Furfural

Base Information

• Chemical Name: Furfural
• CAS No.: 98-01-1
• Molecular Formula: C5H4O2
• Molecular Weight: 96.0856
• Hs Code.: 2932 12 00
• European Community (EC) Number: 202-627-7
• ICSC Number: 0276
• NSC Number: 8841
• UN Number: 1199
• UNII: DJ1HGI319P
• DSSTox Substance ID: DTXSID1020647
• Nikkaji Number: J3.981K
• Wikipedia: Furfural
• Wikidata: Q412429
• Metabolomics Workbench ID: 45777
• ChEMBL ID: CHEMBL189362
• Mol file: 98-01-1.mol

Synonyms:Furaldehyde;Furfural

Chemical Property of Furfural

Chemical Property:

• Appearance/Colour: colourless to reddish-brown oily liquid with almond odour
• Vapor Pressure: 13.5 mm Hg ( 55 °C)
• Melting Point: -36 °C(lit.)
• Refractive Index: n20/D 1.527
• Boiling Point: 161.799 °C at 760 mmHg
• Flash Point: 58.333 °C
• PSA: 30.21000
• Density: 1.145 g/cm³
• LogP: 1.09210
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 95% ethanol: soluble1ML/mL, clear
• Water Solubility.: 8.3 g/100 mL
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 96.021129366
• Heavy Atom Count: 7
• Complexity: 70.5
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

98.5%min ^*data from raw suppliers

Furfural ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 21-23/25-36/37-40-36/37/38
• Safety Statements: 26-36/37/39-45-1/2-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: C1=COC(=C1)C=O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the skin. The substance is irritating to the eyes and respiratory tract. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the liver. Tumours have been detected in experimental animals but may not be relevant to humans.
• Description: Furfural is an essential renewable, non-petroleum based, chemical feedstock which is primarily composed of various agricultural byproducts, including oat husks, wheat bran, corncobs, and sawdust. Chemically, furfural is an organic compound belonging to an aldehyde of furan with the odor of almonds. It is typically produced for industrial purposes, which can be used as a selective solvent in the process of refining lubricating oils and used in the manufacture of transportation fuels to improve the characteristics of diesel fuel and catalytic cracker recycle stocks. Besides, furfural is applied widely for producing resin-bonded abrasive wheels and purifying butadiene needed for the manufacture of synthetic rubber. It is also used to make other furan chemicals, such as furoic acid and furan itself. Other products of furfural include weed killer, fungicide, other solvents and etc. Furfural is a colourless to amber-like oily liquid with an almond-like odour. On exposure to light and air, it turns reddish brown. Furfural is used in making chemicals, as a solvent in petroleum refining, a fungicide, and a weed killer. It is incompatible with strong acids, oxidisers, and strong alkalis. It undergoes polymerisation on contact with strong acids or strong alkalis. Furfural is produced commercially by the acid hydrolysis of pentosan polysaccharides from non-food residues of food crops and wood wastes. It is used widely as a solvent in petroleum refining, in the production of phenolic resins, and in a variety of other applications. Human exposure to furfural occurs during its production and use, as a result of its natural occurrence in many foods and from the combustion of coal and wood.
• Physical properties: Colorless to yellow liquid with an almond-like odor. Turns reddish brown on exposure to light and air. Odor and taste thresholds are 0.4 and 4 ppm, respectively (quoted, Keith and Walters, 1992). Shaw et al. (1970) reported a taste threshold in water of 80 ppm.
• Uses: Solvent refining of lubricating oils, resins, and other organic materials; as insecticide, fungicide, germicide; an intermediate for tetrahydrofuran, furfural alcohol, phenolic and furan polymers Commercially, furfural is produced through hydrolysis of pentosan in agricultural byproducts (e.g., crop wastes). It has a diverse applications which include as a solvent in various manufacturing industries (e.g., petroleum and automotive products), accelerant for vulcanization of rubber, raw material for manufacturing furan derivatives (e.g., tetrahydrofurfuryl alcohol) and synthetic resins, wetting agent, flavoring ingredient for foods (e.g., roasted coffee), fragrance in consumer and personal care products (e.g., fragrance cream, bath products, toiletries), and pesticides for controlling unwanted microorganisms, fungi, weeds, insects, and nematodes. The application methods for pesticidal use include drip irritation, spray boom, sprinkler, and low-pressure back-pack spray. In the manufacture of furfural-phenol plastics such as Durite; in solvent refining of petroleum oils; in the preparation of pyromucic acid. As a solvent for nitrated cotton, cellulose acetate, and gums; in the manufacture of varnishes; for accelerating vulcanization; as insecticide, fungicide, germicide; as reagent in analytical chemistry. In the synthesis of furan derivatives.

