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Continuous tank reactor synthesis of highly substituted sulphobutylether β-cyclodextrins

Savage, T, Mitchell, John C., Trivedi, Vivek, Wicks, Stephen, Waters, L. (2015) Continuous tank reactor synthesis of highly substituted sulphobutylether β-cyclodextrins. International Journal of Pharmaceutics, 495 (2). pp. 862-868. ISSN 0378-5173. (doi:10.1016/j.ijpharm.2015.09.039)

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https://doi.org/10.1016/j.ijpharm.2015.09.039

Abstract

Batch synthesis of sulphobutyl ether β-cyclodextrin (also known as SBE-β-CD or SBECD) is a process effectively divided into three main stages, i.e. initial reagent dissolution, a sulphoalkylation reaction and final reaction quenching. This reaction is followed by downstream processing and purification, and ultimate isolation of the solid SBECD material. However, a feature associated with using this synthetic method is that a high proportion of lower substituted SBECD is observed. There is therefore a need to provide an improved synthetic method for producing higher substituted cyclodextrins. The authors here present a Continuous Tank Reactor (CTR) method for preparing sulphobutyl ether-cyclodextrins. The method comprises first contacting cyclodextrin with a base to form activated cyclodextrin. The method then involves separately contacting the activated cyclodextrin with an 1,4-butane sultone to form sulphoalkyl ether-cyclodextrin. The activation reaction is carried out in batch synthesis mode and the sulphoalkylation reaction is carried out under continuous flow conditions resulting in a novel method for the synthesis of highly derivatised cyclodextrins. The work is particularly concerned with producing controlled substitution in sulphobutyl ether β-cyclodextrins and novel compositions of highly substituted sulphoalkyl ether β-cyclodextrins are described.

Item Type: Article
DOI/Identification number: 10.1016/j.ijpharm.2015.09.039
Uncontrolled keywords: Cyclodextrin, Sulphobutyl ether β-cyclodextrin, Continuous Tank Reactor, SBE-β-CD, SBECD, CD-screen-DAP, Evaporative light scattering detection
Subjects: R Medicine > RS Pharmacy and materia medica
Divisions: Central Services > Universities at Medway
Faculties > Sciences > Medway School of Pharmacy
Depositing User: Vivek Trivedi
Date Deposited: 25 Apr 2019 12:14 UTC
Last Modified: 03 Jun 2019 09:44 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/73629 (The current URI for this page, for reference purposes)
Trivedi, Vivek: https://orcid.org/0000-0001-9304-9214
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