Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors

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...

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Main Authors:	Blacker, A John, Jolley, Katherine E
Format:	Online
Language:	English
Published:	Beilstein-Institut 2015
Online Access:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685760/

id	pubmed-4685760
recordtype	oai_dc
spelling	pubmed-46857602016-01-05 Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors Blacker, A John Jolley, Katherine E Full Research Paper 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. Beilstein-Institut 2015-12-02 /pmc/articles/PMC4685760/ /pubmed/26734089 http://dx.doi.org/10.3762/bjoc.11.262 Text en Copyright © 2015, Blacker and Jolley; licensee Beilstein-Institut. http://www.beilstein-journals.org/bjoc 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. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
repository_type	Open Access Journal
institution_category	Foreign Institution
institution	US National Center for Biotechnology Information
building	NCBI PubMed
collection	Online Access
language	English
format	Online
author	Blacker, A John Jolley, Katherine E
spellingShingle	Blacker, A John Jolley, Katherine E Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors
author_facet	Blacker, A John Jolley, Katherine E
author_sort	Blacker, A John
title	Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors
title_short	Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors
title_full	Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors
title_fullStr	Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors
title_full_unstemmed	Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors
title_sort	continuous formation of n-chloro-n,n-dialkylamine solutions in well-mixed meso-scale flow reactors
description	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.
publisher	Beilstein-Institut
publishDate	2015
url	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685760/
_version_	1613514957151797248

Continuous formation of N-chloro-N,N-dialkylamine solutions in well-mixed meso-scale flow reactors

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