Epoxidation of Canola Oil with Hydrogen Peroxide Catalyzed by Acidic Ion Exchange Resin

Abstract

Canola oil with an iodine value of 112/100 g, and containing 60% oleic acid and 20% linoleic acid, was epoxidised using a peroxyacid generated in situ from hydrogen peroxide and a carboxylic acid (acetic or formic acid) in the presence of an acidic ion exchange resin (AIER), Amberlite IR 120H. Acetic acid was found to be a better oxygen carrier than formic acid, as it produced about 10% more conversion of ethylenic unsaturation to oxirane than that produced by formic acid under otherwise identical conditions. A detailed process developmental study was then performed with the acetic acid/AIER combination. The parameters optimised were temperature (65°C), acetic acid to ethylenic unsaturation molar ratio (0.5), hydrogen peroxide to ethylenic unsaturation molar ratio (1.5), and AIER loading (22%). An iodine conversion of 88.4% and a relative conversion to oxirane of 90% were obtained at the optimum reaction conditions. The heterogeneous catalyst, AIER, was found to be reusable and exhibited a negligible loss in activity.

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

“…The mechanism for this reaction can be seen in Scheme 3. Despite having a higher rate of epoxide formation when formic acid is employed (Dinda et al, 2008), acetic acid is found to be a better choice as 10% higher conversion of ethylenic unsaturation to epoxides is observed compared to formic acid (Mungroo et al, 2008).…”

“…Two common oxidants employed in the industry are performic acid and peracetic acid, generated in-situ using hydrogen peroxide as the oxygen donor and a carboxylic acid such as formic acid (Ni and Salimon, 2012) or acetic acid. While the use of formic acid can be carried out with no catalyst requirement (Ni and Salimon, 2012), acetic acid requires an acid catalyst, either a strong inorganic acid (Dinda et al, 2008), such as HCl, HNO 3 , H 3 PO 4 and the most widely used is H 2 SO 4 , or acidic ion exchange resins (AIER) (Cooney et al, 2011;Mungroo et al, 2008). The mechanism for this reaction can be seen in Scheme 3.…”

“…Mungroo et al (2008) and Dinda et al (2008) studied the catalytic activity of AIER on the epoxidation of canola and cottonseed oil, respectively, using peroxyacetic acid as the oxidant with good oxirane conversion, up to 65%, and selectivity as high as 90%. Borugadda and Goud (2014) reported the epoxidation of castor oil fatty acid methyl esters using Amberlite IR-120(H) for the synthesis of biolubricant base stock.…”

Response surface methodology for optimization of bio‐lubricant basestock synthesis from high free fatty acids castor oil

“…Enhanced rate of per acid formation was anticipated with an increase catalyst loading and hydrogen peroxide concentration followed by an increase in the OOC [49,52]. Figure S7a and b describes the effect of catalyst loading and hydrogen peroxide on the course of epoxide formation.…”

Castor Oil Based Epoxy/Clay Nanocomposite for Advanced Applications

“…However, in spite of such versatility, some of the disadvantages like low toughness, high brittleness and non-biodegradability restricting their utilizations in many advanced applications. Also, the global concern regarding the degradability of polymeric materials in environment compelled the scientists to explore the renewable resources in the production of useful materials (Velayutham et al, 2012;Yang et al, 2011;Biermann et al, 2000;Mungroo et al, 2008;Singh, et al, 2012). Therefore, to overcome such limitations, bio based epoxy resins were produced from vegetable oils.…”