Influence of carboxylic acid in the production of epoxidized soybean oil by conventional and ultrasound-assisted methods
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ORIGINAL ARTICLE
Influence of carboxylic acid in the production of epoxidized soybean oil by conventional and ultrasound-assisted methods Dayanne L. H. Maia 1 & Fabiano A. N. Fernandes 1 Received: 3 July 2020 / Revised: 2 November 2020 / Accepted: 6 November 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract This study investigated the production of epoxidized soybean oil by conventional and ultrasound-assisted methods. Epoxidized soybean oil was synthesized by reacting soybean oil, hydrogen peroxide, and carboxylic acid (formic or acetic acid). Sulfuric acid was used as a peroxidation catalyst. The effects of sonication, the carboxylic acid (formic and acetic acid), peroxidation catalyst (H2SO4), and temperature (50, 60, and 80 °C) were evaluated on the yield and productivity of epoxidized soybean oil. The reaction was carried out for 5 h in the conventional method and for 3 h in the ultrasound-assisted method. In both conventional and ultrasound-assisted methods, soybean oil yields into epoxidized soybean oil surpassed 90% only when formic acid and sulfuric acid were applied. The conventional method occurred faster than the sonochemical method for yields of up to 90%. The ultrasound-assisted method was the best technological option to attain a product of high purity (98%). The sonochemical method could be considered a promising technology if the ultrasound equipment’s limitations can be overcome. Keywords Soybean oil . Epoxidation . Acid catalyst . Ultrasound . Sulfuric acid
1 Introduction Vegetable oils are valuable renewable resources, have low cost, are biodegradable, and can be modified by various reactions to develop sustainable products [1]. These oils can be used to obtain epoxides as an alternative to petroleum-based epoxides [2]. Epoxidized soybean oil is employed as a plasticizer and stabilizer for PVC (polyvinyl chloride) [3, 4], and can be used in food packaging [5]. The epoxidation of vegetable oils increases these oils’ reactivity, making them promising intermediates to produce a wide range of materials with applications in plasticizers, lubricants, surface coating formulations, and polymer stabilizers [6–8]. In this process, the increase in the triglyceride reactivity occurs by converting carbon-carbon double bonds to oxirane rings. However, hydroxyl groups’ formation may also occur when the oxirane ring is opened [9]. Epoxidation using vegetable oils with carboxylic acids and hydrogen peroxide can be carried out with or without a catalyst, such as a strong mineral
* Fabiano A. N. Fernandes [email protected] 1
Departamento de Engenharia Química, Universidade Federal do Ceará, Campus do Pici, Bloco 709, Fortaleza, CE 60440-900, Brazil
acid, a heterogeneous acidic ionic exchange resin, a cationic ionic exchange resin, or an enzyme [10–13]. Several strong mineral acids have been studied for epoxidation and sulfuric acid was considered the most effective mineral acid for this reaction [14]. Large-scale industrial plants that produce oil epoxides use hydrogen peroxide and carb
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