A study was carried out to compare the epoxidation of unsaturated vegetable oils using dioxirane intermediates generated in situ using Oxone to that by the peracid/hydrogen peroxide method. Epoxidized oils are typically synthesized using hydrogen peroxide, as well as acetic or formic acid. This synthesis requires heating and catalysts and generates acidic waste. Recently, advances have been made in the process of using Oxone (potassium peroxymonosulfate) and ketones to generate in situ dioxiranes to epoxidize alkenes. The dioxirane method allows for room temperature reactions and eliminates the use of peroxides and acids. Epoxidation of soybean oil, hempseed oil and sucrose soyate using in situ generated dioxiranes was carried out and parameters such as molar ratios and addition rates were studied. The data show that optimum reaction conditions are reached when molar ratios of Oxone and unsaturation are 1.6:1 and the Oxone addition rate is 1 mL min^–1. As a comparison, epoxidations using the acetic acid/hydrogen peroxide method were carried out and cured materials were prepared from the epoxidized compounds. Negligible differences were identified in the materials prepared from both synthetic pathways. An environmental sustainability assessment using green chemistry principles was also conducted for both methods to evaluate their safety and efficiency with respect to multiple criteria including minimizing waste generation and energy consumption. The analysis shows that, although the peracid method is atom economic and generates less waste, the dioxirane method offers better occupational safety and requires less energy, demonstrating the tradeoffs involved with either pathway if one is to be selected. © 2021 Society of Chemical Industry

中文翻译：

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生物基油的环氧化方法比较：由Oxone生成的二环氧乙烷中间体与由过氧化氢衍生的过酸

进行了一项研究，以比较使用Oxone原位生成的二环氧乙烷中间体与过酸/过氧化氢方法进行的不饱和植物油的环氧化。环氧化油通常使用过氧化氢以及乙酸或甲酸合成。该合成需要加热和催化剂，并产生酸性废物。近来，在使用氧酮（过氧一硫酸钾）和酮的过程中取得了进展，以原位生成二恶英酮以环氧化烯烃。二环氧乙烷法可在室温下反应，而无需使用过氧化物和酸。大豆油，大麻油和蔗糖大豆油的原位环氧化进行了二恶英的生成，并研究了诸如摩尔比和添加速率的参数。数据显示，当Oxone与不饱和物的摩尔比为1.6：1且Oxone添加速率为1 mL min ^–1时，可以达到最佳反应条件。作为比较，使用乙酸/过氧化氢方法进行环氧化，并由环氧化的化合物制备固化的材料。从两种合成途径制备的材料中鉴定出的差异可忽略不计。还针对这两种方法使用了绿色化学原理进行了环境可持续性评估，以针对包括减少废物产生和能源消耗在内的多个标准评估其安全性和效率。分析表明，尽管过酸法是原子经济的，并且产生的废物较少，但是二环氧乙烷法提供了更好的职业安全性，并且所需的能源更少，这表明了如果要选择其中一种途径，都需要权衡取舍。©2021化工协会