Allyl alcohol

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Allyl alcohol
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-propenol, Allyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.156 Edit this at Wikidata
KEGG
  • InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2 checkY
    Key: XXROGKLTLUQVRX-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O/c1-2-3-4/h2,4H,1,3H2
    Key: XXROGKLTLUQVRX-UHFFFAOYAC
  • C=CCO
Properties
C3H6O
Molar mass 58.080 g·mol−1
Density 0.854 g/ml
Melting point −129 °C
Boiling point 97 °C
Miscible
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 21 °C
Explosive limits 2.5–18.0%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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. Allyl alcohol is the smallest representative of the allylic alcohols.

Production

Allyl alcohol can be obtained by many methods.[1] The hydrolysis of allyl chloride is the traditional route:

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

Hydrolysis of this acetate gives allyl alcohol. Alternatively, propylene can be oxidized to acrolein, which upon hydrogenation gives the alcohol.

Other methods

In principle allyl alcohol can be obtained by dehydrogenation of propanol. In the laboratory, it has been prepared by the reaction of glycerol and formic acid.[2] Allyl alcohols in general can be prepared by allylic oxidation of allyl compounds by selenium dioxide.

Applications

Allyl alcohol is mainly converted 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.[1]

Safety

Allyl alcohol is more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lacrymator.[1]

References

  1. ^ a b c Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_425
  2. ^ Oliver Kamm and C. S. Marvel (1941). "Allyl alcohol". Organic Syntheses; Collected Volumes, vol. 1, p. 42.

External links

See also

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