2-FORMYLFURAN

2-Formylfuran is a heterocyclic aldehyde. 
2-Formylfuran can be produced from agricultural raw materials containing pentosans and lignocellulosic feedstock.

CAS Number: 98-01-1
EC Number: 202-627-7
IUPAC Name: Furan-2-carbaldehyde
Chemical Formula: C5H4O2

Other names: FURFURAL, 2-Furaldehyde, furan-2-carbaldehyde, 98-01-1, 2-Furancarboxaldehyde, Furaldehyde, Furfuraldehyde, Fural, 2-Formylfuran, 2-Furanaldehyde, 2-Furancarbonal, Furancarbonal, Furfurole, 2-Furfural, Furfurylaldehyde, 2-Furfuraldehyde, Pyromucic aldehyde, Furale, Furole, Furol, 2-Furylaldehyde, 2-Furylcarboxaldehyde, 2-Furyl-methanal, Furfurale, Furyl-methanal, 2-Furylmethanal, 2-Furil-metanale, Furan-2-carboxaldehyde, 2-furancarbaldehyde, Quakeral, Fufural, alpha-Furole, 2-Formylofuran, 2-Formyl furan, 2-Furankarbaldehyd, Nci-C56177, alpha-Furfuraldehyde, Furfural (natural), Rcra waste number U125, Furaldehydes, Caswell No. 466, FEMA No. 2489, furan-2-aldehyde, NSC 8841, CCRIS 1044, HSDB 542, CHEBI:34768, UNII-DJ1HGI319P, .alpha.-Furole, EINECS 202-627-7, DJ1HGI319P, MFCD00003229, EPA Pesticide Chemical Code 043301, BRN 0105755, 2-furancarboxyaldehyde, DTXSID1020647, AI3-04466, NSC-8841, DTXCID50647, EC 202-627-7, 5-17-09-00292 (Beilstein Handbook Reference), NCGC00091328-01, FURFURAL (IARC), FURFURAL [IARC], Furfurale [Italian], 2-Formylofuran [Polish], 2-Furankarbaldehyd [Czech], CAS-98-01-1, 2-Furil-metanale [Italian], RCRA waste no. U125, Hydrojasmal, Furfuralu, a-furfuraldehyde, Qo furfural, a-Furole, alpha-furaldehyde, 2-furanal, Furfural ACS grade, furan-2 carbaldehyde, FURFURALDEHYDES, Furfural, 99%, 2-Furaldehyde, 8CI, 2-furan-carboxaldehyde, 2-Furanocarboxyaldehyde, FURFURAL [FHFI], FURFURAL [HSDB], FURFURAL [FCC], FURFURAL [MI], 2-Furylaldehyde xypropane, U1199, WLN: T5OJ BVH, BIDD:ER0698, FURAL/PYROMUCIC ALDEHYDE, Furfural, ACS reagent, 99%, CHEMBL189362, QSPL 006, QSPL 102, FEMA 2489, Furan-2-carbaldehyde (Furfural), NSC8841, Furfural, >=98%, FCC, FG, Furfural, for synthesis, 98.0%, STR00358, Tox21_111114, Tox21_202191, Tox21_300170, BDBM50486229, Furaldehydes [UN1199] [Poison], STL283124, AKOS000118907, Furfural, analytical reference material, Furfural 100 microg/mL in Acetonitrile, USEPA/OPP Pesticide Code: 043301, Furfural, natural, >=98%, FCC, FG, Furfural, SAJ first grade, >=99.0%, NCGC00091328-02, NCGC00091328-03, NCGC00091328-04, NCGC00253954-01, NCGC00259740-01, 1ST21046, BP-31002, DB-003668, CS-0015696, F0073, NS00003316, EN300-18110, ASCORBIC ACID IMPURITY A [EP IMPURITY], A845786, Q412429, doi:10.14272/HYBBIBNJHNGZAN-UHFFFAOYSA-N.1, F1294-0048, InChI=1/C5H4O2/c6-4-5-2-1-3-7-5/h1-4, furfural; furfuraldehyde; furfurol; 2-furaldehyde; 2-furancarboxaldehyde; furan-2-carboxaldehyde

2-Formylfuran is also obtained from xylose, via dehydration. 
2-Formylfuran has various interesting properties, such as it thermosets easily, has physical strength and exhibits resistance to corrosion. 

2-Formylfuran appears as colorless or reddish-brown mobile liquids with a penetrating odor. 
Flash point is 140°F. 

Denser than water and soluble in water. 
Vapors heavier than air. 

2-Formylfuran may be toxic by ingestion, skin absorption or inhalation.
2-Formylfuran is an aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group. 

2-Formylfuran has a role as a Maillard reaction product and a metabolite. 
2-Formylfuran is a member of furans and an aldehyde. 

2-Formylfuran derives from a furan.
2-Formylfuran is a natural product found in Vitis rotundifolia, Campsis grandiflora, and other organisms.

2-Formylfuran is an organic compound with the formula C4H3OCHO. 
2-Formylfuran is a colorless liquid, although commercial samples are often brown. 

2-Formylfuran has an aldehyde group attached to the 2-position of furan. 
2-Formylfuran is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. 

The name 2-Formylfuran comes from the Latin word furfur, meaning bran, referring to its usual source. 
2-Formylfuran is only derived from lignocellulosic biomass, i.e., its origin is non-food or non-coal/oil based. 

Aside from ethanol, acetic acid and sugar 2-Formylfuran is one of the oldest renewable chemicals.
2-Formylfuran is also found in many processed foods and beverages.

2-Formylfuran dissolves readily in most polar organic solvents, but it is only slightly soluble in either water or alkanes.
2-Formylfuran participates in the same kinds of reactions as other aldehydes and other aromatic compounds. 

2-Formylfuran exhibits less aromatic character than benzene, as can be seen from the fact that furfural is readily hydrogenated to tetrahydrofurfuryl alcohol. 
When heated in the presence of acids, 2-Formylfuran irreversibly polymerizes, acting as a thermosetting polymer.

2-Formylfuran may be obtained by the acid catalyzed dehydration of 5-carbon sugars (pentoses), particularly xylose.
2-Formylfurans may be obtained from pentosans obtained from hemicellulose present in lignocellulosic biomass.

Between 3% and 10% of the mass of crop residue feedstocks can be recovered as 2-Formylfuran, depending on the type of feedstock. 
In the laboratory, 2-Formylfuran can be synthesized from plant material by heating with sulfuric acid or other acids.

With the purpose to avoid toxic effluents, an effort to substitute sulfuric acid with easily separable and reusable solid acid catalysts has been studied around the world.
The formation and extraction of xylose and subsequently 2-Formylfuran can be favored over the extraction of other sugars with varied conditions, such as acid concentration, temperature, and time.

In industrial production, some lignocellulosic residue remains after the removal of the 2-Formylfuran.
2-Formylfuran is dried and burned to provide steam for the operation of the furfural plant. 

Newer and more energy efficient plants have excess residue, which is or can be used for co-generation of electricity, cattle feed, activated carbon, mulch/fertiliser, etc.
2-Formylfuran is found in many foods: coffee (55–255 mg/kg) and whole grain bread (26 mg/kg).

2-Formylfuran is an important renewable, non-petroleum based, chemical feedstock. 
2-Formylfuran can be converted into a variety of solvents, polymers, fuels and other useful chemicals by a range of catalytic reduction.

Hydrogenation of 2-Formylfuran provides furfuryl alcohol (FA), which is used to produce Furan resins, which are exploited in thermoset polymer matrix composites, cements, adhesives, casting resins and coatings.
Further hydrogenation of 2-Formylfuran leads to tetrahydrofurfuryl alcohol (THFA), which is used as a solvent in agricultural formulations and as an adjuvant to help herbicides penetrate the leaf structure.

In another application as a feedstock, palladium-catalyzed decarbonylation on 2-Formylfuran manufactures industrially furan.
Another important solvent made from 2-Formylfuran is methyltetrahydrofuran. 

2-Formylfuran is used to make other furan derivatives, such as furoic acid, via oxidation, and furan itself via palladium catalyzed vapor phase decarbonylation.
2-Formylfuran is also a specialized chemical solvent.

There is a good market for value added chemicals that can be obtained from 2-Formylfuran.
2-Formylfuran is used in the manufacture of furfural-phenol plastics such as Durite; in solvent refining of petroleum oils and in the preparation of pyromucic acid. 

2-Formylfuran is used as a solvent for nitrated cotton, cellulose acetate and gums; for accelerating vulcanization; in the synthesis of furan derivatives.
2-Furancarboxaldehyde, also known as 2-Formylfuran or a-furole, belongs to the class of organic compounds known as aryl-aldehydes. 

2-Formylfurans are compounds containing an aldehyde group directly attached to an aromatic ring. 
Based on a literature review a significant number of articles have been published on 2-Formylfuran.

