Highly Efficient Chemical Process To Convert Mucic Acid into Adipic Acid and DFT Studies of the Mechanism of the Rhenium‐Catalyzed Deoxydehydration

Abstract

The production of bulk chemicals and fuels from renewable bio-based feedstocks is of significant importance for the sustainability of human society. Adipic acid, as one of the most-demanded drop-in chemicals from a bioresource, is used primarily for the large-volume production of nylon-6,6 polyamide. It is highly desirable to develop sustainable and environmentally friendly processes for the production of adipic acid from renewable feedstocks. However, currently there is no suitable bio-adipic acid synthesis process. Demonstrated herein is the highly efficient synthetic protocol for the conversion of mucic acid into adipic acid through the oxorhenium-complex-catalyzed deoxydehydration (DODH) reaction and subsequent Pt/C-catalyzed transfer hydrogenation. Quantitative yields (99 %) were achieved for the conversion of mucic acid into muconic acid and adipic acid either in separate sequences or in a one-step process.

Microwave-assisted fast conversion of lignin model compounds and organosolv lignin over methyltrioxorhenium in ionic liquids

“…These results are consistent with the work of Kühn et al, in which MTO was reduced by the hydroxyl of the substrate to MDO that is responsible for the C-O bond activation. [20][21][22][23][24][25] This finding matches well with the GC-MS results (see ESI E2) in which the trace amounts of ketone was produced via reduction of MTO by the hydroxyl. The excellent results obtained from model compounds motivated us to investigate the conversion of organolsolv lignin, a more realistic lignin feedstock.…”

“…Trace amount of ketone was detected by GC-MS as well, which could be generated from the interaction between the substrate and MTO to form methyldioxorhenium (MDO). [20][21][22][23][24][25] The experimentally observed vibrational fundamentals of pure CH 3 ReO 3 and CH 3 ReO 3 in the reaction are presented in Figure 2. The concentration ratio of the catalyst and substrate 1 is 1:1 in [Bmim]NTf 2 (100 mg) under 240 W within 30 second, which is examined by IR.…”

Engineering Aspergillus niger for galactaric acid production: elimination of galactaric acid catabolism by using RNA sequencing and CRISPR/Cas9

“…in skincare products, or, more importantly, can be chemically converted to monomers for polymer production. It can be reduced to adipic acid [1] which is a precursor for Nylon or converted to 2,5-furandicarboxylic acid (FDCA) [2, 3]. FDCA is considered as promising renewable that has the potential to replace the fossil-based terephthalic acid.…”

Polymerization of ϵ‐Caprolactam to Nylon‐6 Catalyzed by Barium σ‐Borane Complex under Mild Condition

“…Due to the mild nature of the catalyst, this protocol provides an easy means of synthesizing nylon-6, for the first time with a precise and predictable molecular weight. [3][4][5][6][7][8][9][10] The industrial production of nylon-6 is commonly carried out by means of anionic polymerization, which is performed hydrolytically at 250°C or at a relatively lower temperature of 150°C in the presence of an initiator. The widespread utility of these durable high-strength materials is manifested from the various applications in the form of fibers, industrial yarns, floor covering and engineering plastics or films.…”

“…The widespread utility of these durable high-strength materials is manifested from the various applications in the form of fibers, industrial yarns, floor covering and engineering plastics or films. [3][4][5][6][7][8][9][10] The industrial production of nylon-6 is commonly carried out by means of anionic polymerization, which is performed hydrolytically at 250°C or at a relatively lower temperature of 150°C in the presence of an initiator. [2] With the increase in environmental regulation toward reduction of industrial energy consumption and carbon dioxide (CO 2 ) emission, significant efforts are being made to develop a greener and more efficient technology for making nylon.…”