A Family of Water‐Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid. Issue 12 (11th May 2020)

• Record Type: Journal Article
• Authors: Byrne, Fergal P.; Nussbaumer, Clara M.; Savin, Elise J.; Milescu, Roxana A.; McElroy, Con R.; Clark, James H.; van Vugt‐Lussenburg, Barbara M. A.; van der Burg, Bart; Meima, Marie Y.; Buist, Harrie E.; Kroese, E. Dinant; Hunt, Andrew J.; Farmer, Thomas J.
• Is Part Of: ChemSusChem. Volume 13:Issue 12(2020)
• Page Start: 3212
• Page End: 3221
• Publication Date: 2020-05-11
• Subjects: dipolar aprotic solvent -- low-toxicity solvent -- membranes -- solvent effects -- succindiamide; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.202000462
• Languages: English
• ISSNs: 1864-5631

Abstract

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. Abstract : Succinic success : Three new dipolar aprotic solvents are synthesized catalytically from succinic acid. Interestingly, all are water immiscible, an unusual property for dipolar aprotic solvents. Tested in a Heck reaction, metal–organic framework synthesis, and membrane fabrication, they perform comparably to traditional dipolar aprotic solvents such as N ‐methyl‐2‐pyrrolidone, and in silico and in vitro tests suggest no alarming indications of toxicity.