Journal of Chemical Technology and Biotechnology, Vol.92, No.3, 526-533, 2017
Ketalization of epoxidized methyl oleate using acidic resins
BACKGROUND: Fatty acid dioxolanes can be used as bioplasticizers or biolubricants, replacing petroleum-derived products. Dioxolanes can be obtained by reaction of epoxides or glycols with ketones under acidic conditions. Brnsted and Lewis acids have been reported as catalysts of the reaction. However, acidic resins have not been used so far. These heterogeneous catalysts offer high activity, reusability as well as low price. In this work, ketalization of epoxidized methyl oleate with acetone was evaluated using acidic resins (Dowex-50WX2, Amberlyst-15 and Amberlite-IR120) at low temperature (35-55 degrees C). RESULTS: Total conversion of epoxide was obtained with Amberlyst-15, while amaximum conversion of 20% was afforded with Dowex-50WX2. However, Dowex-50WX2 was more selective to the dioxolane (max. 95% selectivity) than Amberlyst-15 (max. 76% selectivity). Amberlite IR120 afforded the lowest conversion of epoxide (max. 3%). The activation energy of the ketalization catalyzed with Amberlyst-15 was calculated as 12.53 kcal mol(-1). CONCLUSION: A new application of acidic resins in the ketalization of fatty epoxides at low temperatures was described. The effects of resin crosslinking and temperature were evaluated. Three kinds of products were detected: dioxolane, glycol and ketone. Several reaction pathways were proposed for ketalization over each resin. (C) 2016 Society of Chemical Industry