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A Family of Water‐Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid
Author(s) -
Byrne Fergal P.,
Nussbaumer Clara M.,
Savin Elise J.,
Milescu Roxana A.,
McElroy Con R.,
Clark James H.,
VugtLussenburg Barbara M. A.,
Burg Bart,
Meima Marie Y.,
Buist Harrie E.,
Kroese E. Dinant,
Hunt Andrew J.,
Farmer Thomas J.
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202000462
Subject(s) - solubility , chemistry , in silico , succinic acid , toxicity , organic chemistry , catalysis , biochemistry , gene
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.