Production of biobased HMF derivatives by reductive amination

Abstract

5-(Hydroxymethyl)furfural (HMF) has recently attracted a significant amount of revived attention as a renewable building block for the conversion to a wide range of useful derivatives. A simple procedure for the conversion of HMF to (5-alkylaminomethyl-furan-2-yl)methanol has now been developed. Reactions were conducted without the use of a catalyst and under very mild conditions. As a proof of concept, a small library of derivatives was produced from HMF and several aliphatic and aromatic amines in high yields and requiring only minimal purification. This route presents a novel way for the production of furan-based renewable building blocks

Novel Ordered Mesoporous Carbon Based Sulfonic Acid as an Efficient Catalyst in the Selective Dehydration of Fructose into 5-HMF: the Role of Solvent and Surface Chemistry

“…13 In the current research, it is known to a great extent 3 that the distribution of products and in particular the selectivity toward HMF formation is highly dependent on the type (physicochemical properties) of the catalyst, reaction solvent, and temperature and development of new selective and effective protocols for this process has attracted broad research activity. [14][15][16][17] The first important issue in developing an economically and environmentally benign process for HMF formation is a green solvent in terms of easy separation, purity of the final product and low E factor [E-factor=total waste (kg)/product (kg)]. 2,18 Although from the standpoint of advance green and sustainable chemistry using water as a reaction solvent is a long-standing goal and thus often preferable, the difficulty in separating and purifying highly water soluble HMF, the higher possibility of rehydrating HMF in water, and the deactivation of the acid catalysts are important issues that need to be respected.…”

The Production of 5‐Hydroxymethylfurfural from Fructose in Isopropyl Alcohol: A Green and Efficient System

“…Low efficiency in synthesis and high solubility in water pose difficulties in HMF mass production processes, especially for isolation and purification. [5] In most reported methods for the transformation of biomass or derivatives into HMF, the HMF is obtained in solution and the yield is reported by using HPLC or GC. However, developing efficient separation methods is very important in order to make the industrial-scale production of HMF economically viable.…”

Ruthenium‐Catalyzed Conversion of Levulinic Acid to Pyrrolidines by Reductive Amination

“…[22] The hydrogenation step was accomplished with formic acid produced from acidic dehydration of biomassbased carbohydrates. The advantages of the new route are its good atom economy and that it avoids the energy-intense extraction of LA from its aqueous solution with formic acid.…”