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Diamines for Polymer Materials via Direct Amination of Lipid‐ and Lignocellulose‐based Alcohols with NH 3
Author(s) -
Pingen Dennis,
Schwaderer Judith B.,
Walter Justus,
Wen Jiaqi,
Murray George,
Vogt Dieter,
Mecking Stefan
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800365
Subject(s) - reductive amination , amination , chemistry , organic chemistry , furan , hydroxymethyl , furfural , catalysis , selectivity , nitrile , polymer chemistry , polymer
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 H 2 concentration is a rate‐limiting factor. Reducing the partial pressure of H 2 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.