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Cas Database

98-01-1

98-01-1

Identification

  • Product Name:Furfural

  • CAS Number: 98-01-1

  • EINECS:202-627-7

  • Molecular Weight:96.0856

  • Molecular Formula: C5H4O2

  • HS Code:2932 12 00

  • Mol File:98-01-1.mol

Synonyms:Pyromucic aldehyde;2-Furil-metanale [Italian];Bran oil;2-Furyl-methanal;Furyl-methanal;2-Furfural;Furfuraldehyde;Furol;Furfurol;Quakeral;2-Furanaldehyde;2-Furaldehyde;1/C5H4O2/c6-4-5-2-1-3-7-5/h1-4;2-Furil-metanale;Furfurale [Italian];RCRA waste no. U125;2-Furancarbonal;furan-2-carbaldehyde;Furfural (natural);NCI-C56177;2-Furankarbaldehyd [Czech];EPA Pesticide Chemical Code 043301;FEMA No. 2489;RCRA waste number U125;2-Furylcarboxaldehyde;2-Formylfuran;Furancarbonal;Artificial oil of ants;Furfurale;5-17-09-00292 (Beilstein Handbook Reference);2-Furancarboxaldehyde;2-Formylofuran [Polish];Furaldehydes [UN1199] [Poison];Furfurylaldehyde;Furale;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT,IrritantXi

  • Hazard Codes:T,Xi

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H331 Toxic if inhaled H335 May cause respiratory irritation H351 Suspected of causing cancer

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. See Notes. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Seek medical attention if you feel unwell. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . Vapor may irritate eyes and respiratory system. Liquid irritates skin and may cause dermatitis. (USCG, 1999) Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Aggressive airway management may be necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 m1/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aldehydes and Related Compounds/

  • Fire-fighting measures: Suitable extinguishing media Use water spray, dry chemical, "alcohol resistant" form, or carbon dioxide. use water spray to keep fire-exposed containers cool. Special Hazards of Combustion Products: Irritating vapors are generated when heated (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. 1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quantities, absorb on paper towels. Evaporate in a safe place ... Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn the paper in a suitable location away from combustible materials. For large quantities, cover with sodium bisulfite, add a small amt of water & mix. ... After 1 hr, flush with large amt of water & wash site with soap solution.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong bases, strong acids, strong oxidants and food and feedstuffs. Keep in the dark. Well closed. Ventilation along the floor. Store in an area without drain or sewer access.Keep in air tight container and protect from light

  • Exposure controls/personal protection:Occupational Exposure limit valuesAfter reviewing available literature, NIOSH provided comments to OSHA on August 1, 1988, regarding the "Proposed Rule on Air Contaminants" (29 CFR 1910, Docket No. H-020). In these comments, NIOSH questioned whether the PELs proposed for furfural (TWA 2 ppm (skin)) were adequate to protect workers from recognized health hazards.Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Furfural
  • Packaging:50ml
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  • Manufacture/Brand:TRC
  • Product Description:Furfural
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  • Manufacture/Brand:TRC
  • Product Description:Furfural
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  • Product Description:Furfural(1mg/LinAcetonitrile)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Furfural >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Furfural >98.0%(GC)
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Furaldehyde
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Furaldehyde
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Furfural Furfural for synthesis. CAS 98-01-1, molar mass 96.08 g/mol., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
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Relevant articles and documentsAll total 547 Articles be found

Mesoporous tantalum phosphates: Preparation, acidity and catalytic performance for xylose dehydration to produce furfural

Xing, Yanran,Yan, Bo,Yuan, Zifei,Sun, Keqiang

, p. 59081 - 59090 (2016)

Mesoporous tantalum phosphates (TaOPO4-m) with varying P/Ta molar ratios (m = 0.41-0.89) were prepared, comprehensively characterized by ICP-AES, N2 physisorption, small-angle XRD, TEM, Raman, FT-IR, NH3-TPD and IR of pyridine adsorption and employed to catalyze the dehydration of xylose to produce furfural in a biphasic batch reactor. The physicochemical properties of these TaOPO4-m samples were affected significantly by variation of m. More ordered mesopores were formed in the sample with a higher m. On the other hand, the density of acidity decreased but the ratio of Br?nsted acidity to Lewis acidity (B/L) increased with the increase in m. TaOPO4-0.84, which showed adequate mesoporosity and a high B/L ratio, was identified as the best performing catalyst among these TaOPO4-m catalysts in terms of high furfural selectivity (ca. 72 mol%). Correlating the catalyst performance with its acid property showed that the xylose consumption rate decreased with the increasing B/L ratio, while furfural selectivity showed a volcano-type dependence on the B/L ratio. Besides, the huge decrease in the furfural selectivity after poisoning the Br?nsted acid sites by adding 2,6-dimethyl pyridine revealed a kind of Br?nsted acid catalysis for selective furfural production.

Dehydration of xylose over sulfated tin oxide catalyst: Influences of the preparation conditions on the structural properties and catalytic performance

Suzuki, Takeshi,Yokoi, Toshiyuki,Otomo, Ryoichi,Kondo, Junko N.,Tatsumi, Takashi

, p. 117 - 124 (2011)

Various sulfated metal oxides were tested as solid acid catalyst for the dehydration of xylose to furfural under milder conditions. On the basis of our findings that sulfated tin oxide exhibited the highest catalytic activity, the effects of the content of SO42- group and the calcination temperature on the structural properties and catalytic performance were investigated, and the reusability of the sulfated tin oxide catalyst was evaluated. The acid property on the sulfated tin oxide catalyst was characterized by in situ FT-IR observations of the CO-adsorbed sample. Finally, the reaction mechanism of dehydration of xylose over the SO4 2-/SnO2 catalyst was considered.

Improving Biocatalytic Synthesis of Furfuryl Alcohol by Effective Conversion of D-Xylose into Furfural with Tin-Loaded Sulfonated Carbon Nanotube in Cyclopentylmethyl Ether-Water Media

Li, Qi,Hu, Yun,Tao, Yong-You,Zhang, Peng-Qi,Ma, Cui-Luan,Zhou, Yu-Jie,He, Yu-Cai

, p. 3189 - 3196 (2021)

Carbon nanotube (CNT) was utilized as as the precursor to synthesize solid acid (tin-loaded sulfonated carbon nanotube, SO42?/SnO2-CNT) for catalyzing D-xylose into furfural. Fourier transform infrared spectroscopy, Roman spectroscopy, X-ray diffraction analysis, and scanning electron microscope techniques were used for characterizing SO42?/SnO2-CNT. Different loading of D-xylose (20–100?g/L) were converted into furfural (81.6–299.1?mM) at 41.9–61.2% yield by SO42?/SnO2-CNT (3.5 wt%) within 15?min at 180 °C in cyclopentylmethyl ether-water (1:2, v:v) biphasic media. Subsequently, whole-cells of recombinant Escherichia coli CG-19 cells expressing reductase catalyzed D-xylose-derived furfural at 35 ℃ and pH 7.5. Within 3?h, the prepared D-xylose (81.6–299.1?mM) could be converted into furfuryl alcohol at 32.7–61.2% yield (based on the D-xylose loading). Sequential conversion of D-xylose with SO42?/SnO2-CNT and reductase catalysts was established for the effective production of furfuryl alcohol. Graphic Abstract: [Figure not available: see fulltext.]

Kiselewa et al.

, p. 1133;engl.Ausg.S.1073 (1954)

Conversion of xylose, xylan and rice husk into furfural via betaine and formic acid mixture as novel homogeneous catalyst in biphasic system by microwave-assisted dehydration

Delbecq, Frederic,Wang, Yantao,Len, Christophe

, p. 520 - 525 (2016)

Dehydration of D-xylose and direct transformation of xylan into furfural were achieved by means of betaine-formic acid (HCOOH) catalytic system. All reactions were microwave-assisted and carried out in a CPME-water biphasic system. At 170?°C, in a pH range between 1.9 and 2.3, highest yields of 80% and 76% were obtained respectively for the pentose and the polysaccharide. Time dependence of the dehydration and influence of the temperature on the reaction kinetics were studied. Besides, at 190?°C, using the optimized condition of the reaction, rice husk was also employed as a source of furfural with a single stage reaction.

