MOLECULES
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2022
·Vol. 27
·期 20
·6851
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IF 4.927
Rui Fan,Yanxiang Gao
Nowadays, subcritical water extraction (SWE) techniques are extensively investigated worldwide, while the thermal reactions that inevitably occur under subcritical water conditions are rarely studied. In order to investigate the behaviors of the different reactions during SWE of bioactive compounds from licorice, the Maillard reaction process was accessed via their products and the hydrolytic reaction was analyzed according to the kinetic parameters. In addition, the contents of total phenolics and flavonoids in the extracts obtained at the different temperatures were determined and total antioxidant capacities were evaluated by HPLC-ABTS+. The results showed that flavonoids and phenolics from licorice as well as new compounds generated via the Maillard reaction contributed to the antioxidant activity of the extracts. The fluorescence, color and absorbance of the extracts showed that the degree of the Maillard reaction increased with the rise of the extraction temperature. The kinetics of extraction for glycyrrhizic acid showed that it was firstly extracted by diffusion, and then was hydrolyzed into glycyrrhetinic acid 3-O-mono-β-D-glucuronide and glycyrrhetinic acid following a first-order mechanism. These findings could provide deep insights into the SWE process and a new method for producing glycyrrhetinic acid 3-O-mono-β-D-glucuronide and glycyrrhetinic acid.Keywords:glycyrrhizic acid;glycyrrhetinic acid;glycyrrhetinic acid 3-O-mono-β-D-glucuronide;antioxidant;Maillard reaction
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ACS Catalysis
·
2022
·
IF 13.7
Weipeng Song,Huai Liu,Junhua Zhang,Yong Sun,Lincai Peng
Furfural represents one of the most valuable biomass-derived platform molecules. Its selective production with a smart and tractable catalytic system is highly attractive for technical implementation, yet remains challenging. We herein report a promising protocol involving the mature Hβ zeolites in pure 1,4-dioxane to convert hemicellulose-related sugars into furfural with high rate and impressive selectivity under mild operating conditions. Furfural yields as high as 93.6% (from xylose) and 85.9% (from xylan) were accomplished at 140 °C in 40 min. The solvent 1,4-dioxane served as a shield to maintain the crystal structure and acidic center of Hβ as well as to inhibit the polymerization of furfural. The synergistic action of Hβ with 1,4-dioxane largely promoted the selective conversion of xylose to furfural, as the multiple immobilized acid sites of Hβ in 1,4-dioxane medium accelerated xylose-to-xylulose isomerization. The dehydration process was favorable based on its apparent activation energy of 39.1 kJ mol–1, leading to a high turnover frequency of 53.8 h–1. Density functional theory calculations revealed that the superior catalytic behavior could be ascribed to the higher adsorption of xylose than 1,4-dioxane, allowing xylose molecules to fully access the open Al sites of Hβ and the low Gibbs free energy barrier of xylose isomerization to xylulose in 1,4-dioxane over the Hβ catalyst. Moreover, the heterogeneous zeolite catalyst and the single low-boiling-point solvent 1,4-dioxane (101 °C) were readily recovered from the product with outstanding reusability. This contribution not only opens a high potential avenue for the selective production of furfural but also sheds light on the coordination mechanism of Hβ zeolite and 1,4-dioxane toward developing tailored processes.
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DALTON TRANSACTIONS
·
2022
·Vol. 51
·期 45
·17441-17453
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IF 4.569
Yuewen Shao,Mingzhu Guo,Mengjiao Fan,Kai Sun,Guoming Gao,Chao Li,Félix Mérimé Bkangmo Kontchouo,Lijun Zhang,Shu Zhang,Xun Hu
One-pot conversion of furfural, a biomass-derived platform chemical, to gamma-valerolactone (GVL), a fuel additive and green solvent, involves multiple steps of hydrogenation. Among these reactions, the deep hydrogenation of the furan ring in furfural interrupts GVL formation over Ni or Co-based catalysts. In this study, a method of alloying Ni and Co with Fe over a ZSM-5 support was proposed for tackling excessive activity of the catalyst for hydrogenation. The results indicated that the formation of binary NiFe and CoFe alloys in Ni–Co–Fe/ZSM-5 enhanced the dispersion of metallic species, reduction of metal oxides, formation of more Lewis acidic sites, and the adsorption of the C–O functionality of the furan ring, while lowering the capability for adsorption/activation of H2 and the adsorption of the CC group of the furan ring. These factors together reduced the activity for the hydrogenation of the furan ring in furfural, but enhanced the hydrogenation of the CO in ethyl levulinate (EL). The kinetic study confirmed that the hydrogenation of EL was the rate-determining step. The coordination of the dual alloys, NiFe and CoFe, in the bifunctional Ni–Co–Fe/ZSM-5 catalyst rendered superior activity for selective one-pot conversion of furfural to GVL with a yield of 85.7%.
