File:Furfural.svg · Wikimedia Commons · See Wikimedia Commons
furfural
Sign in to saveAlso known as Fural, 2-Furancarboxaldehyde, Furfuraldehyde, 2-Furfuraldehyde, 2-furaldehyde, Furaldehyde, 2-Furanaldehyde, 2-Furylcarboxaldehyde
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 , meaning bran, referring to its usual source. Furfural is derived only from dried biomass. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest known organic chemicals available readily purif
Chemical data
- Formula
- C5H4O2
- Molecular weight
- 96.08 g/mol
- IUPAC name
- furan-2-carbaldehyde
- SMILES
- C1=COC(=C1)C=O
- InChIKey
- HYBBIBNJHNGZAN-UHFFFAOYSA-N
- XLogP
- 0.4
- Polar surface area
- 30.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 96.021
Show 15 more facts
- Commons category
- Furfural
- immediately dangerous to life or health
- 393
- NIOSH Pocket Guide ID
- 0297
- chemical formula
- C₅H₄O₂
- density
- 1.16
- melting point
- -36.5
- boiling point
- 161.75
- vapor pressure
- 2
- flash point
- 140
- solubility
- 8
- lower flammable limit
- 2.1
- upper flammable limit
- 19.3
- ionization energy
- 9.21
- time-weighted average exposure limit
- 20
- canonical SMILES
- C1=COC(=C1)C=O
via Wikidata · CC0
~7 min read
Article
8 sectionsContents
- History
- Properties
- Production
- Uses and occurrence
- Safety
- See also
- References
- External links
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 , meaning bran, referring to its usual source. Furfural is derived only from dried biomass. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest known organic chemicals available readily purified from natural precursors.
== History == Furfural was first isolated in 1821 (published in 1832) by the German chemist Johann Wolfgang Döbereiner, who produced a small sample as a byproduct of formic acid synthesis. 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; he also determined furfural's empirical formula (C5H4O2). George Fownes named this oil "furfurol" in 1845 (from furfur (bran), and oleum (oil)). In 1848, the French chemist Auguste Cahours determined that furfural was an aldehyde. Determining the structure of furfural required some time: the furfural molecule contains a cyclic ether (furan), which tends to break open when it's treated with harsh reagents. In 1870, German chemist Adolf von Baeyer speculated about the structure of the chemically similar compounds furan and 2-furoic acid. Additional research by German chemist Heinrich Limpricht supported this idea. From work published in 1877, Baeyer had confirmed his previous belief on the structure of furfural. By 1886, furfurol was being called "furfural" (short for "furfuraldehyde") and the correct chemical structure for furfural was being proposed. By 1887, the German chemist Willy Marckwald had inferred that some derivatives of furfural contained a furan nucleus. In 1901, the German chemist Carl Harries determined furan's structure through work with succindialdehyde and 2-methylfuran, thereby also confirming furfural's proposed structure.