Abstract
After a short section of safety aspects related to 2-nitroethanol, the paper describes a powerful methodology for developing flow processes based on a proof of concept (1), an optimization and modeling analysis (2), and a long run study in a mini-plant (3). The proof of concept is the initial stage where the solubilities and concentrations are fixed, taking into account the rough kinetics with a mass transfer understanding. It is followed by a complete kinetic analysis including activation energy to model the reaction under various conditions to optimize different targets (yield not being the only driver!). The last section shows the operation of a mini-plant including a microreactor and work-up unit operations. The approach is extremely powerful as it enables the study at laboratory scale of all the features that are usually associated with a pilot plant namely: stability over time on stream, solvent recirculation, model prediction, and robustness.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Sedelmeier, G.; Novartis AG: WO 2008/119804 A1, 2008.
Hessel, V.; Loeb, P.; Loewe, H. In Microreactors in Organic Synthesis and Catalysis; Wirth, T., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008.
Roberge, D. M.; Ducry, L.; Bieler, N.; Cretton, P.; Zimmermann, B. Chem. Eng. Technol. 2005, 28, 318.
Yoshida, J.-I.; Nagaki, A.; Yamada, T. Chem. Eur. J. 2008, 14, 7450.
Hessel, V.; Kralisch, D.; Kockmann, N.; Noel, T.; Wang, Q. ChemSusChem 2013, 6, 746.
Damm, M.; Glasnov, T. N.; Kappe, C. O. Org. Process Res. Dev. 2010, 14, 215.
Hessel, V.; Cortese, B.; deCroon, M.H. J. M. Chem. Eng. Sci. 2011, 66, 1426.
de Bellefon, C.; Tanchoux, N.; Caravieilhes, S.; Grenouillet, P.; Hessel, V. Angew. Chem. Int. Ed. 2000, 39, 3442.
McMullen, J. P.; Jensen, K. F. Org. Process Res. Dev. 2010, 14, 1169.
Kambe, S.; Yasuda, H. Bull. Chem. Soc. Jpn. 1968, 41, 1444.
Hays, J. T.; Hager, G. F.; Engelmann, H. M.; Spurlin, H. M. J. Am. Chem. Soc. 1951, 73, 5369.
Grob, C.; Jenny, E. F. DE1118772, 1970.
Borah, J. C.; Gogoi, S.; Boruwa, J.; Barua, N. B. Synth. Commun. 2005, 35, 873.
Hen, L. N.; Russel, W. 1969; Vol. US Patent 3426084.
Noland, W. E. Org. Synth. 1973, Coll. Vol. 5, 833.
Meyer, R. Explosivstoffe; 6th ed.; VCH: Weinheim, 1985.
Roberge, D. M.; Gottsponer, M.; Eyholzer, M.; Kockmann, N. Chem. Today 2009, 27, 8.
Holvey, C. P.; Roberge, D. M.; Gottsponer, M.; Kockmann, N.; Macchi, A. Chem. Eng. Process. 2011, 50, 1069.
Gorski, I.M.; Makarow, S.P. Berichte der deutschen chemischen Gesellschaft (A and B Series) 1934, 67, 996.
Brandes, E.; Gödde, M.; Hirsch, W. Green Process. Synth. 2012, 1, 345.
Kockmann, N.; Roberge, D. M. Chem. Eng. Process. 2011, 50, 1017.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made.
The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder.
To view a copy of this licence, visit https://creativecommons.org/licenses/by/4.0/.
About this article
Cite this article
Roberge, D.M., Noti, C., Irle, E. et al. Control of Hazardous Processes in Flow: Synthesis of 2-Nitroethanol. J Flow Chem 4, 26–34 (2014). https://doi.org/10.1556/JFC-D-13-00016
Published:
Issue Date:
DOI: https://doi.org/10.1556/JFC-D-13-00016