Proceedings of the IConSSE FSM SWCU 2015, pp. BC.90–96 ISBN: 978-602-1047-21-7
SWUP
BC.90
Study catalytic oxidation of α
-pinene using hydrogen peroxide-ironIII chloride
Merry Pradhita, Masruri , Mohammad Farid Rahman
a
Department of Chemistry, Brawijaya University, Jl. Veteran Malang 65145, Indonesia
Abstract
Indonesia has abundance source of alpha-pinene, and mainly can be isolated from turpentine oils. This oils itself, was harvested from pine tree
Pinus merkusii Junh. de Vr. This paper reveals the recent investigation on oxidation of -pinena using hydrogen
peroxide catalyzed by ironIII chloride. Meanwhile the end objective of this study basically was derivatization of -pinene to provide basic and fine chemicals for industry
and pharmaceuticals. A green oxidator, hydrogen peroxide, commonly provided epoxide group to the alkene double bond of -pinene. However, it was found a diverse oxidation
product was observed during reaction catalyzed by ironIII chloride. Analysis of the oxidation product was performed by using gas chromatography-mass spectrometry and
infrared spectrophotometry.
Keywords
-pinene, carvone, catalytic, oxidation, turpentine oil
1. Introduction
Indonesia as a tropical country has wide area for forestry. And also, its natural products and natural oils harvested from forestry is an indispensable product including the essential
oils. Pine forestry generally grows species of Pine merkusii Junh. de Vr, along island of
Indonesia and produces turpentine oils beside its gum rosin. It was reported in 2013, total production was recorded about 11,851 ton Perum Perhutani, 2014. It was predicted
increase by ten during a decade. However, this production was exported directly as raw turpentine oils.
-pinene contains in turpentine oils as major component. Recent investigation reported that -pinene composed turpentine oil harvested from local forestry in average
88 from total component Amini et al., 2014. This high composition leads to purification of -pinene of turpentine oil for further application Masruri et al., 2007. Previous result
described -pinena has activity to inhibit bacterial growth and also possible for antiseptic Masruri et al., 2007; Leite et al., 2007, bioactivity as anti-inflammation in neuronal cell
Khotimah et al., 2006. Besides, it was also reported application -pinene as starting material in organic synthetic for adhesive, finishing product, ink, and perfumery Sarwar, 2012.
Transformation of -pinene into fine chemicals by oxidation reaction was also reported by other researcher. It applied various different oxidation agents. For example,
hydrogen peroxide H
2
O
2
using some catalyst such as titaniumVI, ironIII, zirconiumIV, titanium-supported silica, and solid acid H
5
PW
11
TiO
40
. Some products were reported such as verbenol 4-9, verbenone 2-10, dan campholenic aldehyde 2-9 Maksimchuk
et
Corresponding author. Tel.: +62 341 575838 ext 111; E-mail address: masruriub.ac.id
M. Pradhita, Masruri, M.F. Rahman
SWUP
BC.91
al., 2005. Reaction was generally undertaken in room temperature until 50
o
C Maksimchuk et al., 2005. However, low selectivity and yield was always reported see Figure 1.
Figure 1. Scheme of oxidation reaction of -pinene.
Oxidation using hydrogen peroxide is interesting process since the by-product resulted is water. It is known as a green oxidator. It has efficiency of oxygen atom to convert organic
substances by 47 Noyori et al., 2003. According to Hasan and co-worker, oxidation using hydrogen peroxide is economically and ecologically advantageous. It was easily to manage,
handle, low cost, and only provided water as by product Hasan et al., 2011. Thus, applying hydrogen peroxide basically follows the principles of green oxidation. This study will report
oxidation of -pinene using hydrogen proxide and catalyzed by ironIII chloride. The result was expected can open the way to control selectivity and further application of Indonesian
turpentine oils.
2. Materials and methods 2.1
