Efficient Catalytic Oxidation of 5‐Hydroxymethylfurfural to 2,5‐Furandicarboxylic Acid by Magnetic Laccase Catalyst

Wang, Kefeng; Liu, Chunlei; Sui, Kunyan; Chen, Guo; Liu, Chun-Zhao

doi:10.1002/cbic.201800008

Cited by 52 publications

(44 citation statements)

References 29 publications

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“…In previous research laccases have been used either in free form [22] or immobilized [12]. In both cases, TEMPO was used as a mediator.…”

Section: Enzymatic Conversion Of Hmf Dff Hmfa and Ffa By Other Enzymesmentioning

confidence: 99%

“…90% FDCA was obtained with oxidation of FFA after 96 h with the same enzyme [11]. A fungal laccase, with TEMPO as a mediator, was able to produce 90.2% FDCA and 8.2% FFA after 96 h [12]. The only enzyme that was capable of almost complete conversion of HMF to FDCA was HMF oxidase, an FAD-dependent oxidase that was able to oxidase HMF to 92% FFA and 8% FDCA in 5 h, and at higher enzyme concentrations to 95% FDCA after 24 h [13,14].…”

mentioning

confidence: 99%

“…1 Schematic representation of oxidation routes of HMF to FDCA by different enzymes (E). Examples of enzymes for E1, E2 and E3 were taken from literature [11][12][13][14]. AAO aryl-alcohol oxidase, HMFO HMF oxidase, UPO unspecific fungal peroxidase, Lac laccase the mechanism of action of a specific enzyme, isolated enzymes have to be used.…”

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confidence: 99%

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Enzymatic conversion reactions of 5-hydroxymethylfurfural (HMF) to bio-based 2,5-diformylfuran (DFF) and 2,5-furandicarboxylic acid (FDCA) with air: mechanisms, pathways and synthesis selectivity

Cajnko

Novak

Grilc

et al. 2020

Biotechnol Biofuels

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Background: 2,5-Furandicarboxylic acid (FDCA) is one of the top biomass-derived value-added chemicals. It can be produced from fructose and other C6 sugars via formation of 5-hydroxymethilfurfural (HMF) intermediate. Most of the chemical methods for FDCA production require harsh conditions, thus as an environmentally friendly alternative, an enzymatic conversion process can be applied. Results: Commercially available horseradish peroxidase (HRP) and lignin peroxidase (LPO), alcohol (AO) and galactose oxidase (GO), catalase (CAT) and laccase (LAC) were tested against HMF, 2,5-diformylfuran (DFF), 5-hydroxymethyl-2-furoic acid (HMFA) and 5-formyl-2-furoic acid (FFA). Enzyme concentrations were determined based on the number of available active sites and reactions performed at atmospheric oxygen pressure. AO, GO, HRP and LPO were active against HMF, where LPO and HRP produced 0.6 and 0.7% of HMFA, and GO and AO produced 25.5 and 5.1% DFF, respectively. Most of the enzymes had only mild (3.2% yield or less) or no activity against DFF, HMFA and FFA, with only AO having a slightly higher activity against FFA with an FDCA yield of 11.6%. An effect of substrate concentration was measured only for AO, where 20 mM HMF resulted in 19.5% DFF and 5 mM HMF in 39.9% DFF, with a K m value of 14 mM. Some multi-enzyme reactions were also tested and the combination of AO and CAT proved most effective in converting over 97% HMF to DFF in 72 h. Conclusions: Our study aimed at understanding the mechanism of conversion of bio-based HMF to FDCA by different selected enzymes. By understanding the reaction pathway, as well as substrate specificity and the effect of substrate concentration, we would be able to better optimize this process and obtain the best product yields in the future.

