. After all of the DCM was
evaporated, we weighed the round bottom flask as m(r.b.f with oil) = 51.2112 g. The mass of
oil drops is 0.0939 g. We also extracted the remaining 4/5 part with 10ml of 5% NaOH
solution. During this extraction, the aqueous phase containing Eugenolate, NaOH, and water is
located at the top, organic phase containing Acetyleugenol in DCM is located at the bottom
part. We took the bottom part and added Na 2SO4 to it. Finally, we obtained Acetyleugenol by
pouring the liquid phase into the tared Erlenmeyer flask. After rotatory evaporation, we got
0.04289 g of Acetyleugenol. Then we added acid to the top part which was the aqueous phase
and the reaction produced a very cloudy yellow emulsion. After that, we did separation with
8ml DCM three times. After the 1st extraction our phases divided clearly, e.g., the cloudy
emulsion became white and the other one became yellow. Then we did rotatory evaporation
with the organic phase to remove solvent and obtained 0.6122 g of yellow viscous liquid.
Figure 3: The last extraction; the obtained liquid

§ 4 Results and Discussion

In this experiment, we conducted many chemical methods at the same time so it will be wise
to explain each of the results separately. The first part of the experiment was more time-
consuming than the other steps but relatively easy. We got 30 ml of a mixture of oils from
5.008 g of cloves in an hour. The first run was slowed after obtaining significant amounts of
liquid to avoid the foam and other impurities because our water was running out. However,
in the second run, the distillation went two times faster than the first one. The problem with
the first run is the time necessary to heat the oil. The temperature in both runs stayed the
same, just in 1st run our thermometer had a problem with its mercury inside.
Then the distilled white non-transparent liquid was extracted with DCM and in this process,
we observed two phases: a clear one and a white cloudy one. From the picture, we can see
that a clear solution is located below so it should be organic because DCM has a higher
density than water. Then we divided our extract into 1/5 and 4/5 parts with a graduated
cylinder. The 1/5 part is used for the determination of the total content of eugenol and
Acetyleugenol in the clove. The volume of 1/5 part is 4.25 ml and from this sample, we
obtained 0.0939 g of oil. The solution is homogenous so the total mass obtained oil mixture
should be 0.0939g*5 = 0.4695 g.
The second part is the direct application of this characteristic reaction:

Hydrolysis of esters will not occur because 5% NaOH solution is not basic enough to perform
the nucleophilic attack (Jirovetz et. al).
From the second part, we can find the amounts of eugenol and Acetyleugenol independently:
5∗0.04289
m ( acetyleugenol )= =0.05361 g
4
However, if we look at the mass of eugenol from the third part then we clearly see that the
5∗0.6122 g
mass of measured eugenol exceeds the total mass we found early (i.e., g > 0.4695
4
– 0.05361 g). In theory, these two values should be the same, however, due to some issues,
there is an 84% difference between them which is very significant. First of all, let us calculate
the yield by using both values. The literature says that 18% of the weight of clove flower buds
are essential oils. The eugenol and Acetyleugenol content in the essential oil is 89% and 5-
15% respectively (Jirovetz et. al). So, the mass of theoretical eugenol and Acetyleugenol
would be these:
5 .008 g∗18 %∗(10 ± 5 ) %
m ( acetyleugenol )= =0. 09014 ± 0.04507 g
100 %∗100 %
5 .008∗18 %∗89 %
m ( eugenol )= =0. 8023 g
100 %∗100 %
Now let us calculate the yield of eugenol and Acetyleugenol:
0.4159 g
%yield of eugenol= ∗100 %=51.84 % (95.38 % ¿the3 rd measurement)
0.8023 g
0. 05361 g
%yield of acetyl eugenol= ∗100 %=77.8 ± 41.15 %
0.09014 ± 0.04507 g

Similarly, content of eugenol and Acetyleugenol in the cloves are found to be:
0.4159 g
%content of eugenol= ∗100 %=8.3 % (15 .28 % ¿the 3 rd measurement)
5.008 g
0. 05361 g
%content of acetyl eugenol= ∗100 %=1.07 %
5.008 g
Then the total essential oil comes from eugenol and Acetyleugenol for cloves will be 9.37%.
The color and viscosity of liquid is a good sign that is the eugenol (Britannica).
The oil also contains significant amounts of both β-cariofileno and α-humulen which are
nonpolar compounds and cannot react with NaOH so they should be extracted with
Acetyleugenol (Jirovetz et. al). This situation means that we obtained lesser amount of
Acetyleugenol than we thought. To analyze this situation and determine the qualitative
composition of distillate we need other techniques. The findings are acceptable (except the
3rd measurement); however, I calculated yield in this way because we did not used all of clove
initially. Therefore, calculating yield from incomplete distillation of cloves would not be
accurate. On other hand, the literature gives ranges of values where I can choose the best
option to make my calculations accurate and scientifically significant. The exclusion of 3 rd
measurement is because we cannot measure the weight of round bottom flask properly
(values are changing) before and after the addition of extract. And we do not have much time
to dry it with anhydrous sodium sulphate which may be another reason.
§ 5 Conclusion
In this experiment, we used steam distillation, several extractions, acid-base neutralizations,
and rotatory evaporation to obtain individual eugenol and its acetyl derivative. We found that
5.008 g cloves would give 0.46g (from 30 ml) mixture of essential oils which is 9.37%
recovery. During those steps we met with various difficulties and some of them are the
possible sources of error. The profound one is the result of last extraction which resulted in
the 84% positive error in weight of eugenol. This measurement shows us how to avoid typical
kinds of errors next time. In conclusion, we obtained necessary liquid with a quite good
results and learnt valuable lessons in this experiment.

§ 6 References
Britannica, T. Editors of Encyclopaedia (2022, September 15). clove. Encyclopedia Britannica.
https://www.britannica.com/plant/clove

Jirovetz L, Buchbauer G, Stoilova I, Stoyanova A, Krastanov A, Schmidt E. Chemical

composition and antioxidant properties of clove leaf essential oil. J Agric Food
Chem. 2006;54(17):6303–6307.

Fieser, L. F., & Williamson, K. L. (1992). Organic experiments. L.F. Fieser, K.L. Williamson (7th
ed.). D.C. Heath.

Williamson, K. L., & Masters, K. M. (2011). Macroscale and Microscale Organic Experiments
(6th ed.). Cengage Learning, Inc.