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ACS Sustainable Chemistry & Engineering
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2022
·
IF 9.224
Lei Zhang,Jingyu Wang,Renliang Huang,Mei Cui,Wei Qi,Zhimin He,Rongxin Su
Cellulose nanocrystals (CNCs) are renewable and multifunctional plant-based nanoparticles that are industrially produced by controlled sulfuric acid hydrolysis, resulting in a large amount of acid–sugar mixture, which has potential to be recovered and concentrated for reuse. However, the removal of sugar from the acid–sugar mixture, which was produced by cellulose biomass hydrolysis, is essential before acid recycling. In this study, the acid–sugar mixture was separated from the CNC hydrolysate, and then, a combination process of diffusion dialysis (DD) using anion-exchange membranes and electrodialysis (ED) was used to remove the sugar from the acid–sugar mixture. The operation parameters were optimized and Fenton oxidation (FO) was applied to degrade sugar with a decrease in the chemical oxygen demand (CODCr) in the wastewater. As a result, 98.8% sulfuric acid was totally recovered in a practical process, with 92.2% recovery by diffusion dialysis and 87.1% by electrodialysis, and more than 90% sugar was rejected. CODCr in the wastewater decreased to <500 mg/L by FO treatment. Furthermore, CNCs prepared with the recovered sulfuric acid showed a crystallinity, surface charge, and morphology similar to that prepared with fresh acid. Therefore, this combination process of DD and ED is a green and economic feasible way for acid recycling for sustainable CNC production.
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FUEL
·
2022
·
IF 8.035
Wenran Gao,Yiling Wan,Shanhui Zhao,Muhammad Asif Akhtar,Kuan Ding,Bin Li,Yinlong Wu,Shoujun Zhang,Shu Zhang
Ketonization of biomass-derived oxygenates is promising for sustainable production of platform chemicals, but the catalyst activity will be severely inhibited by furanic compounds. To investigate the mechanism of the inhibition effect, furanic compounds with different side functional groups were chosen for co-ketonization with propanoic acid over CeO 2 . Results from 12 h continuous reaction showed that conversion of propanoic acid changed slightly when furan was co-fed with propanoic acid, while decreased significantly from 100 % for sole propanoic acid feeding to <55 % when co-feeding with furfural and furfuralcohol. Therefore, the inhibition ability followed the order of furfural ≈ furfuralcohol ≫ furan, which agreed well with the coke yield on the spent catalysts (51 %, 47 %, and 22 %, respectively). DFT calculation indicated that furfural and furfuralcohol, with the adsorption energy of 17–19 kJ·mol −1 , were much easier to adsorb on the catalyst than furan (11 kJ·mol −1 ). However, the lack of α-H of these furanic compounds led to their conversion into aromatic coke components. It is evidenced that the oxygenated side groups, rather than the furan ring, are responsible for the inhibition effect. Successive ketonization-combustion-ketonization tests revealed that simple air calcination can hardly recover the activity of the spent CeO 2 . This investigation gives new insights into the inhibitory impact of furans on the ketonization activity.
