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

TY - JOUR

T1 - A Family of Water Immiscible, Dipolar Aprotic, Diamide Solvents from Succinic Acid

AU - Byrne, Fergal Patrick

AU - Nussbaumer, Clara M

AU - Savin, Elise J

AU - Milescu, Roxana A

AU - McElroy, Con R

AU - Clark, James H

AU - van Vugt-Lussenburg, Barbara M A

AU - van der Burg, Bart

AU - Meima, Marie Y

AU - Buist, Harrie E

AU - Kroese, Dinant

AU - Hunt, Andrew J

AU - Farmer, Thomas J

N1 - © 2020 The Authors

PY - 2020/5/11

Y1 - 2020/5/11

N2 - 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.

AB - 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.

U2 - 10.1002/cssc.202000462

DO - 10.1002/cssc.202000462

M3 - Article

C2 - 32220058

SN - 1864-5631

VL - 13

JO - ChemSusChem

JF - ChemSusChem

ER -