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MADIABU et al., Orient. J. Chem., Vol. 34(6), 3118-3122 (2018)
ingredients in fragrance, so lyrame Schiff base has
good stabilty and less volatile.Its properties enhance
the recilience of fragrance blend.
10 cm), then panelist wrote some codes to identify
the solution. Panelist’s eyes must be parallel with
the tube, when they did the test.The room condition
must have good light exposure and no reflection to
increase the test accuracy.
Aldehyde compound is reacted with amine
trapping agent in condensation reaction to form
Schiff base and water as a by-product. Water must
be eliminated to prevent turbidity and two phases
formed in product solution. Generally, eliminating
water from product occurs under vacuum, instead
using high temperature at atmospheric pressure to
prevent Schiff bases product is not decomposing3.
The reaction of Schiff base synthesis as follows:
GC-MS. Lyrame schiff base solution was
diluted by ethanol, then analysed using GC-MS.The
analysis on condition of GC–MS could be seen at
Table 1 below. Chemical composition of lyrame was
confirmed by comparing fragmentation result with
existing library.
Table 1: GC-MS Analysis condition
Information
Colomn
Capillary colomn : HP-5
(5% Phenyl Methyl
Siloxane 3250C)
Helium
Carrier Gas
Carrier Gas Pressure
Injector Temperature
Injection Volume
Injection Technique
Split Ratio
7,0531 psi
1000C
0,2 µL
Split
80 : 1
Fig. 1. The formation reaction of Schiff base
Methyl anthranilate was often used as
amine trapping agent in Schiff base’s synthesis.
Methyl anthranilate generally gives Schiff bases
that are yellow solid or viscous, yellow liquid. An
excess methyl anthranilate was used to make Schiff
base become more liquid. Methyl anthranilate is a
primary amine which will react spontaneously with an
alkyl aldehyde7, terpened aldehyde7,8, or terpened-like
aldehyde7 such as lyral. When methyl anthranilate
reacts with lyral, Schiff base called lyrame is formed.
Temperature Program (Colomn)
Initial Temperature
Temperature Rate
Final temperature
Interval
1000C hold for 5 min.
150C per minutes
2500C hold for 5 min.
25 min.
RESULT AND DISCUSSION
Lyrame was produced by simple
condensation reaction. Amine group in methyl
anthranilate would act as a nucleophillic, attacking
the carbonyl group in lyral by 1,2 addition, then
hydroxyl group was protonized and eliminated water
molecules. The lyrame mechanism synthesis is
shown at Figure 2.
Gaschromatograpyandmassspectrometry
(GC-MS) have been the most important techniques
in the perfumes industry because perfume ingridient
is quite complex, a polar, and (semi) volatile9,10,11
.
In this study, we aim to prepare lyrame Schiff Base
using simple condensation reaction and to analyze
spectral molecular ion fragment to ensure molecular
structure lyrame Schiff base using GC-MS.
ExPERIMENTAL
Synthesis of Lyrame
9,070 g methyl anthranilate solution was
mixed with lyral solution in beaker glass.The mixture
solution was heated and stirred at temperature about
110 50C for 30 minutes.
Characterization of Lyrame
Color test. Lyrame Schiff base was
added to reaction tube (diameter = 1.3 cm; height =
Fig. 2. Mechanism of lyrame formation reaction