Epoxidation of karanja (Pongamia glabra) oil catalysed by acidic ion exchange resin

Abstract

Epoxidation of karanja (Pongamia glabra) oil catalysed by acidic ion exchange resinKaranja oil with an iodine value of 89 g/100 g was epoxidised in situ with aqueous hydrogen peroxide and acetic acid in the presence of Amberlite IR-120 acidic ion exchange resin as catalyst. The effect of the operating variables on the oxirane oxygen content, as well as on the oxirane ring stability and the iodine value of the epoxidised karanja oil, were determined. The variables studied were stirring speed, hydrogen peroxide-to-ethylenic unsaturation molar ratio, acetic acid-to-ethylenic unsaturation molar ratio, temperature, and catalyst loading. The effects of these parameters on the conversion to the epoxidised oil were studied and the optimum conditions for the maximum oxirane content were established. The proposed kinetic model takes into consideration the two side reactions, namely, epoxy ring opening involving the formation of hydroxy acetate and hydroxyl groups, and the reaction between the peroxyacid and the epoxy group. The kinetic and adsorption constants of the rate equations were estimated by the best fit using Marquardt's algorithm. Good agreement between experimental and predicted data validates the proposed kinetic model. From the estimated kinetic constants, the apparent activation energy for the epoxidation reaction was found to be 11 kcal/mol. Keywords: Epoxidation, peroxyacetic acid, karanja oil (Pongamia glabra), acidic ion exchange resin, kinetics.Eur. J. Lipid Sci. Technol. 109 (2007) 575-584 DOI 10.1002/ejlt.200600298 575 IntroductionEpoxidation of plant oils (triacylglycerols), commonly referred to as "vegetable oils", is a commercially important reaction as the epoxides obtained from these renewable resources, and from their transesterification products, have wide applications in materials such as plasticisers and polymer stabilisers [1][2][3].Fats and oils are renewable resources that can be treated chemically or enzymatically to produce materials that can often act as replacement for materials derived from petroleum. Fatty epoxides can be used directly as plasticisers that are compatible with polyvinyl chloride (PVC) and stabilisers for PVC resins to improve flexibility, elasticity, and toughness and to impart stability to the polymer towards heat and UV radiation. Due to the high reactivity of the oxirane ring, epoxides also act as a raw material for a variety of chemicals, such as alcohols, glycols, alkanolamines, carbonyl compounds, olefinic compounds, and polymers like polyesters, polyurethanes, and epoxy resins. Epoxidised oil with a higher oxirane oxygen value and a lower iodine value is considered to be of better quality [4][5][6]. Today, one of the most important epoxidised vegetable oils is epoxidised soybean oil (ESO), and its worldwide production is about 200,000 t/year [7].On an industrial scale, the epoxidation of plant oils is currently carried out with the "Prileschajew reaction", in which the unsaturated oils react with a percarboxylic acid, such as peroxyacetic acid or peroxyf...

Selective epoxidation of natural triglycerides using acidic ion exchange resin as catalyst

“…SO 4 In the presence of AIER Iodine value Soybean oil [17] 18.3 -130 Palm Olein [6] 14.8 --Vegetable oil [16] -1 1 . 6 -Rubber seed oil [4] 15.7 -120 Karanja oil [18,19] 14. 9 11.0 89 Mahua oil [20] 14.5 -88 Cottonseed oil [10] 11.7 10.1 106 Jatropha oil [21] 14.1 -105…”

Interpenetrating Polymer Network (IPN) with Epoxidized and Acrylated Bioresins and their Composites with Glass and Jute Fibres

“…1; Petrovic et al 2002;Goud et al 2006Goud et al , 2007Cai et al 2008;Dinda et al 2008;Mungroo et al 2008;Goud et al 2010;Manthey et al 2011;Carbonell-Verdu et al 2015). Hemp oil (156 g, 1 mol), acetic acid (40 g, 0.67 mol), and Amberlite IR-120 (23.4 g, 15% by weight of hemp oil) were mixed thoroughly for 30 min from room temperature to 40 °C.…”

Chemo-enzymatic functionalisation of lignocellulose materials using oxiranes

“…However, in vitro preliminary studies in this work have been dedicated to demonstrate the possibility of coupling oxiranes onto lignin model compounds. The generation of oxiranes from unsaturated oils has been studied partly due to their importance as intermediates in the synthesis of polymers and as products resulting from the production of peroxy acids which are used as additives of polymers, lubricants and detergents [9][10][11][12][13][14]. Normally their production is achieved using strong mineral acids like concentrated sulfuric acid as catalysts.…”