CAS Number: 98-01-1
EC Number: 202-627-7
Molecular Formula: C4H3OCHO
Molar Mass: 96.09 g/mol
FURFURAL is an organic compound with the formula C4H3OCHO.
FURFURAL is a colorless liquid, although commercial samples are often brown.
FURFURAL has an aldehyde group attached to the 2-position of furan.
FURFURAL 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 FURFURAL usual source.
FURFURAL is only derived from lignocellulosic biomass, i.e., FURFURAL origin is non-food or non-coal/oil based.
FURFURAL is also found in many processed foods and beverages.
FURFURAL, also known as 2-Furaldehyde is based on waste corn cob used in the synthesis of pharmaceutical, industrial and agricultural chemicals.
The chemical compound furfural is an industrial chemical derived from a variety of agricultural byproducts, including corncobs, oat and wheat bran, and sawdust.
The name furfural comes from the Latin word furfur, meaning bran, referring to FURFURAL usual source.
FURFURAL, or furan-2-carbaldehyde, is an oily liquid formed when sugars from lignocellulosic biomasses such as corncobs, sawdust, and oat hulls dehydrate.
This is a natural process that is the basis of the commercial production of furfural.
In the first half of the 19th century, chemists such as Johann W. Döbereiner at the University of Jena (Germany) and John Stenhouse at Glasgow University discovered furfural in the distillation products of various biomaterials.
FURFURAL did not become an industrial product until Quaker Oats (Chicago) began to produce FURFURAL on a large scale from oat hulls.
FURFURAL, one of the earliest sustainable chemical feedstocks, is used to synthesize a wide range of industrial chemicals, including solvents, resins, plastics, and furan derivatives.
As the hazard information table shows, FURFURAL must be handled with an abundance of caution.
FURFURAL is one of several five-carbon oxygenated hydrocarbons that make up the aroma of canned pumpkin you might use to make your Thanksgiving pumpkin pie.
Oddly, this odor differs significantly from that of the six-carbon compounds, such as former Molecule of the Week cis-3-hexen-1-ol, that emanates from freshly cut pumpkins.
Recently, furfural, “the sleeping beauty bio-renewable chemical” has gained a renewed attention as a potential chemical for the production of biofuels and biochemicals.
FURFURAL is the most commonly produced industrial chemical because FURFURAL production is very flexible.
FURFURAL is one of the top value-added chemicals that can be produced from biomass.
FURFURAL and its derivatives have been extensively used in plastics, pharmaceutical and agrochemical industries.
FURFURAL is a natural precursor to a range of furan-based chemicals and solvents such as dihydropyran, methyltetrahydrofuran, tetrahydrofuran, methylfuranfurfuryl alcohol, tetrahydrofurfuryl alcohol and furoic acid.
FURFURAL and its derivatives have been widely applied as fungicides and nematicides, transportation fuels, gasoline additives, lubricants, resins, decolorizing agents, jet fuel blend stocks, drugs, insecticides, bio-plastics, flavor enhancers for food and drinks, rapid all-weather repair system for bomb-damaged runways and pot holes and also for wood modification and book preservation.
FURFURAL is a naturally occurring furan aldehyde with many commercial uses, e.g., industrial manufacturing, food flavoring, fragrance in personal care products, pesticide.
FURFURAL is not expected to be persistent in the environment.
FURFURAL is rapidly absorbed and eliminated after inhalation, dermal, and oral exposures.
FURFURAL has higher dermal toxicity than by oral and inhalation routes.
FURFURAL is a skin, mucous membrane, and respiratory irritant.
The main toxicity targets are respiratory system, nervous system, liver, and kidneys.
FURFURAL is not classifiable regarding FURFURAL carcinogenicity to humans.
FURFURAL is moderately toxic to aquatic species.
FURFURAL is an organic compound obtained during the dehydration of sugars.
FURFURALs IUPAC name is furan-2-carbaldehyde.
The word, furfural comes from the Latin word furfur that stands for bran, FURFURAL usual source.
Sugars present in a variety of agricultural byproducts such as corn cobs, oats, wheat bran, and sawdust are used to produce furfural.
FURFURAL is commonly used in many processed foods and beverages.
FURFURAL is a colourless liquid that darkens on exposure to air.
FURFURAL is the best-known member of the furan family.
FURFURAL meaning is furfuraldehyde or also called 2-furaldehyde.
FURFURAL is also an important source of other furans.
The boiling point of furfuraldehyde is 161.70C.
The chemical formula for furfuraldehyde or furfural aldehyde is C4H3O-CHO.
