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
相关论文
共 17 条
[11]   Rapid Determination of Reaction Kinetics with an Automated Microfluidic System [J].
McMullen, Jonathan P. ;
Jensen, Klavs F. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (02) :398-407
[12]   Straightforward hetero Diels-Alder reactions of nitroso dienophiles by microreactor technology [J].
Monbaliu, Jean-Christophe M. R. ;
Cukalovic, Ana ;
Marchand-Brynaert, Jacqueline ;
Stevens, Christian V. .
TETRAHEDRON LETTERS, 2010, 51 (44) :5830-5833
[13]   SYNTHETIC ELABORATION OF DIOSPHENOLS .3. REPLACEMENT OF ENOLIC OXYGEN BY HYDROGEN [J].
PONARAS, AA ;
ZAIM, O ;
PAZO, Y ;
OHANNESIAN, L .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1110-1112
[14]  
Rasheed M, 2011, CHIM OGGI, V29, P53
[15]   M-CHLOROPERBENZOIC ACID OXIDATION OF 2-TRIMETHYLSILYLOXY-1,3-DIENES - SYNTHESIS OF ALPHA-HYDROXY AND ALPHA-ACETOXY ENONES [J].
RUBOTTOM, GM ;
GRUBER, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (08) :1599-1602
[16]   Diels-Alder cycloadditions by microwave-assisted, continuous flow organic synthesis (MACOS): the role of metal films in the flow tube [J].
Shore, Gjergji ;
Organ, Michael G. .
CHEMICAL COMMUNICATIONS, 2008, (07) :838-840
[17]   Modular microreaction systems for homogeneously and heterogeneously catalyzed chemical synthesis [J].
Snyder, DA ;
Noti, C ;
Seeberger, PH ;
Schael, F ;
Bieber, T ;
Rimmel, G ;
Ehrfeld, W .
HELVETICA CHIMICA ACTA, 2005, 88 (01) :1-9