Direct Reductive Amination of HMF to 5-(Aminomethyl)-2-furanmethanol Using Supported Iridium-based Catalysts

Ruiz, Doris; Morales, Karen; Maki-Arvela, Paeivi; Chimentao, Ricardo J.; Murzin, Dmitry Yu.

Abstract

In this work, partial reductive amination of 5-hydroxymethylfurfural (HMF) with gaseous ammonia over iridium supported on gamma-Al2O3, TiO2, SiO2 and carbon has been studied. The influence of the support and pressure was investigated in the valorization under mild conditions of HMF to 5-(aminomethyl)-2-furanmethanol (AMFM). The catalysts were characterized by TEM, SEM-EDS, N2 sorption Isotherms, TGA, CO-Chemisorption, TPR, XRD, NH3-TPD, ICP-AES and XPS. The maximum activity and high rates were obtained for all catalytic systems. At 50 minutes of the reaction the Ir/C catalyst achieved 93 % of conversion and exhibited the highest yield and selectivity of 92 % and 99 % respectively, to the desired product 5-(aminomethyl)-2-furanmethanol. The main properties that influence activity and selectivity are related to the amount of iridium on the surface and catalyst acidity. After the third cycle, 63 % and 59 % of selectivity and yield to AMFM respectively at 93 % of conversion were obtained. Reductive amination is widely used in pharmaceutical and agrochemical industries for the synthesis of valuable molecules. In this work, reductive amination of biomass derived HMF over supported Ir-based catalysts under mild conditions is an efficient method for the 5-(aminomethyl)-2-furanmethanol (AMFM) synthesis. Catalysts with high acidity and metal on surface stand out for its efficiency and versatility in synthesizing a valuable primary amine as AMFM. image

Más información

Título según WOS: Direct Reductive Amination of HMF to 5-(Aminomethyl)-2-furanmethanol Using Supported Iridium-based Catalysts
Título de la Revista: CHEMPLUSCHEM
Volumen: 89
Número: 12
Editorial: WILEY-V C H VERLAG GMBH
Fecha de publicación: 2024
DOI:

10.1002/cplu.202400453

Notas: ISI