Title
A Family of Water-Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid
Author
Byrne, F.P.
Nussbaumer, C.M.
Savin, E.J.
Milescu, R.A.
McElroy, C.R.
Clark, J.H.
van Vugt-Lussenburg, B.M.A.
van der Burg, B.
Meima, M.Y.
Buist, H.E.
Kroese, E.D.
Hunt, A.J.
Farmer, T.J.
Publication year
2020
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), and N,N′-dimethyl-N,N′-dibutylsuccindiamide (MBSA). They were synthesized catalytically by 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 in which 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 polyethersulfone. 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. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Subject
Low-toxicity solvent
Membranes
Solvent effects
Succindiamide
Silica
Toxicity
Dipolar aprotic solvent
Integrated approach
Polyethersulfones
Prediction model
Reporter gene assays
Silica catalyst
Solventless system
Useful properties
Solvents
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http://resolver.tudelft.nl/uuid:a52b5261-2183-4130-9b46-34d4c1e05545
DOI
https://doi.org/10.1002/cssc.202000462
TNO identifier
876167
ISSN
1864-5631
Source
ChemSusChem, 13 (13), 3213-3221
Document type
article