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

Dai, Jinhang; Li, Fukun; Fu, Xun

doi:10.1002/cssc.202001955

Cited by 59 publications

(42 citation statements)

References 72 publications

(55 reference statements)

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“… [17–23] . Recent advances in catalytic transformation of renewable chitin biomass to N‐containing fine chemicals within last decade have been reviewed [24] . Some examples were summarized in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

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: 99%

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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“…One route is that biomass materials such as cellulose and lignin serve as renewable carbon sources to produce the intermediates, followed by incorporating N-functional groups using NH 3 , thus affording N-containing chemicals (He et al 2020). The other one is to directly synthesize N-containing chemicals from N-containing biomass feedstocks such as chitin and chitosan (Chen et al 2021;Dai et al 2020;Hülsey et al 2018;Shi et al 2021), which is free of use of external NH 3 and thus leads to significantly reduced energy consumption. Currently, utilization of N-containing biopolymers as raw materials to produce chemicals and materials received less attention compared to cellulose and lignin.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic access to enantiopure N-containing furfuryl alcohol from chitin-derived N-acetyl-D-glucosamine

Hao

Zong

Wang

et al. 2021

Bioresour. Bioprocess.

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Background Chiral furfuryl alcohols are important precursors for the synthesis of valuable functionalized pyranones such as the rare sugar L-rednose. However, the synthesis of enantiopure chiral biobased furfuryl alcohols remains scarce. In this work, we present a chemoenzymatic route toward enantiopure nitrogen-containing (R)- and (S)-3-acetamido-5-(1-hydroxylethyl)furan (3A5HEF) from chitin-derived N-acetyl-D-glucosamine (NAG). Findings 3-Acetamido-5-acetylfuran (3A5AF) was obtained from NAG via ionic liquid/boric acid-catalyzed dehydration, in an isolated yield of approximately 31%. Carbonyl reductases from Streptomyces coelicolor (ScCR) and Bacillus sp. ECU0013 (YueD) were found to be good catalysts for asymmetric reduction of 3A5AF. Enantiocomplementary synthesis of (R)- and (S)-3A5HEF was implemented with the yields of up to > 99% and the enantiomeric excess (ee) values of > 99%. Besides, biocatalytic synthesis of (R)-3A5HEF was demonstrated on a preparative scale, with an isolated yield of 65%. Conclusions A two-step process toward the chiral furfuryl alcohol was successfully developed by integrating chemical catalysis with enzyme catalysis, with excellent enantioselectivities. This work demonstrates the power of the combination of chemo- and biocatalysis for selective valorization of biobased furans. Graphic abstract

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“…Therefore, a novel concept of shell biorefinery has been suggested on account of the massive potential of chitin valorization. Shell biorefinery consists of the sustainable conversion of chitin into several nitrogen-rich chemicals for pharmaceuticals, cosmetics, textiles, water treatment, household cleansers, soaps, and carbon dioxide sequestration, which benefits both the economy and the environment [ 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

The Effect of Molecular Weight on the Antimicrobial Activity of Chitosan from Loligo opalescens for Food Packaging Applications

et al. 2021

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The growing requirement for sustainable processes has boosted the development of biodegradable plastic-based materials incorporating bioactive compounds obtained from waste, adding value to these products. Chitosan (Ch) is a biopolymer that can be obtained by deacetylation of chitin (found abundantly in waste from the fishery industry) and has valuable properties such as biocompatibility, biodegradability, antimicrobial activity, and easy film-forming ability. This study aimed to produce and characterize poly(lactic acid) (PLA) surfaces coated with β-chitosan and β-chitooligosaccharides from a Loligo opalescens pen with different molecular weights for application in the food industry. The PLA films with native and depolymerized Ch were functionalized through plasma oxygen treatment followed by dip-coating, and their physicochemical properties were assessed by Fourier-transform infrared spectroscopy, X-ray diffraction, water contact angle, and scanning electron microscopy. Their antimicrobial properties were assessed against Escherichia coli and Pseudomonas putida, where Ch-based surfaces reduced the number of biofilm viable, viable but nonculturable, and culturable cells by up to 73%, 74%, and 87%, respectively, compared to PLA. Biofilm growth inhibition was confirmed by confocal laser scanning microscopy. Results suggest that Ch films of higher molecular weight had higher antibiofilm activity under the food storage conditions mimicked in this work, contributing simultaneously to the reuse of marine waste.

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

Cited by 59 publications

References 72 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

Chemoenzymatic access to enantiopure N-containing furfuryl alcohol from chitin-derived N-acetyl-D-glucosamine

The Effect of Molecular Weight on the Antimicrobial Activity of Chitosan from Loligo opalescens for Food Packaging Applications

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