High-Temperature Diels-Alder Reactions: Transfer from Batch to Continuous Mode

被引:25
作者
Abele, Stefan [1 ]
Hoeck, Stefan [2 ]
Schmidt, Gunther [1 ]
Funel, Jacques-Alexis [1 ]
Marti, Roger [2 ]
机构
[1] Actel Pharmaceut Ltd, CH-4123 Allschwil, Switzerland
[2] ZHAW Zurich Univ Appl Sci, Inst Chem & Biol Chem, CH-8820 Wadenswil, Switzerland
关键词
CHEMISTRY;
D O I
10.1021/op200320w
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The transfer of a Diels-Alder reaction of (cyclohexa-1,5-dien-1-yloxy)trimethylsilane 1 with alpha-acetoxyacrylonitrile 2 and acrylonitrile 8, respectively, from batch to continuous mode is presented, using standard and widely available laboratory equipment. A standard microwave-based system was used as probe for the transfer to flow reactors. Temperature and residence time have been optimized in small coiled-tube reactors and confirmed with two production runs in a flow reactor. The inherent increase in safety caused by the small volumes at high temperatures and the achieved productivity (approximately 100 g/h using acrylonitrile) are offering advantages over the batch mode which suffers from thermokinetic limitations for scale-up.
引用
收藏
页码:1114 / 1120
页数:7
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