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147

Glycerol Esters from the Reaction of Glycerol with


Dicarboxylic Acid Esters
Gladys H.P. Choa,b, S.K. Yeongb,*, T.L. Ooib, and C.H. Chuaha
a

Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur, Malaysia,


and bAOTD-MPOB, Bandar Baru Bangi, Selangor Darul Ehsan, Malaysia

ABSTRACT: Mono- and di-esterified glycerols were synthesized by the base catalyzed reaction of glycerol with aliphatic dicarboxylic acid esters (C2C9): 2,3-dihydroxy-propyl oxalate (2),
1,3 dioxalyloxy propan-2-ol (3), 1,3-dimethoxyoxalyloxy propan2-ol (5), 2,3-dihydroxy-propyl malonate (6), 2,3-dihydroxy-propyl
methyl malonate (7), 2,3-dihydroxy-propyl methyl succinate (8),
1,3-dimethoxysuccinyloxy propan-2-ol (9), 2,3-dihydroxy-propyl
methyl glutarate (10), 1,3-dimethoxyglutaryloxy propan-2-ol
(11), 2,3-dihydroxy-propyl methyl azelate (14), and 1,3dimethoxyazelyloxy propan-2-ol (15). Their structures were elucidated by spectrometric methods. Compounds 8, 10, 2,3-dihydroxy-propl methyl adipate (12) and 14 were found to possess
surface active properties and the ability to reduce the interfacial
tension between paraffin and water.
Paper no. S1511 in JSD 9, 147152 (Qtr 2, 2006).
KEY WORDS: Diglycerol ester, dimethyl ester, glycerol,
monoglycerol ester.

The synthesis of monoglycerides from different mono-acyl


donors (free fatty acids, fatty acid alkyl ester, and vinyl ester)
with glycerol have been studied extensively by numerous researchers (1,2). However, the synthesis of glycerol esters
from di-acyl donors was limited.
The synthesis of long chain dicarboxylic acid glycerides
from japanic acid, COOH(CH2)20COOH, and palmitic acid,
CH3(CH2)14COOH, with glycerol, to produce ,-japanin-palmitin glycerides and ,-japanin--palmitin glycerides, was
described by Nagano and Tanaka (3). The synthesis of two
diglyceride (1,3-dioleoyl and 1,3-distearoyl ester) molecules
linked together with a short chain dibasic acid (fumaric acid,
succinic acid, and adipic acid) at position 2 was reported (4,5).
These esters can be edible and digestible since fumaric and
succinic acids occur as metabolites in the Krebs cycle for the
*To whom correspondence should be addressed at AOTD-MPOB, Lot
9&11, Jalan P10/14, 43650 Bandar Baru Bangi, Selangor Darul Ehsan,
Malaysia. E-mail: yeong@mpob.gov.my
Abbreviations: APCI, atmospheric pressure chemical ionization;
CIMS, chemical ionization with mass spectrometry; EI, electron impact; FTIR, Fourier transform infrared; GC, gas chromatography;
GCMS, gas chromatography with mass spectrometry; HPLC, high-performance liquid chromatography; IR, infrared; LCMS, liquid chromatography with mass spectrometry.
COPYRIGHT 2006 BY AOCS PRESS

metabolism of fats. In addition, this synthetic ester [bis-(glycerol 1,3-distearate) succinate] possesses lubrication properties
(5). Mono- and di-esterified glycerol esters which are useful for
the synthesis of biodegradable polymers and surfactants were
synthesized from the enzymatic esterification of glycerol with
adipic, sebacic acids, and their dimethyl ester derivatives (6).
The synthesis of oligoesters from oxalic acid and glycerol
was reported by Alksnis and colleagues (7). Polyester films,
which are useful in surface coatings industries, were synthesized from glycerol with different chain lengths of aliphatic
and aromatic dicarboxylic acids (8,9).
As there are only limited reports on the synthesis of glycerol with short carbon chain dicarboxylic acid esters, the
present study on synthesis of glycerol ester by the transesterification of glycerol with dicarboxylic acid esters (C2C9)
represents a contribution to this subject.
Parameters that affect the transesterification were examined in order to optimize the yield of products. In this study,
the reaction of glycerol with dimethyl succinate was used as
a model, as the formation of monoester can be conveniently
used to monitor the progress of reaction.