Dehydration of D-xylose into furfural over bimetallic salts of heteropolyacid in DMSO/H2O mixture

Guo, Xiaoqian,Guo, Feng,Li, Yishan,Zheng, Zhangqin,Xing, Zhexu,Zhu, Zihan,Liu, Ting,Zhang, Xin,Jin, Ying

, p. 18 - 25 (2018)

Dehydration of D-xylose to yield furfural was carried out using bimetallic salts of a heteropolyacid as the catalyst at 160–220 °C in the DMSO/H2O mixtures. The effect of Sn/Cs molar ratio of the bimetallic salts of 12-tungstophosphoric acid (PW) obtained by ultrasound-assisted coprecipitation on dehydration of D-xylose was investigated. The resultant catalysts were characterized by X-ray diffraction, N2 adsorption, field emission scanning electron microscopy and energy dispersive X-ray (EDX). It was found that the Sn-Cs codoped PW catalysts retained the Keggin crystal structure of PW. Sn0.625Cs0.5PW was the most active catalyst in the dehydration of D-xylose into furfural. The maximum D-xylose conversion (close to 100 wt %) and furfural yield (63 wt %) were achieved at 200 °C for 3 h in DMSO/H2O mixtures. It was found that 16.7 wt % Sn0.625Cs0.5PW on a chitosan-derived support displayed similar catalytic activity to that of Sn0.625Cs0.5PW and good stability after recycling six times.

The role of xylulose as an intermediate in xylose conversion to furfural: insights via experiments and kinetic modelling

Ershova,Kanervo,Hellsten,Sixta

, p. 66727 - 66737 (2015)

An experimental work has been performed to study the relevance of xylulose as an intermediate in xylose conversion to furfural in aqueous solution. The furfural formation was investigated at the temperature range from 180 to 220 °C during non-catalyzed and acid-catalyzed conversion of xylose in a stirred microwave-assisted batch reactor. The separate experiments on xylulose and furfural conversions were carried out under similar conditions. The maximum furfural yields obtained from xylose were 48 mol% and 65 mol% for the non-catalyzed and the acid-catalyzed processes, respectively. It was shown that the furfural yield is significantly lower from xylulose than from xylose. Furthermore, the effects of initial xylose concentration and the formation of xylulose were investigated in a mechanistic modeling study. A new reaction mechanism was developed taking into account the xylulose formation from xylose. Based on the experimental results and the proposed reaction model, it was concluded that xylose isomerization to xylulose with subsequent furfural formation is not a primary reaction pathway. The obtained kinetic parameters were further used for plug flow reactor simulations to evaluate furfural yields achievable by an optimized continuous operation.

Furfural production in a biphasic system using a carbonaceous solid acid catalyst

Gómez Millán, Gerardo,Phiri, Josphat,M?kel?, Mikko,Maloney, Thad,Balu, Alina M.,Pineda, Antonio,Llorca, Jordi,Sixta, Herbert

, (2019)

The formation of furfural from xylose was investigated under heterogeneously catalyzed conditions with Starbon450-SO3H as a catalyst in a biphasic system. Experiments were performed based on a statistical experimental design. The variables considered were time and temperature. Starbon450-SO3H was characterized by scanning electron microscopy, N2-physisorption, thermogravimetric analysis, diffuse reflectance infrared Fourier transform, Raman spectroscopy, pyridine titration and X-ray photoelectron spectroscopy. The results indicate that sulfonated Starbon450-SO3H can be an effective solid acid catalyst for furfural formation. A maximum furfural yield and selectivity of 70 mol% was achieved at complete xylose conversion under optimum experimental conditions. The present paper suggests that functionalized Starbon450-SO3H can be employed as an efficient solid acid catalyst that has significant hydrothermal stability and can be reused for several cycles to produce furfural from xylose.

Synergy effect between solid acid catalysts and concentrated carboxylic acids solutions for efficient furfural production from xylose

Doiseau, Aude-Claire,Rataboul, Franck,Burel, Laurence,Essayem, Nadine

, p. 176 - 184 (2014)

An efficient furfural formation from xylose was demonstrated combining a concentrated aqueous solution of acetic acid and solid acid catalysts. Higher furfural yields and selectivities were obtained by comparison to the catalytic performances obtained in pure water. The evident synergy effect observed at 150 °C between the aqueous carboxylic acid solution and the solid acid catalysts is tentatively explained by the occurrence of two phenomena: 1) the contribution of Lewis acid sites which would operate in cooperation with the homogeneous weak Br?nsted acidity brought by the aqueous acetic acid solution. According to the literature, the two steps mechanism involving the xylose-xylulose isomerization over Lewis acid sites and the successive Br?nsted acid catalyzed cyclodehydration to furfural would be the prevailing reaction pathway in the heterogeneous-homogenous catalytic system at 150 °C. 2) an enhancement of the surface solid acid coverage by the carbohydrate and furfural owing to the presence of carboxylic acid in the aqueous solution as shown by comparative liquid phase adsorption experiments done in pure water and in aqueous acetic acid solutions. Among a series of solid acid catalysts, ZrW, Cs2HPW12O40, HY (Si/Al = 15), K10 and NbOH, the latter one, NbOH used non-calcinated was shown to be active, selective and stable in the aqueous acetic acid media. HY and K10 are as active and selective for furfural formation but suffer for a strong Al leaching which precludes their utilization as true solid acid catalyst in acetic acid media.

Furfural production from xylose + glucose feedings and simultaneous N 2-stripping

Agirrezabal-Telleria,Requies,Gueemez,Arias

, p. 3132 - 3140 (2012)

The current furfural manufacturing process is based on homogeneous catalysts as well as steam as the stripping agent. Novel xylose-dehydration research studies include heterogeneous catalysts with high acidity and tailored selectivity. This work aims to evaluate the effect of additional glucose with the xylose feeding during simultaneous N2-stripping of furfural catalyzed by ion-exchange resins. Given the low batch performance of Amberlyst 70, the N2-stripping data showed high furfural yields and selectivity in the condensate stream. The different continuous feeding configurations showed that xylose/glucose ratios similar to the real pentosan-rich biomass could be fed achieving furfural yields of 75% at 200 °C. Moreover, the proposed study serves as a preliminary study to achieve high xylose conversion and relatively low glucose dehydration rates, showing its potential as a possible future process for the upgrading of carbohydrates to furan-based fuel additives.

Efficient, stable, and reusable silicoaluminophosphate for the one-pot production of furfural from hemicellulose

Bhaumik, Prasenjit,Dhepe, Paresh L.

, p. 2299 - 2303 (2013)

Development of stable, reusable, and water-tolerant solid acid catalysts in the conversion of polysaccharides to give value-added chemicals is vital because catalysts are prone to undergo morphological changes during the reactions. With the anticipation that silicoaluminophosphate (SAPO) catalysts will have higher hydrothermal stability, those were synthesized, characterized, and employed in a one-pot conversion of hemicellulose. SAPO-44 catalyst at 170 C within 8 h could give 63% furfural yield with 88% mass balance and showed similar activity up to at least 8 catalytic cycles. The morphological studies revealed that SAPO catalysts having hydrophilic characteristics are stable under reaction conditions.

Unveiling the role of choline chloride in furfural synthesis from highly concentrated feeds of xylose

Jiang,Verrier,Ahmar,Lai,Ma,Muller,Queneau,Pera-Titus,Jér?me,De Oliveira Vigier

, p. 5104 - 5110 (2018)

Furfural is a biomass derived compound used for the synthesis of fuels and chemicals. Herein we show that choline chloride allows the conversion of highly concentrated feeds of xylose (up to 50 wt%) to furfural (up to 75%) and that it can be recycled. Such a beneficial effect was observed from the formation of a choline xyloside intermediate exhibiting higher reactivity than xylose.

Supported task-specific ionic liquid catalyst for highly efficient and recyclable aerobic oxidation of benzyl alcohols

Liu, Lin,Ma, Juanjuan,Sun, Zhen,Zhang, Jianping,Huang, Jingjing,Li, Shanzhong,Tong, Zhiwei

, p. 68 - 71 (2011)

A novel catalytic system was prepared by impregnating ionic liquid immobilized 2,2,6,6-tetramethylpiperidyl-1-oxyl (TEMPO) and copper salt onto various silica supports. This catalytic system was capable of rapidly converting different benzylic and allylic alcohols into the corresponding aldehydes under O2 atmosphere with high conversion. Recycling results showed that the catalyst could be easily recovered and reused.

