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CAS NO: 98-01-1
EC NO: 202-627-7

Furfuraldehyde is an organic compound with the formula C4H3OCHO. 
Furfuraldehyde is a colorless liquid, although commercial samples are often brown. 
Furfuraldehyde has an aldehyde group attached to the 2-position of furan.
Furfuraldehyde 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 furfural comes from the Latin word furfur, meaning bran, referring to its usual source.
 Furfuraldehyde 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 it is one of the oldest renewable chemicals.
Furfuraldehyde is also found in many processed foods and beverages.

Furfuraldehyde was first isolated in 1821 (published in 1832) by the German chemist Johann Wolfgang Döbereiner, who produced a small sample as a byproduct of formic acid synthesis.
In 1840, the Scottish chemist John Stenhouse found that the same chemical could be produced by distilling a wide variety of crop materials, including corn, oats, bran, and sawdust, with aqueous sulfuric acid; he also determined furfural's empirical formula (C5H4O2).
George Fownes named this oil "furfurol" in 1845 (from furfur (bran), and oleum (oil)).
In 1848, the French chemist Auguste Cahours determined that furfural was an aldehyde.
Determining the structure of furfural required some time: the furfural molecule contains a cyclic ether (furan), which tends to break open when it's treated with harsh reagents. 
In 1870, German chemist Adolf von Baeyer speculated (correctly) about the structure of the chemically similar compounds furan and 2-furoic acid.
By 1886, furfurol was being called "furfural" (short for "furfuraldehyde") and the correct chemical structure for furfural was being proposed.
By 1887, the German chemist Willy Marckwald had inferred that some derivatives of furfural contained a furan nucleus.In 1901, the German chemist Carl Harries determined furan's structure by synthesizing it from succindialdehyde, thereby also confirming furfural's proposed structure.

Furfuraldehyde remained relatively obscure until 1922,  when the Quaker Oats Company began mass-producing it from oat hulls.
Today, furfural is still produced from agricultural byproducts like sugarcane bagasse and corn cobs. 
The main countries producing furfural today are the Dominican Republic, South Africa and China.

Furfuraldehyde dissolves readily in most polar organic solvents, but it is only slightly soluble in either water or alkanes.

Furfuraldehyde participates in the same kinds of reactions as other aldehydes and other aromatic compounds. 
Furfuraldehyde 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, furfural irreversibly polymerizes, acting as a thermosetting polymer.

Furfuraldehyde may be obtained by the acid catalyzed dehydration of 5-carbon sugars (pentoses), particularly xylose.

C5H10O5 → C5H4O2 + 3 H2O
These sugars 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 furfural, depending on the type of feedstock. Furfuraldehyde and water evaporate together from the reaction mixture, and separate upon condensation. 
The global production capacity is about 800,000 tons as of 2012. 
China is the biggest supplier of furfural, and accounts for the greater part of global capacity. 
The other two major commercial producers are Illovo Sugar in the Republic of South Africa and Central Romana in the Dominican Republic 

In the laboratory, furfural 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 furfural 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 furfural.
This residue 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.

Uses and occurrence
Furfuraldehyde is found in many foods: coffee (55–255 mg/kg) and whole grain bread (26 mg/kg).

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

Hydrogenation of furfural 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 furfuryl alcohol 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 furfural manufactures industrially furan.

Another important solvent made from furfural is methyltetrahydrofuran. 
Furfuraldehyde is used to make other furan derivatives, such as furoic acid, via oxidation, and furan itself via palladium catalyzed vapor phase decarbonylation.

Furfuraldehyde is also a specialized chemical solvent.

There is a good market for value added chemicals that can be obtained from furfural.

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

Chemical Properties    
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.

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.

