Extraction of limonene from orange peels

Lara A. El Said
CHEM 237
Texas A&M - Qatar

(R)-(+)-Limonene
ABSTRACT: Limonene was extracted from orange peels by performing steam distillation and extraction.
0.4298 g of the product limonene was recovered in 2.945 % recovery. The purity of limonene was found
to be 19.34 % pure by the GC test.

Natural products which are chemicals extracted from

natural sources are important for the daily life uses.
Natural products are used in many materials that are
used by people almost daily such as food, clothing,
perfumes, dyes, and even in drugs (medicine). [1] The oil
available in the peel of citrus fruits consists of the
natural product, (R)-(+)-limonene which is one of the
most common and used fragrance. [2] (R)-(+)-limonene
contains oxidation products which allow limonene to act
as a skin penetration enhancer. [3]
Steam distillation was used in order to extract the
limonene oil from the orange peels. The extracted
limonene oil was separated, the bottom layer was the

1
Clement, B. A.; Harding, K.E. In Organic Chemistry
Lab Manual; Stranz M, McCauley, M., 10th ed.; Cengage
Learning: Mason, OH 45040, USA, 2011; 167-170

2
Matura,

M. ; Goossens, A.; Bordalo, O.; Garcia-Bravo,

B.; Magnusson, K.; Wrangsj, K.; Karlberg, AT. Amer.
Acad. Of Dermat. 2002, 47, 709-714.

Citrus Oils: Comporsition, Advanced Analytical

Techniques,
Contaminants,
and
Biological
Activity; Giovanni Dugo, Luigi Mondello, 1st ed.; Taylor
& Francis Inc.: Bosa Roca, US, 2010; v.49, ch.13, 542543.

aqueous layer and the top layer was the organic layer.
Limonene oil was run through IR spectroscopy and GC
tests. The IR spectrum was analyzed and showed the
presence of certain functional groups. At the frequency
2918.29 cm-1 exists a strong stretched alkane bond. A
stretched variable peak at 1645.11 cm -1 was indicative
of a stretched alkene which contains a carbon-carbon
double bond.
The medium stretched peak indicated at 1436.40 cm -1
shows the existence of an aromatic group with a
carbon-carbon double bond. These functional groups
proves the product to be a cyclic terpene which is
limonene. The GC test determined the purity of the
sample of the product which is 19.34 % purity.
14.5959 g of orange peels were obtained and placed
in a round flask. About 50 ml of water was added to the
peels. The distillation setup was done, joints were
greased and claisen heads were used for stability.
The round flask containing the orange peels was heated
at a 500. Cotton was added to the round flask for
insulation to heat faster. When about 20-30 ml of the
solution of limonene and water was obtained. The
solution was placed in a separatory funnel with 10 ml of
ethyl acetate for extraction. The bottom layer which is
the aqueous layer was disposed, the top layer which is
the organic layer was obtained and a drying agent
which is calcium chloride was added to the organic
layer to get rid of water. The organic layer was placed
in the recrystallization dish with water heated at 300
in order for the ethyl acetate to evaporate. Once ethyl
acetate evaporated and the limonene product was left
behind, the limonene was placed in a vial and weighed
to be 0.4298 g with a recovery of 2.945% recovery.

Limonene: 0.24298 g (2.945 % recovery). IR

cm-1: 2918.29 (s,sh), 1645.11 (var,sh), 1436.40 (m,sh)

Figure1: IR spectrum of