Switchable synthesis of furfurylamine and tetrahydrofurfurylamine from furfuryl alcohol over RANEY® nickel

Abstract

Switchable reductive amination of furfuryl alcohol to tetrahydrofurfurylamine and furfurylamine was realized by adding/not adding H2 over a RANEY® Ni catalyst.

Selective Synthesis of Furfurylamine by Reductive Amination of Furfural over Raney Cobalt

“…This can be ascribed to the poor hydrogenation activity of Ru/C under reductive amination conditions. Based on our previous DFT calculation, the adsorption energy of NH 3 on Ru is higher than those for Pd, Pt, Rh, Ni and Co, indicating that more metal active sites would be occupied by competitive occupation process of NH 3 . Thus the activity of Ru was greatly inhibited, and resulted in the formation of large amount of furfurine (2,4,5‐tris(α‐furyl)‐2‐imidazoline), which was derived from furfurylimine .…”

“…Unexpectedly, further increasing the partial pressure of ammonia led to a decrease in furfurylamine selectivity accompanied by the formation of furfurine, which was formed by the rearrangement of furfuramide in heating above 100 °C . Based on our previous research, in the reductive amination, hydrogen and ammonia would compete to adsorb on the same metal active sites, a variation of the ratio of hydrogen and ammonia could impact greatly on the hydrogenation process . Therefore, the decrease in furfurylamine selectivity with excessively high ammonia pressure can be ascribed to the occupation of ammonia on the metal sites, which suppressed the hydrogenation capability of the metal catalyst.…”

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

“…Polymeric compounds are also generally present (the structures in Figure 4a re representativeso ft he dimericc ompounds). [157] 4x was prepared startingf rom the careful glycidylation (using TBABa s ap hase-transfer catalyst) of furfuryl amine (a product of the reductive amination of furfuryl alcohol with ammonia; Scheme16) [158] to avoid cross-linking on the epoxide. [156] 4v was reacted with renewable diamines for the synthesis of PHU networks with high renewable content.…”

“…Therefore, compared to 2k,the synthesis of amonomer bearingafuran ring (for Diels-Alderr eactionw ith maleimide) and more than one 5CC functionality was required. [157] 4x was prepared startingf rom the careful glycidylation (using TBABa s ap hase-transfer catalyst) of furfuryl amine (a product of the reductive amination of furfuryl alcohol with ammonia; Scheme16) [158] to avoid cross-linking on the epoxide. The re-sulting diglycidyl furfurylamine was quantitatively carbonated in DMF using LiBr as the catalyst at 80 8C, 9bar CO 2 for 5h.…”

Improved conversion of bamboo shoot shells to furfuryl alcohol and furfurylamine by a sequential catalysis with sulfonated graphite and biocatalysts

“…[46][47][48][49][50] Recently, these materials have gained a considerable interest to synthesize organonitrogen and hydroxy compounds from biomass feedstocks. [51][52][53][54][55] Organonitrogen chemical FAM and hydroxy compound FFA, two kinds of important furan molecules, [51][52][53] could be manufactured from the abundant, renewable and inexpensive BSS. First, BSS was effectively catalyzed to FF with Sn-graphite (3.6 wt% dosage) within 30 min at 180 C. Subsequently, the bioreduction and bioamination of BSS-derived FF were conducted under mild reaction conditions.…”