Direct carbonylation of nitrobenzene to phenylisocyanate using gas-liquid slug flow in microchannel

Chemical Engineering Journal

Volumn 180, Issue , 2012, Pages 250-254

  Takebayashi, Yoshihiro ^a   Sue, Kiwamu ^a   Yoda, Satoshi ^a   Furuya, Takeshi ^a   Mae, Kazuhiro ^b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Carbon monoxide; Interfacial area to volume ratio; Mass transfer; Microreactor; Non phosgene isocyanate synthesis; Palladium catalyst

Indexed keywords

BATCH REACTIONS; GAS-LIQUID INTERFACE; GAS-LIQUID INTERFACIAL AREAS; GAS-LIQUID SLUG FLOW; INNER DIAMETERS; INTERFACIAL AREA-TO-VOLUME RATIO; LIQUID SLUG; LIQUID SLUG LENGTH; MICRO-FLOW; MICRO-REACTOR; MICROREACTION SYSTEMS; MICROTUBE; PALLADIUM CATALYST; PER UNIT VOLUME; PHENYLISOCYANATE; REACTANT MIXTURES;

CARBON MONOXIDE; CARBONYLATION; CATALYSTS; GASES; LIQUIDS; MASS TRANSFER; MICROCHANNELS; NITROBENZENE; SYNTHESIS (CHEMICAL); TUBES (COMPONENTS);

PHASE INTERFACES;

EID: 84455202320     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2011.11.031     Document Type: Article

References (25)

1. Ozaki S. Recent advances in isocyanate chemistry. Chem. Rev. 1972, 72:457-496.
2. R.J. Slocombe, H. Flores, T.H. Cleveland, Method of making organic isocyanates, U.S. Patent 2,680,127 (1954).
3. Hardy W.B., Bennett R.P. The direct conversion of aromatic nitro compounds to isocyanates by carbon monoxide. Tetrahedron Lett. 1967, 961-962.
4. Tafesh A.M., Weiguny J. A review of the selective catalytic reduction of aromatic nitro compounds into aromatic amines, isocyanates, carbamates, and ureas using CO. Chem. Rev. 1996, 96:2035-2052.
5. Cenini S., Ragaini F. Catalytic Reductive Carbonylation of Organic Nitro Compounds 1997, Kluwer, Dordrecht.
6. Paul F. Catalytic synthesis of isocyanates or carbamates from nitroaromatics using Group VIII transition metal catalysts. Coord. Chem. Rev. 2000, 203:269-323.
7. Doku G.N., Verboom W., Reinhoudt D.N., van den Berg A. On-microchip multiphase chemistry - a review of microreactor design principles and reagent contacting modes. Tetrahedron 2005, 61:2733-2742.
8. Hessel V., Angeli P., Gavriilidis A., Löwe H. Gas-liquid and gas-liquid-solid microstructured reactors: contacting principles and applications. Ind. Eng. Chem. Res. 2005, 44:9750-9769.
9. Kobayashi J., Mori Y., Kobayashi S. Multiphase organic synthesis in microchannel reactors. Chem. Asian J. 2006, 1:22-35.
10. Watts P., Wiles C. Recent advances in synthetic micro reaction technology. Chem. Commun. 2007, 443-467.
11. Chen G.W., Yue J., Yuan Q. Gas-liquid microreaction technology: recent developments and future challenges. Chin. J. Chem. Eng. 2008, 16:663-669.
12. Kashid M.N., Kiwi-Minsker L. Microstructured reactors for multiphase reactions: state of the art. Ind. Eng. Chem. Res. 2009, 48:6465-6485.
13. Wiles C., Watts P. Recent advances in micro reaction technology. Chem. Commun. 2011, 47:6512-6535.
14. Yasukawa T., Ninomiya W., Ooyachi K., Aoki N., Mae K. Efficient oxidative dehydrogenation of lactate to pyruvate using a gas-liquid micro flow system. Ind. Eng. Chem. Res. 2011, 50:3858-3863.
15. Yasukawa T., Ninomiya W., Ooyachi K., Aoki N., Mae K. Enhanced production of ethyl pyruvate using gas-liquid slug flow in microchannel. Chem. Eng. J. 2011, 167:527-530.
16. Miller P.W., Long N.J., de Mello A.J., Vilar R., Passchier J., Gee A. Rapid formation of amides via carbonylative coupling reactions using a microfluidic device. Chem. Commun. 2006, 546-548.
17. Miller P.W., Long N.J., de Mello A.J., Vilar R., Audrain H., Bender D., Passchier J., Gee A. Rapid multiphase carbonylation reactions by using a microtube reactor: applications in positron emission tomography 11C radiolabeling. Angew. Chem. Int. Ed. 2007, 46:2875-2878.
18. Miller P.W., Audrain H., Bender D., deMello A.J., Gee A.D., Long N.J., Vilar R. Rapid carbon-11 radiolabelling for PET using microfluidics. Chem. Eur. J. 2011, 17:460-463.
19. Rahman M.T., Fukuyama T., Kamata N., Sato M., Ryu I. Low pressure Pd-catalyzed carbonylation in an ionic liquid using a multiphase microflow system. Chem. Commun. 2006, 2236-2238.
20. Fukuyama T., Rahman T., Kamata N., Ryu I. Radical carbonylations using a continuous microflow system. Beilstein J. Org. Chem. 2009, 5.
21. Murphy E.R., Martinelli J.R., Zaborenko N., Buchwald S.L., Jensen K.F. Accelerating reactions with microreactors at elevated temperatures and pressures: profiling aminocarbonylation reactions. Angew. Chem. Int. Ed. 2007, 46:1734-1737.
22. Kelly C.B., Lee C., Mercadante M.A., Leadbeater N.E. A continuous-flow approach to palladium-catalyzed alkoxycarbonylation reactions. Org. Process Res. Dev. 2011, 15:717-720.
23. Csajági C., Borcsek B., Niesz K., Kovács I., Székelyhidi Z., Bajkó Z., Ürge L., Darvas F. High-efficiency aminocarbonylation by introducing CO to a pressurized continuous flow reactor. Org. Lett. 2008, 10:1589-1592.
24. Balogh J., Kuik Á., Ürge L., Darvas F., Bakos J., Skoda-Földes R. Double carbonylation of iodobenzene in a microfluidics-based high throughput flow reactor. J. Mol. Catal. A: Chem. 2009, 302:76-79.
25. Thermophysical properties of fluid systems, NIST Chemistry WebBook, . http://webbook.nist.gov./chemistry/fluid/.