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
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2022
·
IF 8.025
Xinyi Xing,Xian Shi,Rui Hu,Ying Guan,Hui Gao,Siquan Xu
In this work, a series of (x)Hf-β zeolite catalysts were prepared by a simple wet impregnation method and used as bifunctional catalysts with Lewis and Brønsted acid sites for synthesizing 5-hydroxymethylfurfural (5-HMF) from cellulose in H 2 O (NaCl) -THF biphasic system. Characterization analysis of (x)Hf-β zeolite catalysts with ICP-OES, N 2 adsorption-desorption isotherm, XRD, FTIR , SEM, NH 3 -TPD and Py-FTIR indicated that the catalysts possessed favorable pore structure, appropriate acid strength and acidity. A superior 86.3 % cellulose conversion and 53.4 % 5-HMF yield could be obtained at 200 °C for 4 h by using (5 %)Hf-β zeolite as the catalyst. In addition, the catalytic system provided a favorable 5-HMF yield from other carbohydrates, including glucose (85.1 %), sucrose (80.6 %), starch (65.1 %), maltose (65.0 %), dextran (59.9 %), and Moso bamboo (21.9 %). Nevertheless, the recyclability of (5 %)Hf-β zeolite catalyst was unsatisfactory and the 5-HMF yield showed a downtrend from 53.4 % to 24.4 % after 5 cycles. The catalyst has promising potential for converting biomass materials into high-value platform compounds.
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高影响因子
FUEL
·
2022
·
IF 8.035
Wansi Lin,Yuan Cheng,Huai Liu,Junhua Zhang,Lincai Peng
The design of high-efficiency heterogeneous catalyst plays a central role for catalytic transfer hydrogenation (CTH) of biomass-derived furfural (FAL) into furfuryl alcohol (FOL). Herein, a novel zirconium doped polyacrylonitrile (PAN) nanofiber (Zr@PAN) was assembled via electrospinning technology. Systematic characterizations revealed that the high catalytic activity for CTH of FAL into FOL was provided by the cooperative effect between Lewis acid and Lewis base sites due to the chelation effect between zirconium ions and cyano-groups on PAN. Besides, a kinetic model specifying this reaction has been set up and showed a good correlation (R 2 > 0.94) between the measured and predicted data, which can effectively monitor the process and tailor the reaction conditions to attain the desired product. Although the activity of Zr-20@PAN decreased after three cycles of recovery, the introduction of bridging agent, such as lignin and tea polyphenol, can solve the recovery defect well due to their abundant hydroxyl group or carboxyl group.
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2022
·
IF 5.895
Linhui Feng,Heping Cui,Pusen Chen,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
An Amadori rearrangement product (ARP) derived from ribose (Rib) and glutathione (GSH) was prepared and identified as N-(1-deoxy-d-ribulos-1-yl)-glutathione by ultraperformance liquid chromatography–tandem mass spectrometry and NMR. Thermal treatment of the ARP aqueous solution was conducted, and a relatively high temperature was found to accelerate the degradation of the ARP. The concentration of furans formed at 120 °C was more than 6.39 times that at 100 °C, and especially, the high temperature favored the formation of furfural and 4-hydroxy-5-methyl-3(2H)-furanone through deoxyosone dehydration. The promoting role of extra-added GSH or its constituent amino acids was investigated in the volatile formation during thermal processing of the ARP. Both, the added GSH and its constituent amino acids, could timely capture glyoxal (GO) and methylglyoxal (MGO) to facilitate Strecker degradation, which improved pyrazine formation. Compared with glycine and glutamic acid, cysteine was the most effective extra-added amino acid to react with GO and MGO to produce pyrazine and methylpyrazine. More importantly, the cysteine degraded from extra-added GSH effectively accelerated the generation of sulfur-containing volatile compounds through the reaction of cysteine degradation products with furans and shorter-chain α-dicarbonyl compounds.
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高影响因子
FUEL
·
2022
·
IF 8.035
Yaqi Duan,Zhenhan Tao,Aiguo Zhu,Christophe Len,Yantao Wang,Weiran Yang
The integration and cascade utilization of the entire lignocellulosic biomass components to obtain high value-added chemicals or fuels are of high interest. Herein, a strategy combined the chemo-catalytic and hydrothermal liquification processes was developed for the conversion of raw biomass into high value-added furanic compounds and fuels. Firstly, optimal 58% yield of furfural and 40% yield of 5-methylfurfural were co-produced from hemicellulose and cellulose components of hemp stalk powder (HSP) using formic acid and NaI as the catalysts. Then, the lignin-rich solid residue left after chemo-catalytic process, can be simply converted into bio-oil and hydrochar via hydrothermal liquefaction with a high energy recovery efficiency (88%). Elemental analysis of the bio-oils and hydrochars, as well as the adsorbing capacity of the hydrochars were also investigated and discussed. The pioneering study on simultaneously production of furfural and 5-methylfurfural, as well as the cascade valorization strategy using a green, simple and efficient way may unwrap a new direction for the entire biomass utilization.