Reported found in several essential oils from plants of the Pinaceae family, in the essential oil from Cajenne linaloe, in the oil from leaves of Trifolium pratense and Trifolium incarnatum, in the distillation waters of several essential oils, such as ambrettee and angelica seeds, in Ceylon cinnamon essential oil, in petitgrain oil, ylang-ylang, lavender, lemongrass, calamus, eucalyptus, neroli, sandalwood, tobacco leaves and others Also reported found in many foods including apple, apricot, citrus peel oils and juices, berries, guava, grapes, pineapple, asparagus, kohlrabi, celery, onion, leek, potato, tomato, cinnamon, mustard, bread, cheeses, meats, fsh, cognac, rum, whiskies, cider, grape wine, cocoa, coffee, tea, barley, peanuts, popcorn, pecans, oats, honey, soybeans, passion fruit, plums, mushroom, mango, tamarind, fruit brandies, whiskey malt, white bread, rum, bourbon, cardamom, coriander seed, calamus, corn oil, malt, wort and other sources

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). 
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 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.

furfural: 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.

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.

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, it darkens and gradually decomposes.
Furfuraldehyde 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.

furfural (C4H3O-CHO), also called 2-furaldehyde, best known member of the furan family and the source of the other technically important furans. 
Furfuraldehyde is a colourless liquid (boiling point 161.7 °C; specific gravity 1.1598) subject to darkening on exposure to air. 
Furfuraldehyde dissolves in water to the extent of 8.3 percent at 20 °C and is completely miscible with alcohol and ether.

A span of about 100 years marked the period from discovery of furfural in the laboratory to the first commercial production in 1922. 
The subsequent industrial development provides an excellent example of the industrial utilization of agricultural residues. 
Corncobs, oat hulls, cottonseed hulls, rice hulls, and bagasse are the major raw material sources, the annual replenishment of which ensures a continuing supply. 
In the manufacturing process, lots of the raw material and dilute sulfuric acid are steamed under pressure in large rotary digesters. The furfural formed is removed continuously with steam, and concentrated by distillation; the distillate, on condensation, separates into two layers. 
The bottom layer, comprising wet furfural, is dried by vacuum distillation to obtain furfural of minimum 99 percent purity.

Furfuraldehyde 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. 
Furfuraldehyde 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 furfural is an important source. Condensation with phenol provides furfural-phenolic resins for a variety of uses.

When vapours of furfural and hydrogen are passed over a copper catalyst at elevated temperature, furfuryl alcohol is formed. 
This important derivative is used in the plastics industry for the production of corrosion-resistant cements and cast-molded items. 
The similar hydrogenation of furfuryl alcohol over a nickel catalyst gives tetrahydrofurfuryl alcohol, from which are derived various esters and dihydropyran.

In its reactions as an aldehyde, furfural bears a strong resemblance to benzaldehyde. 
Thus, it undergoes the Cannizzaro reaction in strong aqueous alkali; it dimerizes to furoin, C4H3OCO-CHOH-C4H3O, under the influence of potassium cyanide; it is converted to hydrofuramide, (C4H3O-CH)3N2, by the action of ammonia. 
However, furfural differs markedly from benzaldehyde in a number of ways, of which autoxidation will serve as an example. 
On exposure to air at room temperature, furfural is degraded and cleaved to formic acid and formylacrylic acid. 
Furoic acid is a white crystalline solid useful as a bactericide and preservative. 
Its esters are fragrant liquids used as ingredients in perfumes and flavourings.

Furfuraldehyde appears as 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.
Colourless to yellow oily liquid which browns on storage, pungent, sweet, bread-like, caramellic, cinnamon-almond-like flavour, odour resembles benzaldehyde
Furfuraldehyde is an aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group. 
Furfuraldehyde has a role as a Maillard reaction product and a metabolite. 
Furfuraldehyde is a member of furans and an aldehyde. 
Furfuraldehyde derives from a furan.
Furfuraldehyde is a natural product found in Vitis rotundifolia, Campsis grandiflora, and other organisms with data available.