EXPERIMENTAL PROCEDURES
Materials. Glycerol (99.2%) was purchased from Fisher
Chemicals (Leicestershire, United Kingdom). The dicarboxylic acid esters (dimethyl oxalate, dimethyl malonate,
dimethyl succinate, dimethyl glutarate, dimethyl adipate,
and dimethyl azelate) and molecular sieves (4 ) were purchased from Fluka (Buchs, Switzerland), and potassium hydroxide was purchased from Merck (Darmstadt, Germany).
The solvents used were high-performance liquid chromatography (HPLC) grade.
Methods. The alcoholysis was performed in a 250-mL
three-necked flask equipped with a reflux condenser, thermometer, and a sampling port. The flask was heated to
80C in a water bath, and its contents were stirred magnetically. The reagents used were in a molar ratio, 4 mol of glycerol to 1 mol of acid ester; the reaction was catalyzed by 0.2
wt% of potassium hydroxide and 2 wt% of molecular sieves.
On completion of the reaction, the reaction mixture was
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148
G.H.P. CHO ET AL.

washed with water and the glycerol ester extracted with


chloroform.
Spectrometric analysis. A Nicolet magna FT-IR 550 (Madison, Wisconsin) spectrometer was used to record the
Fourier transform infrared (FTIR) spectra. Gas chromatographic (GC) analyses of glycerol esters were performed
on an Agilent 6890N (Palo Alto, California) gas chromatograph equipped with a flame ionization detector. An Agilent DB Wax (Palo Alto, California) 30 m 0.32 mm 0.25
m column was used for the separation. The oven temperature was programmed from 60 to 230C at 2C/min. The
injector port was set at 240C and detector at 260C. Gas
chromatography with mass spectrometry (GCMS) was
performed on an Agilent 6893 (Palo Alto, California) series gas chromatograph fitted with an Agilent DB Wax
(Palo Alto, California) 30 m 0.32 mm 0.25 m capillary
column and temperature programming was similar to the
GC conditions. Liquid chromatography with mass spectrometry (LCMS) was performed on PE Sciex API 100
LCMS (Wellesley, Massachusetts) fitted with an SGE GL
Wakosil (United States) 150 mm 2 mm 5 m C-18 column, PerkinElmer LC Series 2000 LC pump, and Whatman zero air generator. Distilled water with 0.1% of formic
acid and methanol with 0.1% of formic acid in a 55:45
ratio served as the mobile phase for flow injector analysis
(FIA). HPLC was performed on a Jasco PU-1580 (Tokyo,
Japan) fitted with an Inertsil Octadecylsilane-3 (United
States), 25 cm long, 4.6 mm internal diameter, with a 5 m
particle size 8 reversed-phase column. Distilled water and
methanol in a 55:45 ratio served as the mobile phase. The
measurements of surface tension were performed by using
the Sigma 70 tensiometer (Finland). Interfacial tensions
were measured by using the same instrument and paraffin
oil was used as the lighter phase. Cloud points were determined by heating 25 mL of 10% (vol/vol) glycerol ester
solution in a standard test jar. The cloud point was determined by visual observation. The temperature at which the
solution becomes obviously turbid was recorded as the
cloud point. The reproducibility of cloud point measurement is 0.2C.

