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4337
Hydration of R-pinene under various conditions was studied and compared with the literature.
Optimal reaction conditions have been established for the hydration of R-pinene and crude turpentine
oil in the absence of catalyst and using a low volume of acetone. A detailed reaction product analysis
is reported. The main hydration product, R-terpineol, was obtained at a yield of 67 wt % of the
initial R-pinene by reacting with 15% aqueous sulfuric acid and an excess of acetone in an oil bath
heated to 80-85 C over the course of 4 h. A progressive transformation of R-terpineol to 4-(2hydroxypropyl)-1-methylcyclohexanol (1,8-terpine) takes place as the hydration time exceeds 4 h.
A crude turpentine oil sample was also hydrated under conditions similar to those of R-pinene. The
R-terpineol yield was 77 wt % of the initial R-pinene in the crude turpentine oil. The chemical analysis
of the crude turpentine oil before and after hydration was carried out, and the distribution of the
products was discussed.
Keywords: Hydration; R-pinene; R-terpineol; essential oil; turpentine; yield; emulsifier
INTRODUCTION
Pakdel et al.
Table 1. Composition of Crude Turpentine Oil before
and after Hydration for 4 ha
wt %
compound
before
after
R-pinene
-pinene
3-carene
terpinolene
R-terpineol
limonene
eucalyptol
-terpineol
-terpineol
-terpinene
camphene
fenchyl alcohol
-myrcene
camphor
1-methyl-4-isopropylbenzene
1,7,7-trimethyltricycloheptane
borneol
1,8-terpine
R-terpinene
other organic compounds
52.0
11.4
4.2
nd
3.9
3.3
nd
1.4
nd
1.0
0.8
0.7
0.6
0.4
0.3
0.2
0.1
nd
0.1
nq
nd
nd
4.4
2.7
40.1
7.9
0.3
1.1
1.1
11.7
2.5
6.3
nd
nd
nd
0.2
5.8
2.6
1.4
nq
total
80.4
89.7
response factora
standard deviation
R-pinene
3-carene
limonene
camphene
R-terpineol
2.34
2.14
2.33
2.29
2.59
0.12
0.07
0.09
0.07
0.14
3h
4h
7h
16 h
-pinene
R-pinene
camphene
1-methyl-4-(1-methylethyl)7-oxabicyclo[2.2.1]heptane
terpinolene
limonene
eucalyptol
R-terpinene
-terpinene
fenchyl alcohol
borneol
R-terpineol
-terpineol
1,8-terpine
1.8
1.6
3.2
nd
nd
nd
2.5
nd
nd
nd
2.3
nd
nd
nd
1.4
1.5
nd
8.4
nd
nd
12.5
6.1
5.3
57.8
nd
3.0
nd
8.3
nd
1.0
14.2
6.5
5.2
58.0
1.8
2.5
nd
5.0
2.3
1.1
16.5
8.2
7.6
45.8
2.8
6.3
2.5
5.0
1.8
1.6
10.4
5.2
4.5
29.5
3.8
7.1
total
99.7
98.80
97.90
74.30
Pakdel et al.
Table 4. Comparison of the Yields (%) of r-Terpineol
after Hydration for 4 h Carried out with and without
Emulsifier
without emulsifier
with emulsifier
58.14
60.17
59.16a
50.91
49.03
49.97a
Average.
20
27.10
27.05
37.60
24
R-pinene
75.5
77.2
66.4
68.1
aThe values for weight percent are based on the initial mass of
R-pinene.
(3)
(4)
(5)
(6)
(7)
(8)
(9)
(10)
(11)
(12)
(13)
(14)
LITERATURE CITED
(1) Valkanas, G.; Inconomou, N. Reactions in the terpene
series. I. Hydration of R-pinene. Helv. Chim. Acta. 1963,
46, 1089-1096.
(2) Williams, C. M.; Whittaker, D. Rearrangements of
pinane derivatives. Part II. Products of acid-catalysed