Names | |
---|---|
Preferred IUPAC name (Furan-2-yl)methanol | |
Other names Furan-2-ylmethanol Furfuryl alcohol 2-Furanmethanol 2-Furancarbinol 2-(Hydroxymethyl)furan | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.388 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C5H6O2 | |
Molar mass | 98.10 g/mol |
Appearance | colorless liquid |
Odor | burning odor [2] |
Density | 1.128 g/cm3 |
Melting point | −29 °C (−20 °F; 244 K) |
Boiling point | 170 °C (338 °F; 443 K) |
miscible | |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 65 °C; 149 °F; 338 K [2] |
Explosive limits | 1.8% - 16.3% [2] |
Lethal dose or concentration (LD, LC): | |
LC50 (median concentration) | 397 ppm (mouse, 6 hr) 85 ppm (rat, 6 hr) 592 ppm (rat, 1 hr) [3] |
LCLo (lowest published) | 597 ppm (mouse, 6 hr) [3] |
NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 50 ppm (200 mg/m3) [2] |
REL (Recommended) | TWA 10 ppm (40 mg/m3) ST 15 ppm (60 mg/m3) [skin] [2] |
IDLH (Immediate danger) | 75 ppm [2] |
Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents. [4]
Furfuryl alcohol is manufactured industrially by hydrogenation of furfural, which is itself typically produced from waste bio-mass such as corncobs or sugar cane bagasse. As such furfuryl alcohol may be considered a green chemical. [5] One-pot systems have been investigated to produce furfuryl alcohol directly from xylose using solid acid catalysts. [6]
It undergoes many reactions including Diels–Alder additions to electrophilic alkenes and alkynes. Hydroxymethylation gives 1,5-bis(hydroxymethyl)furan. Hydrolysis gives levulinic acid. Upon treatment with acids, heat and/or catalysts, furfuryl alcohol can be made to polymerize into a resin, poly(furfuryl alcohol). Hydrogenation of furfuryl alcohol can proceed to give hydroxymethyl derivative of tetrahydrofuran and 1,5-pentanediol. The etherification reaction of furfuryl alcohol with alkyl or aryl halide (e.g. benzyl chloride) in the liquid-liquid-liquid triphase system with the help of a phase transfer catalyst also reported. [7] In the Achmatowicz reaction, also known as the Achmatowicz rearrangement, furfuryl alcohol is converted to a dihydropyran.
The primary use of furfuryl alcohol is as a monomer for the synthesis of furan resins. [4] [8] These polymers are used in thermoset polymer matrix composites, cements, adhesives, coatings and casting/foundry resins. Polymerization involves an acid-catalyzed polycondensation, usually giving a black cross-linked product. [9] A highly simplified representation is shown below.
Because of its low molecular weight, furfuryl alcohol can impregnate the cells of wood, where it can be polymerized and bonded with the wood by heat, radiation, and/or catalysts or additional reactants. The treated wood (e.g. "Kebony") has improved moisture-dimensional stability, hardness, and decay and insect resistance; catalysts can include zinc chloride, citric, and formic acid, as well as borates. [10] [11]
Furfuryl alcohol has been used in rocketry as a fuel which ignites hypergolically (immediately and energetically in contact) with white fuming nitric acid or red fuming nitric acid oxidizer. [12] The use of hypergolics avoids the need for an igniter. Mixtures of furfuryl alcohol and aniline in different proportions were used in American MGM-5 Corporal ballistic missile and WAC Corporal and Aerobee sounding rockets. [13] Mixture of 41% of furfuryl alcohol, 41% of xylidine and 18% of methanol, called Furaline, was used in France for experimental rocket engines for aircraft, developed by SEPR. [13]
In late 2012, Spectra, a concept liquid rocket engine using white fuming nitric acid as the oxidizer to furfuryl alcohol fuel was static tested by Copenhagen Suborbitals. [14] [15]
The median lethal dose for furfuryl alcohol ranges from 160 to 400 mg/kg (mouse or rabbit, oral).[ citation needed ]
A hypergolic propellant is a rocket propellant combination used in a rocket engine, whose components spontaneously ignite when they come into contact with each other.
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.
Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula CH
3NO
2. It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent. As an intermediate in organic synthesis, it is used widely in the manufacture of pesticides, explosives, fibers, and coatings. Nitromethane is used as a fuel additive in various motorsports and hobbies, e.g. Top Fuel drag racing and miniature internal combustion engines in radio control, control line and free flight model aircraft.
Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It 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. Furfural is only derived from dried biomass. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest organic chemicals available readily purified from natural precursors.
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.
Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.
Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.
Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.
Tetraethyl orthosilicate, formally named tetraethoxysilane (TEOS), ethyl silicate is the organic chemical compound with the formula Si(OC2H5)4. TEOS is a colorless liquid. It degrades in water. TEOS is the ethyl ester of orthosilicic acid, Si(OH)4. It is the most prevalent alkoxide of silicon.
The Achmatowicz reaction, also known as the Achmatowicz rearrangement, is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by the Polish chemist 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 sulfuric acid. Additional reaction steps, alcohol protection with methyl orthoformate and boron trifluoride) and then ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.
2,5-Furandicarboxylic acid (FDCA) is an organic chemical compound consisting of two carboxylic acid groups attached to a central furan ring. It was first reported as dehydromucic acid by Rudolph Fittig and Heinzelmann in 1876, who produced it via the action of concentrated hydrobromic acid upon mucic acid. It can be produced from certain carbohydrates and as such is a renewable resource, it was identified by the US Department of Energy as one of 12 priority chemicals for establishing the “green” chemistry industry of the future. Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety.
A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle.
2-Methyltetrahydrofuran (2-MeTHF) is an organic compound with the molecular formula C5H10O. It is a highly flammable, mobile liquid. It is mainly used as a replacement for Tetrahydrofuran (THF) in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations (as, unlike THF, it is not miscible with water). It is derived from sugars via furfural and is occasionally touted as a biofuel.
Methoxymethylfurfural is an organic compound derived from dehydration of sugars and subsequent etherification with methanol. This colorless liquid is soluble in a wide range of solvents including lower alcohols. The molecule is a derivative of furan, containing both aldehyde and ether (methoxymethyl) functional groups. MMF has been detected in the leaves and roots of Chilean Jaborosa magellanica (Solanaceae). It has a typical odor suggestive of maraschino cherries. MMF can be made from a wide range of carbohydrate containing feedstocks including sugar, starch and cellulose using a chemical catalytic process and is a potential "carbon-neutral" feedstock for fuels and chemicals.
2-Furoic acid is an organic compound, consisting of a furan ring and a carboxylic acid side-group. Along with other furans, its name is derived from the Latin word furfur, meaning bran, from which these compounds were first produced. The salts and esters of furoic acids are known as furoates. 2-Furoic acid is most widely encountered in food products as a preservative and a flavouring agent, where it imparts a sweet, earthy flavour.
Dionisios G. Vlachos is an American chemical engineer, the Allan & Myra Ferguson Endowed Chair Professor of Chemical Engineering at the University of Delaware and director of the Catalysis Center for Energy Innovation, a U.S. Department of Energy - Energy Frontiers Research Center. Throughout his career at University of Delaware and the University of Minnesota, he has advanced the study of catalysts and reaction engineering including catalytic applications in biomass utilization, alkane conversion and zeolites. He is a fellow of the American Association for the Advancement of Science and recipient of the Wilhelm Award of the American Institute of Chemical Engineers (2011).
Itaconic anhydride is the cyclic anhydride of itaconic acid and is obtained by the pyrolysis of citric acid. It is a colourless, crystalline solid, which dissolves in many polar organic solvents and hydrolyzes forming itaconic acid. Itaconic anhydride and its derivative itaconic acid have been promoted as biobased "platform chemicals" and bio- building blocks.) These expectations, however, have not been fulfilled.
Furan resin refers to polymers produced from various furan compounds, of which the most common starting materials are furfuryl alcohol and furfural. In the resin and in the cured polyfurfurol, the furan rings are not connected by conjugation. The resins are generally used as binders for sand castings. The furan monomer is typically converted to a free-flowing resin with mild acid catalysis. Curing is achieved using strong acid.
Tetrahydrofurfuryl alcohol (THFA) is an organic compound with the formula HOCH2C4H7O. In terms of its structure, it consists of a tetrahydrofuran ring substituted in the 2-position with a hydroxymethyl group. It is a colorless liquid that is used as a specialty solvent and synthetic intermediate, e.g. to 3,4-dihydropyran. It is prepared by hydrogenation of furfural. It is a precursor to 1,5-pentanediol.