Highly Efficient Silica-Supported Peroxycarboxylic Acid for the Epoxidation of Unsaturated Fatty Acid Methyl Esters and Vegetable Oils

Abstract

A silica-supported peroxycarboxylic acid oxidant, 2-percarboxyethyl silica (SiO2@(CH2)2COOOH), was successfully prepared and used for the epoxidation of fatty acid methyl esters (FAMEs) and vegetable oils. Among the oxidants prepared under different conditions, C-SiO2@(CH2)2COOOH (TEOS:CTES = 2:1) had the highest surface area, pore volume, and peroxide value. It also exhibited the highest activity for the epoxidation reactions. For methyl linoleate, 92.76% yield of epoxidized product was obtained at room temperature. Other unsaturated FAMEs with 1 and 3 double bonds were also efficiently converted to their epoxides. Moreover, the oxidant was also successfully applied to the epoxidation of vegetable oils, olive oil, and linseed oil with high product yield at room temperature. Finally, the used oxidant was regenerated through a simple oxidation process with H2O2 and recycled at least 5 times without much drop in the reactivity.

Performance controlled via surface oxygen-vacancy in Ti-based oxide catalyst during methyl oleate epoxidation

“… 2 , 3 However, various energy policies in different countries that encourage the use of electric vehicles to lower the demand for biodiesel suppressed the demand for FAME. Hence, the epoxidation reaction can be the solution towards the utilization of the FAME producing higher-value chemicals, especially, epoxide products 4 which are used in as plasticizers 5 , stabilizer in PVC, intermediates in polyurethane polyols 6 , lubricants 7 , cosmetics, precursors of various polymer 8 , wood impregnation, biofuel additives 9 , and in pharmaceuticals 10 . So far, the low-temperature liquid-phase epoxidation reaction was described by Prileshajew, as shown in Supplementary Figures S1 .…”

One pot peroxidation of oleic acid rich Azadirachta indica oil over bio‐waste derived heterogeneous catalyst

“…Table gives the comparison of IV C of various oils for different types of catalysts including homogeneous, heterogeneous (polymeric and metallic) catalysts that are reported in the literature . In the present work, all the experiments were conducted for a limited period to show the dependent variables effect on the IV C .…”

“…However, the use of homogeneous molybdenum catalyst per reaction was only 1 %. Another work, by Benaniba et al is comparable because they also used a tungsten‐based catalyst for sunflower oil epoxidation and reported a promising result after 8 h. Recent development of organometallic oxidant by Yao et al showed the performance in peroxidation of olive oil and linseed oil. They reported a high conversion, i.e.…”

“…Table 5 gives the comparison of IV C of various oils for different types of catalysts including homogeneous, heterogeneous (polymeric and metallic) catalysts that are reported in the literature. [2,[22][23][24][25][26][27][28][29][30][31][32] In the present work, all the experiments were conducted for a limited period to show the dependent variables effect on the IV C . For comparison purposes, another experiment was conducted at the local optimal values with an extended reaction period of 10 h and the IV C was 84.3 %.…”

“…Soybean oil [23] Al 2 O 3 5 8 0 2 4 9 7 Oleic acid methyl ester [24] Ti-silicas 20 70 24 20 Vegetable oil mixture [2] Ti(IV)-grafted silica 8 -24 85 Oleic acid [25] Silica-sulphuric acid 5 70 24 88 FAME [26] [C 3 SO 3 HMIM][HSO 4 ] 1 2 8 5 2 3 0 Canola oil [27] Amberlite IR-120 20 100 5 35 Mahua oil [22] H 2 SO 4 3.12 30 10 60 Mahua oil [22] HNO 3 3.12 30 10 36 Soybean oil [28] Ti/SiO 2 2.5 80 26.7 34.78 Soybean oil [29] Amberlite IR-120 15 75 7 96.9 Soybean oil [30] [MoO 2 (acac) 2 ]/ TBHP 1 110 24 83.2 Sunflower oil [31] WO 5 O ¼ P(NMe 2 ) 3 25 55 8 75.5 Olive oil [32] Oxidant SiO 2 @ (CH 2 ) 2 COOOH 710 Ambient 12 87.9 Linseed oil [32] Oxidant SiO 2 @ (CH 2 ) 2 COOOH 710 Ambient 9 92.4 Present work WNH-Zn 20 60 10 84.3…”