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FICHA CATALOGRÁFICA ELABORADA PELA BIBLIOTECA DO INSTITUTO
DE QUÍMICA DA UNICAMP
T235m
Teixeira, Sergio.
Modificações catalíticas de óleos vegetais para a
produção de insumos químicos / Sergio Teixeira. –
Campinas – SP:[s.n], 2006.
Orientador: Ulf Schuchardt.
Tese - Universidade Estadual de Campinas, Instituto
de Química.
1. Óleos vegetais. 2. Catálise. 3. Antioxidantes.
4. Surfactantes. I. Schuchardt, Ulf. II. Universidade
Estadual de Campinas. Instituto de Química. III. Título.
Título em inglês: Catalytic modifications of vegetable oils for the production of chemical
products
Palavras-chaves em inglês: Vegetable oils, Catalysis, Antioxidants, Surfactants
Área de concentração: Química Inorgânica
Titulação: Doutor em Ciências
Banca examinadora: Ulf Schuchardt (orientador), Caio Glauco Sanches (membro),
Luiz Pereira Ramos (membro), Francisco B. T. Pessine (membro), Nelson E. C. Durán
(membro), Inés Joekes (suplente), Pedro L. O. Volpe (suplente), Daniel B. Arellano
(suplente)
Data de defesa: 26/06/2006
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Edenol 3205 (1H-RMN)
9 Dec 2005
Acquisition Time (sec) 2.6667
300.07
Frequency (MHz)
CDCl3
Solvent
Camila edenol 3250 cdcl3 dez07cmgH7
1H
Number of Transients 16
6000.00
Temperature (grad C) 30.000
Comment
Nucleus
Sweep Width (Hz)
Dec 7 2005
Date
Original Points Count 16000
Points Count
16384
1.23
No. H = 489
3.64
CH3OCO
CH3 terminal
No.
1
2
3
4
5
6
(ppm)
0.86
1.23
1.47
1.60
1.71
2.28
Height
0.169
1.000
0.106
0.081
0.033
0.148
17.38
3.0
No.
7
8
9
10
11
12
(ppm)
2.62
2.88
2.95
3.09
3.64
7.25
Height
0.006
0.021
0.022
0.018
0.555
0.021
No.
Annotation
1
CH3 terminal
2 CH2's entre os oxiranos
3
No. H = 489
4
OOCCH25 H's do oxirano do 18:1
6 os oxiranos de 18:2 e ou
7
CH3OCO
8
Chloroform-d
1.51
0.43
31.30
2.5
(ppm)
[0.76 .. 0.99]
[1.66 .. 1.75]
[0.76 .. 3.79]
[2.18 .. 2.37]
[2.57 .. 2.67]
[2.83 .. 3.16]
[3.53 .. 3.73]
7.25
356.13
2.0
No.
1
2
3
4
5
6
7
8
9
10
11
(ppm)
[0.78 .. 0.99]
[0.99 .. 2.16]
[2.16 .. 2.43]
[2.44 .. 2.44]
[2.48 .. 2.50]
[2.59 .. 2.66]
[2.83 .. 3.15]
[3.33 .. 3.41]
[3.42 .. 3.49]
[3.54 .. 3.75]
[7.23 .. 7.27]
1.60
1.71
2.62
2.95
2.88
3.09
1.21 2.15
3.5
1.47
CH2's entre os oxiranos
H's do oxirano do 18:1
38.89
0.86
2.28
OOCCH2H's dos oxiranos de 18:2 e ou 18:3
1.5
41.17
1.0
Value
41.17
356.13
31.30
0.04
0.43
1.51
17.38
2.15
1.21
38.89
1.00
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DUJLOD.RULJLQDOOHYRXDRFRQVXPRGRVJUXSRVHSy[LGRHjIRUPDomRGHSURGXWRV
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FRQWHQKDPJUXSRVHSy[LGR$DUJLOD 0RQW+3$:PRVWURXVHUXPFDWDOLVDGRUEDVWDQWH
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HSy[LGRV GH ROHDWR OLQROHDWR H OLQROHQDWR D JDPD GH
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Edenol modificado (fração residual)
9 Dec 2005
Acquisition Time (sec) 2.6667
300.07
Frequency (MHz)
CDCl3
Solvent
Comment
Nucleus
Sweep Width (Hz)
Camila edenol mod res cdcl3 dez07cmgH1
1H
Number of Transients 16
6000.00
Temperature (grad C) 30.000
Dec 7 2005
Date
Original Points Count 16000
Points Count
16384
No. total H = 735
H's dos CH2's de etileno glicol
1.28
3.63
CH3OCO
0.86
1.59
2.27
desl.~ 1,68 - 1,73 (CH2 de oxiranos)
3.72
2.95
OH ou -CH-OH
ausente
134.90
4.0
No.