RESULTS AND DISCUSSION


The glycerol esters (Fig. 1, Table 1) were synthesized by the
base catalyzed reaction of glycerol with aliphatic dicarboxylic
acid esters (dimethyl oxalate, dimethyl malonate, dimethyl succinate, dimethyl glutarate, dimethyl adipate, and dimethyl azelate). This study consists of 11 new and four reported compounds. The new compounds are 2, 3, 5, 6, 7, 8, 9, 10, 11, 14,
and 15. The general scheme of synthesis is illustrated in
Scheme 1. Synthesized compounds are identified and described herein.
Products identified from reaction of glycerol with dimethyl oxalate. (i) 4-Hydroxymethyl-1,3-dioxolan-2-one (1). Infrared (IR)
max cm1: 3414, 2946, 1751, 1217. EI/GCMS m/z (rel.
int.): 118 [M+, 6], 117 (M+ H, 100%), 75 (C3H7O2+, 10),
JOURNAL OF SURFACTANTS AND DETERGENTS, VOL. 9, NO. 2 (QTR 2, 2006)

61 (C2H5O2+, 15), 57 (C3H5O+, 50). Atmospheric pressure


chemical ionization (APCI)/LCMS m/z (rel. int.): 119
[(M+H)+, 100%].
(ii) 2,3-Dihydroxy-propyl oxalate (2). IR max cm1: 3414,
2946, 1751, 1644, 1405, 1217. EI/GCMS m/z (rel. int.): 147
(M+ OH, 4), 103 (C3H3O4+, 100%), 89 (C2HO4+, 23), 73
(C2HO3+, 10), 61 (C2H5O2+, 30). APCI/LCMS m/z (rel.
int.): 165 [(M+H)+, 100%].
(iii) 1,3-Dioxalyloxy propan-2-ol (3). IR max cm1: 3414,
2946, 1751, 1644, 1405, 1217. EI/GCMS m/z (rel. int.): 147
(C5H7O5+, 2), 103 (C3H3O4+, 100%), 89 (C2HO4+, 17), 73
(C2HO3+, 9), 61 (C2H5O2+, 23). APCI/LCMS m/z (rel.
int.): 237 [(M+H)+, 100%].
(iv) 2,3-Dihydroxy-propyl methyl oxalate (4). IR max cm1:
3414, 2946, 1751, 1644, 1405, 1217. EI/GCMS m/z (rel. int.):
147 (M+ OCH3, 10), 103 (C3H3O4+, 100%), 117 (C4H5O4+,
5), 87 (C3H3O3+, 6), 75 (C3H7O2+, 45), 59 (C2H3O2+, 43).
APCI/LCMS m/z (rel. int.): 179 [(M+H)+, 100%].
(v) 1,3-Dimethoxyoxalyloxy propan-2-ol (5). IR max cm1:
3414, 2946, 1751, 1644, 1405, 1217. EI/GCMS m/z (rel.
int.): 233 (M+ OCH3, 6), 147 (C5H7O5+, 5), 103 (C3H3O4+,
100%), 87 (C3H3O3+, 2), 75 (C3H7O2+, 44), 59 (C2H3O2+,
37). APCI/LCMS m/z (rel. int.): 265 [(M+H)+, 100%].
Products identified from reaction of glycerol with dimethyl malonate. (i) 2,3-Dihydroxy-propyl malonate (6). IR max cm1: 3404,
2955, 1737, 1642, 1444, 1206. EI/GCMS m/z (rel. int.): 103
(C3H3O4+, 100%), 87 (C3H3O3+, 1), 75 (C3H7O2+, 69), 61
(C2H5O2+, 83), 59 (C2H3O2+, 3). APCI/LCMS m/z (rel.
int.): 179 [(M+H)+, 100%].
(ii) 2,3-Dihydroxy-propyl methyl malonate (7). IR max cm1:
3404, 2955, 1737, 1642, 1444, 1206. EI/GCMS m/z (rel.
int.): 133 (C5H9O4+, 10), 117 (C3H3O4+, 100%), 75
(C3H7O2+, 17), 61 (C2H5O2+, 28), 59 (C2H3O2+, 20).
APCI/LCMS m/z (rel. int.): 193 [(M+H)+, 100%].
Products identified from reaction of glycerol with dimethyl succinate. (i) 2,3-Dihydroxy-propyl methyl succinate (8). IR max cm1:
3408, 2953, 1727, 1641, 1433, 1217. EI/GCMS m/z (rel.
int.): 189 (M+ OH, 1), 175 (M+ OCH3, 5), 147 (C6H11O4+,
5), 115 (C5H7O3+, 100%), 59 (C2H3O2+, 20). APCI/LCMS
m/z (rel. int.): 207 [(M+H)+, 100%].
(ii) 1,3-Dimethoxysuccinyloxy propan-2-ol (9). IR max cm1:
3408, 2953, 1727, 1641, 1433, 1217. EI/GCMS m/z (rel.
int.): 320 [M+, 2], 289 (M+ OCH3, 5), 189 (C8H13O5+, 7),
175 (C7H11O5+, 10), 115 (C5H7O3+, 100%), 59 (C2H3O2+,
20). APCI/LCMS m/z (rel. int.): 321 [(M+H)+, 100%].
Products identified from reaction of glycerol with dimethyl glutarate. (i) 2,3-Dihydroxy-propyl methyl glutarate (10). IR max cm1:
3443, 2951, 1726, 1640, 1444, 1216. EI/GCMS m/z (rel. int.):
220 [M+, 3], 203 (M+ OH, 1), 189 (M+ OCH3, 10), 129
(C6H9O3+, 100%), 101 (C5H9O2+, 45), 59 (C2H3O2+, 53).
APCI/LCMS m/z (rel. int.): 221 [(M+H)+, 100%].
(ii) 1,3-Dimethoxyglutaryloxy propan-2-ol (11). IR max cm1:
3443, 2951, 1726, 1640, 1444, 1216. EI/GCMS m/z (rel. int.):
289 (M+ C(=O)OCH3, 5), 189 (C8H13O5, 7), 129 (C6H9O3+,
100%), 101 (C5H9O2+, 10), 87 (C4H7O2+, 11), 59 (C2H3O2+,
20). APCI/LCMS m/z (rel. int.): 349 [(M+H)+, 100%].

