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 its usual source. A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... Corn redirects here. ... Binomial name Avena sativa Carolus Linnaeus (1753) The Oat (Avena sativa) is a species of cereal grain, and the seeds of this plant. ... Species T. aestivum T. boeoticum T. compactum T. dicoccoides T. dicoccon T. durum T. monococcum T. spelta T. sphaerococcum References:   ITIS 42236 2002-09-22 For the indie rock group see: Wheat (band). ... wheat bran Bran is the hard outer layer of cereal grains, and consists of combined aleurone and pericarp. ... Sawdust is composed of fine particles of wood. ... Latin is an ancient Indo-European language originally spoken in Latium, the region immediately surrounding Rome. ...

Furfural is an aromatic aldehyde, with the ring structure shown at right. Its chemical formula is C₅H₄O₂. In its pure state, it is a colorless oily liquid with the odor of almonds, but upon exposure to air it quickly becomes yellow. In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... An aldehyde. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... Binomial name Prunus dulcis (Mill. ...

History

Furfural was first isolated in 1832 by the German chemist Johann Wolfgang Döbereiner, who formed a very small quantity of it as a byproduct of formic acid synthesis. At the time, formic acid was formed by the distillation of dead ants, and Döbereiner's ant bodies probably contained some plant matter. 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, and he determined that this chemical had an empirical formula of C₅H₄O₂. In 1901, the German chemist Carl Harries deduced furfural's structure. A chemist pours from a Florence flask. ... Johann Wolfgang Döbereiner Johann Wolfgang Döbereiner (December 13, 1780 – March 24, 1849) was a German chemist. ... Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. ... Laboratory distillation set-up using, without a fractionating column 1: Heat source 2: Still pot 3: Still head 4: Thermometer/Boiling point temperature 5: Condenser 6: Cooling water in 7: Cooling water out 8: Distillate/receiving flask 9: Vacuum/gas inlet 10: Still receiver 11: Heat control 12: Stirrer speed... Subfamilies Aenictinae Aenictogitoninae Aneuretinae Apomyrminae Cerapachyinae Dolichoderinae Dorylinae Ecitoninae Formicinae Leptanillinae Leptanilloidinae Myrmeciinae Myrmicinae Nothomyrmeciinae Ponerinae Proceratiinae Pseudomyrmecinae Ants are social insects that belong to the same order as the wasps and bees. ... Motto: (Latin for No one provokes me with impunity)1 Anthem: Multiple unofficial anthems Capital Edinburgh Largest city Glasgow Official language(s) English, Gaelic, Scots 2 Government Constitutional monarchy  - Queen Queen Elizabeth II  - Prime Minister of the UK Tony Blair MP  - First Minister Jack McConnell MSP Unification    - by Kenneth I... John Stenhouse (October 31, 1809 – December 31, 1880) was a Scottish chemist. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... In chemistry, the empirical formula of a chemical is a simple expression of the relative number of each type of atom (called a chemical element) in it. ... Carl Dietrich Harries ( 1866 - 1923 ) was a German Chemist. ...

Except for occasional use in perfume, furfural remained a relatively obscure chemical 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. Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, objects, and living spaces a pleasant smell. ... The official logo for Quaker Oats. ... This article or section does not cite its references or sources. ... Look up corn in Wiktionary, the free dictionary. ...

Properties

Furfural's physical properties are summarized in the table at right. Furfural dissolves readily in most polar organic solvents, but is only slightly soluble in either water or alkanes. Organic chemistry is a specific discipline within the subject of chemistry. ... Water is a chemical substance that is essential to all known forms of life. ... An alkane is an acyclic saturated hydrocarbon. ...

Chemically, furfural participates in the same kinds of reactions as other aldehydes and other aromatic compounds. The aromatic stability of furfural is not as great as in benzene, and furfural participates in hydrogenation and other addition reactions more readily than many other aromatics. Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... Hydrogenation is a chemical reaction in which unsaturated bonds between carbon atoms are reduced by attachment of a hydrogen atom to each carbon. ... An addition reaction, in chemistry, is in its simplest terms a organic reaction where two or more molecules combine to form a larger one. ...

When heated above 250 °C, furfural decomposes into furan and carbon monoxide, sometimes explosively. Furan, also known as furane and furfuran, is an aromatic heterocyclic organic compound, produced when wood, especially pine-wood, is distilled. ... Carbon monoxide, with the chemical formula CO, is a colourless, odourless and tasteless gas. ...

When heated in the presence of acids, furfural irreversibly solidifies into a hard thermosetting resin. Resin of a pine Insect trapped in resin. ...

