128. Acrolein

Nomenclature

CAS number: 107-02-8
2-Propenal; acrylic aldehyde; acrylaldehyde; acraldehyde; Aqualin (Shell); Magnacide (Baker).
C3H4O; mol wt 56.06.
C 64.27%, H 7.19%, O 28.54%.

Description and references

Prepd industrially by passing glycerol vapors over magnesium sulfate heated to 330-340°. Lab prepn by heating a mixture of anhydr glycerol, acid potassium sulfate and potassium sulfate in the presence of a small amount of hydroquinone and distilling in the dark: H. Adkins, W. H. Hartung, Org. Synth. coll. vol. I, 15 (1941). Formation from glycerol by the action of B. amaracrylus: Voisenet, Compt. Rend. 188, 941, 1271 (1929); by B. welchii: Humphreys, J. Infect. Dis. 35, 282; Chem. Zentralbl. 1925, II, 309. Toxicity study: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951). Review: L. G. Hess et al., in Kirk-Othmer Encyclopedia of Chemical Technology vol. 1 (Wiley-Interscience, New York, 3rd ed., 1978) pp 277-297. Review of toxicology and human exposure: Toxicological Profile for Acrolein (PB91-180307, 1990) 157 pp.

Chemical structure

Properties

Liquid with pungent odor. Flammable, poisonous. mp 88°. d0 0.8621; d20 0.8389; d50 0.8075. bp760 52.5°; bp200 17.5°; bp100 2.5°; bp60 7.5°; bp1.0 64.5°. nD19 1.4022. Sol in 2 to 3 parts water; in alcohol, ether. Flash pt, open cup: <0°F (18°C). Vapor pressure at 20°: 210 mm Hg. Unstable, polymerizes (especially under light or in the presence of alkali or strong acid) forming disacryl, a plastic solid. Absorption spectrum: Lüthy, Z. Phys. Chem. 107, 291, 298 (1923). LD50 orally in rats: 0.046 g/kg (Smyth).

Caution

Potential symptoms of overexposure are irritation of eyes, skin and mucous membranes; decreased pulmonary function; delayed pulmonary edema; chronic respiratory disease. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 6. See also Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 186.

Use

Manuf colloidal forms of metals; making plastics, perfumes; warning agent in methyl chloride refrigerant. Has been used in military poison gas mixtures. Used in organic syntheses. Aquatic herbicide.