Difference between revisions of "Furfural"
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Revision as of 15:12, 30 January 2016
| Names | |
|---|---|
| IUPAC name
Furan-2-carbaldehyde
| |
| Other names
Fural, furan-2-carboxaldehyde, furfuraldehyde, 2-furaldehyde, pyromucic aldehyde
| |
| Properties | |
| C5H4O2 | |
| Molar mass | 96.09 |
| Appearance | Colorless oil |
| Odor | Almond-like |
| Density | 1.16 g/mL (20 °C) |
| Melting point | −37 °C (−35 °F; 236 K) |
| Boiling point | 162 °C (324 °F; 435 K) |
| 83 g/L | |
| Vapor pressure | 2 mmHg (20°C) |
| Hazards | |
| Flash point | 62 °C (335 K, 144 °F) |
| Related compounds | |
| Related compounds
|
Furan |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Furfural is an organic compound, a heterocyclic aldehyde, with the chemical formula C5H4O2. It is derived from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust.
Contents
Properties
Chemical
Hydrogenating furfural yields tetrahydrofuran and derivatives, such as 2-methyltetrahydrofuran, and furfuryl alcohol.
Palladium-catalyzed decarbonylation of furfural will yield furan.
When heated in the presence of acids, furfural irreversibly solidifies into a hard thermosetting resin.
Physical
Furfural is a colorless oily liquid, with an almond-like smell, which quickly darkens when exposed to air. It is poorly soluble in water and alkanes. Furfural is however soluble in most polar organic solvents.
Availability
Furfural is sold by many chemical suppliers.
Preparation
Furfural can be obtained by heating hemicellulose with dilute sulfuric acid. Through this process, the hemicellulose undergoes hydrolysis to yield these sugars, mainly xylose. Under the same conditions of heat and acid, xylose and other five carbon sugars undergo dehydration, losing three water molecules, resulting furfural:
- C5H10O5 → C5H4O2 + 3 H2O
Corn cobs, which are cheaply and readily available, can be used as a source of sugars, offering a good yield. Fresh corn cobs have been found to have a better yield than older ones.[1][2]
D-Ribose will form furfural on heating with sulfuric acid.[3]
Projects
- Make furfuryl alcohol
- Make 2-methyltetrahydrofuran
- Make tetrahydrofuran[4]
- Make furan
Handling
Safety
Furfural is toxic and should be handled with care. It is a skin irritant and chronic skin exposure can lead to skin allergy as well as an unusual susceptibility to sunburn.
Storage
Furfural should be stored in closed bottles, away from air to prevent it from turning brown.
Disposal
Furfural can be safely burned.
References
- ↑ http://www.orgsyn.org/demo.aspx?prep=cv1p0280
- ↑ http://pubs.acs.org/doi/abs/10.1021/ie50161a032
- ↑ http://pubs.acs.org/doi/abs/10.1021/ja01241a001
- ↑ http://www.google.com/patents/WO2014118806A1?cl=en