Production

Many plant materials contain the polysaccharide hemicellulose, a polymer of sugars containing five carbon atoms each. When heated with sulfuric acid, hemicellulose undergoes hydrolysis to yield these sugars, principally xylose. Under the same conditions of heat and acid, xylose and other five carbon sugars undergo dehydration, losing three water molecules to become furfural: Polysaccharides (sometimes called glycans) are relatively complex carbohydrates. ... A hemicellulose can be any of several heteropolymers (matrix polysaccharides) present in almost all cell walls along with cellulose. ... Polymer is a term used to describe large molecules consisting of repeating structural units, or monomers, connected by covalent chemical bonds. ... Magnification of typical sugar showing monoclinic hemihedral crystalline structure. ... Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ... Xylose or wood sugar is an aldopentose — a monosaccharide containing five carbon atoms and including an aldehyde functional group. ...

C₅H₁₀O₅ → C₅H₄O₂ + 3 H₂O Xylose or wood sugar is an aldopentose — a monosaccharide containing five carbon atoms and including an aldehyde functional group. ... Water is a chemical substance that is essential to all known forms of life. ...

For crop residue feedstocks, about 10% of the mass of the original plant matter can be recovered as furfural. Furfural and water evaporate together from the reaction mixture, and separate upon condensation.

Global total capacity of production is about 450,000 ton. China is the biggest supplier of this product and they have about a half of global capacity.

In the laboratory, synthesis of furfural from corn cobs takes place by reflux with concentrated sulfuric acid ^[1]. Diagram of typical reflux apparatus. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ...

Uses

Furfural is used as a solvent in petrochemical refining to extract dienes (which are used to make synthetic rubber) from other hydrocarbons. For other uses, see Solvent (disambiguation). ... Petrochemicals are chemical products made from raw materials of petroleum (hydrocarbon) origin. ... Refining is the process of purification of a substance, usually used of a natural resource that is almost in a usable form, but which is more useful in its pure form. ... Dienes are hydrocarbons which contain two double bonds. ... Latex being collected from a tapped rubber tree Rubber is an elastic hydrocarbon polymer which occurs as a milky colloidal suspension (known as latex) in the sap of several varieties of plants. ... Hydrocarbons are refined at oil refineries and processed at chemical plants A hydrocarbon is a chemical compound that consists only of the elements carbon (C) and hydrogen (H). ...

Furfural, as well as its derivative furfuryl alcohol, can be used either by themselves or in together with phenol, acetone, or urea to make solid resins. Such resins are used in making fiberglass, some aircraft components, and automotive brakes. Furfuryl alcohol, also called furanmethanol or furancarbinol, is an organic compound containing a furan substitited with a hydroxymethyl group. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Urea is an organic compound of carbon, nitrogen, oxygen and hydrogen, with the formula CON2H4 or (NH2)2CO. Urea is also known as carbamide, especially in the recommended International Non-proprietary Names (rINN) in use in Europe. ... Bundle of fiberglass Fiberglass or glassfibre is material made from extremely fine fibers of glass. ... An Airbus A380, currently the worlds largest airliner An aircraft is any vehicle or craft capable of atmospheric flight. ... A brake is a device for slowing or stopping the motion of a machine or vehicle, and to keep it from starting to move again. ...

Furfural is also used as a chemical intermediate in the production of the solvents furan and tetrahydrofuran. Hydroxymethylfurfural has been identified in a wide variety of heat processed foods. Furan, also known as furane and furfuran, is an aromatic heterocyclic organic compound, produced when wood, especially pine-wood, is distilled. ... For other uses of THF, see THF (disambiguation) Tetrahydrofuran is a heterocyclic organic compound. ... Hydroxymethylfurfural, HMF or 5-(Hydroxymethyl)furfural is an aldehyde and a furan compound formed during the thermal decomposition of sugars and carbohydrates. ...

Safety

When ingested or inhaled, furfural can cause symptoms similar to those of intoxication, including euphoria, headache, dizziness, nausea, and eventual unconsciousness and death due to respiratory failure. Contact with furfural irritates the skin and respiratory tract and can cause the lungs to fill with fluid. ... It has been suggested that this article or section be merged with Epidermis (skin). ... In humans the respiratory tract is the part of the anatomy that has to do with the process of respiration or breathing. ...

Chronic skin exposure can lead to a skin allergy to the substance, as well as an unusual susceptibility to sunburn. In toxicity studies, furfural has led to tumors, mutations, and liver and kidney damage in animals. An allergy can refer to several kinds of immune reactions including Type I hypersensitivity in which a persons body is hypersensitised and develops IgE type antibodies to typical proteins. ... Tumor (American English) or tumour (British English) originally means swelling, and is sometimes still used with that meaning. ... In biology, mutations are changes to the genetic material (either DNA or RNA). ... The liver is an organ in some animals, including mammals (and therefore humans), birds, and reptiles. ... The kidneys are bean-shaped excretory organs in vertebrates. ...

References

1. ^ Organic Syntheses, Coll. Vol. 1, p.280 (1941); Vol. 1, p.49 (1921) Article

Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...

External links

• Links to external chemical sources.