-

Suggitt et al.

, p. 373,376 (1947)

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High performance mesoporous zirconium phosphate for dehydration of xylose to furfural in aqueous-phase

Cheng, Liyuan,Guo, Xiangke,Song, Chenhai,Yu, Guiyun,Cui, Yuming,Xue, Nianhua,Peng, Luming,Guo, Xuefeng,Ding, Weiping

, p. 23228 - 23235 (2013)

The conversion of sugars to chemicals in aqueous-phase is especially important for the utilization of biomass. In current work, zirconium phosphate obtained by hydrothermal methods using organic amines as templates has been examined as a solid catalyst for the dehydration reaction of xylose to furfural in aqueous-phase. The use of dodecylamine and hexadecylamine in the synthesis process results in mesoporous zirconium phosphate with uniform pore width of ~2 nm and in morphology of nanoaggregates, which is characterized by powder X-ray diffraction, N2 isothermal sorption, NH3 temperature-programmed desorption, FT-IR, and 31P MAS NMR spectroscopy. When used as a catalyst for xylose dehydration to furfural in aqueous-phase, the mesoporous zirconium phosphate presents excellent catalytic performance with high conversions up to 96% and high furfural yields up to 52% in a short time of reaction. Moreover, the catalyst is easily regenerated by thermal treatment in air and shows quite stable activity. The open structure with numerous active sites of the Bronsted/Lewis acid sites is responsible for the high catalytic efficiency of mesoporous zirconium phosphate.

Conversion of xylose into furfural using lignosulfonic acid as catalyst in ionic liquid

Wu, Changyan,Chen, Wei,Zhong, Linxin,Peng, Xinwen,Sun, Runcang,Fang, Junjie,Zheng, Shaobo

, p. 7430 - 7435 (2014)

Preparation of biopolymer-based catalysts for the conversion of carbohydrate polymers to new energies and chemicals is a hot topic nowadays. With the aim to develop an ecological method to convert xylose into furfural without the use of inorganic acids, a biopolymer-derived catalyst (lignosulfonic acid) was successfully used to catalyze xylose into furfural in ionic acid ([BMIM]Cl). The characteristics of lignosulfonic acid (LS) and effects of solvents, temperature, reaction time, and catalyst loading on the conversion of xylose were investigated in detail, and the reusability of the catalytic system was also studied. Results showed that 21.0% conversion could be achieved at 100 °C for 1.5 h. The method not only avoids pollution from conventional mineral acid catalysts and organic liquids but also maked full use of a byproduct (lignin) from the pulp and paper industry, thus demonstrating an environmentally benign process for the conversion of carbohydrates into furfural.

Enhanced Furfural Yields from Xylose Dehydration in the Γ-Valerolactone/Water Solvent System at Elevated Temperatures

Sener, Canan,Motagamwala, Ali Hussain,Alonso, David Martin,Dumesic, James A.

, p. 2321 - 2331 (2018)

High yields of furfural (>90 %) were achieved from xylose dehydration in a sustainable solvent system composed of γ-valerolactone (GVL), a biomass derived solvent, and water. It is identified that high reaction temperatures (e.g., 498 K) are required to achieve high furfural yield. Additionally, it is shown that the furfural yield at these temperatures is independent of the initial xylose concentration, and high furfural yield is obtained for industrially relevant xylose concentrations (10 wt %). A reaction kinetics model is developed to describe the experimental data obtained with solvent system composed of 80 wt % GVL and 20 wt % water across the range of reaction conditions studied (473–523 K, 1–10 mm acid catalyst, 66–660 mm xylose concentration). The kinetic model demonstrates that furfural loss owing to bimolecular condensation of xylose and furfural is minimized at elevated temperature, whereas carbon loss owing to xylose degradation increases with increasing temperature. Accordingly, the optimal temperature range for xylose dehydration to furfural in the GVL/H2O solvent system is identified to be from 480 to 500 K. Under these reaction conditions, furfural yield of 93 % is achieved at 97 % xylan conversion from lignocellulosic biomass (maple wood).

Production of furfural from xylose and corn stover catalyzed by a novel porous carbon solid acid in γ-valerolactone

Zhu, Yuanshuai,Li, Wenzhi,Lu, Yijuan,Zhang, Tingwei,Jameel, Hasan,Chang, Hou-Min,Ma, Longlong

, p. 29916 - 29924 (2017)

A resorcinol-formaldehyde resin carbon (RFC) catalyst with a well-developed, ordered, mesoporous framework was prepared using a soft template method at room temperature. The carbon was sulfonated in water using sulfanilic acid under mild atmospheric conditions. The sulfonated RFC (S-RFC) was characterized by N2 adsorption-desorption, elemental analysis, TEM, XPS, and FT-IR. It was determined that S-RFC is an efficient solid acid catalyst for furfural production from xylose and corn stover in γ-valerolactone (GVL). The effects of reaction time, reaction temperature, catalyst loading, substrate dosage and water concentration were investigated. 80% furfural yield and 100% xylose conversion were obtained from xylose at 170 °C in 15 min with 0.5 g catalyst. Comparatively, 68.6% furfural yield was achieved from corn stover at 200 °C in 100 min when using 0.6 g catalyst. Since there was no discernable decrease in furfural yield after multiple conversions utilizing the same catalyst, the recyclability of the catalyst is considered good.

Reactive Extraction Enhanced by Synergic Microwave Heating: Furfural Yield Boost in Biphasic Systems

Huskens, Jurriaan,Lange, Jean-Paul,Ricciardi, Luca,Verboom, Willem

, (2020)

Reactive extraction is an emerging operation in the industry, particularly in biorefining. Here, reactive extraction was demonstrated, enhanced by microwave irradiation to selectively heat the reactive phase (for efficient reaction) without unduly heating the extractive phase (for efficient extraction). These conditions aimed at maximizing the asymmetries in dielectric constants and volumes of the reaction and extraction phases, which resulted in an asymmetric thermal response of the two phases. The efficiency improvement was demonstrated by dehydrating xylose (5 wt percent in water) to furfural with an optimal yield of approximately 80 mol percent compared with 60–65 mol percent under conventional biphasic conditions, which corresponds to approximately 50 percent reduction of byproducts.

One-step Preparation of Carbon-based Solid Acid Catalyst from Water Hyacinth Leaves for Esterification of Oleic Acid and Dehydration of Xylose

Laohapornchaiphan, Jutitorn,Smith, Christopher B.,Smith, Siwaporn Meejoo

, p. 3178 - 3186 (2017)

Carbon-based solid acid catalysts were successfully obtained via one-step hydrothermal carbonization (HTC) of water hyacinth (WH) in the presence of p-toluenesulfonic acid (PTSA). Increasing the HTC temperature from 180 to 240 °C resulted in carbonaceous materials with increased sulfur content and less adsorbed water. The material obtained at 220 °C (WH-PTSA-220) contains the highest amount of acid sites and promotes the highest initial rate of two transformations, that is, methanolysis of oleic acid and dehydration of xylose to furfural. While all PSTA-treated WH catalysts gave comparable fatty acid conversions (≈97 %) and furfural yields (≈60 %) after prolonged reaction times, the WH-PTSA-240 system bearing a relatively low acid density maintains the most favorable reusability profile. Higher HTC temperatures (220–240 °C) improved the catalyst reusability profiles due to graphitization and hydrophobicity of the carbon surface. The catalyst systems derived herein from biomass may have potential applications in biorefining platforms, utilizing the conversion of waste biomass to chemicals.

