Cu(0)-mediated living radical polymerisation in dimethyl lactamide (DML); an unusual green solvent with limited environmental impact

Abstract

The synthesis of poly-acrylates, methacrylates and styrene derivatives by SET-LRP is reported in a user and environmentally friendly “green” solvent, dimethyl lactamide (DML).

SET-LRP in biphasic mixtures of fluorinated alcohols with water

“…8,[51][52][53] The SET-LRP of BA also resulted in biphasic systems when dimethyl lactamide was used as a solvent. 54 Meanwhile, a biphasic reaction mixture containing Cu(II)Br 2 solution in alcohol separated from the immiscible polymer solution in alcohol was observed during the SET-LRP of 2-ethylhexyl acrylate in TFE. 20 These developments together with the development of SET-LRP of N-isopropylacrylamide catalyzed by Cu(0) generated in situ by the reduction of Cu(II)Br 2 with NaBH 4 in water led to the elaboration of "programmed" biphasic SET-LRP systems that are produced by design.…”

Photoinduced Upgrading of Lactic Acid-Based Solvents to Block Copolymer Surfactants

“…Biomass-derived platform chemicals are gaining momentum in both industry and academia because of dwindling of fossil fuel resources and environmental concerns. − In this regard, lactic acid is one of the top feedstock given its ready availability from renewable carbohydrates via fermentation or chemocatalytic routes, , and its facile conversion into a number of important derivatives such as fine and commodity chemicals, biodegradable polymers, and fuel precursors. − Among them, ethyl lactate (EL) and N , N -dimethyl lactamide (DML) are in the portfolio of available green biosolvents suitable to replace traditional chemicals because they offer an appealing combination of properties including high boiling point, high solvency power, negligible toxicity, and 100% biodegradability that translate into important environmental benefits and performance advantages. − The use of EL, for example, enabled to improve the green angle of numerous organic transformations such as olefin metathesis and cycloaddition reactions. The instability of Cu­(I)­X/N–ligand complexes toward disproportionation in DML and EL also facilitated their application as efficient green reaction media in Cu(0)-mediated SET-LRP reactions. , However, the potential of these simple and cheap lactic acid deriavatives goes beyond their academic use as they have been used in many industrial applications including the preparation of agrochemical and cleaning formulations, polymeric membranes in a safe workplace, among others. ,− …”

“…13−16 The use of EL, for example, enabled to improve the green angle of numerous organic transformations such as olefin metathesis 17 and cycloaddition 18 reactions. The instability of Cu(I)X/N−ligand complexes toward disproportionation in DML 19 and EL 20 also facilitated their application as efficient green reaction media in Cu(0)mediated SET-LRP reactions. 21,22 However, the potential of these simple and cheap lactic acid deriavatives 23 goes beyond their academic use as they have been used in many industrial applications including the preparation of agrochemical 24 and cleaning formulations, 25 polymeric membranes in a safe workplace, 26 among others.…”

SET-LRP in the Neoteric Ethyl Lactate Alcohol

“…In spite of these appealing features, EtLa was never employed as a solvent for SET-LRP. However, dimethyl lactamide, a synthesized derivative of lactic acid, showed promising properties . The applications of SET-LRP at the interface of polymer science with biology and medicine is widely spread and provides various applications .…”