Synthesis of polyamides from diols and diamines with liberation of H 2

Boopathy Gnanaprakasam, Ekambaram Balaraman, Chidambaram Gunanathan, David Milstein

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43 Citations (Scopus)

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 M n 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.

Original languageEnglish
Pages (from-to)1755-1765
Number of pages11
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume50
Issue number9
DOIs
Publication statusPublished - May 1 2012

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Keywords

  • alcohol dehydrogenation
  • amidation
  • catalysis
  • catalysts
  • dihydrogen
  • homogeneous catalysis
  • pincer
  • pincer complex
  • polyamides
  • ruthenium complex

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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