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“…In previous research laccases have been used either in free form [22] or immobilized [12]. In both cases, TEMPO was used as a mediator.…”

Section: Enzymatic Conversion Of Hmf Dff Hmfa and Ffa By Other Enzymesmentioning

confidence: 99%

mentioning

confidence: 99%

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Enzymatic conversion reactions of 5-hydroxymethylfurfural (HMF) to bio-based 2,5-diformylfuran (DFF) and 2,5-furandicarboxylic acid (FDCA) with air: mechanisms, pathways and synthesis selectivity

Cajnko

Novak

Grilc

et al. 2020

Biotechnol Biofuels

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“…The laccase-mediator system (LMS) has been used for the removal of residual lignin in biomass [13,40], or the treatment of recalcitrant pollutants, such as antibiotics [39] or other drugs [41], pesticides [42], industrial textile wastewater [43], and even synthetic fragrances [44]. LMS has been also used for the oxidative synthesis of platform chemicals [45].…”

Section: Structural Aspects Mode Of Action and Redox Properties Of mentioning

confidence: 99%

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

et al. 2019

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There is a high number of well characterized, commercially available laccases with different redox potentials and low substrate specificity, which in turn makes them attractive for a vast array of biotechnological applications. Laccases operate as batteries, storing electrons from individual substrate oxidation reactions to reduce molecular oxygen, releasing water as the only by-product. Due to society’s increasing environmental awareness and the global intensification of bio-based economies, the biotechnological industry is also expanding. Enzymes such as laccases are seen as a better alternative for use in the wood, paper, textile, and food industries, and they are being applied as biocatalysts, biosensors, and biofuel cells. Almost 140 years from the first description of laccase, industrial implementations of these enzymes still remain scarce in comparison to their potential, which is mostly due to high production costs and the limited control of the enzymatic reaction side product(s). This review summarizes the laccase applications in the last decade, focusing on the published patents during this period.

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“…Both intermediates are then further oxidized to 5-formyl-2-furancarboxylic acid (FFCA), which is finally transformed to FDCA [25]. Several reaction systems with different oxidants are used to activate the oxygen species for catalytic oxidation of HMF such as oxygen, air, H 2 O 2 , and KMnO 4 [26]. Oxygen or air are normally preferred for HMF oxidation due to the broad availability, low price, and benignity to the environment.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Metal-Based Catalysts for the Catalytic Aerobic Oxidation of 5-Hydroxymethyl-Furfural to 2,5-Furandicarboxylic Acid

et al. 2020

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Biomass can be used as an alternative feedstock for the production of fuels and valuable chemicals, which can alleviate the current global dependence on fossil resources. One of the biomass-derived molecules, 2,5-furandicarboxylic acid (FDCA), has attracted great interest due to its broad applications in various fields. In particular, it is considered a potential substitute of petrochemical-derived terephthalic acid (PTA), and can be used for the preparation of valuable bio-based polyesters such as polyethylene furanoate (PEF). Therefore, significant attempts have been made for efficient production of FDCA and the catalytic chemical approach for FDCA production, typically from a biomass-derived platform molecule, 5-hydroxymethylfurfural (HMF), over metal catalysts is the focus of great research attention. In this review, we provide a systematic critical overview of recent progress in the use of different metal-based catalysts for the catalytic aerobic oxidation of HMF to FDCA. Catalytic performance and reaction mechanisms are described and discussed to understand the details of this reaction. Special emphasis is also placed on the base-free system, which is a more green process considering the environmental aspect. Finally, conclusions are given and perspectives related to further development of the catalysts are also provided, for the potential production of FDCA on a large scale in an economical and environmentally friendly manner.

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Efficient Catalytic Oxidation of 5‐Hydroxymethylfurfural to 2,5‐Furandicarboxylic Acid by Magnetic Laccase Catalyst

Cited by 52 publications

References 29 publications

Enzymatic conversion reactions of 5-hydroxymethylfurfural (HMF) to bio-based 2,5-diformylfuran (DFF) and 2,5-furandicarboxylic acid (FDCA) with air: mechanisms, pathways and synthesis selectivity

Enzymatic conversion reactions of 5-hydroxymethylfurfural (HMF) to bio-based 2,5-diformylfuran (DFF) and 2,5-furandicarboxylic acid (FDCA) with air: mechanisms, pathways and synthesis selectivity

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

Recent Developments in Metal-Based Catalysts for the Catalytic Aerobic Oxidation of 5-Hydroxymethyl-Furfural to 2,5-Furandicarboxylic Acid

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