A Method to Identify Best Available Technologies (BAT) for Hydrogenation Reactors in the Pharmaceutical Industry

J. Flow Chem. 2012, 2(3), 77–82

http://www.akademiai.com/content/8652651g3378x686/?p=ab7c1bc4cd7740e1855623297649f542&pi=3

http://www.akademiai.com/content/8652651g3378x686/fulltext.pdf

Journal of Flow Chemistry
Publisher	Akadémiai Kiadó
ISSN	2062-249X (Print) 2063-0212 (Online)
Subject	Flow Chemistry
Issue	Volume 2, Number 3/September 2012
Pages	77-82
DOI	10.1556/JFC-D-12-00014

Authors

Tuong Doan¹, Petr Stavárek¹, Claude Bellefon^{1 * Author for correspondence: claude.debellefon@lgpc.cpe.fr}

¹CNRS, CPE Lyon University of Lyon Villeurbanne France

Abstract

A methodology that may be applied to help in the choice of a continuous reactor is proposed. In this methodology, the chemistry is first described through the use of eight simple criteria (rate, thermicity, deactivation, solubility, conversion, selectivity, viscosity, and catalyst). Then, each reactor type is also analyzed from their capability to answer each of these criteria. A final score is presented using “spider diagrams.” Lower surfaces indicate the best reactor choice. The methodology is exemplified with a model substrate nitrobenzene and a target pharmaceutical intermediate, N-methyl-4-nitrobenzenemethanesulphonamide, and for three different continuous reactors, i.e., stirred tank, fixed bed, and an advanced microstructured reactor. Comparison with the traditional batch reactor is also provided.

lyon france...........

 

 

 

Curtius reaction..........Flow Synthesis

A Modular Flow Reactor for Performing Curtius Rearrangements as a Continuous Flow Process.		Link: 10.1039/b801631n
Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N.; Smith, C. D.; Tierney, J. P.
Org. Biomol. Chem. 2008, 6, 1577-1586.
Abstract: The use of a mesofluidic flow reactor is described for performing Curtius rearrangement reactions of carboxylic acids in the presence of diphenylphosphoryl azide and trapping of the intermediate isocyanates with various nucleophiles.

http://pubs.rsc.org/en/Content/ArticleLanding/2008/OB/b801631n#!divAbstract

A modular flow reactor for performing Curtius rearrangements as a continuous flow process

Marcus Baumann,^a   Ian R. Baxendale,^a   Steven V. Ley,*^a  Nikzad Nikbin,^a   Christopher D. Smith^a and   Jason P. Tierney^b  

^a

Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk;
Fax: +44 1223 336442 ;
Tel: +44 1223 336398

^b

Neurology Lead Discovery Chemistry, Neurology CEDD, GlaxoSmithKline R and D, New Frontiers Science Park (North), Third Avenue, Harlow, UK

Org. Biomol. Chem., 2008,6, 1577-1586

DOI: 10.1039/B801631N

Azide Monoliths as Convenient Flow Reactors for Efficient Curtius Rearrangement Reactions.		Link: 10.1039/b801634h
Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N.; Smith, C. D.
Org. Biomol. Chem. 2008, 6, 1587-1593.
Abstract: The preparation and use of an azide-containing monolithic reactor is described for use in a flow chemistry device and in particular for conducting Curtius rearrangement reactions via acid chloride inputs.

http://pubs.rsc.org/en/Content/ArticleLanding/2008/OB/b801634h#!divAbstract

Azide monoliths as convenient flow reactors for efficient Curtiusrearrangement reactions

Marcus Baumann,^a   Ian R. Baxendale,^a   Steven V. Ley,*^a  Nikzad Nikbin^a and   Christopher D. Smith^a  

^a

Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk;
Fax: +44 1223 336442 ;
Tel: +44 1223 336398

Org. Biomol. Chem., 2008,6, 1587-1593

DOI: 10.1039/B801634H

An Efficient, Asymmetric Organocatalyst-mediated Conjugate Addition of Nitroalkanes to Unsaturated Cyclic and Acyclic Systems

An Efficient, Asymmetric Organocatalyst-mediated Conjugate Addition of Nitroalkanes to Unsaturated Cyclic and Acyclic Systems 
C.E.T. Mitchell, S.E. Brenner, J. Garcia-Fortanet and S.V. Ley, Org. Biomol. Chem. 2006, 4, 2039-2049.
http://pubs.rsc.org/en/content/articlelanding/2006/ob/b601877g/unauth#!divAbstract 

5-Pyrrolidin-2-yltetrazole is a versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enones. Using this catalyst, this transformation requires short reaction times, tolerates a broad substrate scope, and possibly proceeds via generation of an iminium species.

Multi-step synthesis using modular flow reactors: the preparation of yne-ones and their use in heterocycle synthesis

Multi-step synthesis using modular flow reactors: the preparation of yne-ones and their use in heterocycle synthesis 

I.R. Baxendale, S.C. Schou, J. Sedelmeier, S.V. Ley, Chem. Eur. J. 2010, 16, 89-94.

 http://onlinelibrary.wiley.com/doi/10.1002/chem.200902906/abstract

 

Multi-step in flow: The palladium-catalysed acylation of terminal alkynes for the synthesis of yneones as well as their further transformation to various heterocycles in a continuous-flow mode is presented. Furthermore, an extension of the simple flow configuration that allows for easy batch splitting and the generation of a heterocyclic library is described (see scheme).