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. 2023 May 27;15(11):2477.
doi: 10.3390/polym15112477.

Enzymatic and Synthetic Routes of Castor Oil Epoxidation

Juliana A S Montenegro  1 , Andreas Ries  2 , Ingridy D S Silva  3 , Carlos B B Luna  3 , Antônia L Souza  4 , Renate M R Wellen  1   3   4
Affiliations

Enzymatic and Synthetic Routes of Castor Oil Epoxidation

Juliana A S Montenegro et al. Polymers (Basel). .

Abstract

Epoxidation of castor oil in synthetic and enzymatic routes was carried out in order to promote a system with less environmental impact. The epoxidation reactions of castor oil compounds upon addition of lipase enzyme with and without acrylic immobilization and with reaction times of 24 and 6 h, as well as the synthetic compounds upon addition of Amberlite resin and formic acid, were investigated using Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance in hydrogen molecules (1H-NMR). The analysis indicated that the enzymatic reactions (6 h) and synthetic reactions provided a conversion from 50 to 96% and epoxidation from 25 to 48%, resulting from peak stretching and signal disintegration in the hydroxyl region due to the appearance of H2O in the interaction of peracid with catalyst. In systems without toluene, a dehydration event with a peak absorbance of 0.02 AU, indicating a possible vinyl group at 2355 cm-1 in enzymatic reactions without acrylic immobilization, was observed and resulted in a selectivity of 2%. In the absence of a solid catalyst, an unsaturation conversion of castor oil above 90% was achieved; however, this catalyst is necessary for the epoxidation to take place, whereas the lipase enzyme becomes able of epoxidizing and dehydrating the castor oil upon changing the time or reaction system. The conversation from 28 to 48% of solid catalysts (Amberlite and lipase enzyme) displays their importance to the instauration conversion of castor oil into oxirane rings.

Keywords: 1H-NMR; FTIR; castor oil; epoxidation; lipase enzyme.

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Conflict of interest statement

There is no conflict of interest.

Figures

Figure 1
Figure 1
FTIR spectra of castor oil and the synthetic reactions’ products.
Figure 2
Figure 2
Spectra zoom for the hydroxyl (a) and unsaturation (b) regions of the synthetic reactions.
Figure 3
Figure 3
FTIR spectra for the epoxy region of the synthetic reactions.
Figure 4
Figure 4
FTIR spectra for the enzymatic epoxidations. * With toluene; ** without toluene.
Figure 5
Figure 5
Zoom of FTIR spectra of hydroxyl (a) and unsaturation (b) regions for the enzymatic reactions at 24 h.
Figure 6
Figure 6
FTIR spectra of the epoxy region for the enzymatic reactions at 24 h.
Figure 7
Figure 7
FTIR spectra of the epoxy region for the 6 h enzymatic reactions. * With toluene; ** without toluene.
Figure 8
Figure 8
1H-NMR spectra for the enzymatic reactions. * With toluene; ** without toluene.
Figure 9
Figure 9
1H-NMR spectra for the synthetic reactions.
See this image and copyright information in PMC

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