Furfuraldehyde is used in solvent extraction in petroleum refinin, used as a solvent for rubber cements, resins, and dyes, also used as a flavoring agent and chemical intermediate
Furfuraldehyde is used to make furan-based chemicals; Decomposes into furan above 250 deg C.
Polymerizes into furan-based resins in the presence of strong acid, One of the aldehydes in smoke, e.g., soldering, and present in many foods.
Generally recognized as safe as a food flavor.
Was used in high concentrations as a herbicide and fungicide

Industry Uses of Furfuraldehyde:
- Abrasives
- Intermediates
- Solvents (which become part of product formulation or mixture)

General Manufacturing Information of Furfuraldehyde:    
Industry Processing Sectors
- All other basic organic chemical manufacturing
- Nonmetallic mineral product manufacturing (includes clay, glass, cement, concrete, lime, gypsum, and other nonmetallic mineral product manufacturing.
- Plastic material and resin manufacturing

About Furfuraldehyde
Helpful information
Furfuraldehyde is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.

Furfuraldehyde is used in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Furfuraldehyde is most likely to be released to the environment.

Article service life
Release to the environment of Furfuraldehyde can occur from industrial use: industrial abrasion processing with low release rate (e.g. cutting of textile, cutting, machining or grinding of metal).
Furfuraldehyde can be found in products with material based on: stone, plaster, cement, glass or ceramic.
Widespread uses by professional workers
Furfuraldehyde is used in the following products: fertilisers and coating products.
Furfuraldehyde is used in the following areas: agriculture, forestry and fishing.
Other release to the environment of Furfuraldehyde is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use as reactive substance.
Formulation or re-packing
Furfuraldehyde is used in the following products: polymers. 
Release to the environment of Furfuraldehyde can occur from industrial use: formulation of mixtures.

Uses at industrial sites
Furfuraldehyde is used in the following products: polymers and extraction agents.
Furfuraldehyde has an industrial use resulting in manufacture of another substance (use of intermediates).
Furfuraldehyde is used in the following areas: scientific research and development and health services.
Furfuraldehyde is used for the manufacture of: chemicals and metals.
Release to the environment of Furfuraldehyde can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, for thermoplastic manufacture and as processing aid.
Release to the environment of Furfuraldehyde can occur from industrial use: manufacturing of the substance.

2-formyl furan

2-Furancarboxaldehyde (furfural)
2-Furylaldehyde xypropane
Cyclic aldehyde
furancarboxaldehyde (furfural)
furfural (2-furancarboxaldehyde)
Pyromucic aldehyde
FEMA 2489
Furfuraldehyde, synthesis grade
Furfuraldehyde,2-Furaldehyde, Furan-2-carboxaldehyde
AKOS BBS-00003199
Pyromucic aldehyde
Artificial ant oil
Artificial oil of ants
2-Formyl furan
Rcra waste number U125
NSC 8841
2-Furancarboxaldehyde, homopolymer
Bran oil
Furfuraldehyde (natural)
Ant Oil, artificial
Furfuraldehydee [Italian]
Caswell No. 466
2-Formylofuran [Polish]
2-Furankarbaldehyd [Czech]
2-Furil-metanale [Italian]
FEMA No. 2489
CCRIS 1044
HSDB 542
EINECS 202-627-7
RCRA waste no. U125
EPA Pesticide Chemical Code 043301
BRN 0105755
Qo furfural
Ant Oil
Furfuraldehyde ACS grade
furan-2 carbaldehyde
Furfuraldehyde, 99%
2-Furaldehyde, 8CI
2-Furylaldehyde xypropane
EC 202-627-7
5-17-09-00292 (Beilstein Handbook Reference)
Furfuraldehyde, ACS reagent, 99%
Furfuraldehyde, >=98%, FCC, FG
Furfuraldehyde, for synthesis, 98.0%
Furfuraldehyde, analytical reference material
Furfuraldehyde 100 microg/mL in Acetonitrile
Furfuraldehyde, natural, >=98%, FCC, FG
Furfuraldehyde, SAJ first grade, >=99.0%


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