Direct Synthesis of Polyamides via Catalytic Dehydrogenation of Diols and Diamines

We report a direct synthesis of polyamides via catalytic dehydrogenation of diols and diamines. A PNN pincer ruthenium complex, the Milstein catalyst, was used for this reaction and polyamides with number average molecular weight from ∼10 to 30 kDa could be obtained from a wide variety of diols and...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-02, Vol.133 (5), p.1159-1161
Main Authors: Zeng, Hanxiang, Guan, Zhibin
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Catalysis
Diamines - chemistry
Hydrogenation
Nylons - chemical synthesis
Nylons - chemistry
Ruthenium - chemistry
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Summary:We report a direct synthesis of polyamides via catalytic dehydrogenation of diols and diamines. A PNN pincer ruthenium complex, the Milstein catalyst, was used for this reaction and polyamides with number average molecular weight from ∼10 to 30 kDa could be obtained from a wide variety of diols and diamines bearing aliphatic or aromatic, linear or cyclic spacers. Because of the high catalytic selectivity of primary amine over secondary amine, polyamines could be conveniently incorporated into linear polyamides without tedious protection/deprotection steps. Compared with conventional condensation method, this catalytic system avoids the requirement of stoichiometric preactivation or in situ activation reagents and provides a much cleaner process with high atomic economy.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja106958s