Glyoxal

Glyoxal

Names
Preferred IUPAC name Oxaldehyde
Systematic IUPAC name Ethanedial
Other names Glyoxal Oxalaldehyde
Identifiers
CAS Number	107-22-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:34779 Y
ChemSpider	7572 Y
ECHA InfoCard	100.003.160
KEGG	C14448 Y
PubChem	7860
UNII	50NP6JJ975 Y
InChI InChI=1S/C2H2O2/c3-1-2-4/h1-2H Y Key: LEQAOMBKQFMDFZ-UHFFFAOYSA-N Y InChI=1/C2H2O2/c3-1-2-4/h1-2H Key: LEQAOMBKQFMDFZ-UHFFFAOYAX
SMILES C(=O)C=O
Properties
Chemical formula	C2H2O2
Molar mass	58.04 g·mol−1
Density	1.27 g/cm3
Melting point	15 °C (59 °F; 288 K)
Boiling point	51 °C (124 °F; 324 K)
Thermochemistry
Specific heat capacity (C)	1.044 J/(K·g)
Hazards
NFPA 704	1 2 1
Flash point	−4 °C (25 °F; 269 K)
Autoignition temperature	285 °C (545 °F; 558 K)
Related compounds
Related aldehydes	acetaldehyde glycolaldehyde propanedial methylglyoxal
Related compounds	glyoxylic acid glycolic acid oxalic acid pyruvic acid diacetyl acetylacetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Glyoxal is an organic compound with the chemical formula OCHCHO. It is a yellow-colored liquid that evaporates to give a green-colored gas. Glyoxal is the smallest dialdehyde (two aldehyde groups). Its structure is more complicated than typically represented because the molecule hydrates and oligomerizes. It is produced industrially as a precursor to many products.

Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid.

Commercial glyoxal is prepared either by the gas-phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-phase oxidation of acetaldehyde with nitric acid. Global nameplate capacity is around 220,000 tons, with production rates less, due to overcapacity mostly in Asia. Most production is done via the gas-phase oxidation route.

The first commercial glyoxal source was in Lamotte, France, started in 1960. The single largest commercial source is BASF in Ludwigshafen, Germany, at around 60,000 tons per year. Other production sites exist also in the US and China. Commercial bulk glyoxal is made and reported as a 40%-strength solution in water.

Glyoxal may be synthesized in the laboratory by oxidation of acetaldehyde with selenious acid. The preparation of anhydrous glyoxal entails heating solid glyoxal hydrate(s) with phosphorus pentoxide and condensing the vapors in a cold trap. The experimentally determined Henry's law constant of glyoxal is: