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Novel access to verbenone via ruthenium nanoparticles-catalyzed oxidation of α-pinene in neat water
Applied Catalysis A: General ( IF 5.5 ) Pub Date : 2017-11-21 , DOI: 10.1016/j.apcata.2017.11.016
Mariem Rauchdi , Mustapha Ait Ali , Alain Roucoux , Audrey Denicourt-Nowicki

Aqueous suspensions of Ru(0) nanoparticles, stabilized with hydroxyethylammonium salts and possessing sizes around 2 nm, proved to be active and selective in the mild oxidation of α-pinene in the presence of tert-butylhydroperoxide, in neat water. Verbenone, a product of great interest for fine chemistry, was obtained as major product with yield up to 41% under optimized conditions. 2-hydroxy-3-pinanone was identified as a co-product of the reaction, but with very low amount (<7%). Kinetic investigations allowed determining the potential reaction intermediates and by-products. Moreover, mechanistic studies with radical scavengers confirmed that α-pinene oxidation mainly implies both carbon- and oxygen-centered radicals.



中文翻译:

新颖访问马鞭草烯酮通过的钌微粒催化氧化α蒎烯在纯的水

Ru(0)纳米粒子的水悬浮液,用羟乙基铵盐稳定并具有大约2 nm的大小,被证明在纯净水中在叔丁基过氧化氢存在下在α-pine烯的轻度氧化中具有活性和选择性。获得了对精细化学非常感兴趣的产品马鞭草酮,它是在优化的条件下收率高达41%的主要产品。已确定2-羟基-3-吡喃酮酮是反应的副产物,但含量极低(<7%)。动力学研究可以确定潜在的反应中间体和副产物。此外,用自由基清除剂进行的机理研究证实,α-pine烯氧化主要是指以碳和氧为中心的自由基。

更新日期:2017-11-21
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