1
2
3
4
5
6
7
8
(ppm)
0.86
1.28
1.59
2.27
2.95
3.63
3.72
7.25
24.44
3.5
Height
0.242
0.781
0.186
0.229
0.100
1.000
0.081
0.060
56.04
3.0
No.
Annotation
1 1,68 - 1,73 (CH2 de oxir
2
ausente
3
No. total H = 735
4
OH ou -CH-OH
5 dos CH2's de etileno gl
6
CH3OCO
7
Chloroform-d
(ppm)
[1.70 .. 1.95]
[1.70 .. 1.95]
[0.69 .. 4.31]
[2.85 .. 3.09]
[3.12 .. 4.14]
[3.61 .. 3.66]
7.25
No.
1
2
3
4
5
6
519.68
2.5
(ppm)
[0.79 .. 2.12]
[2.12 .. 2.58]
[2.88 .. 3.10]
[3.10 .. 4.25]
[5.44 .. 5.47]
[7.24 .. 7.27]
2.0
1.5
1.0
Value
519.68
56.04
24.44
134.90
0.58
1.00
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Edenol modificado (fração residual)
9 Dec 2005
Acquisition Time (sec) 0.8000
75.46
Frequency (MHz)
CDCl3
Solvent
Camila edenol mod res cdcl3 dez07cmgC
13C
Number of Transients 20000
20000.00
Temperature (grad C) 30.000
Comment
Nucleus
Sweep Width (Hz)
Dec 7 2005
Date
Original Points Count 16000
Points Count
CH2's de etileno glicol
16384
Chlorof orm-d
29.16
51.41
CH3OCO
24.92
34.06
77.00
C´s ligados a OH's
14.09
31.88
174.08
C=O
(ppm)
14.09
22.68
24.92
29.16
29.70
31.88
34.06
37.93
51.41
160
Height
0.182
0.184
0.295
0.262
0.143
0.144
0.368
0.030
0.330
150
No. (ppm)
10 62.25
11 73.26
12 74.44
13 77.00
14 79.05
15 80.15
16 82.48
17 83.78
18 174.08
140
Height
0.047
0.054
0.022
0.942
0.022
0.037
0.027
0.022
0.082
130
120
110
100
90
80
70
37.93
62.25
74.44
73.26
83.78
82.48
80.15
79.05
C's de etileno glicol
170
No.
1
2
3
4
5
6
7
8
9
22.68
CH3 terminal
60
50
40
30
20
No.
Annotation
(ppm)
1
CH3 terminal
[12.14 .. 16.03]
2
CH3OCO
[49.04 .. 53.09]
3
C's de etileno glicol
[60.34 .. 63.60]
4
C´s ligados a OH's
[72.29 .. 75.33]
5
Chloroform-d
77.00
6 CH2's de etileno glicol [75.14 .. 85.23]
7
C=O
[170.83 .. 176.78]
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Applied Catalysis A: General 318 (2007) 213–217
www.elsevier.com/locate/apcata
Alumina-catalyzed epoxidation of unsaturated fatty esters
with hydrogen peroxide
Jorge Sepulveda 1, Sergio Teixeira, Ulf Schuchardt *
Instituto de Quı́mica, Universidade Estadual de Campinas, PO Box 6154, 13083-970 Campinas, SP, Brazil
Received 12 July 2006; received in revised form 31 October 2006; accepted 5 November 2006
Available online 6 December 2006
Abstract
Two commercial aluminas and one produced by the sol–gel process were compared for the epoxidation of unsaturated fatty esters using
anhydrous or aqueous hydrogen peroxide as oxidant and ethyl acetate as solvent. The aluminas show a good catalytic activity and excellent
selectivity towards the epoxides. The sol–gel alumina was more efficient and when using aqueous hydrogen peroxide could be recycled several
times.
