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

Byrne, F.P., Nussbaumer, C.M., Savin, E.J. , Milescu, R.A., McElroy, Con, 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. and Farmer, T.J. (2020) A Family of Water-Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid. ChemSusChem, 13 (12). pp. 3212-3221. ISSN 1864-5631

Full content URL: https://doi.org/10.1002/cssc.202000462

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Item Type:Article
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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), 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.

Additional Information:cited By 8
Keywords:Silica, Integrated approach, Polyethersulfones, Prediction model, Reporter gene assays, Silica catalyst, Solventless system, Toxicity, Dipolar aprotic solvent
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
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ID Code:54740
Deposited On:30 May 2023 13:36

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