The Swern Oxidation: Development of a High-Temperature Semicontinuous Process
The Swern Oxidation: Development of a High-Temperature Semicontinuous Process
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DOI：
10.1021/op800057d
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发表时间：
2008-06
影响因子：
3.4
通讯作者：
J. R. McConnell;J. E. Hitt;E. Daugs;Troy A. Rey
中科院分区：
文献类型：
--
作者：
J. R. McConnell;J. E. Hitt;E. Daugs;Troy A. Rey
Swern氧化被广泛用于将醇氧化成其各自的羰基化合物。然而，用于斯韦恩氧化的低温操作条件(<；−60°C)限制了其在放大操作中的应用。关于Swern氧化的工艺开发工作表明，在线反应器系统可用于成功地形成羰基化合物的烷氧基硫酸盐前体。两种试剂流，包括醇/二甲亚砜/二氯甲烷和草酰氯，在常温下加载到直列式反应器，使温度上升到40°C。烷氧基氯化硫中间体直接排放到三乙胺中完成反应。在750Gal中试装置上，证明了0.1Gal、1.4Gal、1.4Gal的S在串联反应器中的停留时间为0.1Gal、1.4Gal、−。
The Swern oxidation has been widely exploited for the oxidation of alcohols to their respective carbonyl compounds. The cryogenic operating conditions (<−60 °C) employed for the Swern oxidation, however, limit its utility for scale-up operations. Process development efforts on the Swern oxidation have demonstrated that an in-line reactor system can be used for the successful formation of the alkoxysulfonium salt precursor of the carbonyl compound. Two reagent streams, consisting of the alcohol/dimethylsulfoxide/methylene chloride and the oxalyl chloride, are loaded at ambient temperature to an in-line reactor, allowing the temperature to rise to 40 °C. The alkoxysulfonium chloride intermediate is discharged directly into triethylamine to complete the reaction. Residence times of 0.1−1.4 s in the in-line reactor were demonstrated to produce successful results in 750-gal pilot-plant equipment.