Low-Temperature Continuous-Flow Dehydration of Xylose Over Water-Tolerant Niobia–Titania Heterogeneous Catalysts

Moreno-Marrodan, Carmen,Barbaro, Pierluigi,Caporali, Stefano,Bossola, Filippo

, p. 3649 - 3660 (2018)

The sustainable conversion of vegetable biomass-derived feeds to useful chemicals requires innovative routes meeting environmental and economical criteria. The approach herein pursued is the synthesis of water-tolerant, unconventional solid acid monolithic catalysts based on a mixed niobia–titania skeleton building up a hierarchical open-cell network of meso- and macropores, and tailored for use under continuous-flow conditions. The materials were characterized by spectroscopic, microscopy, and diffraction techniques, showing a reproducible isotropic structure and an increasing Lewis/Br?nsted acid sites ratio with increasing Nb content. The catalytic dehydration reaction of xylose to furfural was investigated as a representative application. The efficiency of the catalyst was found to be dramatically affected by the niobia content in the titania lattice. The presence of as low as 2 wt % niobium resulted in the highest furfural yield at 140 °C under continuous-flow conditions, by using H2O/γ-valerolactone as a safe monophasic solvent system. The interception of a transient 2,5-anhydroxylose species suggested the dehydration process occurs via a cyclic intermediates mechanism. The catalytic activity and the formation of the anhydro intermediate were related to the Lewis acid sites (LAS)/Br?nsted acid sites (BAS) ratio and indicated a significant contribution of xylose–xylulose isomerization. No significant catalyst deactivation was observed over 4 days usage.

Root et al.

, p. 158,161,164 (1959)

Catalytic dehydration of xylose to furfural: Vanadyl pyrophosphate as source of active soluble species

Sádaba, Irantzu,Lima, Sérgio,Valente, Anabela A.,López Granados, Manuel

, p. 2785 - 2791 (2011)

The acid-catalysed, aqueous phase dehydration of xylose (a monosaccharide obtainable from hemicelluloses, e.g., xylan) to furfural was investigated using vanadium phosphates (VPO) as catalysts: the precursors, VOPO4· 2H2O, VOHPO4·0.5H2O and VO(H 2PO4)2, and the materials prepared by calcination of these precursors, that is, γ-VOPO4, (VO) 2P2O7 and VO(PO3)2, respectively. The VPO precursors were completely soluble in the reaction medium. In contrast, the orthorhombic vanadyl pyrophosphate (VO)2P 2O7, prepared by calcination of VOHPO4· 0.5H2O at 550 °C/2 h, could be recycled by simply separating the solid acid from the reaction mixture by centrifugation, and no drop in catalytic activity and furfural yields was observed in consecutive 4 h-batch runs (ca. 53% furfural yield, at 170 °C). However, detailed catalytic/characterisation studies revealed that the vanadyl pyrophosphate acts as a source of active water-soluble species in this reaction. For a concentration of (VO) 2P2O7 as low as 5 mM, the catalytic reaction of xylose (ca. 0.67 M xylose in water, and toluene as solvent for the in situ extraction of furfural) gave ca. 56% furfural yield, at 170 °C/6 h reaction.

Furfural formation from D-xylose: The use of different halides in dilute aqueous acidic solutions allows for exceptionally high yields

Marcotullio,De Jong

, p. 1291 - 1293 (2011)

Starting from the results achieved in a previous work on the effects of Cl- ions on furfural formation in aqueous acid solution [Marcotullio, G. et al., Green Chem. 2010, 12, 1739], the general effect of different halides is addressed. Experimental results show the halides to influence at least two distinct steps in the reaction leading from d-xylose to furfural under acidic conditions, via different mechanisms. The nucleophilicity of the halides appears to be critical for the dehydration, but not for the initial enolization reaction. By combining different halides synergic effects become evident resulting in very high selectivities and furfural yields.

Production of furfural from xylose at atmospheric pressure by dilute sulfuric acid and inorganic salts

Rong, Chunguang,Ding, Xuefeng,Zhu, Yanchao,Li, Ying,Wang, Lili,Qu, Yuning,Ma, Xiaoyu,Wang, Zichen

, p. 77 - 80 (2012)

In this paper, the dehydration of xylose to furfural was carried out under atmospheric pressure and at the boiling temperature of a biphasic mixture of toluene and an aqueous solution of xylose, with sulfuric acid as catalyst plus an inorganic salt (NaCl or FeCl3) as promoter. The best yield of furfural was 83% under the following conditions: 150 mL of toluene and 10 mL of aqueous solution of 10% xylose (w/w), 10% H2SO4 (w/w), 2.4 g NaCl, and heating for 5 h. FeCl3 as promoter was found to be more efficient than NaCl. The addition of DMSO to the aqueous phase in the absence of an inorganic salt was shown to improve the yield of furfural.

Catalytic cyclodehydration of xylose to furfural in the presence of zeolite H-Beta and a micro/mesoporous Beta/TUD-1 composite material

Lima, Sérgio,Antunes, Margarida M.,Fernandes, Auguste,Pillinger, Martyn,Ribeiro, Maria Filipa,Valente, Anabela A.

, p. 141 - 148 (2010)

The batch-wise and aqueous phase cyclodehydration of d-xylose to furfural (FUR) at 170 °C has been investigated in the presence of a composite material consisting of zeolite Beta nanocrystals (Si/Al = 12) embedded in a purely siliceous TUD-1 mesoporous matrix (BEATUD), characterised by elemental analysis, powder XRD, TEM and N2 sorption. After 8 h the xylose conversion reached 98% and the FUR yield was 74%. The initial reaction rates for BEATUD and the bulk nanocrystalline zeolite Beta (BEA) were similar when expressed on the basis of the total amount of acid sites (Lewis + Br?nsted) determined through FTIR analysis of adsorbed pyridine. However, the FUR yields at high xylose conversions of ca. 98% were higher for BEATUD (74%) than for bulk BEA (54%). TGA and DSC analyses for recovered catalysts showed that BEATUD possessed a lower amount of carbonaceous matter after a catalytic run, suggesting that the improved performance of the composite may be due to favourable competitive adsorption effects caused by the surrounding silica matrix. By thermally removing the carbonaceous matter between consecutive batch runs, BEATUD could be repeatedly reused without loss of catalytic performance.

Catalytic conversion of xylose to furfural by p-toluenesulfonic acid (Ptsa) and chlorides: Process optimization and kinetic modeling

Sajid, Muhammad,Rizwan Dilshad, Muhammad,Saif Ur Rehman, Muhammad,Liu, Dehua,Zhao, Xuebing

, (2021)

Furfural is one of the most promising precursor chemicals with an extended range of downstream derivatives. In this work, conversion of xylose to produce furfural was performed by employing p-toluenesulfonic acid (pTSA) as a catalyst in DMSO medium at moderate temperature and atmospheric pressure. The production process was optimized based on kinetic modeling of xylose conversion to furfural alongwith simultaneous formation of humin from xylose and furfural. The synergetic effects of organic acids and Lewis acids were investigated. Results showed that the catalyst pTSA-CrCl3·6H2 O was a promising combined catalyst due to the high furfural yield (53.10%) at a moderate temperature of 120? C. Observed kinetic modeling illustrated that the condensation of furfural in the DMSO solvent medium actually could be neglected. The established model was found to be satisfactory and could be well applied for process simulation and optimization with adequate accuracy. The estimated values of activation energies for xylose dehydration, condensation of xylose, and furfural to humin were 81.80, 66.50, and 93.02 kJ/mol, respectively.

Efficient catalytic conversion of corn stalk and xylose into furfural over sulfonated graphene in γ-valerolactone

Ma, Jianru,Li, Wenzhi,Guan, Shengnan,Liu, Qiying,Li, Qingqing,Zhu, Chaofeng,Yang, Tao,Ogunbiyi, Ajibola Temitope,Ma, Longlong

, p. 10569 - 10577 (2019)

Sulfonated graphene (SG) was prepared and employed to convert corn stalk and xylose into furfural. Transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS) and Fourier transform infrared spectroscopy (FT-IR) were used to characterize SG. The effects of reaction time, temperature, substrate loading, catalyst dosage and solvents on the reaction were researched and optimized. SG exhibited high catalytic activity in the conversion of xylose and corn stalk to furfural. A fairly high furfural yield of 96% was achieved at 150 °C from xylose and a 71.9% furfural yield was obtained when using a 10.7 ratio (mass ratio: xylose to SG) at 140 °C. While a 48% furfural yield was obtained from corn stalk (based on the starting combined moles of xylan and glucan in corn stalk; yield was >100%, if based on only xylan) using a substrate loading (corn stalk to catalyst mass ratio) of 2.14 and a 19% 5-hydroxymethylfurfural (5-HMF) yield was obtained. What's more, a 43.9% yield of furfural was obtained in only 20 min. In addition, the reusability of SG was also investigated and shown to have good stability for xylose dehydration.

