57512-44-4Relevant academic research and scientific papers
Continuous Production of Biorenewable, Polymer-Grade Lactone Monomers through Sn-Β-Catalyzed Baeyer–Villiger Oxidation with H2O2
Yakabi, Keiko,Mathieux, Thibault,Milne, Kirstie,López-Vidal, Eva M.,Buchard, Antoine,Hammond, Ceri
, p. 3652 - 3659 (2017/09/13)
The Baeyer–Villiger oxidation is a key transformation for sustainable chemical synthesis, especially when H2O2 and solid materials are employed as oxidant and catalyst, respectively. 4-substituted cycloketones, which are readily available from renewables, present excellent platforms for Baeyer–Villiger upgrading. Such substrates exhibit substantially higher levels of activity and produce lactones at higher levels of lactone selectivity at all values of substrate conversion, relative to non-substituted cyclohexanone. For 4-isopropyl cyclohexanone, which is readily available from β-pinene, continuous upgrading was evaluated in a plug-flow reactor. Excellent selectivity (85 % at 65 % conversion), stability, and productivity were observed over 56 h, with over 1000 turnovers (mol product per mol Sn) being achieved with no loss of activity. A maximum space–time yield that was almost twice that for non-substituted cyclohexanone was also obtained for this substrate [1173 vs. 607 g(product) kg(catalyst)?1 cm?3 h?1]. The lactone produced is also shown to be of suitable quality for ring opening polymerization. In addition to demonstrating the viability of the Sn-β/H2O2 system to produce renewable lactone monomers suitable for polymer applications, the substituted alkyl cyclohexanones studied also help to elucidate steric, electronic, and thermodynamic elements of this transformation in greater detail than previously achieved.
Preparation and Catalytic Property of Multi-walled Carbon Nanotubes Supported Keggin-Typed Tungstosilicic Acid for the Baeyer-Villiger Oxidation of Ketones
Yang, Zhiwang,Xu, Xueqing,Li, Tianjing,Zhang, Nana,Zhao, Xia,Chen, Wenlong,Liang, Xixi,He, Xinli,Ma, Hengchang
, p. 1955 - 1960 (2015/12/24)
Multi-walled carbon nanotubes (MWCNTs) supported HSiW/MWCNTs was successfully prepared and characterized by Fourier transform infrared spectoscopy, X-ray powder diffraction, transmission electron microscopy and N2 adsorption-desorption test. Its catalytic performance for the catalytic Baeyer-Villiger oxidation of cyclic ketones with 30 % H2O2 as oxidants was investigated. It was found that HSiW/MWCNTs was very efficient to transform of some cycloketones to the corresponding lactones with high conversions as well as selectivities. Factors affecting the oxidations and the reusability of the catalyst were also investigated. It was found that the catalyst can be reused seven times in the catalytic oxidation reaction of cyclopentanone without obviously catalytic activity losing in the oxidation. Graphical Abstract: A supported solid acid of HSiW/MWCNTs was used as efficient catalyst for the Baeyer-Villiger oxidation of ketones. High cyclopentanone conversion (98 %) and ε- valerolactone selectivity (99 %) were obtained. The catalyst can be reused at least seven runs in the oxidation of cyclopentanone.
Preparation of silica-supported sulfate and its application as a stable and highly active solid acid catalyst
Yang, Zhi-Wang,Niu, Leng-Yuan,Jia, Xiao-Jie,Kang, Qiao-Xiang,Ma, Zhen-Hong,Lei, Zi-Qiang
experimental part, p. 798 - 802 (2011/12/21)
Silica sulfate was prepared by a simple procedure, and proved to be an efficient and recyclable solid acid catalyst. SO3H groups were successfully introduced to silica surface while keeping its structure intact, as proved by XRD patterns and SEM images of the catalyst. With the catalysis of the supported sulfate materials, many of the ketones are efficiently transformed into the corresponding lactones with 30% hydrogen peroxide. In addition, the high performance of silica sulfate as a heterogeneous catalyst was further demonstrated for the esterification of varieties of carboxylic acid with ethanol.
Clean and selective Baeyer-Villiger oxidation of ketones with hydrogen peroxide catalyzed by Sn-palygorskite
Lei, Ziqiang,Zhang, Qinghua,Wang, Rongmin,Ma, Guofu,Jia, Chengguo
, p. 5779 - 5785 (2007/10/03)
An environmentally benign and selective Baeyer-Villiger oxidation system is introduced. Palygorskite-supported Sn complexes were prepared by a simple procedure. Cyclic ketones and acyclic ketones were oxidized by hydrogen peroxide in a reaction catalyzed by palygorskite-supported Sn complexes, affording corresponding lactones or esters with selectivity for the product of 90-99%. The influence of the solvents, reaction temperature, the amount of catalyst used and the reaction time on the catalytic activity and product selectivity were investigated in detail. The catalyst is cheap, easy to be prepared in large scale and can be recycled.
Baeyer-Villiger oxidation of ketones with hydrogen peroxide catalyzed by Sn-palygorskite
Lei, Ziqiang,Zhang, Qinghua,Luo, Jujie,He, Xiaoyan
, p. 3505 - 3508 (2007/10/03)
Palygorskite-supported Sn complexes were prepared by a simple procedure. Cyclic ketones and acyclic ketones were oxidized by hydrogen peroxide in a reaction catalyzed by palygorskite-supported Sn complexes, affording corresponding lactones or esters with selectivity for the product of 90-100%. The catalysts can be recycled for several times without significant decline in catalytic activity.
Chiral 6,7-dihydrooxepin-2(5H)-ones and the azepinone analogues: Conformation and diastereofacial selectivity in addition to the enones
Sato, Masayuki,Uehara, Fumiaki,Aizawa, Koh-Ichi,Kaneko, Chikara,Satoh, Shun-Ichi,Furuya, Toshio
, p. 633 - 636 (2007/10/02)
Diastereofacial selectivity in addition to the enones of 6- and 7-substituted dihydrooxepinones was studied. The addition occurred preferentially from the face anti to the substituent and 7-substituted substrates showed higher diastereofacial selectivity than the 6-substituted substrates. An explanation for the observed diastereofacial selectivity is proposed.