# 2006 Elsevier B.V. All rights reserved.
Keywords: Epoxidation; Methyl oleate; Alumina; Hydrogen peroxide; Vegetable oils
1. Introduction
The application of modified vegetable oils in the chemical
industry is becoming more and more important because of their
availability from renewable resources. Epoxidized vegetable
oils play an important role as building blocks for the
preparation of chemical intermediates that are the basis for a
wide variety of consumer products [1]. Epoxidized oils can be
used as PVC-plasticizers and stabilizers, reactive diluents for
paints, intermediates in the production of polyurethane-polyols,
as well as components of lubricants and adhesives [2].
The catalytic epoxidation of oleochemicals has been the
subject of many academic and industrial investigations [3,4].
However, the only commercial source of epoxidized oils is the
Prileshajev reaction which uses short chain percarboxylic acids
[5]. Other methods for the epoxidation of unsaturated fatty
compounds include the use of dioxiranes [6], the generation of
peracids from aldehydes and molecular oxygen [7], chemoenzymatic ‘‘self-epoxidation’’ catalyzed by immobilized
Novozym 4351 [8], and transition metal catalyzed C C
epoxidations using alkylhydroperoxides [9].
The use of hydrogen peroxide as oxidant in epoxidation is
attractive both from the environmental and the economic
standpoint. It is cheap, readily available and gives water as the
only by-product. Many different catalytic systems for the
epoxidation using hydrogen peroxide as oxidant have been
developed in recent years. Catalysts based on titanium [10],
manganese [11], tungsten [12] and rhenium [13] have been
described.
In recent papers [14,15] good activity and selectivity in the
epoxidation of limonene, cyclohexene, 1-octene and pinene by
anhydrous and aqueous H2O2 catalyzed by alumina were
reported. However, no detailed work was conducted with bulk
substrates such as methyl oleate. In the present work a
comparison of different aluminas in the epoxidation of fatty
esters with anhydrous and aqueous hydrogen peroxide is
reported.
2. Experimental
2.1. Reagents/materials
* Corresponding author. Tel.: +55 19 3788 3071; fax: +55 19 3788 3023.
E-mail address: [email protected] (U. Schuchardt).
1
On leave from the Instituto de Investigaciones en Catálisis y Petroquı́micaINCAPE-(UNL-CONICET), Santiago del Estero 2654, 3000 Santa Fe, Argentina.
0926-860X/$ – see front matter # 2006 Elsevier B.V. All rights reserved.
doi:10.1016/j.apcata.2006.11.004
Ethyl acetate (Quimis, p.a.), methanol (Quimis, p.a.), secbutanol (Merck, HPLC grade), oleic acid (Merck, extra pure),
hydrogen peroxide (Interox, 70%, w/w aqueous solution),
214
J. Sepulveda et al. / Applied Catalysis A: General 318 (2007) 213–217
aluminum oxide for chromatography (Fluka, 0.05–0.15 mm),
aluminum oxide for column chromatography (Acros Organics,
activated, acidic, 0.1–0.5 mm), aluminum tri-sec-butoxide
(Aldrich, 99.99%), oxalic acid (Synth, p.a.), di-n-butyl ether
(Fluka, >99%) and soybean oil (Cargill) were used as received.
The solution of anhydrous hydrogen peroxide (24%, w/w) in
ethyl acetate was prepared from aqueous H2O2 (70%, w/w) in
ethyl acetate by azeotropic distillation with a Dean-Stark
apparatus [14].
2.6. Epoxidation of methyl esters of soybean oil
2.2. Methods
2.7. Dehydration of 1,4-butanediol
The products were identified by gas chromatography–mass
spectroscopy (GC–MS) using a Hewlett-Packard 5890 gas
chromatograph equipped with a AT-Wax column and interfaced
with a Hewlett-Packard 5971A mass spectrometer. Helium was
used as the carrier gas. A similarly equipped Hewlett-Packard
5890 gas chromatograph using nitrogen as the carrier gas and a
flame ionization detector was used for product quantification,
with the help of calibration curves.
The aluminas were analyzed by XRD with a Shimadzu XD3A diffractometer, using Cu Ka radiation, with a step size of
0.028 and counting time of 1 s. The surface area was determined
in a Micrometrics ASAP 2010 device by nitrogen adsorption–
desorption at 77 K, using the BET method.
Liquid phase catalytic dehydration of 1,4-butanediol was
employed in order to study the acidic sites of alumina. The
experiments were carried out in a Parr autoclave (Parr
Instruments Co.). Alumina (300 mg), 20 mmol of 1,4butanediol and 30 mL of 1,4-dioxane (solvent) were placed
into the reactor. The mixture was heated to 210 8C under
vigorous stirring to start the reaction. The products of
the reaction were quantified by GC analysis, using
calibration curves and di-n-butyl ether (10 mmol) as internal
standard.
