Furan
Overview
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans.
Furan is a colorless, flammable, highly volatile
Volatility (chemistry)
In chemistry and physics, volatility is the tendency of a substance to vaporize. Volatility is directly related to a substance's vapor pressure. At a given temperature, a substance with higher vapor pressure vaporizes more readily than a substance with a lower vapor pressure.The term is primarily...
liquid with a boiling point
Boiling point
The boiling point of an element or a substance is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid....
close to room temperature. It is toxic and may be carcinogenic. Furan is used as a starting point to other specialty chemicals.
The name furan comes from the Latin furfur, which means bran
Bran
Bran is the hard outer layer of grain and consists of combined aleurone and pericarp. Along with germ, it is an integral part of whole grains, and is often produced as a by-product of milling in the production of refined grains. When bran is removed from grains, the grains lose a portion of their...
.
Unanswered Questions
Discussions
Encyclopedia
Furan is a heterocyclic
organic compound
, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans.
Furan is a colorless, flammable, highly volatile
liquid with a boiling point
close to room temperature. It is toxic and may be carcinogenic. Furan is used as a starting point to other specialty chemicals.
. The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele
in 1780. Another important derivative, furfural
, was reported by Johann Wolfgang Döbereiner
in 1831 and characterised nine years later by John Stenhouse
. Furan itself was first prepared by Heinrich Limpricht
in 1870, although he called it tetraphenol.
, or by the copper-catalyzed oxidation of 1,3-butadiene
:
In the laboratory, furan can be obtained from furfural
by oxidation to furan-2-carboxylic acid, followed by decarboxylation.. It can also be prepared directly by thermal decomposition
of pentose
-containing materials, cellulosic solids especially pine-wood.
is a classic way to synthesize furans, although many syntheses have been developed. One of the simplest synthesis methods for furans is the reaction of 1,4-diketone
s with phosphorus pentoxide
(P2O5) in the Paal-Knorr Synthesis
. The thiophene
formation reaction of 1,4-diketones with Lawesson's reagent
also forms furans as side products. 2,4-Disubstituted furans can be synthesized by sulfone
-mediated cyclization of 1,3-diketones
s of electron
s on the oxygen atom is delocalized
into the ring, creating a 4n+2 aromatic system (see Hückel's rule
) similar to benzene
. Because of the aromaticity, the molecule is flat and lacks discrete double bond
s. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization
is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system.
Due to its aromaticity, furan's behavior is quite dissimilar to that of the more typical heterocyclic ether
s such as tetrahydrofuran
.
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. The class of compounds containing such rings are also referred to as furans.
Furan is a colorless, flammable, highly volatile
Volatility (chemistry)
In chemistry and physics, volatility is the tendency of a substance to vaporize. Volatility is directly related to a substance's vapor pressure. At a given temperature, a substance with higher vapor pressure vaporizes more readily than a substance with a lower vapor pressure.The term is primarily...
liquid with a boiling point
Boiling point
The boiling point of an element or a substance is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid....
close to room temperature. It is toxic and may be carcinogenic. Furan is used as a starting point to other specialty chemicals.
History
The name furan comes from the Latin furfur, which means branBran
Bran is the hard outer layer of grain and consists of combined aleurone and pericarp. Along with germ, it is an integral part of whole grains, and is often produced as a by-product of milling in the production of refined grains. When bran is removed from grains, the grains lose a portion of their...
. The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele
Carl Wilhelm Scheele
Carl Wilhelm Scheele was a German-Swedish pharmaceutical chemist. Isaac Asimov called him "hard-luck Scheele" because he made a number of chemical discoveries before others who are generally given the credit...
in 1780. Another important derivative, furfural
Furfural
Furfural is an organic compound derived from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word , meaning bran, referring to its usual source....
, was reported by Johann Wolfgang Döbereiner
Johann Wolfgang Döbereiner
Johann Wolfgang Döbereiner was a German chemist who is best known for work that foreshadowed the periodic law for the chemical elements.- Life and work :...
in 1831 and characterised nine years later by John Stenhouse
John Stenhouse
John Stenhouse FRS FRSE FIC FCS was a Scottish chemist. In 1854, he invented one of the first practical respirators.He was a co-founder of the Chemical Society in 1841.-Life:...
. Furan itself was first prepared by Heinrich Limpricht
Heinrich Limpricht
Heinrich Limpricht was a German chemist. Limpricht was a pupil of Friedrich Wöhler; he worked on the chemistry of furans and pyrroles, discovering furan in 1870....
in 1870, although he called it tetraphenol.
Production
Industrially, furan is manufactured by the palladium-catalyzed decarbonylation of furfuralFurfural
Furfural is an organic compound derived from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word , meaning bran, referring to its usual source....
, or by the copper-catalyzed oxidation of 1,3-butadiene
1,3-Butadiene
1,3-Butadiene is a simple conjugated diene with the formula C4H6. It is an important industrial chemical used as a monomer in the production of synthetic rubber. When the word butadiene is used, most of the time it refers to 1,3-butadiene....
:
In the laboratory, furan can be obtained from furfural
Furfural
Furfural is an organic compound derived from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word , meaning bran, referring to its usual source....
by oxidation to furan-2-carboxylic acid, followed by decarboxylation.. It can also be prepared directly by thermal decomposition
Thermal decomposition
Thermal decomposition, or thermolysis, is a chemical decomposition caused by heat. The decomposition temperature of a substance is the temperature at which the substance chemically decomposes....
of pentose
Pentose
A pentose is a monosaccharide with five carbon atoms. Pentoses are organized into two groups. Aldopentoses have an aldehyde functional group at position 1...
-containing materials, cellulosic solids especially pine-wood.