P -Hydroxybenzenesulfonic acid-formaldehyde solid acid resin for the conversion of fructose and glucose to 5-hydroxymethylfurfural

Li, Wenzhi,Zhang, Tingwei,Xin, Haosheng,Su, Mingxue,Ma, Longlong,Jameel, Hason,Chang, Hou-Min,Pei, Gang

, p. 27682 - 27688 (2017)

A novel solid p-hydroxybenzenesulfonic acid-formaldehyde resin (SPFR) was prepared via a straightforward hydrothermal method. The catalytic properties of SPFR solid acids were evaluated in the dehydration reaction of fructose and glucose to 5-hydroxymethylfurfural (HMF). SEM, TEM, N2 adsorption-desorption, elemental analysis (EA), thermogravimetric analysis (TGA), and FT-IR were used to explore the effects of catalyst structure and composition on the HMF preparation from fructose. The effects of reaction time and temperature on the dehydration of fructose and glucose were also investigated. An HMF yield as high as 82.6% was achieved from fructose at 140 °C after 30 min, and 33.0% was achieved from glucose at 190 °C in 30 min. Furthermore, the recyclability of SPFR for the HMF production from fructose in 5 cycles was good.

The optimization of formic acid hydrolysis of xylose in furfural production

Yang, Wandian,Li, Pingli,Bo, Dechen,Chang, Heying

, p. 53 - 61 (2012)

Formic acid, a byproduct of furfural process, can be an effective catalyst for dehydration of xylose into furfural. Due to the low corrosion resistance, easy to be separated and reused, there is a growing interest in the use of formic acid as catalyst. In this study, response surface methodology (RSM) was used to optimize the hydrolysis process in order to obtain high furfural yield and selectivity. Three important parameters, initial xylose concentration (40-120 g/L), temperature (170-190 °C), formic acid concentration (5-15 g/L) were optimized. The optimum initial xylose concentration, formic concentration, reaction temperature were 40 g/L, 10 g/L, and 180 °C, respectively. Under these conditions, the maximum furfural yield of 74% and selectivity of 78% were achieved.

Mesoporous Nb2O5 as solid acid catalyst for dehydration of d-xylose into furfural

García-Sancho,Rubio-Caballero,Mérida-Robles,Moreno-Tost,Santamaría-González,Maireles-Torres

, p. 119 - 124 (2014)

The acid-catalyzed dehydration of d-xylose to furfural has been investigated in a biphasic water-toluene system, using a mesoporous Nb 2O5 catalyst prepared by a neutral templating route. The catalytic behavior was compared with a commercial Nb2O5. Materials were characterized by XRD, XPS, TEM, NH3-TPD, Raman spectroscopy and N2 sorption. The d-xylose conversion and furfural yield over the mesoporous niobia were found to increase with reaction temperature and time, in such a way that at 170 °C and 90 min, a d-xylose conversion and a furfural yield were higher than 90% and 50%, respectively. However, the commercial crystalline niobia displayed a low activity. The stability of the mesoporous catalyst has been demonstrated by XRD and N 2 sorption, and corroborated by the absence of significant niobium leaching in solution.

Cleavage of DNA by proton-coupled electron transfer to a photoexcited, hydrated Ru(II) 1,10-phenanthroline-5,6-dione complex

Poteet, Steven A.,Majewski, Marek B.,Breitbach, Zachary S.,Griffith, Cynthia A.,Singh, Shreeyukta,Armstrong, Daniel W.,Wolf, Michael O.,MacDonnell, Frederick M.

, p. 2419 - 2422 (2013)

Visible light irradiation of a ruthenium(II) quinone-containing complex, [(phen)2Ru(phendione)]2+ (12+), where phendione = 1,10-phenanthroline-5,6-dione, leads to DNA cleavage in an oxygen independent manner. A combination of NMR analyses, transient absorption spectroscopy, and fluorescence measurements in water and acetonitrile reveal that complex 1 2+ must be hydrated at the quinone functionality, giving [(phen) 2Ru(phenH2O)]2+ (1H2O2+, where phenH2O = 1,10-phenanthroline-6-one-5-diol), in order to access a long-lived 3MLCThydrate state (τ ~ 360 ns in H2O) which is responsible for DNA cleavage. In effect, hydration at one of the carbonyl functions effectively eliminates the low-energy 3MLCTSQ state (RuIII phen-semiquinone radical anion) as the predominant nonradiative decay pathway. This 3MLCT SQ state is very short-lived (2O2+* has photophysical properties similar to the 3MLCT state in [Ru(phen) 3]2+* with the added functionality of basic sites at the ligand periphery. Whereas [Ru(phen)3]2+* does not show direct DNA cleavage, the deprotonated form of 1H2O 2+* does via a proton-coupled electron transfer (PCET) mechanism where the peripheral basic oxygen sites act as the proton acceptor. Analysis of the small molecule byproducts of DNA scission supports the conclusion that cleavage occurs via H-atom abstraction from the sugar moieties, consistent with a PCET mechanism. Complex 12+ is a rare example of a ruthenium complex which 'turns on' both reactivity and luminescence upon switching to a hydrated state.

Dehydration of biomass to furfural catalyzed by reusable polymer bound sulfonic acid (PEG-OSO3H) in ionic liquid

Zhang, Zhang,Du, Bin,Quan, Zheng-Jun,Da, Yu-Xia,Wang, Xi-Cun

, p. 633 - 638 (2014)

Polymer bound sulfonic acid (PEG-OSO3H) is active for the dehydration of biomass to furfural. The furfural yield is improved when MnCl2 is added to the reaction mixture. The catalyst was mild, non-volatile, and non-corrosive and can be recycled multiple times (>10) without an intermediate regeneration step and no significant leaching of -OSO3H groups is observed.

The formation of 2-furaldehyde and formic acid from pentoses in slightly acidic deuterium oxide studied by 1H NMR spectroscopy

Ahmad, Tania,Kenne, Lennart,Olsson, Kjell,Theander, Olof

, p. 309 - 320 (1995)

The title reaction at 96 deg C and pD 1.5, 3.0, or 4.5 was followed by 1H NMR spectroscopy.The rate on pentose degradation increased in the order: arabinose ca. xyloseribose2-pentuloses.At pD 1.5, the rate of 2-furaldehyde formation increased in the same order.Increasing pD strongly accelerated the degradation of the aldoses but slightly retarded that of the ketoses.Increasing pD also retarded the formation of 2-furaldehyde, particularly from the ketoses, and increased its deuterium content at H-α (from 8-25 to 50-83 atom percent) and H-3 (from 79-100 to 100 atom percent).This is explained by assuming that 2-furaldehyde had formed mainly via acyclic intermediates, with reversible formation of a 3-deoxypentosulose.The formation of formic acid was slow and did not proceed via 2-furaldehyde.As evident from experiments with 1- or 5-13C-substituted aldopentoses, the formic acid was derived exclusively from the terminal pentose carbons, C-1 being somewhat more important than C-5.Keywords: Formic acid; 2-Furaldehyde; Pentose

Highly efficient and selective CO2-adjunctive dehydration of xylose to furfural in aqueous media with THF

Morais, Ana Rita C.,Bogel-Lukasik, Rafal

, p. 2331 - 2334 (2016)

The selective dehydration of xylose into furfural using high-pressure CO2 as an effective and more sustainable catalyst in an H2O/THF system is reported for the first time. The conversion of d-xylose into furfural above 83 mol% with a furfural yield of 70 mol% and a selectivity of 84% was achieved with only 50 bar of CO2 pressure within 1 hour at 180 °C.

