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Fast synthesis of optically active polyamides containing l-methionine linkages in ionic liquid via a microwave-assisted process

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Abstract

Several optically active aromatic polyamides have been synthesized via direct polycondensation of chiral diacid monomer 1 containing l-methionine moiety with diverse aromatic diamines 2a–2h in a green medium, namely 1,3-dipropylimidazolium bromide as a room temperature ionic liquid. In order to evaluate the advantages of microwave promotion of these polymerization reactions, we compared microwave irradiation (method I) with conventional oil bath heating (method II) by means of reaction rates, conversions, and inherent viscosities. The inherent viscosities of resulting polymers were ranging between 0.47–0.65 and 0.35–0.57 dL/g in methods I and II, respectively. These polymers were characterized by means of 1H-NMR, FT-IR, elemental, organosolubility, differential scanning calorimetry, and thermal gravimetric analysis techniques. The obtained polymers show thermal stability up to 273 °C under nitrogen atmosphere and good solubility in polar organic solvents. Polymerization reactions proceeded in higher yields and moderate inherent viscosities under microwave irradiation conditions besides the dramatically shorter reaction times and achieving the more pure products.

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Acknowledgements

We wish to express our gratitude to the Research Affairs Division Isfahan University of Technology (IUT), Isfahan for partial financial support. Further financial support from National Elite Foundation (NEF) and Center of Excellency in Sensors and Green Chemistry Research (IUT) is gratefully acknowledged.

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Authors and Affiliations

  1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, I.R., Iran

    Shadpour Mallakpour & Hojjat Seyedjamali

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  1. Shadpour Mallakpour
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  2. Hojjat Seyedjamali
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Correspondence to Shadpour Mallakpour.

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Mallakpour, S., Seyedjamali, H. Fast synthesis of optically active polyamides containing l-methionine linkages in ionic liquid via a microwave-assisted process. Colloid Polym Sci 287, 1111–1116 (2009). https://doi.org/10.1007/s00396-009-2080-6

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  • DOI: https://doi.org/10.1007/s00396-009-2080-6

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