Organic Chemistry Laboratory Formal Report

Limonene Isolation from Orange

Peels by Steam Distillation

CHEMISTR
Y

20
1L

Kyle Tanchuling, Trish Uson, Angelica Uy*, Carlo Uy

Department of Chemistry, College of Science

*Corresponding author; e-mail: Uyangelica24@yahoo.com

Abstract
Distillation method is an important commercial process for purification of
materials. Extraction of the limonene oil was conducted using one type of
method called steam distillation. The oil collected from distilling the sample
was then analyzed through performing addition tests. And the chemical
reactions that took place lead to the identification of its olefinic group.

Keywords: distillation, terpenes, limonene, alkenes

Introduction
For centuries, human beings have known that volatile oils with a variety of fragrances
and flavors could be isolated from certain plants. These compounds occur in all parts of
the plants and are called essential oils. They are of great commercial importance in the
perfume and flavoring industries, and many also have been used medicinally. The
chemical constituents of essential oils have a wide variety of structures; many of them
contain rings or more double bonds.
After many years of carrying out structural determinations on these interesting and
challenging compounds, chemists began to detect some patterns that most of these
compounds are composed of multiple 5 carbon atoms. Whole families of compounds
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were discovered and classified according to their molecular formulas. These natural
products, all of which had multiples of 5 carbon atoms in their structures, were called
terpenes. Terpenes are natural liquid products and many examples are known with 10,
15, 20, 25, 30, and 40 carbon atoms. C 10 terpenes are known as monoterpenes, which
is used in many industries. All terpenes are built up of isoprene units, normally by a
head-to-tail joining:

Monoterpene oil is commonly found in the peels of citrus fruits, known as limonene, to
enhance fragrances and flavors, and also for adhesives, polymers, and even used as
solvent.

Organic Chemistry Laboratory Formal Report

The concentration and isolation of an essential oil from a natural product has had a
dramatic impact on the development of medicine and food chemistry. The process often
used in isolating these oils is called steam distillation. Steam distillation is an important
technique that has significant commercial applications. It is a special type of distillation
for temperature sensitive materials by taking advantage of their volatility in steam by codistilling these temperature sensitive materials with water.
The objective of this experiment is to isolate limonene from the peel of oranges and to
characterize its olefinic groups by performing addition tests.
Results and discussion
In this experiment, limonene was isolated from the peel of oranges. Since limonene can
decompose at higher temperature, normal distillation is not suitable. Steam distillation
was then used, and this method is especially for immiscible liquids, which in this case
are water and limonene. The addition of water depressed the temperature of the
compound, evaporated it at a lower temperature, prevented limonene from
decomposing because of its high boiling point (see Table 1.), and applied pressure in
the individual vapor so the liquid cannot reach the boiling point fast enough. The hot
steam opened the pockets in the orange peels, allowing volatile oil to be released.
Since limonene is volatile, it can vaporize at a temperature lower than its boiling point.
So as the temperature increases, the volatile molecules vaporized and condensed on
the cooler surface of the condenser. Most of the distillate was water, but a separable
small portion of it was the limonene oil in a high state of purity.

Organic Chemistry Laboratory Formal Report

Table 1. Physical and Chemical Properties

Limonene

Molecular Weight

Boiling Point

Melting Point

(g/mol)
136.23

(C)
-40

(C)
168

Water
Potassium

18.02

Permanganate
Cyclohexane

158.03
84.16

Decomposes
6.47

100

80.7

The limonene oil extracted was further analyzed by addition tests. Two test tubes were
prepared and filled with approximately 1mL of potassium permanganate solution
(KMnO4). On the first test tube a few drops of limonene oil was added, and a sudden
decolorization was observed. This decolorization was due to the reaction between
KMnO4 and limonene oil. KMnO4 is known to be a strong oxidizing agent, which is why
limonene underwent oxidative cleavage and caused the solution to turn into brown.
Under alkaline conditions, the manganate(VII) ions was first reduced to green
manganate(IV) ions

And eventually into a dark brown solid manganese(IV) oxide.

Organic Chemistry Laboratory Formal Report

Together with this reduction reaction for KMnO4 is the oxidation reaction for limonene

This chemical reaction proved that limonene contains C-C double bonds, and is
therefore an alkene.
On the second test tube, a few drops of cyclohexane was added. This exhibited no
reaction, for cyclohexane, as one of alkanes, is in most occasions unreactive.
Conversely, KMnO4 cannot oxidate alkanes.
The purpose of this experiment was to extract limonene from orange peels using
methods of steam distillation and to determine its olefinic group. The limonene oil was
successfully isolated and was later identified to contain C-C double bonds in its
structure, and is therefore categorized as an alkene.
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Organic Chemistry Laboratory Formal Report

Experimental methodology
The outer colored rind of three oranges was grated and added to a 400mL of distilled
water in a 500mL round-bottomed flask. Five boiling chips were added to the flask and
the distillation apparatus was set up. The flask was heated and allowed to boil, but not
too strongly, until 100mL of the distillate was collected. A dropping pipette was used to
carefully remove the oil layer and into the test tube.
In two other test tubes, about 1mL of potassium permanganate (KMnO 4) was measured.
On the first test tube, a few drops of limonene oil were added. And on the second test
tube, a few drops of cyclohexane (C6H12) were added.
References
Ege, S.N. Organic Chemistry: Structure and Reactivity; Houghton Mifflin Company:
Boston, 1999; p 706
Suggs, J.W. Organic Chemistry; Barrons Educational Series Inc.: New York, 2002; p
454
http://www.chemguide.co.uk/organicprops/alkenes/kmno4.html (retrieved on Sept 19,
2016)
http://www.lalaessentialoils.com/steam-distillation.html (retrieved on Sept 17, 2016)
http://www.umsl.edu/~orglab/documents/distillation/dist.htm (retrieved on Sept 16, 2016)