A mixture of methyl esters of soybean oil
(2.5 g = 14.6 mmol of double bonds), aqueous hydrogen
peroxide (60 mmol), di-n-butyl ether (10 mmol, internal
standard), and ethyl acetate (10 mL) was heated under reflux
with magnetic stirring. A sample was taken and the reaction
started by addition of the alumina (300 mg). The products were
quantified by GC analysis.
3. Results and discussion
3.1. Characterization of the alumina catalysts
2.3. Synthesis of the sol–gel alumina
The sol–gel alumina was obtained by hydrolysis of
aluminum sec-butoxide (10.0 g, 40.6 mmol) dissolved in
15 mL of sec-butanol [16]. To this suspension an aqueous
solution of oxalic acid (7.5 mL, 0.75 mol L 1) was added
dropwise under vigorous stirring. The mixture was refluxed for
3 h and the gel obtained was dried at 70 8C for 24 h and then
treated under a flow of synthetic air at 100, 200 and 400 8C, for
24 h each, generating g-Al2O3.
The behavior of alumina in the dehydration of 1,4butanediol has been monitored in order to evaluate the acidic
character of the solids [17,18]. This reaction is essentially a
liquid phase dehydration and tetrahydrofuran (THF) is
produced with high selectivity (>99%) at 210 8C. The good
conversion observed for sol–gel and Acros aluminas (Fig. 1) in
the dehydration can be explained by the higher density and/or
strength of the acidic sites. Fluka alumina was not very active
under these conditions and no catalytic activity was observed at
lower reaction temperatures (100–160 8C).
2.4. Esterification of oleic acid
28.2 g (0.1 mol) of oleic acid and 100 mL (2.36 mol) of
methanol saturated with gaseous HCl (ca. 8%, w/w) were
refluxed for 1 h. The mixture was cooled, transferred to an
extraction funnel and washed with a saturated aqueous solution
of NaCl until the pH of the washings was neutral and, finally,
washed twice with distillated water. The ester obtained was
dried with anhydrous magnesium sulfate and distilled in a
Kugelrohr apparatus (180 8C, 10 mbar). Yield: 98%.
2.5. Epoxidation of methyl oleate with alumina
In a typical experiment 300 mg of alumina, 10 mmol of
hydrogen peroxide, 5 mmol of methyl oleate and 10 mL ethyl
acetate were mixed in a 50 mL round bottom flask. The reaction
was carried out at 80 2 8C under vigorous stirring and
samples were taken at regular periods for GC analysis. An
initial amount of methyl palmitate in the starting material was
used as an internal standard.
Fig. 1. Dehydration of 1,4-butanediol catalyzed by aluminas. Conditions:
300 mg of catalyst; 20 mmol of 1,4-butanediol; 30 mL of 1,4-dioxane; 210 8C.
J. Sepulveda et al. / Applied Catalysis A: General 318 (2007) 213–217
215
Table 1
BET surface area of the aluminas and initial activity in the epoxidation of
methyl oleate
Fig. 2. Epoxidation of methyl oleate using Fluka alumina with anhydrous and
aqueous hydrogen peroxide. Conditions: H2O2/oleate = 2 (mol/mol); methyl
oleate/catalyst = 5 (w/w); 80 2 8C.
3.2. Epoxidation of methyl oleate
The results for the epoxidation of methyl oleate with H2O2
as oxidant in the presence of Fluka alumina are shown in Fig. 2.
From the profile of the epoxidation with aqueous (70%, w/w)
and anhydrous (24%, w/w) hydrogen peroxide it is clear that the
aqueous solution is the better choice.
At the beginning of the reaction, the conversion of methyl
oleate is similar when aqueous 70 wt% or anhydrous 24 wt%
hydrogen peroxide are used. However, aqueous hydrogen
peroxide is more efficient in the rehydration of the surface,
maintaining the number of catalytic sites high. The effect of
water on the surface of alumina has already been discussed in
early papers [16,19].
Fig. 3 shows the results for different aluminas in the
epoxidation of methyl oleate with aqueous hydrogen peroxide.
