Solventless Amination of Lignin and Natural Phenolics using 2‐Oxazolidinone

Abstract

Reactive amine compounds are critical for a vast array of useful chemicals in society, yet a limited number of them are derived from renewable resources. This study developed an efficient route to obtain aminated building blocks from phenolic resources derived from nature, such as lignin and tannic acid, for enhancing their utility in applications such as epoxy resins, nylons, polyurethanes, and other polymeric materials. The reaction utilized a carbon storage compound, 2‐oxazolidinone as a solvent and as a reagent circumventing the need of hazardous chemistry of conventional amination routes such as those involving formaldehyde. Both free acids and hindered phenolics were readily converted into aminoethyl derivatives resulting in aromatics with primary amine functionality. The aminated compounds, with the potential for enhanced reactivity, can pave the way toward more advanced renewable building blocks.

From waste to resource: advancements in sustainable lignin modification

“…A recent work from Renneckar et al 73 reports an interesting solventless amination of softwood kraft lignin via 2-oxazolidinone (OZD, see Scheme 5). This compound exhibits a non-hazardous nature, according to its Safety Data Sheet (SDS).…”