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Turpentine is one of the essential oils obtained from pine trees and cannot be used for making any
derivatives since it contains several components depending upon the species of the pine trees. We have
succeeded to isolate -pinene with 97 % purity from Indonesian turpentine using continuous low-pressure
distillation. Alpha-pinene can be readily converted into many chemicals having important pharmaceutical
properties including -terpineol by acid-catalyzed hydration process.
Alpha-terpineol is valuable compound widely used for fragrant substance in the cosmetic
industry, anti fungal pharmaceutical industry, disinfectant, odorant in the cleaning industry and mineral
flotation agent in the mining industry. A conventional configuration for this hydration process involves
two steps, chemical reaction in a reactor followed by separation step in a distillation column. In this
study, both chemical reactions and separation by distillation were carried out simultaneously in reactive
distillation. Alpha-pinene 97%, which is distilled from the Indonesian turpentine as feeds and
chloroacetic acid as a catalyst. We simulated this process using Aspen plus and studied effect of the main
parameter, which includes reflux ratio, distillate rate and plate number on the conversion of -pinene to
-terpineol.
Key words: -pinene hydration, -terpineol, reactive distillation, aspen plus
Introduction
Turpentine is one of the essential oils obtained
from pine trees. Highly purified -pinene that has
to reach 97% purity can be obtained by vacuumfractional distillation of turpentine [2].
When treated with water in the presence of
acid catalyst, -pinene is hydrated to complex
mixtures
of
monoterpenes,
alcohol
and
hydrocarbons, although -terpineol predominates.
-terpineol is a valuable compound widely used
for fragrant substance in the cosmetic industry, anti
fungal in pharmaceutical industry [7], disinfectant
[14], odorant in the cleaning industry [1] and
mineral flotation agent in the mining industry [4].
Hydration of -pinene by homogeneous acid
catalysts yielding -terpineol has been studied
since the 1930s, when Charlton and Day (1937)
studied the hydration of -pinene using sulfuric
acid at low temperature [3]. Then, Williams and
Whittaker (1971) investigated the rearrangements
of acid-catalyzed hydration of -pinene in aqueous
and anhydrous acetic acids [13].
Pakdel et al (2001) studied hydration of crude
turpentine oil which contains 52% -pinene and
used sulfuric acid as catalyst in the presence of
acetone. They reported the main hydration product,
-terpineol, was obtained at a yield of 77.2%
-pinene
Composition
(mass fract)
0.9709
Component
-pinene
0.0160
camphene
0.0128
limonene
0.0002
carene
1.10E-09
Table 2.
Chemical Name
Chemical Formula
-pinene
-pinene
camphene
limonene
carene
chloroacetic acid
water
-terpineol
C10H16
C10H16
C10H16
C10H16
C10H16
C2H3ClO2
H2 O
C10H18O
Mw
TB
(g/mol)
(K)
136.24
136.24
136.24
136.24
136.24
94.5
18.02
154.25
429.29
439.19
433.65
450.6
491.9
462.5
373.15
540.84
Table 3.
Component
-pinene
-pinene
camphene
limonene
carene
chloroacetic acid
water
-terpineol
Feed
Distillate
Bottom
mole frac
mole frac
mole frac
0.0480
0.0008
0.0006
0.0000
0.0000
0.0831
0.8675
0.0000
6.94E-14
1.11E-07
2.40E-07
2.48E-10
3.63E-18
1.13E-08
0.9999996
1.25E-13
6.00E-04
2.70E-03
2.20E-03
4.08E-05
1.54E-10
0.2835
0.5478
0.1632
(1)
-pinene
terpene hydrat
-terpineol
+ H2O
(2)
k2
-pinene
-terpineol
(3)
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