A Family of Water Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid

Fergal Patrick Byrne, Clara M Nussbaumer, Elise J Savin, Roxana A Milescu, Con R McElroy, James H Clark, Barbara M A van Vugt-Lussenburg, Bart van der Burg, Marie Y Meima, Harrie E Buist, Dinant Kroese, Andrew J Hunt, Thomas J Farmer

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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.

Original languageEnglish
Number of pages11
Early online date11 May 2020
Publication statusE-pub ahead of print - 11 May 2020

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