Furfural production from rice husk using sulfuric acid and a solid acid catalyst through a two-stage process

Suxia, Ren,Haiyan, Xu,Jinling, Zhu,Shunqing, Li,Xiaofeng, He,Tingzhou, Lei

, p. 1 - 6 (2012)

This study aimed to optimize the conditions for furfural production from rice husk via a two-stage process: acid hydrolysis followed by dehydration using an orthogonal test design and response surface methodology, respectively. Orthogonal test design was utilized in the hydrolysis step; optimum conditions were as follows: 2.5% sulfuric acid (mass fraction), 110 °C reaction temperature, sulfuric acid to rice husk (L/S) ratio of 8 (g/mL), and a reaction time of 3 h. According to the Box-Behnken design, the temperature, amount of catalyst, extractant volume, and reaction time were chosen as four important factors with three levels for the dehydration step. Conditions were further optimized by response surface analysis. The results showed that the optimal conditions were 177 °C, 120 mL extractant volume, 2.1 g of catalyst, and a reaction time of 4.8 h. Under the optimal conditions, the furfural yield reached 8.9%, which is consistent with the estimated value, 8.97%.

A modified biphasic system for the dehydration of d-xylose into furfural using SO42-/TiO2-ZrO2/La 3+ as a solid catalyst

Li, Huiling,Deng, Aojie,Ren, Junli,Liu, Changyu,Wang, Wenju,Peng, Feng,Sun, Runcang

, p. 251 - 256 (2014)

One of the most promising strategies for furfural production is to extract continually the target product from the aqueous solution utilizing organic solvents. With the aim to develop an ecologically viable catalytic pathway for furfural production without the addition of mineral acids, we presented a modified biphasic system using a solid acid (SO42-/ TiO2-ZrO2/La3+) as catalyst for producing furfural from xylose. Different kinds of aprotic organic solvents (DMSO, DMF and DMI) in water phase and 2-butanol in organic phase (MIBK) were investigated as reaction media. Furfural yield and xylose conversion efficiency were dependent on the amounts of aprotic organic solvents and 2-butanol, the solid/liquid ratio, and the volume ratio of the organic phase and the aqueous phase as well as the reaction temperature and time. As a result, DMI showed the best performance on improving furfural yield during the furfural production. 3563.3 μmol of furfural/g of xylose with 97.9% xylose conversion efficiency was obtained after 12 h at 180 °C when the volume ratios of water to DMI and MIBK to 2-butanol were 8:2 and 7:3, respectively.

Synthesis of furfural from d-xylose and corncob with chromium chloride as catalyst in biphasic system

Zhang, Ye,Chen, Mingqiang,Wang, Jun,Hu, Qingsong

, p. 1717 - 1720 (2014)

An efficient process was developed for the conversion of D-xylose into furfural with chromium chloride as catalyst in a biphasic system. The optimal furfural yield of 38.76 % was obtained in the following reaction conditions: reaction temperature 140 °C, reaction time 1 h and the catalyst loading 2 mmol. Sodium chloride used as co-catalyst was found to affect the furfural yield. A higher furfural yield of 52.55 % was achieved in the presence of 3 g of sodium chloride when using chromium chloride catalyst for the dehydration of D-xylose into furfural. The CrCl3·6H2O-NaCl catalytic system could be recycled and its stable activity was showed after three successive runs. Moreover, this work also provided useful information for the production of furfural from biomass. The furfural yield of 23.88 % was achieved when corncob used as starting materials.

Catalytic dehydration of D-xylose to furfural over a tantalum-based catalyst in batch and continuous process

Li, Xing-Long,Pan, Tao,Deng, Jin,Fu, Yao,Xu, Hua-Jian

, p. 70139 - 70146 (2015)

Furfural is a biomass-based bulk chemical and its derivatives have potential applications as renewable fuels and chemicals. A water-tolerant and stable solid acid catalyst modified hydrated tantalum oxide (TA-p) was developed for catalytic conversion of D-xylose to furfural in water-organic solvent biphasic system. This process was performed both in a batch reactor and a continuous fixed-bed reactor. In the batch process, D-xylose conversion and furfural yield were significantly affected by the organic solvent, reaction temperature and reaction time. 1-Butanol, which could be obtained through the fermentation of biomass-based carbohydrates, was selected as organic phase and the highest furfural yield of 59% was achieved with D-xylose conversion of 96% at 180 °C in the continuous process. Moreover, the long-time stability test for 80 h under the optimal conditions showed the excellent stability of TA-p catalyst.

Wolfrom et al.

, p. 3518,3523 (1949)

Conversion of C5 carbohydrates into furfural catalyzed by a Lewis acidic ionic liquid in renewable γ-valerolactone

Wang, Shurong,Zhao, Yuan,Lin, Haizhou,Chen, Jingping,Zhu, Lingjun,Luo, Zhongyang

, p. 3869 - 3879 (2017)

For the purpose of building a green reaction system to produce furfural (FF), the conversion of two important pentoses from hemicellulose, namely xylose and arabinose, was investigated in an aqueous reaction system including a Lewis acidic ionic liquid as a catalyst and renewable γ-valerolactone (GVL) as a co-solvent. The results showed that the introduction of GVL greatly improved the reactivity of pentose and inhibited the secondary decomposition reaction of FF compared to a pure-water reaction system. NMR analysis suggested that the composition of pentose conformers was greatly altered towards a reactive distribution. The highest FF yields were 79.76% (from xylose) and 58.70% (from arabinose), which were obtained at 140 °C. The influence of reaction parameters on pentose conversion was also studied. A comparison between different reaction conditions suggested that arabinose had less reactivity than xylose, leading to its lower conversion rate and FF yield. Furthermore, xylan and real biomass materials were tested in the proposed reaction system, and decent FF yields of up to 69.66% (from xylan) and 47.96% (from corn stalk) were obtained.

Synthesis of furfural from xylose by heterogeneous and reusable nafion catalysts

Lam, Edmond,Majid, Ehsan,Leung, Alfred C. W.,Chong, Jonathan H.,Mahmoud, Khaled A.,Luong, John H. T.

, p. 535 - 541 (2011)

Nafion 117 has been proven as a robust and reusable heterogeneous catalyst for the dehydration of 9.1% (w/w) xylose in dimethyl sulfoxide (DMSO) to yield 60% furfural in 2 h at 150°C. The catalytic high activity promoted shorter reaction times to limit the formation of side-products which otherwise would lead to decreased yields. Within the allowable operating temperature range of Nafion (125 to 175°C), the reaction was kinetically controlled. In corroboration with AFM and SEM imaging, ATR-FTIR confirmed that the Nafion catalytic activity remained unchanged after 15 repeated uses. With excellent chemical and thermal stability under the conditions for xylose dehydration compared to existing solid acid catalysts, this reusable Nafion system could be a step towards the more economical production of furfural from renewable biomass, an intermediate chemical for the preparation of value-added chemicals.

Furfural synthesis from D-xylose in the presence of sodium chloride: Microwave versus conventional heating

Xiouras, Christos,Radacsi, Norbert,Sturm, Guido,Stefanidis, Georgios D.

, p. 2159 - 2166 (2016)

We investigate the existence of specific/nonthermal microwave effects for the dehydration reaction of xylose to furfural in the presence of NaCl. Such effects are reported for sugars dehydration reactions in several literature reports. To this end, we adopted three approaches that compare microwave-assisted experiments with a) conventional heating experiments from the literature; b) simulated conventional heating experiments using microwave-irradiated silicon carbide (SiC) vials; and at c) different power levels but the same temperature by using forced cooling. No significant differences in the reaction kinetics are observed using any of these methods. However, microwave heating still proves advantageous as it requires 30% less forward power compared to conventional heating (SiC vial) to achieve the same furfural yield at a laboratory scale.

Synthesis, kinetic study, and applications of polyethyleneimine supported nano zirconium chromate in oxidation of furfuryl alcohol to corresponding carbonyl compound

Sheikh, Setareh,Goudarzian, Nooredin

, p. 1531 - 1538 (2016)

The efficiency of highly branched polyethyleneimine has been investigated as a support for nano zirconium chromate and subsequent use as a heterogeneous oxidant for selective oxidation of furfuryl alcohol to furfural. These were synthesized using polyethyleneimine to produce a polymer coordinated nano zirconium, a noble and straightforward method for screening high catalytically active polymer nano composites. The one-step systematic derivatization of the polyethyleneimine scaffold led structurally correlated to the stabilization of zirconium nanoparticles and catalysis. Analysis of this polymeric reagent identified the zirconium chromate nano composite that was able to be effective to oxidation reaction in tetrahydrofuran under mild conditions due to the surface area of the nano zirconium chromate per unit volume. Capacity of the reagent and fixation of nano zirconium chromate is confirmed by ICP and atomic absorption technique. Morphology of this nano composite is investigated by SEM and TEM. The kinetic of oxidation of furfuryl alcohol, over heterogeneous catalyst, nano zirconium chromate in THF, were investigated. Power-law rate model was applied to describe the experimental results and obtain the orders of the reaction with respect to furfuryl alcohol, catalyst, and furfural, which were found to be 0.989, 0.991, and ?0.68, respectively, with the activation energy of 76.78?kJ/mol. Graphical abstract: [Figure not available: see fulltext.]

