4509. Glyoxal

Nomenclature

CAS number: 107-22-2
Ethanedial; biformyl; diformyl; oxalaldehyde.
C2H2O2; mol wt 58.04.
C 41.39%, H 3.47%, O 55.13%.
OHCCHO.

Description and references

Prepd by the oxidation of acetaldehyde by nitric or selenious acid: Lubawin, Ber. 8, 768 (1875); Wyss, Ber. 10, 1366 (1877); Klln, Ann. 416, 230 (1918); Riley et al., J. Chem. Soc. 1932, 1881; Ronzio, Waugh, Org. Synth. coll. vol. III, 438 (1955); by hydrolysis of dichlorodioxane: Butler, Cretcher, J. Am. Chem. Soc. 54, 2988 (1932). Review of commercial development: J. F. Bohmfalk et al., Ind. Eng. Chem. 43, 786 (1951). Toxicity study: H. F. Smyth et al., J. Ind. Hyg. Toxicol. 23, 259 (1941). Review: A. B. Boese et al. in Glycols, G. O. Curme, F. Johnston, Eds. (Reinhold, New York, 1952) pp 125-128.

Properties

Yellow prisms or irregular pieces turning white on cooling. d20 1.14. Opaque at 10°, mp 15°. bp776 51°. The vapors are green and burn with a purple flame. Explosive: Mixtures with air may explode! nD20.5 1.3826. Sol in anhydr solvents. pH of a 40% aq soln: 2.1-2.7; d420 1.27. Polymerizes quickly on standing, on contact with water (violent reaction), or when dissolved in solvents contg water. The anhydr polymer changes to the monomer on heating. Solns of the monomer are obtained on heating the polymer with anethole, phenetole, safrole, methyl nonyl ketone, or benzaldehyde. LD50 in rats, guinea pigs (mg/kg): 2020, 760 orally (Smyth).

Derivative

Dihydrate.
(OHCCHO)3.2H2O; mol wt 210.14.
O 60.91%, H 4.80%, C 34.29%.

Properties

Crystalline powder, nonhygroscopic. More sol in hot water than in cold water. Commercially available in anhydr form as crystalline dihydrate, or as a 40% aq soln which may contain polymerization inhibitors.

Caution

Moderately irritating to skin, mucous membranes.

Use

In textiles, organic synthesis, glues, biocides.