Formation of a renewable amide, 3-acetamido-5-acetylfuran, via direct conversion of N-acetyl-d-glucosamine

Drover, Marcus W.; Omari, Khaled W.; Murphy, Jennifer N.; Kerton, Francesca M.

doi:10.1039/c2ra20578e

Cited by 117 publications

(99 citation statements)

References 18 publications

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“…78 In the work of Franich et al, a mechanism of dehydration proceeding via an anhydrosugar intermediate was proposed. In our research, 80 we have proposed a mechanism that proceeds through an open-chain aldose form of the hexose in line with mechanisms proposed for dehydrations of fructose. In 1998, Chen et al pyrolyzed NAG at 200°C for 30 min.…”

Section: 74mentioning

confidence: 69%

“…83 However, when reactions were performed in dipolar aprotic solvents or in some imidazolium ionic liquids in the presence of chloride ions and boric acid, 3A5AF was obtained. 80,84 In both studies, under optimized conditions, 60% yield of 3A5AF could be obtained, which is approximately 30 times greater than the yields via pyrolysis. In reactions performed in organic solvents, the highest yields were obtained in DMA, DMF and DMSO, however, we also noted that significant conversion levels could be achieved in the 'greener' solvents ethyl lactate and PEG.…”

Section: 74mentioning

confidence: 88%

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Green chemistry and the ocean-based biorefinery

et al. 2013

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Research into renewable chemicals, fuels and materials sourced from the oceans at Memorial University and elsewhere is employing green chemical technologies for the transformation of algae and food industry waste streams into useful products. A very small proportion of biomass utilization research is currently focused on these feedstocks and efforts focused in this area could reduce land space competition between food and chemical/fuel production. This perspective highlights some of the achievements and potential opportunities surrounding the use of algae and waste from shellfish and finfish processing. In particular, investigations in this field have used alternative solvents (water, supercritical carbon dioxide and methanol or ionic liquids) extensively. Supercritical Fluid Extraction (SFE) has been used to extract lipids and pigments from algae, and oils from fish-processing plant waste streams. Water can be used to isolate potentially high value biologically-active oligosaccharides from some seaweeds. Biotechnological approaches are showing promise in the separation of biopolymers from shellfish waste streams. Production of new nitrogen-containing bioplatform chemicals (e.g. 3-acetamido-5-acetylfuran) from aminocarbohydrates (chitin, chitosan and N-acetylglucosamine) is being pursued.

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Section: 74mentioning

confidence: 69%

Section: 74mentioning

confidence: 88%

Green chemistry and the ocean-based biorefinery

et al. 2013

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“…60 % of 3A5AF has been obtained by using boric acid as the promoter. Microwave-irradiation was adopted as an efficient heating method and the dehydration reaction was carried out in both ionic liquids (ILs) and organic solvents at 180 and 220°C respectively [34,35]. The exceptional promotional effect of boric acid in NAG conversion has been ascribed to the possible formation of borate-hexose complex, which shifts the hexose-aldose equilibrium to the generation of linear form aldose.…”

Section: Conversion Of Chitin Monomermentioning

confidence: 99%

Novel Catalytic Systems to Convert Chitin and Lignin into Valuable Chemicals

Chen

Yan

2014

Catal Surv Asia

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This review briefs the emerging strategies for the designing of catalysts and catalytic systems to upgrade waste biomass into value-added chemicals, with an emphasis on the efforts and advances in our group. The review covers the valorization of chitin and lignin materials, which are most abundant N-containing and the most abundant aromatic polymers, respectively. In the chitin part, we show case existing examples on chitin monomer and chitin transformation into renewable, N-containing chemicals. Oxidation, hydrolysis, dehydration reactions will be introduced. In lignin part we mainly introduce novel catalyst for lignin hydrogenolysis, in particular Ni based monometallic and bimetallic catalysts. The structure-activity correlations will be discussed in detail. We finally describe some of the undergoing works in the group and highlight a few potential directions worth investigation in the future.

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“…It could be a precursor of polyamide proximicines [149] that are isolated from Verrucosispora, a marine actinomycete. The product formation could be accelerated by the addition of different additives -the highest yield of 60% was achieved when boric-acid was used in 10 mol% concentration in [BMIM][Cl] at 180 • C. The kinetic study of the reaction revealed that the activation energy was 82.8 kJ/mol [150]. The yield can slightly be increased by the addition of NaCl and the application of higher temperature (220 • C) [151].…”

Section: Fundamental Reactions Involving Watermentioning

confidence: 86%

The role of water in catalytic biomass-based technologies to produce chemicals and fuels

2015

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a b s t r a c tWater can have many different roles in catalytic biomass-based technologies to produce chemicals and fuels. Since water is one of the two basic chemicals of nature used during photosynthesis, biomass contains different amount of water, which can be advantageously utilized during the conversion schemes. Water could be the solvent of the reactions or just either the eliminated product or the reactant resulting in hydration and hydrolysis. Since some of these roles are intrinsically part of the natural system, their change could be very difficult or not even possible. Therefore, the designer of the chemistry or the process must understand the possible roles of water at both the molecular and the macroscopic levels.

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Formation of a renewable amide, 3-acetamido-5-acetylfuran, via direct conversion of N-acetyl-d-glucosamine

Abstract: An effective method for transforming an amino-sugar into an N-substituted furan in an ionic liquid is reported. B(OH) 3 significantly improves the yield (60%, 3 min MW heating).

Cited by 117 publications

References 18 publications

Green chemistry and the ocean-based biorefinery

Green chemistry and the ocean-based biorefinery

Novel Catalytic Systems to Convert Chitin and Lignin into Valuable Chemicals

The role of water in catalytic biomass-based technologies to produce chemicals and fuels

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