Journal article
Synthesis of polyamides from diols and diamines with liberation of H2
Journal of Polymer Science, Part A: Polymer Chemistry, Vol.50(9), pp.1755-1765
May/2012
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. (C) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
Details
- Title
- Synthesis of polyamides from diols and diamines with liberation of H2
- Creators
- Boopathy Gnanaprakasam (null)Ekambaram Balaraman (null) - The Weizmann Institute of ScienceChidambaram Gunanathan (null)David Milstein (null) - The Weizmann Institute of Science
- Resource Type
- Journal article
- Publication Details
- Journal of Polymer Science, Part A: Polymer Chemistry, Vol.50(9), pp.1755-1765; May/2012
- Number of pages
- 11
- Language
- English
- DOI
- https://doi.org/10.1002/pola.25943
- Grant note
- This research was supported by the European Research Council under the FP7 framework (ERC No. 246837), the Israel Science Foundation, and the Kimmel Center for Molecular design. D. Milstein is the holder of the Israel Matz Professorial Chair of Organic Chemistry._ALMAME_DELIMITER_
- Record Identifier
- 993262825503596
Metrics
12 Record Views