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ACS Sustainable Chemistry & Engineering
·
2022
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IF 9.224
Ao Xia,Dong Feng,Yun Huang,Xianqing Zhu,Zhengxin Wang,Xun Zhu,Qiang Liao
Anaerobic digestion of furfural wastewater suffers from toxicity to microbes, which reduces its performance. The toxic effects may be eliminated by a sustainable way of conductive material supplementation. In this study, the effect on anaerobic digestion of furfural (0.5–4 g/L) was investigated by adding 0–40 g/L granular activated carbon (GAC) in batch tests. The innovation of this current study is to explore the potential direct interspecies electron transfer (DIET) for the first time in furfural degradation as the sole substrate in anaerobic digestion. The results demonstrated that when furfural was the sole substrate, in the presence of GAC, the peak methane production rate was increased by 46.0%, while the specific methane yield was improved by 24.7%, compared with the control. Additionally, the electroactive Geobacter sulfurreducens abundance in biofilms attached to the surface of GAC was 19.0 folds higher than that in the control. The abundances of the related genes of methane metabolism and furfural degradation in biofilms were 1.1 and 5.8 folds higher than the control by metagenomic analysis, respectively. These lines of evidence suggested that the pathway of furfural metabolism to methane among Moorella species, G. sulfurreducens, and Methanothrix species based on DIET was likely established.
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RSC Advances
·
2022
·Vol. 12
·期 26
·16942-16954
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IF 4.036
Yawei Zhan,Meixin Wang,Tengfei Ma,Zhiqiang Li
In this study, the effect of the γ-valerolactone (GVL)/H2O pretreatment system on bamboo (Neosinocalamus affinis) for enzymatic hydrolysis and ethanol fermentation was investigated. The performance characterization of the pretreated bamboo substrates, including the chemical composition, the structural characteristics, and the ability to produce bioethanol, were evaluated. The recovered substrates were enzymatically hydrolyzed for 48 h and then fermented to bioethanol. For the cellulose in the raw bamboo material, the highest cellulose-to-glucose conversion yield (CGCY) was achieved at 140 °C for 2 h with GVL : H2O = 8 : 2, which was 73.39%, and the cellulose-to-ethanol conversion yield (CECY) was 67.00%. This indicated that 183.5 kg of bioethanol could be produced per ton of bamboo, which was 9.71-folds higher than that directly converted from the untreated raw bamboo powder. Under these conditions, 50.60% of the active lignin can be recovered and be used as a wood-derived feedstock for further high-valued utilization. Meanwhile, the maximum concentration of fermentation inhibitors formed after pretreatment was about 140.9 mmol L−1, and had weak inhibition to the subsequent reaction. It has been shown that the cellulose could be effectively separated from bamboo and converted into bioethanol through the GVL/H2O pretreatment system.
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高影响因子
Biomass Conversion and Biorefinery
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2022
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IF 4.05
Xiao Yaoxin,Zhang Jun,Zhu Lingjun,Shan Rui,Yuan Haoran,Chen Yong
A series of inexpensive electroplating sludge-derived magnetic copper-containing catalysts were developed for the selective hydrogenation of biomass-based furfural (FFR) into furfuryl alcohol (FA) and 2-methylfuran (MF). The specific structural characteristics of as-prepared magnetic copper-containing samples were clearly identified through various techniques, including XRD, XPS, N 2 adsorption–desorption, NH 3 -TPD, SEM and so on. The characterizations revealed that the hydrogen pre-activated magnetic catalysts supplied metallic Cu species, medium acidity and porosity for the catalytic upgrading of FFR in hydrogen atmosphere. As for FFR-to-FA as well as FFR-to-MF transformations, the magnetic copper-containing catalyst with calcination temperature of 800 °C exhibited excellent performance towards the formation of FA and MF, wherein desirable FA yield of 98.5 mol% and MF yield of 71.3 mol% were achieved at reaction temperatures of 160 °C and 240 °C, respectively. The reuse experiments indicated that the recycled catalysts still maintained excellent activity and stability even after four-time recycling. The present study thus highlights a new approach for the resource utilization of electroplating sludge, which also supplies low-cost and efficient catalytic materials for the selective upgrading of various biomass-derived platform molecules.
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