149
GLYCEROL ESTERS

OH

OH

OH

C
H

(C H 2 ) n C

OH

2 n=0

6 n=1

O C

OH

C OH

OH

O C (C H 2 )n

OH

OH

H
O C H3 H

O C

OH
O

O C

(C H 2 ) n

O CH 3

O
(C H 2 ) n

C O CH 3

4 n=0

5 n=0

7 n=1

9 n=2

8 n=2

11 n = 3

10 n = 3

13 n = 4

12 n = 4

15 n = 7

14 n = 7
FIG. 1. Structure of synthesized compounds.

TABLE 1
Composition of Base-Catalyzed Reaction Based on GC Chromatogram
Reaction of
glycerol with
Dimethyl oxalate
Dimethyl malonate
Dimethyl succinate
Dimethyl glutarate
Dimethyl adipate
Dimethyl azelate

Glycerol (%)

Dicarboxylic
acid ester (%)

Monoester (%)

Diester (%)

1.74
1.14
1.01
1.06
1.61
1.57

90.99
71.60
37.09
22.75
7.60
3.55

5.16
27.26
54.03
65.34
75.57
78.75

2.11
nda
7.87
10.85
15.79
16.13

nd, not detected.

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G.H.P. CHO ET AL.

OH

OH

OH
H

+ MeOC(CH2)n COMe

OC(CH2)n COMe

OC(CH2)n COMe

OH

OH

OH

OC(CH2)n COMe

KOH

SCHEME 1. Synthesis of glycerol esters (n = 0, 1, 2, 3, 4, 7).

