Acrolein

Title: Acrolein
CAS Registry Number: 107-02-8
CAS Name: 2-Propenal
Additional Names: acrylic aldehyde; acrylaldehyde; acraldehyde
Trademarks: Aqualin (Shell); Magnacide (Baker)
Molecular Formula: C3H4O
Molecular Weight: 56.06
Percent Composition: C 64.27%, H 7.19%, O 28.54%
Line Formula: CH2=CHCHO
Literature 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.
Properties: Flammable liquid with pungent odor. 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).
Melting point: mp -88°
Boiling point: bp760 52.5°; bp200 17.5°; bp100 2.5°; bp60 -7.5°; bp1.0 -64.5°
Flash point: Flash pt, open cup: <0°F (-18°C)
Index of refraction: nD19 1.4022
Density: d0 0.8621; d20 0.8389; d50 0.8075
Toxicity data: 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.
Acrylamide Acrylic Acid Acrylonitrile Actaplanins Actarit

Acrolein
Propenal.svg Acrolein-3D-balls.png
Acrolein-3D-vdW.png
Identifiers
CAS number 107-02-8 YesY
PubChem 7847
ChemSpider 7559 YesY
UNII 7864XYD3JJ YesY
KEGG C01471 YesY
ChEBI CHEBI:15368 YesY
ChEMBL CHEMBL721 YesY
IUPHAR ligand 2418
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C3H4O
Molar mass 56.06 g mol−1
Appearance Colorless to yellow liquid. Colorless gas in smoke.
Odor irritating
Density 0.839 g/mL
Melting point −88 °C; −126 °F; 185 K
Boiling point 53 °C; 127 °F; 326 K
Solubility in water very soluble
Hazards
MSDS JT Baker MSDS
Main hazards Highly poisonous. Causes severe irritation to exposed membranes. Extremely flammable liquid and vapor.
NFPA 704
NFPA 704.svg
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Flash point −26 °C; −15 °F; 247 K
Autoignition temperature 278 °C; 532 °F; 551 K
Explosive limits 3-31%
Related compounds
Related alkenals Crotonaldehyde

cis-3-Hexenal
(E,E)-2,4-Decadienal

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine.