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Furfuraldehyde is a colourless to amber-like oily liquid with an almond-like odour.
On exposure to light and air, Furfuraldehyde turns reddish brown. Furfural is used in making chemicals, as a solvent in petroleum refining, a fungicide, and a weed killer.
Furfuraldehyde is incompatible with strong acids, oxidisers, and strong alkalis.
CAS: 98-01-1
MF: C5H4O2
MW: 96.08
EINECS: 202-627-7
Synonyms
2-formylofuran;2-Furanaldehyde;2-Furancarbonal;2-Furancarboxaldehyde (furfural);2-Furankarbaldehyd;2-Furfural;2-Furfuraldehyde;2-Furil-metanale;Sodium Ascorbate Impurity A (EP/BP); 2-Furancarboxaldehyde; 2-Furaldehyde; 2-Formylfuran; 2-Furanaldehyde; 2-Furancarbaldehyde; 2-Furancarbonal; 2-Furfural; 2-Furfuraldehyde; 2-Furylaldehyde; 2-Furylcarboxaldehyde;Artificial ant oil; Fural; Furaldehyde; Furan-2-carboxaldehyde; Furancarbonal; Furfuraldehyde; Furfurol; Furfurole; Furfurylaldehyde; Furole; Pyromucic aldehyde; Furfural (As per USP Commenting Opening 50(5))
Furfuraldehyde undergoes polymerisation on contact with strong acids or strong alkalis.
Furfuraldehyde is produced commercially by the acid hydrolysis of pentosan polysaccharides from non-food residues of food crops and wood wastes.
Furfuraldehyde 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.
A colourless liquid,C5H4O2, b.p. 162°C, which darkenson standing in air.
Furfuraldehyde is the aldehydederivative of furan and occurs invarious essential oils and in fuseloil.
Furfuraldehyde is used as a solvent for extractingmineral oils and natural resinsand itself forms resins with somearomatic compounds.
Colorless or reddish-brown mobile liquids with a penetrating odor.
Flash points 140°F.
Denser than water and soluble in water.
Vapors heavier than air.
May be toxic by ingestion, skin absorption or inhalation.
Furfuraldehyde, with the CAS number 98-01-1, is an organic compound classified as an aldehyde and is derived from agricultural byproducts, particularly from the hydrolysis of pentosans found in plant materials.
Furfuraldehyde is a colorless to yellow liquid with a characteristic almond-like odor.
Furfuraldehyde is soluble in water, alcohol, and ether, making it versatile for various applications.
Furfuraldehyde's molecular formula is C5H4O2, and it has a boiling point around 161°C.
Furfuraldehyde is primarily used as a solvent and as an intermediate in the production of various chemicals, including furan, tetrahydrofuran, and other furan derivatives.
Additionally, Furfuraldehyde serves as a precursor for the synthesis of resins and plastics.
Due to its reactivity, Furfuraldehyde can participate in various chemical reactions, including condensation and polymerization.
Furfuraldehyde is also recognized for its potential as a renewable resource in the production of biofuels and biochemicals, contributing to sustainable chemistry practices.
However, safety precautions are necessary, as it can be harmful if inhaled or ingested.
Furfuraldehyde Chemical Properties
Melting point: -36 °C (lit.)
Boiling point: 162 °C (lit.)
Density: 1.16 g/mL at 25 °C (lit.)
Vapor density: 3.31 (vs air)
Vapor pressure: 13.5 mm Hg ( 55 °C)
Refractive index: n20/D 1.527
FEMA: 2489 | FURFURAL
Fp: 137 °F
Storage temp.: Store below +30°C.
Solubility: 95% ethanol: soluble1ML/mL, clear
Form: Liquid
Color: very deep brown
Odor: at 1.00 % in dipropylene glycol. sweet woody almond fragrant baked bread
PH: >=3.0 (50g/l, 25℃)
Explosive limit: 2.1-19.3%(V)
Biological source: synthetic
Odor Type: bready
Water Solubility: 8.3 g/100 mL
FreezingPoint: -36.5℃
Sensitive: Air Sensitive
Merck: 14,4304
JECFA Number: 450
BRN: 105755
Henry's Law Constant: 1.52(x 10-6 atm?m3/mol) at 20 °C (approximate - calculated from water solubility and vapor pressure)
Exposure limits NIOSH REL: IDLH 100 ppm; OSHA PEL: TWA 5 ppm (20 mg/m3); ACGIH TLV: TWA 2 ppm (adopted).
Dielectric constant: 41.9（20℃）
Stability: Stable. Substances to be avoided include strong bases, strong oxidizing agents and strong acids. Flammable.
LogP: 0.41
Surface tension: 43.61mN/m at 293.15K
Surface tension: 41.9mN/m at 20°C
CAS DataBase Reference: 98-01-1(CAS DataBase Reference)
NIST Chemistry Reference: 2-Furancarboxaldehyde(98-01-1)
IARC: 3 (Vol. 63) 1995
EPA Substance Registry System: Furfuraldehyde (98-01-1)
Furfuraldehyde is a colorless to yellow aromatic het erocyclic aldehyde with an almond-like odor.
Turns amber on exposure to light and air.
Furfuraldehyde has a characteristic penetrating odor typical of cyclic aldehydes.
Furfuraldehyde is prepared industrially from pentosans that are contained in cereal straws and brans; these materials are previously digested with diluted H2S04, and the formed furfural steam is distilled.
