Furfuryl alcohol
Overview
 
Furfuryl alcohol, also called 2-furylmethanol or 2-furancarbinol, is an 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...

 containing a furan
Furan
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....

 substituted with a hydroxymethyl
Hydroxymethyl
Hydroxymethyl in the field of chemistry, particularly in organic chemistry, is the name for a substituent with the structural formula -CH2-OH. The hydroxymethyl group consists of a methylene group connected to a hydroxy group. This makes the hydroxymethyl group an alcohol...

 group. It is a clear colorless liquid when pure, but becomes amber colored upon prolonged standing. It possesses a faint burning odor and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents. Upon treatment with acids, heat and/or catalysts
Catalysis
Catalysis is the change in rate of a chemical reaction due to the participation of a substance called a catalyst. Unlike other reagents that participate in the chemical reaction, a catalyst is not consumed by the reaction itself. A catalyst may participate in multiple chemical transformations....

, furfuryl alcohol can be made to polymerize
Polymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...

 into a resin, poly(furfuryl alcohol).

Furfuryl alcohol is manufactured industrially by the catalytic reduction of 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....

 which is obtained from corncob
Corncob
A corncob is the central core of a maize ear.The corn plant's ear is also considered a "cob" or "pole" but it is not fully a "pole" until the ear is shucked, or removed from the plant material around the ear...

 and sugar cane bagasse
Bagasse
Bagasse is the fibrous matter that remains after sugarcane or sorghum stalks are crushed to extract their juice. It is currently used as a biofuel and as a renewable resource in the manufacture of pulp and paper products and building materials....

.
Encyclopedia
Furfuryl alcohol, also called 2-furylmethanol or 2-furancarbinol, is an 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...

 containing a furan
Furan
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....

 substituted with a hydroxymethyl
Hydroxymethyl
Hydroxymethyl in the field of chemistry, particularly in organic chemistry, is the name for a substituent with the structural formula -CH2-OH. The hydroxymethyl group consists of a methylene group connected to a hydroxy group. This makes the hydroxymethyl group an alcohol...

 group. It is a clear colorless liquid when pure, but becomes amber colored upon prolonged standing. It possesses a faint burning odor and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents. Upon treatment with acids, heat and/or catalysts
Catalysis
Catalysis is the change in rate of a chemical reaction due to the participation of a substance called a catalyst. Unlike other reagents that participate in the chemical reaction, a catalyst is not consumed by the reaction itself. A catalyst may participate in multiple chemical transformations....

, furfuryl alcohol can be made to polymerize
Polymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...

 into a resin, poly(furfuryl alcohol).

Furfuryl alcohol is manufactured industrially by the catalytic reduction of 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....

 which is obtained from corncob
Corncob
A corncob is the central core of a maize ear.The corn plant's ear is also considered a "cob" or "pole" but it is not fully a "pole" until the ear is shucked, or removed from the plant material around the ear...

 and sugar cane bagasse
Bagasse
Bagasse is the fibrous matter that remains after sugarcane or sorghum stalks are crushed to extract their juice. It is currently used as a biofuel and as a renewable resource in the manufacture of pulp and paper products and building materials....

. It finds use as a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

, but is primarily used as an ingredient in the manufacture of various chemical products such as foundry resins
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

, adhesives
Adhesive
An adhesive, or glue, is a mixture in a liquid or semi-liquid state that adheres or bonds items together. Adhesives may come from either natural or synthetic sources. The types of materials that can be bonded are vast but they are especially useful for bonding thin materials...

, and wetting agents.

Furfuryl alcohol has been used in rocketry as a fuel which ignites hypergolically (immediately and energetically in contact) with white fuming nitric acid
White fuming nitric acid
White fuming nitric acid is a storable liquid oxidizer used with kerosene and hydrazine rocket fuel. It consists of nearly pure nitric acid . WFNA is commonly specified as containing no more than 2% water and less than 0.5% dissolved nitrogen dioxide or dinitrogen tetroxide.WFNA was sometimes...

 or red fuming nitric acid
Red fuming nitric acid
Red fuming nitric acid is a storable oxidizer used as a rocket propellant. It consists mainly of nitric acid , also containing 13% dinitrogen tetroxide and 3% water. The dissolved nitrogen dioxide is very concentrated and can be found at room temperature...

 oxidizer. The use of hypergolics avoids the need for an igniter.

Furfuryl alcohol is probably a BK channel
BK channel
BK channels , also called Maxi-K or slo1, are ion channels characterized by their large conductance of potassium ions through cell membranes. These channels are activated by changes in membrane electrical potential and/or by increases in concentration of intracellular calcium ion...

 agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...

.

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 has improved moisture-dimensional stability, hardness, and decay and insect resistance; catalysts can include zinc chloride
Zinc chloride
Zinc chloride is the name of chemical compound with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. ZnCl2 itself is hygroscopic and even deliquescent. Samples should therefore be protected from...

, citric
Citric acid
Citric acid is a weak organic acid. It is a natural preservative/conservative and is also used to add an acidic, or sour, taste to foods and soft drinks...

 or formic acid
Formic acid
Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...

, or borates.

Kebonization is a commercially marketed wood-impregnation process using furfuryl alcohol.

External links

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