The activities of the materials in the epoxidation follows the
Fig. 3. Epoxidation of methyl oleate using different aluminas. Conditions:
aqueous H2O2/oleate = 2 (mol/mol); methyl oleate/catalyst = 5 (w/w);
80 2 8C.
Alumina
BET surface
area (m2 g 1)
Initial activity
(% conv. h 1 m 2)
Sol–gel
Acros
Fluka
280
200
195
0.179
0.193
0.174
same order as observed in the dehydration of 1,4-butanediol. As
shown in a proceeding paper [20], weak to moderate acidic sites
are responsible for the catalysis. The different activities can be
explained by the different BET surface areas of the aluminas.
When calculating the initial activities of the aluminas per m2
and hour (Table 1), we find that the activity for epoxide
production is in the same range for commercial and sol–gel
aluminas, which means that only the available surface area is
responsible for the different conversions. A similar result was
already obtained in the epoxidation of several olefins with
hydrogen peroxide in the presence of different commercial
aluminas [15], where the conversion was found to be
independent of the type of alumina used. The same selectivity
for epoxides (>97%) was observed for all aluminas.
3.3. Effect of the molar ratio methyl oleate:hydrogen
peroxide
The influence of the molar ratio methyl oleate:aqueous
hydrogen peroxide on the conversion is shown in Fig. 4. A
molar ratio of 1:4 is sufficient to guarantee an appropriate
conversion. The excess of H2O2 is necessary because part of it
is decomposed by the catalyst to water and oxygen [19].
3.4. Epoxidation of methyl esters of soybean oil
The catalytic results for the epoxidation of methyl esters of
soybean oil with Acros alumina are presented separately for
Fig. 4. Effect of substrate:aqueous H2O2 molar ratio in the epoxidation of methyl
oleate with Acros alumina. Conditions: methyl oleate/catalyst = 5 (w/w);
80 2 8C.
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J. Sepulveda et al. / Applied Catalysis A: General 318 (2007) 213–217
each unsaturated ester in Fig. 5. The methyl linolenate present
was totally epoxidized after 6 h; the conversion of methyl
linolenate was 87% after 9 h. The selectivity for epoxides was
better than 97% for all methyl esters. The conversion using the
alumina catalyst was higher than that obtained by Hoelderich
and coworkers [3] with Ti-MCM-41 and tert-butyl hydroperoxide at 70 8C and oleate/catalyst ratio of 20 g/g. They
observed a conversion of only 50–60% after 24 h.
3.5. Recycling tests
Fig. 5. Epoxidation of methyl esters of soybean oil with Acros alumina.
Conditions: aqueous H2O2/soybean methyl esters = 4 (mol/mol); 2.5 g of
methyl esters; substrate/catalyst = 8 (w/w); 80 2 8C.
The recycling of the catalyst was evaluated for three and four
cycles for Acros and sol–gel aluminas, respectively. In these
experiments the catalyst was filtered after each experiment. In
our previous work [19] we already demonstrated that the
stability of the catalyst with aqueous 70 wt% hydrogen
peroxide was higher than with anhydrous hydrogen peroxide,
allowing the production of 47.4 g of cyclooctene oxide per g of
alumina. With methyl oleate, the sol–gel alumina was used four
times with small loss in conversion efficiency and no significant
changes on selectivity (Fig. 6a). On the other hand, Acros
alumina deactivated more rapidly, reaching a conversion of
50% after three reactions (Fig. 6b).
4. Conclusions
Alumina synthesized by the sol–gel method is shown to be
an inexpensive and efficient catalyst in the epoxidation of
methyl oleate and soybean oil methyl esters with aqueous
hydrogen peroxide as oxidant. A conversion of 95% and
selectivity >97% for the epoxide were obtained after 24 h
without the use of any kind of homogeneous acid. After four
cycles, a conversion of 87% was obtained. These results show
that sol–gel alumina is an alternative catalyst for the
epoxidation of vegetable oils.
Acknowledgements
The authors acknowledge financial support from Fundação
de Amparo à Pesquisa do Estado de São Paulo (FAPESP),
Conselho Nacional de Desenvolvimento Cientı́fico e Tecnológico (CNPq) and Coordenação de Aperfeiçoamento de
Pessoal de Nı́vel Superior (CAPES).
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Fig. 6. Recycling of the sol–gel alumina (a) and Acros alumina (b) in the
epoxidation of methyl oleate. Conditions: substrate/catalyst = 5 (w/w); aqueous
H2O2/oleate = 4 (mol/mol); 80 2 8C.
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