JOURNAL OF SURFACTANTS AND DETERGENTS, VOL. 9, NO. 2 (QTR 2, 2006)

substitution in the glycerol chain. The characteristic fragment


ion shown in compound 5 was m/z 87; 6 and 7 were m/z 101; 8
and 9 were m/z 115; 10 and 11 were m/z 129; 12 and 13 were
m/z 143; and 14 and 15 were m/z 185, respectively. The
acylium ion, M+ 31, is due to the loss of the methoxyl group
by simple -cleavage. In compound 5 it resulted in m/z at 233,
8 in m/z at 175, 9 in m/z at 289, 10 in m/z at 189, and 15 in m/z
at 429, respectively. Another significant ion in methyl ester
cleavage was m/z 59, [CH3OC(=O)]+, which was also due to
the -cleavage in ester linkage (10). Besides that, EIMS indicated that simple cleavage of the hydroxyl group, M-OH, occurred in compound 8 at m/z 189, 10 at m/z 203, and 14 at m/z
259, respectively.
Various parameters that may affect the transesterification
were studied in order to optimize the yield of products. The
first parameter studied was the effect of substrate molar
ratio. The reactions were carried out by varying the glycerol/ester molar ratio. Accumulated studies (1113) suggest that an excess of the acid ester is essential for alcoholysis reaction to be completed. Molar ratios from 1:1 to 6:1,
glycerol to acid ester, were investigated. The optimum ratio
was 4:1 (Fig. 2), whereby the quantity of the monoester was
60% after 8 h. The conversion decreased slightly when the
molar ratio exceeded 4:1. A similar result was obtained by
Roxana and colleagues (13) in 1999 in their study on enzymatic synthesis.
Although similar reactions are known to be catalyzed
by acids, bases, or enzymes (1216), only potassium hydroxide was selected; the resulting base added at several

Percent conversion (%)

Products identified from reaction of glycerol with dimethyl adipate.


(i) 2,3-Dihydroxy-propyl methyl adipate (12). IR max cm1: 3410,
2951, 1724, 1639, 1442, 1213. EI/GCMS m/z (rel. int.): 203
(M+ OCH3, 5), 175 (M+ C(=O)OCH3, 10), 173 (C8H13O4+,
22), 161 (C7H13O4+, 15), 143 (C7H11O3+, 100%), 115
(C6H11O2+, 30), 59 (C2H3O2+, 21). APCI/LCMS m/z (rel.
int.): 235 [(M+H)+, 100%].
(ii) 1,3-Dimethoxyadipyloxy propan-2-ol (13). IR max cm1:
3410, 2951, 1724, 1639, 1442, 1213. EI/GCMS m/z (rel.
int.): 345 (M+ OCH3, 3), 317 (M+ C(=O)OCH3, 7), 303
(C14H23O7+, 15), 143 (C7H11O3+, 100%), 115 (C6H11O2+,
40), 73 (C3H5O2+, 20), 59 (C2H3O2+, 18). APCI/LCMS
m/z (rel. int.): 377 [(M+H)+, 100%].
Products identified from reaction of glycerol with dimethyl azelate. (i) 2,3-Dihydroxy-propyl methyl azelate (14). IR max cm1:
3412, 2950, 1723, 1637, 1443, 1215. EI/GCMS m/z (rel.
int.): 276 [M +, 2], 259 (M + OH, 5), 217 (M +
C(=O)OCH 3, 7), 215 (C 11H 19O 4+, 15), 203 (C 10H 19O 4+,
20), 185 (C 10H 17O 3+, 100%), 157 (C 9H 17O 2+, 20), 59
(C2H3O2+, 25). APCI/LCMS m/z (rel. int.): 277 [(M+H)+,
100%].
(ii) 1,3-Dimethoxyazelyloxy propan-2-ol (15). IR max cm1:
3412, 2950, 1723, 1637, 1443, 1215. EI/GCMS m/z (rel.
int.): 429 (M+ OCH3, 7), 401 (C21H37O7+, 10), 303
(C14H23O7+, 20), 185 (C10H17O3+, 100%), 157 (C9H17O2+,
20), 73 (C3H5O2+, 25), 59 (C2H3O2+, 30). APCI/LCMS
m/z (rel. int.): 461 [(M+H)+, 100%].
All compounds showed broad peak at IR bands at
34043443 cm1 that are characteristic of the OH stretching from glycerol, along with the 17231751 cm1 band
(C=O stretching for glycerol esters), 16371644 cm 1 band
(C=O stretching of dicarboxylic acid esters), and 1230 cm1
band (bending of the C-O-C group in ester).
Chemical ionization with mass spectrometry (CIMS) spectrum gave molecular ion (M+H) peaks for compounds 1, 2, 3,
4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, and 15 at m/z 118, 164, 236,
178, 264, 178, 192, 206, 320, 220, 348, 234, 376, 276, and 460,
which correspond to the molecular formula C4H6O4, C5H8O6, C7H8O9, C6H10O6, C9H12O9, C6H10O6, C7H12O6, C8H14O6,
C13H20O9, C9H16O6, C15H24O9, C10H18O6, C17H28O9,
C13H24O6, and C23H40O9, respectively. The EIMS spectrum
revealed that the most important ions with highest abundance
are associated with cleavage to the oxygen atoms of ester to
produce ions of type [C(=O)(CH2)nC(=O)OCH3]+. These
ions serve the primary function of marking the position of