In 1922, Quaker Oats company started producing furfural from oat hulls for commercial use much after FURFURAL discovery by a German scientist Johann Wolfgang in 1821.
The industrial development of the production of furfural is a great example of how industries utilize agricultural residues.
The major raw material source of furfural such as corncobs, oat hulls, cottonseed hulls, rice hulls, and bagasse are replenished annually ensuring a constant supply of raw material for the production of furfural.
In large rotary digesters, lots of raw material and dilute sulphuric acid are steamed under pressure.
The furfural form is continuously removed with steam and then concentrated with the help of distillation.
The furfural obtained by distillation separates into two layers of condensation and the wet furfural at the bottom is dried with the help of vaccum distillation to obtain furfural with a minimum of 99% purity.
Given below is the dehydration reaction of pentoses under an acid catalyst.
C5H10O5 → C5H10O2 + 3H2O
The furfural price remains stable in the market and is readily available at FURFURAL sigma Aldrich.
Global demands of furfural remain high with China as FURFURAL leading production capacity of 85% and consumption of 75%.
Properties of FURFURAL has a molecular weight of 96.08 g/mol.
FURFURAL is denser than water and water-soluble.
FURFURALs vapours are heavier than air.
FURFURAL has a distinct caramel taste and smells somewhat like benzaldehyde.
FURFURAL has a boiling point of 161.70C.
FURFURAL is considered a major platform chemical that is used in the production of various other chemicals.
FURFURAL strongly resembles benzaldehyde in FURFURAL reactions as an aldehyde.
In the presence of strong aqueous alkali, FURFURAL undergoes a Cannizaro reaction.
FURFURAL dimerizes furoin under the influence of potassium cyanide and by the action of ammonia is converted into hydro furamide (C4H3O-CH)3N2.
On exposure to air at room temperature, furfural degrades into formic acid and formerly acrylic acid.
Furoic or furfural acid is a crystalline solid, white in colour, and is used as a bactericide and a preservative.
FURFURALs esters are fragrant liquids commonly used in perfumes and flavourings.
FURFURAL is an arenecarbaldehyde that is slightly soluble in water and is used as a food flavouring agent.
FURFURAL is also used as a fragrance agent for in-home products or similar industrial products.
FURFURAL is an organic compound obtained upon dehydration of sugars, which is highly soluble in water and organic solvents.
FURFURAL is used as an additive agent in the food industry and also in the production of various fuels and chemicals.
FURFURAL is absent in fresh food but is naturally generated upon heating of sugar-containing food items.
FURFURAL is one of the furan derivatives from hemicellulose present in lignocellulosic.
FURFURAL is naturally obtained upon dehydration of xylose, which is a pentose sugar.
This heterocyclic and aromatic aldehyde consists of an aldehyde side group and a furan ring.
FURFURAL is a colourless liquid and has an oily appearance with an almond-like odour.
FURFURAL has various industrial purposes being a platform chemical that is used in the production of various other chemical compounds.
FURFURAL is also used in the production of furan compounds.
FURFURAL is a heterocyclic aldehyde.
FURFURAL can be produced from agricultural raw materials containing pentosans and lignocellulosic feedstock.
FURFURAL is also obtained from xylose, via dehydration.
Furan has various interesting properties, such as FURFURAL thermosets easily, has physical strength and exhibits resistance to corrosion.
FURFURAL is a raw material for the production of various furan-based chemicals and solvents such as:
Applications of FURFURAL Include:
Selective solvent in refining lubricating oils to produce high-quality motor oil with improved temperature-viscosity properties.
Decolourizing agent to refine crude wood rosin.
Purification of C4 and C5 hydrocarbons for manufacturing synthetic rubber.
Reactive solvent and excellent wetting agent in manufacturing abrasive wheels, brake linings and refractory products for the steel industry.
Chemical feedstock for furfuryl alcohol and other derivatives.
FURFURAL undergoes hydrogenation in the vapor-phase over copper-containing catalysts to form furfuryl alcohol as the predominant product.
FURFURAL may also be used to prepare gel precursors for phenol-furfural aerogels.
FURFURAL has been employed as a standard for the HPLC quantification of furfural in the autohydrolysate liquor obtained from microwave-irradiated maize bran.
FURFURAL may be used in the preparation of γ-valerolactone (GVL) and biofuel 2-methylfuran (51% yield).
Uses of FURFURAL:
Now that we know what the structure of furfural looks like and how FURFURAL's produced, let's talk about a couple of the more important applications FURFURAL can be utilized for.
If we take furfural and convert the aldehyde to an alcohol in what's called a reduction reaction, we get furfuryl alcohol (abbreviated FA).