Technology Process of Furfural

There total 476 articles about Furfural which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) + cyanomethylene triphenylphosphorane (16640-68-9) → furfural (98-01-1) + 3-(furan-2-yl)propanenitrile (21446-61-7) + 2,2-[oxybis(methylene)]bis-furan (4437-22-3) + 3-(furan-2-yl)prop-2-enenitrile (7187-01-1)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; caesium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In toluene; at 150 ℃; for 72h;

DOI:10.1002/ejoc.200600070

Reference yield: 30.6%

methanol (67-56-1) + D-Fructose (57-48-7,18875-34-8) → furfural (98-01-1) + 5-(methoxymethyl)-2-furaldehyde (1917-64-2) + levulinic acid methyl ester (624-45-3)

Guidance literature:

methanol; D-Fructose; Amberlist 15; In water; at 60 ℃; for 3h;

ZSM-12; In methanol; water; at 180 ℃; for 12h; under 48754.9 Torr;

Reference yield: 18.4%

methanol (67-56-1) + D-Fructose (57-48-7,18875-34-8) + D-xylose (6763-34-4) → furfural (98-01-1) + 5-(methoxymethyl)-2-furaldehyde (1917-64-2)

Guidance literature:

aluminium(III) triflate; at 150 ℃; for 1h; under 9375.94 Torr; Product distribution / selectivity;

upstream raw materials:

furan

hydrogen cyanide

N,N-dimethyl-formamide

(2-furyl)methyl alcohol

Downstream raw materials:

(E)-2-(2-(furan-2-yl)vinyl)pyridine

S-benzyl-β-N-(furyl)methylenedithiocarbazate

3,5-diacetyl-4-[2]furyl-1-phenyl-1,4-dihydro-pyridine

(2,3-dimethoxy-phenethyl)-furfuryl-methyl-amine

Refernces

• 1、 Suzuki, Takeshi,Yokoi, Toshiyuki,Otomo, Ryoichi,Kondo, Junko N.,Tatsumi, Takashi. "Dehydration of xylose over sulfated tin oxide catalyst: Influences of the preparation conditions on the structural properties and catalytic performance". . p. 117 - 124. Retrieved 2011.
• 2、 Kiselewa et al.. "". . p. 1133;engl.Ausg.S.1073. Retrieved 1954.
• 3、 Guo, Xiaoqian,Guo, Feng,Li, Yishan,Zheng, Zhangqin,Xing, Zhexu,Zhu, Zihan,Liu, Ting,Zhang, Xin,Jin, Ying. "Dehydration of D-xylose into furfural over bimetallic salts of heteropolyacid in DMSO/H2O mixture". . p. 18 - 25. Retrieved 2018.
• 4、 Gómez Millán, Gerardo,Phiri, Josphat,M?kel?, Mikko,Maloney, Thad,Balu, Alina M.,Pineda, Antonio,Llorca, Jordi,Sixta, Herbert. "Furfural production in a biphasic system using a carbonaceous solid acid catalyst". . . Retrieved 2019.
• 5、 Agirrezabal-Telleria,Requies,Gueemez,Arias. "Furfural production from xylose + glucose feedings and simultaneous N 2-stripping". . p. 3132 - 3140. Retrieved 2012.
• 6、 Jiang,Verrier,Ahmar,Lai,Ma,Muller,Queneau,Pera-Titus,Jér?me,De Oliveira Vigier. "Unveiling the role of choline chloride in furfural synthesis from highly concentrated feeds of xylose". . p. 5104 - 5110. Retrieved 2018.
• 7、 Suggitt et al.. "-". . p. 373,376. Retrieved 1947.
• 8、 Wu, Changyan,Chen, Wei,Zhong, Linxin,Peng, Xinwen,Sun, Runcang,Fang, Junjie,Zheng, Shaobo. "Conversion of xylose into furfural using lignosulfonic acid as catalyst in ionic liquid". . p. 7430 - 7435. Retrieved 2014.
• 9、 Zhu, Yuanshuai,Li, Wenzhi,Lu, Yijuan,Zhang, Tingwei,Jameel, Hasan,Chang, Hou-Min,Ma, Longlong. "Production of furfural from xylose and corn stover catalyzed by a novel porous carbon solid acid in γ-valerolactone". . p. 29916 - 29924. Retrieved 2017.
• 10、 Laohapornchaiphan, Jutitorn,Smith, Christopher B.,Smith, Siwaporn Meejoo. "One-step Preparation of Carbon-based Solid Acid Catalyst from Water Hyacinth Leaves for Esterification of Oleic Acid and Dehydration of Xylose". . p. 3178 - 3186. Retrieved 2017.