A novel approach for the preparation of furandiamines utilizing biomass platform chemicals as substrates via Gabriel synthesis

Abstract

Primary diamines are significant chemical intermediates and raw materials for high-added-value chemical products, which are regarded as essential monomers in the synthesis of polyamides and polyurethanes. Primary diamines are also particularly pronounced in the automotive, aerospace, and pharmaceutical fields. Among them, 2,5-bis(aminomethyl)furan (BAF) has garnered grant attention as a highly promising renewable diamine. In this work, a new route for the reduction preparation of BAF using a platform compound 5-chloromethylfurfural (CMF) utilizing the Gabriel method was developed, which reasonably avoids the disadvantage of molecular internal polymerization that often occurs in traditional routes that converting BAF from 5-hydroxymethylfurfural (HMF) and HMF derivatives. Additionally, under mild reaction conditions, this novel route yields BAF efficiently by employing Ni/SiO₂ as the catalyst. According to the kinetic analysis the reduction process was proved to be predominant. In addition, the analysis of the mechanism showed that compared to other catalysts, Ni/SiO₂ contains more active sites and more hydrogen active components (Ni⁰), achieving an impressive yield of 82.35 % under mild conditions. This work provides a pioneering method for the preparation of BAF, which is crucial for the development of primary diamine preparation.