Synthesis of polyamides from diols and diamines with liberation of H2

TitleSynthesis of polyamides from diols and diamines with liberation of H2
Publication TypeJournal Article
Year of Publication2012
AuthorsGnanaprakasam, B, Balaraman, E, Gunanathan, C, Milstein, D
JournalJournal of Polymer Science Part A: Polymer Chemistry
Volume50
Issue9
Pagination1755–1765
Date PublishedMAY
Abstract

The amidation reaction based on catalytic coupling of alcohols with amines previously reported by us, using the pincer complexes 1 and 2 as catalysts, was applied to the generation of polyamides from nonactivated diols and diamines. A range of polymers was prepared, with Mn up to 26.9 kDa. Unlike the traditional syntheses of polyamides based on carboxylic acid derivatives, which require the use of toxic reagents and generate stoichiometric amounts of waste, this process generates only molecular hydrogen as byproduct. Both aromatic and aliphatic diols and diamines were used. Gel permeation chromatography measurements of the dimethylformamide-soluble polymers and thermal studies of the polyamides were performed. Matrix assisted laser desorption/ionization time-of-flight (MALDI-TOF) spectra are also reported. Thermogravimetric analyses studies indicate that the aromatic polyamides (with the exception of the pyridine-based polyamide) are more thermally stable than the aliphatic ones. This general, environmentally benign method for the synthesis of polyamides is homogeneously catalyzed under neutral conditions by dearomatized ruthenium-pincer complexes 1 and 2 and proceeds in 1,4-dioxane under an inert atmosphere. Conditions for polyamidation in the absence of solvent are also reported, using the pincer complex 2 as catalyst. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

DOI10.1002/pola.25943
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.543
Divison category: 
Catalysis and Inorganic Chemistry