Byrne, Fergal Patrick, Nussbaumer, Clara M, Savin, Elise J et al. (10 more authors) (2020) A Family of Water Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid. ChemSusChem. ISSN 1864-564X
Abstract
Three dipolar aprotic solvents were designed to possess high dipolarity and low toxicity: N , N , N ', N '-tetrabutylsuccindiamide (TBSA), N , N '-diethyl- N , N '-dibutylsuccindiamide (EBSA), N , N '-dimethyl- N , N '-dibutylsuccindiamide (MBSA). They were synthesized catalytically using a K60 silica catalyst in a solventless system. Their water-immiscibility stands out as an unusual and useful property for dipolar aprotic solvents. They were tested in a model Heck reaction, metal-organic framework syntheses, and a selection of polymer solubility experiments where their performances were found to be comparable to traditional solvents. Furthermore, MBSA was found to be suitable for the production of an industrially-relevant membrane from polyethersulphone. An integrated approach involving in silico analysis based on available experimental information, prediction model outcomes and read across data, as well as a panel of in vitro reporter gene assays covering a broad range of toxicological endpoints was used to assess toxicity. These in silico and in vitro tests suggested no alarming indications of toxicity in the new solvents.
Metadata
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Copyright, Publisher and Additional Information: | © 2020 The Authors | ||||
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Institution: | The University of York | ||||
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) | ||||
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Depositing User: | Pure (York) | ||||
Date Deposited: | 20 May 2020 10:10 | ||||
Last Modified: | 06 Jan 2024 00:43 | ||||
Published Version: | https://doi.org/10.1002/cssc.202000462 | ||||
Status: | Published online | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1002/cssc.202000462 |
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Filename: cssc.202000462.pdf
Description: A Family of Water-Immiscible, Dipolar Aprotic, DiamideSolvents from Succinic Acid
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