The Swern oxidation: Development of a high-temperature semicontinuous process

被引：30

作者：

McConnell, J. Russell ^{[1
]}

Hitt, James E. ^{[1
]}

Daugs, Edward D. ^{[1
]}

Rey, Troy A. ^{[1
]}

机构：

[1] Dow Chem Co USA, Midland, MI 48674 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2008年 / 12卷 / 05期

关键词：

D O I：

10.1021/op800057d

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The Swern oxidation has been widely exploited for the oxidation of alcohols to their respective carbonyl compounds. The cryogenic operating conditions (< -60 degrees 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 degrees 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.

引用

页码：940 / 945

页数：6

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[11] STRUCTURE OF THE DIMETHYL SULFOXIDE OXALYL CHLORIDE REACTION-PRODUCT - OXIDATIONS OF HETEROAROMATIC AND DIVERSE ALCOHOLS TO CARBONYL-COMPOUNDS [J].