60
50
40
30
20
10
0
0

10
15
Reaction time (hours)

20

FIG. 2. Effect of glycerol:dimethyl succinate molar ratio at 1:1 (); 2:1


); and 6:1 (
) (80C, 0.2 wt% KOH, and 2 wt%
(); 3:1 (); 4:1 (x); 5:1 (
molecular sieve).

151

Percent conversion (%)

GLYCEROL ESTERS

70
60
50
40
30
20
10
0
0

10

15

20

Reaction time (hours)


FIG. 3. Effect of catalyst (KOH) concentration on the reaction of glycerol
with dimethyl succinate: without catalyst (); 0.1 wt% (); 0.2 wt% (); 0.4
wt% (x); and 0.6 wt% (+) (molar ratio 4:1, 80C, and 2 wt% molecular sieve).

60

80

Percent conversion (%)

Percent conversion (%)

concentrations (00.6 wt%) showed an increase of reaction rate (Fig. 3), but the optimal value was about 0.2
wt%.
The reaction temperature also influences the rate of
reaction and the yield of glycerol esters. Therefore different reaction temperatures were studied to determine the
optimum temperature. Reaction temperatures studied
were 80C, 100C, and 120C. At higher temperatures, the
amount of monoester in the reaction mixture increased
and it reached a maximum level after 6 h when the reaction was carried out at 100 to 120C, whereas it took 8 h
at a lower temperature (Fig. 4). Furthermore, the formation of diester from monoester was faster when the temperature was higher. However, the overall yield at the end
of the reaction was not affected by temperature. In this
case, the formation of both monoester and diester were
produced in an overall yield of 80% after 15 h of reaction
time.
Esterification is a reversible reaction. Water is the byproduct formed during the process and it would cause the
ester to hydrolyze. The equilibrium will shift to the formation of ester if water is removed during the reaction. This
can be done with the assistance of molecular sieves (13). In
this case, molecular sieves were deliberately added to has-