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.
Shaw et al. (1970) reported a taste threshold in water of 80 ppm.
Reactions
Aside from a darkening in color, Furfuraldehyde is relatively stable thermally and does not exhibit changes in physical properties after prolonged heating up to 230°C.
The reactions of Furfuraldehyde are typical of those of the aromatic aldehydes, although some complex side reactions occur because of the reactive ring.
Furfuraldehyde yields acetals, condenses with active methylene compounds, reacts with Grignard reagents, and provides a bisulfite complex.
Upon reduction, furfural yields Furfuraldehyde alcohol; upon oxidation, it yields furoic acid.
Furfuraldehyde can be decarbonylated to furan.
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, Furfuraldehyde is produced through hydrolysis of pentosan in agricultural byproducts (e.g., crop wastes).
Furfuraldehyde 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 Furfuraldehyde-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.
Preparation
Industrially prepared from pentosans that are contained in cereal straws and brans; these materials are previously digested with diluted H2SO4, and the formed furfural steam is distilled.
Production Methods
Furfuraldehyde is obtained commercially by treating pentosan-rich agricultural residues (corncobs, oat hulls, cottonseed hulls, bagasse, rice hulls) with a dilute acid and removing the furfural by steam distillation.
Major industrial uses of furfuraldehyde include:
(1) the production of furans and tetrahydrofurans where the compound is an intermediate;
(2) the solvent refining of petroleum and rosin products;
(3) the solvent binding of bonded phenolic products; and
(4) the extractive distillation of butadiene from other C4 hydrocarbons.
When pentoses, e.g., arabinose, xylose, are heated with dilute HCl, furfuraldehyde is formed, recognizable by deep red coloration with phloroglucinol, or by the formation, with phenylhydrazine, of furfuraldehyde phenylhydrazone C4H3O·CH : NNHC6H5, solid, mp 97 °C.
Reactivity Profile
Furfuraldehyde reacts with sodium hydrogen carbonate. Furfural also can react with strong oxidizers.
An exothermic resinification of almost explosive violence can occur upon contact with strong mineral acids or alkalis.
Furfuraldehyde forms condensation products with many types of compounds, including phenol, amines and urea.
Industrial uses
Also known as furfuraldehyde, furol, and pyromuclealdehyde,furfural is a yellowish liquidwith an aromatic odor, soluble in water and inalcohol, but not in petroleum hydrocarbons. Onexposure, Furfuraldehyde darkens and gradually decomposes.Furfural occurs in different forms in variousplant life and is obtained from complex carbohydratesknown as pentosans, which occur insuch agricultural wastes as cornstalks, corncobs,straw, oat husks, peanut shells, bagasse,and rice.
Furfuraldehyde is used for making syntheticplastics, as a plasticizer in other synthetic resins,as a preservative in weed killers, and as aselective solvent especially for removing aromaticand sulfur compounds from lubricatingoils.
Furfuraldehyde is also used for the making of butadiene,adiponitrile, and other chemicals.
Various derivatives of furfural are not used,and these, known collectively as furans, are nowmade synthetically from formaldehyde andacetylene, which react to form butyl nedole.
Purification Methods
Furfuraldehyde is unstable to air, light and acids.
Impurities include formic acid, .-formylacrylic acid and furan-2-carboxylic acid.
Distil Furfuraldehyde in an oil bath from 7% (w/w) Na2CO3 (added to neutralise acids, especially pyromucic acid).
Redistil Furfuraldehyde from 2% (w/w) Na2CO3, and then, finally fractionally distil it under vacuum.
Furfuraldehyde is stored in the dark.
Impurities resulting from storage can be removed by passage through chromatographic grade alumina.
Furfuraldehyde can be separated from impurities other than carbonyl compounds by the bisulfite addition compound.
The aldehyde is steam volatile.
Furfuraldehyde has been purified by distillation (using a Claisen head) under reduced pressure.
Furfuraldehyde is essential as is the use of an oil bath with temperatures of no higher than 130o which is highly recommended.
When Furfuraldehyde is distilled at atmospheric pressure (in a stream of N2), or under reduced pressure with a free flame (caution: because the aldehyde is flammable), an almost colourless oil is obtained.
After a few days and sometimes a few hours, the oil gradually darkens and finally becomes black.
This change is accelerated by light and occurs more slowly when Furfuraldehyde is kept in a brown bottle.
However, when the aldehyde is distilled under vacuum and the bath temperature kept below 130o during the distillation, the oil develops only a slight colour when exposed to direct sunlight during several days.
The distillation of very impure material should NOT be attempted at atmospheric pressure; otherwise the product darkens very rapidly.
After one distillation under vacuum, a distillation at atmospheric pressure can be carried out without too much decomposition and darkening.
The liquid irritates mucous membranes.
Store Furfuraldehyde in dark containers under N2, preferably in sealed ampoules.
Toxicity evaluation
The limited data in animals are insufficient for deriving a plausible mechanism of toxicity.
Nevertheless, aldehyde functional group is intrinsically reactive and low molecular weight aldehydes such as formaldehyde are known to interact with biologically important macromolecules such as DNA, structural proteins, and enzymes.
This supposition is consistent with the toxic effects observed at multiple sites, i.e., respiratory system, nervous system, liver, and kidneys.
