Blacker, AJ and Jolley, KE (2015) Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors. Beilstein Journal of Organic Chemistry, 11. 2408 - 2417. ISSN 1860-5397
Abstract
The continuous flow synthesis of a range of organic solutions of N, N-dialkyl-N-chloramines is described using either a bespoke meso-scale tubular reactor with static mixers or a continuous stirred tank reactor. Both reactors promote the efficient mixing of a biphasic solution of N,N-dialkylamine in organic solvent, and aqueous sodium hypochlorite to achieve near quantitative conversions, in 72–100% in situ yields, and useful productivities of around 0.05 mol/h with residence times from 3 to 20 minutes. Initial calorimetric studies have been carried out to inform on reaction exotherms, rates and safe operation. Amines which partition mainly in the organic phase require longer reaction times, provided by the CSTR, to compensate for low mass transfer rates in the biphasic system. The green metrics of the reaction have been assessed and compared to existing procedures and have shown the continuous process is improved over previous procedures. The organic solutions of N,N-dialkyl-N-chloramines produced continuously will enable their use in tandem flow reactions with a range of nucleophilic substrates.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2015 Blacker and Jolley; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License(http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
Keywords: | amine; biphasic; chloramine ; chlorination; continuous flow chemistry; CSTR; static mixer; sodium hypochlorite; tube reactor |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 18 Dec 2015 16:13 |
Last Modified: | 12 Feb 2019 13:14 |
Published Version: | http://dx.doi.org/10.3762/bjoc.11.262 |
Status: | Published |
Publisher: | Beilstein-Institut |
Identification Number: | 10.3762/bjoc.11.262 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:92890 |