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

作者：Pingen Dennis; Schwaderer Judith B; Walter Justus; Wen Jiaqi; Murray George; Vogt Dieter; Mecking Stefan^*

来源：ChemCatChem, 2018, 10(14): 3027-3033.

DOI：10.1002/cctc.201800365

• 5-HMF
• catalysis
• direct amination
• long-chain diols
• polyamides

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.

• 出版日期2018-7-19