Dunlop

, p. 204,206 (1948)

Microwave assisted efficient furfural production using nano-sized surface-sulfonated diamond powder

Delbecq, Frederic,Takahashi, Yukari,Kondo, Takeshi,Corbas, Cristobal Cara,Ramos, Encarnacion Ruiz,Len, Christophe

, p. 74 - 78 (2018)

Sulfonated nano-sized diamond powder (S-DP) was tested in a typical water-CPME (1:3, v/v) biphasic system and heated in a commercial monowave microwave oven to promote the dehydration of D-xylose into furfural as industrial platform molecule. This new heterogeneous catalyst with a propyl linker between the support and the sulfonyl group expressed remarkable sufficient hydrophilicity, affinity for D-xylose and catalytic activity in presence of NaCl. The solid can act as a strong acidic catalyst without detectable exchange between proton exclusively localized on the surface of the catalyst and sodium ion. It was also stable at 200 °C even after severe recycling treatment. The final optimized condition requires 10 wt% of the catalyst for a maximum furfural yield of 76% when the mixture is heated for 50 min in the current biphasic system.

The role of metal halides in enhancing the dehydration of xylose to furfural

Enslow, Kristopher R.,Bell, Alexis T.

, p. 479 - 489 (2015)

The dehydration of xylose yields furfural, a product of considerable value as both a commodity chemical and a platform for producing a variety of fuels. When xylose is dehydrated in aqueous solution in the presence of a Bronsted acid catalyst, humins are formed via complex side processes that ultimately result in a loss in the yield of furfural. Such degradative processes can be minimized via the insitu extraction of furfural into an organic solvent. The partitioning of furfural from water into a given extracting solvent can be enhanced by the addition of salt to the aqueous phase, a process that increases the thermodynamic activity of furfural in water. Although the thermodynamics of using salts to improve liquid-liquid extraction are well studied, their impact on the kinetics of xylose dehydration catalyzed by a Bronsted acid are not. The aim of the present study was to understand how metal halide salts affect the mechanism and kinetics of xylose dehydration in aqueous solution. We found that the rate of xylose consumption is affected by both the nature of the salt cation and anion, increasing in the order no salt+++ and no salt---. Furfural selectivity increases similarly with respect to metal cations, but in the order no salt--- for halide anions. Multinuclear NMR was used to identify the interactions of cations and anions with xylose and to develop a model for explaining xylose-metal halide and water-metal halide interactions. The results of these experiments coupled with 18O-labeling experiments indicate that xylose dehydration is initiated by protonation at the C1OH and C2OH sites, with halide anions acting to stabilize critical intermediates. The means by which metal halides affect the formation of humins was also investigated, and the role of cations and anions in affecting the selectivity to humins is discussed. Get your kicks from kinetics: The effect of metal halides on the mechanism and kinetics of xylose dehydration in aqueous solution have been investigated. We found that both the rate of xylose consumption and furfural selectivity are affected by the nature of the salt cation and anion pairing.

Synergistic effect between CaCl2 and Γ-Al2O3 for furfural production by dehydration of hemicellulosic carbohydrates

Fúnez-Nú?ez,García-Sancho,Cecilia,Moreno-Tost,Pérez-Inestrosa,Serrano-Cantador,Maireles-Torres

, (2019)

γ-Al2O3 has successfully been used as solid acid catalyst for xylose dehydration in a water:toluene biphasic system. The addition of alkaline earth metal chlorides improved the partition coefficient, thus facilitating the extraction of furfural from the aqueous phase. In this sense, the best catalytic performance was attained by using CaCl2 and γ-Al2O3 with almost full xylose conversion and a furfural yield of 55% after 50 min, at 150 °C. A 1H NMR study has demonstrated that CaCl2 shifts the α-xylopyranose/β-xylopyranose anomeric equilibrium toward the α-form, more favorable for initiating the dehydration process, and γ-Al2O3 promotes the furfural production. γ-Al2O3 can be reused during ten catalytic cycles without any pretreatment. Finally, the synergistic effect between CaCl2 and γ-Al2O3 could also be inferred from the increase in furfural yield, until a value of 83% after 50 min at 175 °C, by using a hemicellulosic liquor obtained from olive stones.

Furfural from corn stover hemicelluloses. A mineral acid-free approach

Gomez Bernal, Hilda,Bernazzani, Luca,Raspolli Galletti, Anna Maria

, p. 3734 - 3740 (2014)

Furfural was obtained from corn stover hemicelluloses by a microwave-assisted, green and heterogeneously catalyzed two-step cascade process as follows: first step, hydrothermal fractionation of corn stover hemicelluloses, and second step, hydrolysis/dehydration of soluble hemicellulosic sugars over niobium phosphate to yield furfural at moderate temperatures (200 °C), with both steps being performed in water. Furfural yields of up to 23 mol% with respect to the starting raw biomass were reached. This journal is the Partner Organisations 2014.

Hydrochloric acid-catalyzed coproduction of furfural and 5-(chloromethyl)furfural assisted by a phase transfer catalyst

Bhat, Navya Subray,Dutta, Saikat,Onkarappa, Sharath Bandibairanahalli,Vinod, Nivedha

, (2020)

Furfural has been produced in 53percent isolated yield from D-xylose within an aqueous HCl-1,2-dichloroethane biphasic reaction mixture using benzyltributylammonium chloride (BTBAC) as a phase transfer catalyst. The use of BTBAC noticeably improved the yield of furfural compared to that in the control reaction. The reaction was optimized on the reaction temperature, duration, concentration of HCl, and the loading of BTBAC. Furfural and 5-(chloromethyl)furfural (CMF) have also been coproduced from a mixture of pentose and hexose sugars. Under optimized conditions (100 °C, 3 h, 20.2percent HCl, 10 wtpercent BTBAC), CMF and furfural were isolated in 17percent and 53percent yield, respectively, from a mixture of glucose and xylose. In addition, levulinic acid was isolated from the aqueous layer in 31percent yield.

One-pot sustainable synthesis of valuable nitrogen compounds from biomass resources

Carreira, M. Carolina A.,Fernandes, Ana C.,Oliveira, M. Concei??o

, (2022/01/11)

In this work we report a new one-pot process for the sustainable synthesis of 2-furanylquinazolines and 2-furfurylidene derivatives from carbohydrates, including xylose, fructose and xylan, with moderate overall yields, catalyzed by perrhenic acid.

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang

, (2021/09/28)

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

Ethanolysis of selected catalysis by functionalized acidic ionic liquids: An unexpected effect of ILs structural functionalization on selectivity phenomena

Nowakowska-Bogdan, Ewa,Nowicki, Janusz

, p. 1857 - 1866 (2022/02/05)

A series of functionalized hydrogen sulfate imidazolium ILs were synthesized and applied as catalysts in the reaction of glucose, xylose and fructose with ethanol. In this research, an unexpected selectivity phenomenon was observed. It showed that in this reaction functionalized ILs should be considered as a special type of catalyst. Functionalization of alkyl imidazolium ILs, especially the addition of electronegative OH groups, causes a clear and unexpected effect manifested via visible changes in the selectivity of the reaction studied. In the case of fructose, an increase in the number of OH groups affects an increase in the selectivity towards ethyl levulinate from 14.2% for [bmim]HSO4 to 20.1% for [glymim]HSO4 with an additional increase in selectivity to 5-hydroxymethyfurfural. In turn, for xylose, the introduction of OH groups to the alkyl chain was manifested by a decrease in selectivity to furfural as its ethyl acetal and an increase in selectivity to ethylxylosides. This journal is

Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride

Azeez, Sadaf,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri

supporting information, p. 2048 - 2053 (2022/03/31)

A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.

