Non-isocyanate route to amides and polyamides through reactions of aryl N-phenylcarbamates with carboxylic acids
Journal
Journal of Polymer Research
Journal Volume
23
Journal Issue
8
Pages
-
Date Issued
2016
Author(s)
Abstract
In pursuit of green processes for synthesizing organic products and polymers, an efficient route of amide formation has been devised by reacting carbamates with carboxylic acids. Aryl N-phenylcarbamates were utilized as alternative reagents to replace aromatic isocyanates in amides and polyamides syntheses. The results showed that the high-yield of amide products can be produced from phospholene oxide-catalyzed reactions. This non-isocyanate route (NIR) resulted in amides with greater than 90 % amide selectivity and little urea or isocyanate by-product contaminants. The polyamides prepared from the subsequent reaction series between aryl N,N′-diphenyl biscarbamates and hexafluoroisopropylidene bis-benzoic acid (HFI-BBA) yielded soluble polyamides with high molecular weight and high thermal stability. Thus, aryl N-phenylcarbamates are considered as the viable intermediates for the green synthesis of amides or polyamides without using the toxic aromatic isocyanates.
SDGs
Type
journal article