Efficient conversion of N-acetyl-D-glucosamine into nitrogen-containing compound 3-acetamido-5-acetylfuran using amino acid ionic liquid as the recyclable catalyst

Wang, Jiao; Zang, Hongjun; Jiao, Shuolei; Wang, Kang; Shang, Zhen; Li, Huanxin; Lou, Jing

doi:10.1016/j.scitotenv.2019.136293

Cited by 39 publications

(44 citation statements)

References 38 publications

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“…In this study, we prepared several ethanolamine ionic liquids for the conversion of NAG to 3A5AF. Compared with our latest work, [33] the yield of 3A5AF increased by nearly 10 % after using this kind of ionic liquid. The influences of different ILs will be discussed in detail below.…”

Section: Introductionmentioning

confidence: 48%

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Green Conversion of N‐Acetylglucosamine into Valuable Platform Compound 3‐Acetamido‐5‐acetylfuran Using Ethanolamine Ionic Liquids as Recyclable Catalyst

Zang

Jiao

et al. 2021

ChemistrySelect

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N‐acetylglucosamine (NAG) is the monomer of chitin which is the most abundant nitrogen‐containing biomass. Thus, NAG is a potential nitrogen‐rich feedstock for the production of renewable organonitrogen chemicals. In this work, ethanolamine ionic liquids were synthesized easily from inexpensive raw materials and subsequently used as catalysts for NAG conversion to produce 3‐acetamido‐5‐acetylfuran (3A5AF). Using triethanolamine hydrochloride ([TEA]Cl) ionic liquid as the catalyst, a high 3A5AF yield of 62.0 % was obtained at the optimum reaction conditions of 170 °C and 20 min. Moreover, this ionic liquid exhibited good reusability and still had good catalytic activity after recycling five times. High‐performance liquid chromatography‐mass spectrometry (HPLC‐MS) analysis provided the relevant basis for rationalizing the reaction mechanism. Therefore, our study presents an intriguing and sustainable protocol for the direct conversion of NAG.

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Section: Introductionmentioning

confidence: 48%

“…Recently, we found the amino acid ionic liquids can efficiently catalyze NAG conversion into 3A5AF. The yield of 3A5AF reached 52.6 % in 10 min at 180 °C in an oil bath [33] . Substituting microwave conditions may increase the possibility of industrial application.…”

Section: Introductionmentioning

confidence: 96%

Green Conversion of N‐Acetylglucosamine into Valuable Platform Compound 3‐Acetamido‐5‐acetylfuran Using Ethanolamine Ionic Liquids as Recyclable Catalyst

Zang

Jiao

et al. 2021

ChemistrySelect

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“…Recently, a few B(OH) 3 -free methods have been developed. Wang et al [36] reported the conversion of NAG over a glycine chloride ([Gly]Cl) ionic liquid catalyst in DMA, giving a 43 % yield of 3A5AF at 200°C for 10 min. The addition of 100 wt% CaCl 2 improved 3A5AF yield to 53 %.…”

Section: Dehydration Product Of Nagmentioning

confidence: 99%

Towards Shell Biorefinery: Advances in Chemical‐Catalytic Conversion of Chitin Biomass to Organonitrogen Chemicals

Dai

2020

ChemSusChem

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Chitin is the most abundant biopolymer after cellulose but it has not been fully utilized yet. Because of biologically fixed nitrogen, effective conversion of chitin or its derivatives to value‐added organonitrogen compounds is a promising strategy to valorize chitin biomass, which has attracted increasing attention. Recently, a novel concept of shell biorefinery has been proposed on account of the huge potentials of chitin valorization. Until now, a number of valuable organonitrogen chemicals, including amino sugars, amino alcohols, amino acids, and heterocyclic compounds, have been produced from chitin biomass. In this Minireview, the focus is on the recent advances in the synthesis of organonitrogen chemicals employing chitin biomass as starting material via different catalytic processes. An outlook on the challenges and opportunities for more effective valorization of chitin will be given.

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“…It should be stated that sulfolane is a solvent that is structurally similar to DMSO. Furthermore, there is a report on the transformation of GlcNAc into 3-acetamido-5-acetylfuran at temperatures of 160-210 • C in which the formation of the five-membered ring intermediate is shown to be key [28,29]. Hence, there is a possibility that the furanose form (GFNAc) exists more than the pyranose form (GlcNAc).…”

Section: Selectivity To Form Pyranose Ring Versus Furanose Ring Diffementioning

confidence: 99%

Microwave-Assisted Heating Reactions of N-Acetylglucosamine (GlcNAc) in Sulfolane as a Method Generating 1,6-Anhydrosugars Consisting of Amino Monosaccharide Backbones

et al. 2020

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The microwave-assisted heating reaction of N-acetyl glucosamine (GlcNAc) in sulfolane is described. The reaction produces two major products that are assignable to 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucopyranose (AGPNAc) and 1,6-anhydro-2-acetamido-2-deoxy-β-d-glucofuranose (AGFNAc). In order to reveal a general feature of the system, the 3, 5, and 10 min reactions were performed at 140, 160, 180, 200, and 220 °C to clarify the time course changes in the conversion of GlcNAc and the yields of the two produced 1,6-anhydrosugars. Temperature is a crucial factor that significantly affects the conversion of GlcNAc. The yields of AGPNAc and AGFNAc are also drastically changed depending on the reaction conditions. The 5-min reaction at 200 °C is shown to be the optimal condition to generate the 1,6-anhydrosugars with a high efficiency in which AGPNAc and AGFNAc are produced in the yields of 21% and 44%, respectively. Consequently, the microwave-assisted heating reaction of GlcNAc in sulfolane is shown to be a simple and promising pathway to generate 1,6-anhydrosugars consisting of amino monosaccharide backbones, which have high potentials as raw materials leading to biological oligosaccharides and biomimetic polysaccharides.

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Efficient conversion of N-acetyl-D-glucosamine into nitrogen-containing compound 3-acetamido-5-acetylfuran using amino acid ionic liquid as the recyclable catalyst

Cited by 39 publications

References 38 publications

Green Conversion of N‐Acetylglucosamine into Valuable Platform Compound 3‐Acetamido‐5‐acetylfuran Using Ethanolamine Ionic Liquids as Recyclable Catalyst

Green Conversion of N‐Acetylglucosamine into Valuable Platform Compound 3‐Acetamido‐5‐acetylfuran Using Ethanolamine Ionic Liquids as Recyclable Catalyst

Towards Shell Biorefinery: Advances in Chemical‐Catalytic Conversion of Chitin Biomass to Organonitrogen Chemicals

Microwave-Assisted Heating Reactions of N-Acetylglucosamine (GlcNAc) in Sulfolane as a Method Generating 1,6-Anhydrosugars Consisting of Amino Monosaccharide Backbones

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