ten the reaction. The rate of reaction accelerated when


water was constantly removed from the reaction mixture by
the molecular sieve as shown in Figure 5.
In consideration of the above factors, molar ratio of 4:1
of glycerol to ester, reaction temperature at 80C, 0.2 wt%
KOH as catalyst, and 2 wt% of molecular sieves were chosen as the optimum reaction conditions for all the subsequent reactions, which are reactions of glycerol with dimethyl oxalate, dimethyl malonate, dimethyl succinate,
dimethyl glutarate, dimethyl adipate, and dimethyl azelate. The GC composition of the reactions is shown in
Table 1.
The results indicate that long chain dicarboxylic acid esters are easier to react with glycerol and formed glycerol esters than shorter chain length dicarboxylic acid esters. This
is expressed by the yield of glycerol: dimethyl azelate was
highest and followed by dimethyl adipate, dimethyl glutarate, dimethyl succinate, dimethyl malonate, and dimethyl oxalate.
Compounds 8, 10, 12, and 14 with 90% purity were isolated by HPLC and the physical properties were tested.
The measurement of surface tension, interfacial tension,
and cloud point are summarized in Table 2. Surface tension of compounds 8, 10, 12, and 14 were in the range of
30 to 31 mN/m and decreased when the carbon chain
length of dimethyl ester increased (Table 2). These values are close to those of the surface tension of the industrial surfactants, which range from 26 to 28 mN/m (17).
Interfacial tensions of compounds 8, 10, 12, and 14
against paraffin oil were found to be 16.8, 14.5, 10.4, and
9.9 mN/m, respectively (Table 2). Compound 14 has the
lowest interfacial tension compared with compounds 8,
10, and 12. This is probably due to the interaction of the
hydrophobic portion of monoglycerol ester with the liquid surface of paraffin oil. The cloud points of synthesized monoesters were more than 100C (Table 2). From
the literature, mono- and di-glycerides are mild surfactants and widely used in food industries. They also can be
further reacted to produce more complex biosurfactants
such as the phospholipids (18). The synthesized succinate

50
40
Monoester

30
20

Diester

10
0
0

10

15

20

Reaction time (hours)


FIG. 4. The effect of temperature on the reaction of glycerol with dimethyl succinate for monoester at 80C (); 100C (); 120C () and
); 100C (
); 120C (
) (molar ratio 4:1, 0.2 wt%
diester at 80C (
KOH, and 2 wt% molecular sieve).

70

Monoester

60
50
40
30

Diester

20
10
0
0

10

15

Reaction time (hours)

20

FIG. 5. The influence of molecular sieve on the reaction of glycerol with


dimethyl succinate for monoester without molecular sieve () and with 2
) and
wt% molecular sieve (); and for diester without molecular sieve (
with 2 wt% molecular sieve (
) (molar ratio 4:1, 80C, and 0.2 wt% KOH).
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152
G.H.P. CHO ET AL.
TABLE 2
Physical Data of 10% (vol/vol) Monoglycerol Esters
Properties

Temperature
(C)

Compound
8

Compound
10

Compound
12

Compound
14

Appearance

25

Surface tension
(mN/m)

25

30.72

30.53

30.72

30.01

Interfacial tension
(mN/m)

25

16.80

14.50

10.35

9.87

Cloud point (C)

>100

>100

>100

>100

Light yellow Light yellow Light yellow Light yellow


liquid
liquid
liquid
liquid

glycerides (8) could be used in conjunction with harsh detergents like sodium lauryl sulfate to reduce the irritation
of the sulfate ester.

11.

ACKNOWLEDGMENTS
12.

The authors would like to thank the Director General of Malaysian


Palm Oil Board (MPOB) for the permission to publish this article
and the research grant given through MPOB graduate scholarship.
In addition, the authors are also grateful to the University of
Malaya for the facilities provided.

13.

REFERENCES

14.

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[Received August 25, 2006; accepted February 14, 2006]

Gladys H.P. Cho is a masters degree student at the Department of


Chemistry, University of Malaya, Malaysia. She majors in oleochemical chemistry.
Dr. S.K. Yeong is a senior research officer at the Advanced Oleochemical Technology Division, Malaysian Palm Oil Board. Her research involves the development of household and industrial chemical
products from palm based oleochemicals.
Dr. T.L. Ooi is a principal research officer at the Advanced Oleochemical Technology Division, Malaysian Palm Oil Board. He currently heads the Oleochemical Products Development Unit.
Dr. C.H. Chuah is a professor at the Department of Chemistry,
University of Malaya, Malaysia. His research interest is in palm
oil chemistry.