Furfural History Properties Production Uses Safety

**Properties**
General
Name	Furfural

Chemical formula	C₅ H₄ O₂
Formula weight	96.09 amu
Synonyms	2-furancarboxaldehyde, fural, furfuraldehyde, pyromucic aldehyde
CAS number	98-01-1
Phase behavior
Melting point	236.2 K (-36.5 °C)
Boiling point	434.9 (161.7°C)
Triple point	236.8 K (-35.9°C) ? bar
Critical point	670 K (397°C) 55 bar
Enthalpy of fusion	14.37 kJ/ molThe mole (symbol: mol) is one of the seven SI base units and is commonly used in chemistry. It measures the amount of substance of a system and is defined as the amount of substance that contains as many elementary entities as there are atoms in exactly 0
Entropy of fusionThe Entropy of fusion of a substance represents the increase in the degree of disorder involved in the transition from an organized crystalline solid to the disorganized structure of a liquid. It is denoted as ΔS and normally expressed in J / mol ·	61.1 J/mol·K
Enthalpy of vaporization	50.6 kJ/mol
Liquid properties
Δ_fH⁰_liquidThe standard enthalpy of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of that substance from its component elements, at their standard states (the most stable form of the element or compound at 25 degrees Cels	-200.2 kJ/ molThe mole (symbol: mol) is one of the seven SI base units and is commonly used in chemistry. It measures the amount of substance of a system and is defined as the amount of substance that contains as many elementary entities as there are atoms in exactly 0
S⁰_liquidIn chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. By comparing the entropies of products and reactants in a chemical reaction, we can determine whether the reac	218 J/mol·K
C_pHeat capacity (abbreviated C or just C also called thermal capacity is the ability of matter to store heat. The heat capacity of a certain amount of matter is the quantity of heat (measured in Joules) required to raise its temperature by one kelvin. The S	159.5 J/mol·K
DensityFor other meanings of density, see density (disambiguation Density (symbol: rho Greek: rho) is a measure of mass per unit of volume. The higher an object's density, the higher its mass per volume. The average density of an object equals its total mass div	1.16 ×10³ kgThe kilogram (symbol: kg is the SI base unit of mass. A gram is defined as one thousandth of a kilogram. Conversion of units describes equivalent units of mass in other systems. Multiples SI prefixes are used to name multiples and subdivisions of the kilo/ m³
Gas properties
Δ_fH⁰_gas	-151.0 kJ/mol
C_p	90.8 J/mol·K
Safety
Acute effects	Toxic irritant. Can cause headache, dizziness, nausea, and eventual unconsciousness and death. When inhaled, can cause swelling and spasms of the respiratory tract.
Chronic effecs	Repeated exposure can cause skin allergies and photosensitization. Can cause liver and kidney damage.
Flash point	62°C
Autoignition temperature	315°C
Explosive limits	2-19%
More info
Properties	NIST WebBook
MSDS	Hazardous Chemical Database
SI units were used where possible. Unless otherwise stated, standard conditions were used. Disclaimer and references

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.

Furfural is an aromatic aldehyde, with the ring structure shown at right. Its chemical formula is C₅ H₄ O₂. In its pure state, it is a colorless oily liquid with the odor of almonds, but upon exposure to air it quickly becomes yellow.

1 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 emprical formula of C₅H₄O₂. In 1901, the German chemist Carl Harries deduced furfural's structure.

Except for occasional use in perfume, furfural remained a relatively obscure chemical until 1922, when the Quaker Oat Company began mass-producing it from oat hulls. Today, furfural is still produced from agricultural byproducts.

2 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.

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.

When heated above 250°C, furfural decomposes into furan and carbon monoxide, sometimes explosively.

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

3 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.

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.

4 Uses

Furfural is used as a solvent in petrochemical refining to extract dienes (which are used to make synthetic rubber) from other hydrocarbons.

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.

Furfural is also used as a chemical intermediate in the production of the solvents furan and tetrahydrofuran.

5 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.

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.

Furans Aldehydes

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