Synthesis of furans
The Feist-Benary synthesisFeist-Benary synthesis
The Feist-Benary synthesis is an organic reaction between α-halogen ketones and β-dicarbonyl compounds to substituted furan compounds. This condensation reaction is catalyzed by amines such as ammonia and pyridine. The first step in the ring synthesis is related to the Knoevenagel condensation...
is a classic way to synthesize furans, although many syntheses have been developed. One of the simplest synthesis methods for furans is the reaction of 1,4-diketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
s with phosphorus pentoxide
Phosphorus pentoxide
Phosphorus pentoxide is a chemical compound with molecular formula P4O10 . This white crystalline solid is the anhydride of phosphoric acid. It is a powerful desiccant.-Structure:...
(P2O5) in the Paal-Knorr Synthesis
Paal-Knorr synthesis
The Paal–Knorr Synthesis in organic chemistry is a reaction that generates either furans, pyrroles, or thiophenes from 1,4-diketones. It is a synthetically valuable method for obtaining substituted furans and pyrroles, common structural components of many natural products...
. The thiophene
Thiophene
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a flat five-membered ring, it is aromatic as indicated by its extensive substitution reactions. Related to thiophene are benzothiophene and dibenzothiophene, containing the thiophene ring fused with one and two benzene...
formation reaction of 1,4-diketones with Lawesson's reagent
Lawesson's reagent
Lawesson's reagent, or LR, is a chemical compound used in organic synthesis as a thiation agent. Lawesson's reagent was first made popular by Sven-Olov Lawesson, who did not, however, invent it. Lawesson's reagent was first made in 1956 during a systematic study of the reactions of arenes with...
also forms furans as side products. 2,4-Disubstituted furans can be synthesized by sulfone
Sulfone
A sulfone is a chemical compound containing a sulfonyl functional group attached to two carbon atoms. The central hexavalent sulfur atom is double bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.-IUPAC name and...
-mediated cyclization of 1,3-diketones
Chemistry
Furan is aromatic because one of the lone pairLone pair
In chemistry, a lone pair is a valence electron pair without bonding or sharing with other atoms. They are found in the outermost electron shell of an atom, so lone pairs are a subset of a molecule's valence electrons...
s of electron
Electron
The electron is a subatomic particle with a negative elementary electric charge. It has no known components or substructure; in other words, it is generally thought to be an elementary particle. An electron has a mass that is approximately 1/1836 that of the proton...
s on the oxygen atom is delocalized
Delocalized electron
In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or one covalent bond....
into the ring, creating a 4n+2 aromatic system (see Hückel's rule
Hückel's rule
In organic chemistry, Hückel's rule estimates whether a planar ring molecule will have aromatic properties. The quantum mechanical basis for its formulation was first worked out by physical chemist Erich Hückel in 1931...
) similar to benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
. Because of the aromaticity, the molecule is flat and lacks discrete double bond
Double bond
A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...
s. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization
Orbital hybridisation
In chemistry, hybridisation is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties. Hybridised orbitals are very useful in the explanation of the shape of molecular orbitals for molecules. It is an integral part...
is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system.
Due to its aromaticity, furan's behavior is quite dissimilar to that of the more typical heterocyclic ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...
s such as tetrahydrofuran
Tetrahydrofuran
Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...
.
- It is considerably more reactive than benzeneBenzeneBenzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
in electrophilic substitutionElectrophilic substitutionElectrophilic substitution reactions are chemical reactions in which an electrophile displaces a group in a compound, typically but not always hydrogen. Electrophilic aromatic substitution is characteristic of aromatic compounds and is an important way of introducing functional groups onto benzene...
reactions, due to the electron-donating effects of the oxygen heteroatom. Examination of the resonance contributors shows the increased electron density of the ring, leading to increased rates of electrophilic substitution.
- Furan serves as a dieneDieneIn organic chemistry a diene or diolefin is a hydrocarbon that contains two carbon double bonds.Conjugated dienes are functional groups, with a general formula of CnH2n-2. Dienes and alkynes are functional isomers...
in Diels-Alder reactionDiels-Alder reactionThe Diels–Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. The reaction can proceed even if some of the atoms in the newly formed ring are not carbon...
s with electron-deficient dienophiles such as ethyl (E)-3-nitroacrylate. The reaction product is a mixture of isomers with preference for the endo isomer:
- HydrogenationHydrogenationHydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
of furans affords sequentially dihydrofurans and tetrahydrofuranTetrahydrofuranTetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...
s. - In the Achmatowicz reactionAchmatowicz reactionThe Achmatowicz Reaction is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by Osman Achmatowicz Jr. in 1971 furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute...
, furans converted to dihydropyran compounds.
- Hydrogenation
See also
- Simple aromatic ringSimple aromatic ringSimple aromatic rings, also known as simple arenes or simple aromatics, are aromatic organic compounds that consist only of a conjugated planar ring system with delocalized pi electron clouds. Many simple aromatic rings have trivial names. They are usually found as substructures of more complex...
s - FuranoseFuranoseA furanose is a collective term for carbohydrates that have a chemical structure that includes a five-membered ring system consisting of four carbon atoms and one oxygen atom...
- bs4994BS4994BS4994 is the "specification for the design and construction of vessels and storage tanks in reinforced plastics"...
Furan resin as thermoset FRP for chemical process plant equipments - Furantetracarboxylic acidFurantetracarboxylic acidIn chemistry, furantetracarboxylic acid is an organic compound with formula , or 4, which can be viewed as deriving from furan through replacement of the four hydrogen atoms by carboxyl functional groups -OH....
- FuranoflavonoidFuranoflavonoidFuranoflavonoid are flavonoids possessing a furan group.An example of such compound is karanjin, a furanoflavonol....