TY - JOUR
T1 - Utilization of vanillin to prepare sulfated Calix[4]resorcinarene as efficient organocatalyst for biodiesel production based on methylation of palmitic acid and oleic acid
AU - Jumina, Jumina
AU - Kurniawan, Yehezkiel Steven
AU - Lubis, Ali B
AU - larasati, Eleonora
AU - Pranowo, Bambang
AU - Triono, Sugeng
N1 - Publisher Copyright:
© 2023 Published by Elsevier Ltd.
PY - 2023/5/7
Y1 - 2023/5/7
N2 - Recently, biodiesel production from palm oils has been thoroughly investigated to substitute crude oil due to its scarcity. However, the biodiesel production process is time-consuming due to its slow kinetics; thus, concentrated sulfuric acid has been used to fasten the reaction process in some industries. Unfortunately, sulfuric acid is a toxic, corrosive, and non-environmentally friendly catalyst. In this study, we prepared sulfated Calix[4]resorcinarene derived from vanillin as an efficient organocatalyst to replace sulfuric acid. The catalytic activity of sulfated Calix[4]resorcinarenes was evaluated through the methylation of palmitic acid and oleic acid as model compounds due to their abundant amounts in palm oil. The Calix[4]resorcinarene and sulfated Calix[4]resorcinarenes have been obtained through a one-pot reaction in 71.8–98.3% yield. Their chemical structures were confirmed by using FTIR, NMR and HRMS spectrometry analyses. The results showed that the sulfated Calix[4]resorcinarene exhibited high catalytic activity for methyl palmitate and methyl oleate productions in 94.8 ± 1.8 and 97.3 ± 2.1% yield, respectively, which was comparable to sulfuric acid (96.3 ± 1.8 and 95.9 ± 2.5%). The optimum condition was achieved by using 0.020 wt equivalent of organocatalyst for 6 h reaction process at 338 K. The methylation of palmitic acid and oleic acid fits well with the first-order kinetic model (R2 = 0.9940–0.9999) with a reaction rate constant of 0.6055 and 1.1403 h-1, respectively. Further investigation reveals that the hydroxyl group of vanillin plays a pivotal role in the organocatalytic activity of sulfated Calix[4]resorcinarene.
AB - Recently, biodiesel production from palm oils has been thoroughly investigated to substitute crude oil due to its scarcity. However, the biodiesel production process is time-consuming due to its slow kinetics; thus, concentrated sulfuric acid has been used to fasten the reaction process in some industries. Unfortunately, sulfuric acid is a toxic, corrosive, and non-environmentally friendly catalyst. In this study, we prepared sulfated Calix[4]resorcinarene derived from vanillin as an efficient organocatalyst to replace sulfuric acid. The catalytic activity of sulfated Calix[4]resorcinarenes was evaluated through the methylation of palmitic acid and oleic acid as model compounds due to their abundant amounts in palm oil. The Calix[4]resorcinarene and sulfated Calix[4]resorcinarenes have been obtained through a one-pot reaction in 71.8–98.3% yield. Their chemical structures were confirmed by using FTIR, NMR and HRMS spectrometry analyses. The results showed that the sulfated Calix[4]resorcinarene exhibited high catalytic activity for methyl palmitate and methyl oleate productions in 94.8 ± 1.8 and 97.3 ± 2.1% yield, respectively, which was comparable to sulfuric acid (96.3 ± 1.8 and 95.9 ± 2.5%). The optimum condition was achieved by using 0.020 wt equivalent of organocatalyst for 6 h reaction process at 338 K. The methylation of palmitic acid and oleic acid fits well with the first-order kinetic model (R2 = 0.9940–0.9999) with a reaction rate constant of 0.6055 and 1.1403 h-1, respectively. Further investigation reveals that the hydroxyl group of vanillin plays a pivotal role in the organocatalytic activity of sulfated Calix[4]resorcinarene.
U2 - 10.1016/j.heliyon.2023.e16100
DO - 10.1016/j.heliyon.2023.e16100
M3 - Article (Academic Journal)
C2 - 37251819
SN - 2405-8440
VL - 9
JO - Heliyon
JF - Heliyon
IS - 5
M1 - e16100
ER -