An Effective and Inexpensive Hf/ZSM-5 Catalyst for Efficient HMF Formation from Cellulose

Wu, Ningxin,Zhang, Manling,Pan, Xiaomei,Zhang, Jin,Gao, Lijing,Xiao, Guomin

, p. 1984 - 1992 (2020/11/09)

Abstract: The production of 5-hydroxymethylfurfural (HMF) from cellulose is of great significance for the high-value utilization of biomass, although this route currently faces the challenge of low efficiency. In the present work, a series of effective (x)Hf/ZSM-5 catalysts were developed for HMF production from cellulose, and analyzed by BET, XRD, SEM, ICP, NH3-TPD, Py-FTIR techniques. Driven by the (5)Hf/ZSM-5 catalyst, HMF with a yield of up to 67.5% and 17.2% of furfural are simultaneously obtained from cellulose in the H2O(NaCl)/THF biphasic system. Moreover, after four consecutive cycles, (5)Hf/ZSM-5 catalyst still maintained part of its catalytic activity. The 67.5% HMF yield achieved herein is one of the highest yields achieved in the conversion reaction using cellulose as a substrate, and the catalytic performance of the H2O(NaCl)/THF system containing the (5)Hf/ZSM-5 catalyst is even comparable to that of the expensive ionic liquid system. This result reflects the application prospect of (5)Hf/ZSM-5 catalyst in the future industrial production process of HMF. Graphic Abstract: [Figure not available: see fulltext.]

Process route upstream and downstream products

Process route

methanol
67-56-1

methanol

2-(furan-2-yl)-1,3-dioxolane
1708-41-4

2-(furan-2-yl)-1,3-dioxolane

furfural
98-01-1

furfural

2-furoic acid methyl ester
611-13-2

2-furoic acid methyl ester

Conditions
Conditions Yield
With dihydrogen peroxide; vanadia; In water; at 5 ℃; for 9h;
82 % Chromat.
D-glucose
50-99-7

D-glucose

GLUTATHIONE
70-18-8

GLUTATHIONE

1,3-thiazole
288-47-1

1,3-thiazole

Thiophene-2-thiol
7774-74-5

Thiophene-2-thiol

Tetrahydrothiophen-3-one
1003-04-9

Tetrahydrothiophen-3-one

furfural
98-01-1

furfural

2,5-DIMETHYLTHIOPHENE
638-02-8

2,5-DIMETHYLTHIOPHENE

5-Methylfurfural
620-02-0

5-Methylfurfural

1-(2-furyl)-1-ethanone
1192-62-7,80145-44-4

1-(2-furyl)-1-ethanone

2-methylthiophene-3-thiol
2527-76-6

2-methylthiophene-3-thiol

2-Acetylpyrrole
1072-83-9

2-Acetylpyrrole

2-methylfuran-3-thiol
28588-74-1

2-methylfuran-3-thiol

Conditions
Conditions Yield
In water; at 160 ℃; for 2h; pH=7.5;
ascorbic acid
50-81-7,98966-42-8

ascorbic acid

furfural
98-01-1

furfural

2-Methylpyrazine
109-08-0

2-Methylpyrazine

2,5-dimethyl-pyrazine
123-32-0

2,5-dimethyl-pyrazine

1-benzofurane
271-89-6

1-benzofurane

2,5-diformylfurane
823-82-5,163857-09-8

2,5-diformylfurane

1-furfuryl-pyrrole
1438-94-4

1-furfuryl-pyrrole

2,2'-difurylmethane
1197-40-6

2,2'-difurylmethane

2,4-di-tert-Butylphenol
96-76-4

2,4-di-tert-Butylphenol

2-ethyl-5-methypyrazine
13360-64-0

2-ethyl-5-methypyrazine

3-ethyl-2-hydroxy-2-cyclopenten-1-one
21835-01-8

3-ethyl-2-hydroxy-2-cyclopenten-1-one

Conditions
Conditions Yield
With sodium hydroxide; at 143 ℃; for 2h; pH=5; aq. phosphate buffer; Sealed vial;
ascorbic acid
50-81-7,98966-42-8

ascorbic acid

furfural
98-01-1

furfural

2-Methylpyrazine
109-08-0

2-Methylpyrazine

2,5-dimethyl-pyrazine
123-32-0

2,5-dimethyl-pyrazine

2,5-diformylfurane
823-82-5,163857-09-8

2,5-diformylfurane

2-ethyl-3,6-dimethylpyrazine
13360-65-1

2-ethyl-3,6-dimethylpyrazine

2,2'-difurylmethane
1197-40-6

2,2'-difurylmethane

2,4-di-tert-Butylphenol
96-76-4

2,4-di-tert-Butylphenol

3,5-diethyl-2-methyl-pyrazine
18138-05-1

3,5-diethyl-2-methyl-pyrazine

2-ethyl-5-methypyrazine
13360-64-0

2-ethyl-5-methypyrazine

3-ethyl-2-hydroxy-2-cyclopenten-1-one
21835-01-8

3-ethyl-2-hydroxy-2-cyclopenten-1-one

Conditions
Conditions Yield
With sodium hydroxide; at 143 ℃; for 2h; pH=5; aq. phosphate buffer; Sealed vial;
(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

isoascorbic acid
1129294-89-8,98966-42-8

isoascorbic acid

furfural
98-01-1

furfural

3-hydroxy-2-pyrone
496-64-0

3-hydroxy-2-pyrone

2-furanoic acid
88-14-2

2-furanoic acid

(E)-2-Hexenoic acid
13419-69-7

(E)-2-Hexenoic acid

2,3-dihydro-6-propylbenzofuran-3,7-diol
1401094-48-1

2,3-dihydro-6-propylbenzofuran-3,7-diol

3-(2-furoyl)hexanal
1401094-49-2

3-(2-furoyl)hexanal

6-propylbenzofuran-7-ol
1309945-34-3

6-propylbenzofuran-7-ol

Conditions
Conditions Yield
With citric acid; In water; at 60 ℃; for 168h; pH=3.2; Darkness;
(2-furyl)methyl alcohol
98-00-0,25212-86-6,93793-62-5

(2-furyl)methyl alcohol

methanol
67-56-1

methanol

furfural
98-01-1

furfural

2-furoic acid methyl ester
611-13-2

2-furoic acid methyl ester

Conditions
Conditions Yield
With oxygen; potassium carbonate; at 80 ℃; for 24h; chemoselective reaction;
With oxygen; at 60 ℃; for 48h; Time; Catalytic behavior;
D-glucose
50-99-7

D-glucose

2-methylfuran
534-22-5

2-methylfuran

furfural
98-01-1

furfural

2,5-dimethylfuran
625-86-5

2,5-dimethylfuran

5-Methylfurfural
620-02-0

5-Methylfurfural

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

carbon monoxide
201230-82-2

carbon monoxide

hydrogen
1333-74-0

hydrogen

Conditions
Conditions Yield
With 0.5%Co4%Fe/SiO2; In 1-Methylnaphthalene; at 350 ℃; for 1h; Reagent/catalyst;
Conditions
Conditions Yield
propene; With carbon dioxide; carbon monoxide; water; oxygen; molybdenum-bismuth type catalyst; molybdenum-vanadium type catalyst; under 1125.11 Torr;
With sodium hydroxide; In water; at 140 ℃; for 30h; under 24.7525 Torr;
2-amino-1-[2]furyl-2-phenyl-ethanol

2-amino-1-[2]furyl-2-phenyl-ethanol

furfural
98-01-1

furfural

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
Erhitzen auf Temperaturen oberhalb des Schmelzpunkts;
furfural
98-01-1

furfural

poly(methacrylic acid)
79-41-4,25087-26-7,50867-57-7

poly(methacrylic acid)

benzaldehyde
100-52-7

benzaldehyde

propionic acid
802294-64-0,79-09-4

propionic acid

acrylic acid
79-10-7

acrylic acid

Conditions
Conditions Yield
isobutene; With water; oxygen; Oxidation catalyst I (first oxidation catalyst) was prepared according to Example 1 of EP 0 267 556 A2; at 360 ℃; Gas phase;
Oxidation catalyst II (second oxidation catalyst) was prepared according to Example 1 ofEP 0 376 117 A1; at 300 ℃; Product distribution / selectivity; Gas phase;

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