Beckmann Rearrangement of Cyclohexanone Oxime in a Microreactor Setup with Internal Recirculation

被引:11
作者
Zuidhof, Niek T. [1 ]
de Croon, Mart H. J. M. [1 ]
Schouten, Jaap C. [1 ]
Tinge, Johan T. [2 ]
机构
[1] Eindhoven Univ Technol, Dept Chem Engn & Chem, Lab Chem Reactor Engn, NL-5600 MB Eindhoven, Netherlands
[2] R&D BV Ind Chem, DSM Chem Technol, Geleen, Netherlands
关键词
E-Caprolactam; Beckmann rearrangement; Cyclooctane solution; Internal recirculation; EPSILON-CAPROLACTAM;
D O I
10.1002/ceat.201300088
中图分类号
TQ [化学工业];
学科分类号
0817 ;
摘要
Beckmann rearrangement of cyclohexanone oxime dissolved in cyclooctane with oleum to epsilon-caprolactam was demonstrated in a microreactor setup with internal recirculation operated in continuous mode. The core of the setup comprised a 316 stainless-steel micromixer consisting of 17 split-and-recombine units connected to a delay loop, a 316 stainless-steel microchannel reactor with an internal diameter of 0.250 mm and a length of 0.50 m. At 100 degrees C, the conversion of cyclohexanone oxime was complete and the selectivity towards epsilon-caprolactam was approximately 99 %. The solvent cyclooctane reduces the observed purity of the produced oleum/epsilon-caprolactam. This reduction in purity might be a severe hurdle for usage of a solvent on the industrial scale in the Beckmann rearrangement of cyclohexanone oxime in oleum to epsilon-caprolactam.
引用
收藏
页码:1387 / 1394
页数:8
相关论文
共 17 条
[1]  
[Anonymous], 1950, CH Patent, Patent No. 267114
[2]  
ARNDT O, 1980, Patent No. 4242275
[3]  
Beckmann E., 1886, BER DTSCH CHEM GES, V19, P988, DOI DOI 10.1002/CBER.188601901222
[4]  
H Lu, 2010, CN Patent, Patent No. [101851203 A, 101851203]
[5]  
Horn P., 1981, Patent No. [US4257950(A), 4257950]
[6]  
Luo G., 2010, CN Patent, Patent No. [101,891,681 A, 101891681]
[7]   Mechanism of the Beckmann rearrangement in sulfuric acid solution [J].
Nguyen, MT ;
Raspoet, G ;
Vanquickenborne, LG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (04) :821-825
[8]  
Schlack P., 1952, DE Patent, Patent No. [860,357, 860357]
[9]  
Smeets T. M., 2004, Process for preparing caprolactam by admixture of cyclohexanone oxime to a reaction mixture under turbulent flow conditions, Patent No. [113,287, 113287]
[10]   *DIE BECKMANNSCHE UMLAGERUNG DES CYCLOHEXANONOXIMS KINETIK DER REAKTIONS-ENDPHASE .1. [J].
WICHTERLE, O ;
ROCEK, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1951, 16 :591-598