2-Formylfuran best known member of the furan family and the source of the other technically important furans. 
2-Formylfuran is a colourless liquid (boiling point 161.7 °C; specific gravity 1.1598) subject to darkening on exposure to air. 

2-Formylfuran dissolves in water to the extent of 8.3 percent at 20 °C and is completely miscible with alcohol and ether.
2-Formylfuran is used as a selective solvent for refining lubricating oils and rosin, and to improve the characteristics of diesel fuel and catalytic cracker recycle stocks. 

2-Formylfuran is employed extensively in the manufacture of resin-bonded abrasive wheels and for the purification of butadiene needed for the production of synthetic rubber. 
The manufacture of nylon requires hexamethylenediamine, of which 2-Formylfuran is an important source. 

Condensation with 2-Formylfuran provides furfural-phenolic resins for a variety of uses.
2-Formylfuran is an organic compound produced from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. 

The name 2-Formylfuran comes from the Latin word furfur, meaning bran, referring to its usual source.
Aside from ethanol, acetic acid and sugar 2-Formylfuran is one of the oldest renewable chemicals.

2-Formylfuran 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, 2-Formylfuran is an organic compound belonging to an aldehyde of furan with the odor of almonds. 

2-Formylfuran 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. 

2-Formylfuran 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.

2-Formylfuran is a colourless to amber-like oily liquid with an almond-like odour. 
On exposure to light and air, 2-Formylfuran turns reddish brown. 

2-Formylfuran is used in making chemicals, as a solvent in petroleum refining, a fungicide. 
2-Formylfuran is incompatible with strong acids, oxidisers, and strong alkalis.
 
2-Formylfuran undergoes polymerisation on contact with strong acids or strong alkalis. 
2-Formylfuran is produced commercially by the acid hydrolysis of pentosan polysaccharides from non-food residues of food crops and wood wastes. 

2-Formylfuran 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.

2-Formylfuran is a colorless to yellow aromatic het erocyclic aldehyde with an almond-like odor. 
Turns amber on exposure to light and air.

2-Formylfuran has a characteristic penetrating odor typical of cyclic aldehydes. 
2-Formylfuran 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.

2-Formylfuran is produced through hydrolysis of pentosan in agricultural byproducts (e.g., crop wastes). 
2-Formylfuran 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.
2-Formylfuran is the aldehydederivative of furan and occurs invarious essential oils and in fuseloil. 

2-Formylfuran is used as a solvent for extractingmineral oils and natural resinsand itself forms resins with somearomatic compounds.
2-Formylfuran 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: the production of furans and tetrahydrofurans where the compound is an intermediate; the solvent refining of petroleum and rosin products; the solvent binding of bonded phenolic products; and the extractive distillation of butadiene from other C4 hydrocarbons.
2-Formylfuran reacts with sodium hydrogen carbonate. 
2-Formylfuran also can react with strong oxidizers.

An exothermic resinification of almost explosive violence can occur upon contact with strong mineral acids or alkalis. 
2-Formylfuran is a yellowish liquidwith an aromatic odor, soluble in water and inalcohol, but not in petroleum hydrocarbons. 

2-Formylfuran darkens and gradually decomposes.2-Formylfuran 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. 
2-Formylfuran 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. 

2-Formylfuran is also used for the making of butadiene,adiponitrile, and other chemicals.
Various derivatives of 2-Formylfuran are not used,and these, known collectively as furans, are nowmade synthetically from formaldehyde andacetylene, which react to form butyl nedole.
2-Formylfuran is used for lube oil refining and butadiene extraction; as a solvent for wood resin, nitrated cotton, cellulose acetate, and gums; in the produc tion of phenolic plastics, thermosetting resins, refined petroleum oils, dyes, and varnishes; in the manufacture of pyromucic acid, vulcanized rubber, insecticides, fungicides, herbicides, germicides, furan derivatives, polymers, and other organic chemicals.

APPLICATION:
2-Formylfuran undergoes hydrogenation in the vapor-phase over copper-containing catalysts to form furfuryl alcohol as the predominant product. 
2-Formylfuran may also be used to prepare gel precursors for phenol-furfural aerogels.

2-Formylfuran has been employed as a standard for the HPLC quantification of furfural in the autohydrolysate liquor obtained from microwave-irradiated maize bran. 
2-Formylfuran may be used in the preparation of γ-valerolactone (GVL) and biofuel 2-methylfuran (51% yield).