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Catalytic behavior of melamine glyoxal resin towards consecutive oxidation and oxy-Michael addition

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Abstract

Synthesis of melamine glyoxal resin involves a catalyst-free, one pot reaction between melamine and glyoxal in DMF. The synthesized resins have a similar morphological arrangement to that of layered materials as depicted by their XRD pattern and Raman spectra. The catalytic behavior of melamine glyoxal resin (MGR) have been studied in allylic oxidation of cyclohexene and simultaneous Michael addition. The MGR/solvent/O2 oxidant system can be regarded as a metal-free, additive-free, cost-effective and environmentally benign catalytic system. The oxidative behavior of MGR is attributed to its ability to generate in situ organic peroxide species during the course of reaction. Generation of peroxide species is confirmed by the KI/starch test and further confirmed by the complete suppression effect of TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) over oxidation. The activity for Michael addition can be attributed to the presence of a higher content of nitrogen atoms, which serves as the active site. In oxidation, 28.1% conversion of cyclohexene with 37.19 and 62.81% selectivities for cyclohexenol and cyclohexenone were observed, respectively. In consecutive oxidation and oxy-Michael addition, 31.5% conversion of cyclohexene was observed with selectivities of 61.6% for cyclohexenone and 38.4% for alkoxy product.

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Acknowledgments

We acknowledge KOSEF for A3, NRL (36379-1), BK21 projects and MOCIE for Nano Center for Fine Chemicals Fusion Technology.

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Authors and Affiliations

  1. Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemical Fusion Technology, Department of Chemistry, Inha University, Incheon, 402-751, Korea

    Mohd. Bismillah Ansari, Eko Adi Prasetyanto, Jun Lee & Sang-Eon Park

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  1. Mohd. Bismillah Ansari
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  2. Eko Adi Prasetyanto
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  3. Jun Lee
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  4. Sang-Eon Park
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Correspondence to Sang-Eon Park.

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Ansari, M.B., Prasetyanto, E.A., Lee, J. et al. Catalytic behavior of melamine glyoxal resin towards consecutive oxidation and oxy-Michael addition. Res Chem Intermed 36, 677–684 (2010). https://doi.org/10.1007/s11164-010-0169-7

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