FA is used in the manufacture of things like cement, adhesives, castings, and coatings.
Uses and Occurrence of FURFURAL:
FURFURAL is found in many foods: coffee (55–255 mg/kg) and whole grain bread (26 mg/kg).
FURFURAL is an important renewable, non-petroleum based, chemical feedstock.
FURFURAL 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.
FURFURAL is used to make other furan derivatives, such as furoic acid, via oxidation, and furan itself via palladium catalyzed vapor phase decarbonylation.
FURFURAL is also a specialized chemical solvent.
There is a good market for value added chemicals that can be obtained from furfural.
Function and Uses of FURFURAL:
Large quantities of FURFURAL are used in solvent extraction in the petroleum refining industry.
FURFURAL is also used as a solvent (for nitrated cotton, cellulose acetate and gums), to accelerate vulcanization, as an ingredient of phenolic resins (Durite), as an intermediate in the synthesis of furan derivatives, as a weed killer, as a fungicide and as a flavouring agent.
FURFURAL has been identified in 150 foods, including fruits, vegetables, beverages, bread and bread products.
The highest reported concentrations were found in wheat bread (0.8–14 ppm) [mg/kg], cognac (0.6–33 ppm), rum (22 ppm), malt whisky (10–37 ppm), port wine (2–34 ppm) and coffee (55–255 ppm).
The concentrations of FURFURAL in juices were 0.01–4.93 ppm.
FURFURAL is an ingredient contained in many fragrances and flavours.
FURFURAL may be found in fragrances used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries, in flavours of oral care products as well as in non-cosmetic products such as household cleaners and detergents.
FURFURAL in the in the fragrance compound is reported to be 0.036% or less.
FURFURAL in Practice:
FURFURAL has an aromatic odour reminiscent of almonds.
This biomass-based chemical is a hetero-aromatic aldehyde with exceptional physical properties.
Production of FURFURAL:
FURFURAL 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.
FURFURAL 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.
We mentioned previously that furfural was a renewable chemical feedstock.
The reason this is the case actually stems from how FURFURAL's made.
FURFURAL can be produced on large industrial scales by taking plant mass and treating FURFURAL with an acid.
When this happens, the 5-carbon sugar molecules undergo a dehydration (loss of water) reaction to give furfural.
Depending on the type of plant matter that's used, anywhere between 3% and 10% of the original plant mass can be recovered as furfural.
Obviously, plants are constantly growing and being produced, that's why furfural is considered a 'green' or renewable source of chemical feedstocks.
FURFURAL could potentially represent an important source of organic compounds once petroleum resources start to dry up.
History of FURFURAL:
FURFURAL 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 FURFURAL'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 FURFURAL from succindialdehyde, thereby also confirming furfural's proposed structure.
FURFURAL remained relatively obscure until 1922, when the Quaker Oats Company began mass-producing FURFURAL 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.
Structure of FURFURAL:
Let's get started by looking at the structure of furfural.
FURFURAL is an aldehyde of furan and is a yellow oily liquid in pure form, but tends to turn brown upon prolonged exposure to air and moisture.
An aldehyde is an organic functional group that has a carbonyl group (carbon-oxygen double bond) attached to a hydrogen and some other carbon-based side chain.
Furan is an aromatic five-membered ring that has an oxygen atom embedded within the ring system.
Notice that the aldehyde portion of the molecule is bonded to the carbon that's directly adjacent to the oxygen of the furan ring.
Due to the polar nature of FURFURAL, FURFURAL will dissolve quite readily and form solutions with a variety of polar organic solvents like methanol, ethanol, chloroform, and dimethyl sulfoxide (DMSO).
FURFURAL will not, however, dissolve in water and particularly non-polar solvents like hexane.
Properties of FURFURAL:
FURFURAL dissolves readily in most polar organic solvents, but FURFURAL is only slightly soluble in either water or alkanes.
FURFURAL participates in the same kinds of reactions as other aldehydes and other aromatic compounds.
FURFURAL exhibits less aromatic character than benzene, as can be seen from the fact that furfural is readily hydrogenated to tetrahydrofurfuryl alcohol.
When FURFURAL is heated in the presence of acids, furfural irreversibly polymerizes, acting as a thermosetting polymer.
Safety of FURFURAL:
FURFURAL is carcinogenic in lab animals and mutagenic in single cell organisms, but there is no data on human subjects.
FURFURAL is classified in IARC Group 3 due to the lack of data on humans and too few tests on animals to satisfy Group 2A/2B criteria.
FURFURAL is hepatotoxic.
The median lethal dose is high 650–900 mg/kg (oral, dogs), consistent with FURFURAL pervasiveness in foods.
