Diamines for Polymer Materials via Direct Amination of Lipid- and Lignocellulose-based Alcohols with NH3

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2018
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Wen, Jiaqi
Murray, George
Vogt, Dieter
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10.1002/cctc.201800365
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ChemCatChem ; 10 (2018), 14. - pp. 3027-3033. - ISSN 1867-3880. - eISSN 1867-3899
Abstract
Via an all‐catalytic route, long‐chain diamines were prepared by the catalytic direct amination of long‐chain diols, derived from plant oils. High conversion was achieved with good selectivity, with the amount of nitrile impurities formed suppressed to a low level. From the lignocellulose‐based 5‐hydroxymethylfurfural (5‐HMF), or from bis(hydroxymethyl)furan, 2,5‐bis(aminomethyl)furan (BAMF) was generated. 5‐HMF was converted in a one‐pot, one‐step direct amination and reductive amination using ammonia. In both cases, the reaction proceeded very efficiently. In the combined amination and reductive amination, the H2 concentration is a rate‐limiting factor. Reducing the partial pressure of H2 also shortened the reaction time required significantly. Polycondensation of the long‐chain diamines with long‐chain diacids led to higher molecular weight polyamides, illustrating the quality of the diamines obtained by this synthetic approach as monomers.
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ISO 690PINGEN, Dennis, Judith Barbara SCHWADERER, Justus WALTER, Jiaqi WEN, George MURRAY, Dieter VOGT, Stefan MECKING, 2018. Diamines for Polymer Materials via Direct Amination of Lipid- and Lignocellulose-based Alcohols with NH3. In: ChemCatChem. 10(14), pp. 3027-3033. ISSN 1867-3880. eISSN 1867-3899. Available under: doi: 10.1002/cctc.201800365
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@article{Pingen2018Diami-42968,
  year={2018},
  doi={10.1002/cctc.201800365},
  title={Diamines for Polymer Materials via Direct Amination of Lipid- and Lignocellulose-based Alcohols with NH<sub>3</sub>},
  number={14},
  volume={10},
  issn={1867-3880},
  journal={ChemCatChem},
  pages={3027--3033},
  author={Pingen, Dennis and Schwaderer, Judith Barbara and Walter, Justus and Wen, Jiaqi and Murray, George and Vogt, Dieter and Mecking, Stefan}
}
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