|Jmol-3D images||Image 1|
|Molar mass||58.08 g mol−1|
|Melting point||−129 °C|
|Boiling point||97 °C|
|Solubility in water||Miscible|
|EU classification||Toxic (T)
the environment (N)
S38, S45, S61
|Flash point||21 °C; 70 °F; 294 K|
|Autoignition temperature||378 °C; 712 °F; 651 K|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C or 77 °F, 100 kPa)
Allyl alcohol (IUPAC name: 2-propenol) is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid, but it is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Today allyl alcohol can be obtained by many methods. Allyl alcohol is the smallest representative of the allylic alcohols.
Allyl alcohol was first prepared in 1856 by Auguste Cahours and August Hofmann by saponification of allyl iodide. Today allyl alcohol is produced commercially by the Dow and Shell corporations through the hydrolysis of allyl chloride:
- CH2CHCH2Cl + NaOH → CH2CHCH2OH + NaCl
Allyl alcohol can also be made by the rearrangement of propylene oxide, a reaction that is catalyzed by potassium alum at high temperature. The advantage of this method relative to the allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" of propylene to allyl acetate:
- CH2=CHCH3 + 1/2 O2 + CH3CO2H → CH2CHCH2O2CCH3 + H2O
In principle, allyl alcohol can be obtained by dehydrogenation of propanol. In the laboratory, it has been prepared by the reaction of glycerol with oxalic or formic acids. Allyl alcohols in general can be prepared by allylic oxidation of allyl compounds by selenium dioxide.
Allyl alcohol is converted mainly to glycidol, which is a chemical intermediate in the synthesis of glycerol, glycidyl ethers, esters, and amines. Also, a variety of polymerizable esters are prepared from allyl alcohol, e.g. diallyl phthalate.
Allyl alcohol is more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lacrymator.
- Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. pg. 7-11 doi:10.1002/14356007.a01_425
- Oliver Kamm and C. S. Marvel (1941), "Allyl alcohol", Org. Synth.; Coll. Vol. 1: 42
- Cohen, Julius (1900). Practical Organic Chemistry 2nd Ed.. London: Macmillan and Co., Limited. p. 96.
- International Chemical Safety Card 0095
- NIOSH Pocket Guide to Chemical Hazards 0017
- Institut national de recherche et de sécurité (2004). "Alcool allylique." Fiche toxicologique n° 156. Paris:INRS. (French)
- State of Michigan public information on allyl alcohol
- Occupational exposure guidelines
- Datasheet regulatory information