Synthesis of Amidation Agents and Their Reactivity in Condensation Reactions

Abstract

Nowadays, the development of new approaches which smartly bypass the use of harsh reaction conditions and hazardous chemicals covers a pivotal role. In this research paper the synthesis, characterization, and application of novel libraries of triazine bis-quaternary ammonium salts, employed as coupling agents to produce amides is reported. Full characterization of the novel compounds by ¹H and ¹³C NMR, FT-IR spectroscopy, ESI-HRMS, and elemental analysis is provided. Furthermore, a comparison in terms of activity of the preformed triazine compounds versus in situ formulations has been evaluated for the formation of amides in the presence of phenylethylamine and different aliphatic or aromatic acids. A possible correlation between the chemical structure of the triazine and their reactivity for the formation of the triazine bis-quaternary ammonium salts is also reported. Moreover, best performing condensation agents have been further tested for the cross-linking of collagen powder as possible wet white tanning systems, for sustainable and environmentally friendly leather tanning.

Key words

1,3,5-triazine bis-quaternary ammonium salts - amidation agents - collagen cross-linking - green chemistry - sustainable leather tanning

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