The Occupational Safety and Health Administration has set a permissible exposure limit for furfural at 5 ppm over an eight-hour time-weighted average (TWA), and also designates furfural as a risk for skin absorption.
Reactions and Hazards of FURFURAL:
Air & Water Reactions:
FURFURAL is sensitive to light and air.
Soluble in water, with mixing.
Special Hazards of Combustion Products:
Irritating vapors are generated when heated.
Vapor may irritate eyes and respiratory system.
Liquid irritates skin and may cause dermatitis.
FURFURAL 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.
FURFURAL forms condensation products with many types of compounds, including phenol, amines and urea.
Identifiers of FURFURAL:
CAS Number: 98-01-1
ECHA InfoCard: 100.002.389
PubChem CID: 7362
CompTox Dashboard (EPA): DTXSID1020647
Chemical Name: FURFURAL
Synonyms: 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; NSC 8841; Pyromucic aldehyde; α-Furole
CAS Number: 98-01-1
Molecular Formula: C₅H₄O₂
Appearance: Light Yellow to Very Dark Brown Oil
Molecular Weight: 96.08
Storage: 4°C, Hygroscopic
Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
Typical Properties of FURFURAL:
Chemical formula: C5H4O2
Molar mass: 96.085 g·mol−1
Appearance: Colorless oil
Density: 1.1601 g/mL (20 °C)
Melting point: −37 °C (−35 °F; 236 K)
Boiling point: 162 °C (324 °F; 435 K)
Solubility in water: 83 g/L
Vapor pressure: 2 mmHg (20 °C)
Magnetic susceptibility (χ): −47.1×10−6 cm3/mol
Molecular Weight: 96.08
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 1
Exact Mass: 96.021129366
Monoisotopic Mass: 96.021129366
Topological Polar Surface Area: 30.2 Å²
Heavy Atom Count: 7
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Melting point: mp -36.5°
Boiling point: bp760 161.8°; bp100 103°; bp20 67.8°; bp1.0 18.5°
Flash point: Flash pt, closed cup, 140°F (60°C); open cup, 155°F (68°C)
Index of refraction: nD20 1.5261
Density: d425 1.1563
Toxicity data: LD50 orally in rats: 127 mg/kg (Jenner)
Specifications of FURFURAL:
CAS number: 98-01-1
EC index number: 605-010-00-4
EC number: 202-627-7
Hill Formula: C₅H₄O₂
Molar Mass: 96.09 g/mol
HS Code: 2932 12 00
Quality Level: 100
Vapor density: 3.31 (vs air)
Vapor pressure: 13.5 mmHg ( 55 °C)
Autoignition temp.: 599 °F
Expl. lim.: 19.3 %
Refractive index: n20/D 1.525 (lit.)
bp: 162 °C (lit.)
mp: −36 °C (lit.)
Density: 1.16 g/mL at 25 °C (lit.)
SMILES string: [H]C(=O)c1ccco1
InChI key: HYBBIBNJHNGZAN-UHFFFAOYSA-N
Names of FURFURAL:
Preferred IUPAC name of FURFURAL:
Other names of FURFURAL:
FURFURAL, furan-2-carboxaldehyde, fural, furfuraldehyde, 2-furaldehyde, pyromucic aldehyde
Synonyms of FURFURAL:
Artificial ant oil
Artificial ant oil
Artificial oil of ants
Rcra waste number U125
Ant Oil, artificial
Caswell No. 466
FEMA No. 2489
RCRA waste no. U125
EPA Pesticide Chemical Code 043301
FURFURAL ACS grade
WLN: T5OJ BVH
5-17-09-00292 (Beilstein Handbook Reference)
FURFURAL, ACS reagent, 99%
FURFURAL, >=98%, FCC, FG
FURFURAL, for synthesis, 98.0%
Furaldehydes [UN1199] [Poison]
FURFURAL, analytical reference material
FURFURAL 100 microg/mL in Acetonitrile
FURFURAL, natural, >=98%, FCC, FG
FURFURAL, SAJ first grade, >=99.0%
UNII-N4G9GAT76C component HYBBIBNJHNGZAN-UHFFFAOYSA-N
furfural (furfuraldehyde) redist
furfural-refined flavor grade
2-Furaldehyd [German] [ACD/IUPAC Name]
2-Furaldehyde [ACD/IUPAC Name]
2-Furaldéhyde [French] [ACD/IUPAC Name]
2-Furancarboxaldehyde [ACD/Index Name]
Aceton [German] [ACD/IUPAC Name]
T5OJ BVH [WLN]
FURFURAL-d4 (Stabilized with BHT)