Allyl alcohol

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Allyl alcohol
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 107-18-6 YesY
PubChem 7858
ChemSpider 13872989 YesY
KEGG C02001 YesY
ChEBI CHEBI:16605 YesY
ChEMBL CHEMBL234926 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H6O
Molar mass 58.08 g mol−1
Density 0.854 g/ml
Melting point −129 °C
Boiling point 97 °C (207 °F; 370 K)
Solubility in water Miscible
Hazards
MSDS External MSDS
EU Index 603-015-00-6
EU classification Toxic (T)
Dangerous for
the environment (N)
R-phrases R10, R23/24/25,
R36/37/38, R50
S-phrases (S1/2), S36/37/39,
S38, S45, S61
NFPA 704
Flammability code 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., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 21 °C (70 °F; 294 K)
Autoignition temperature 378 °C (712 °F; 651 K)
Explosive limits 2.5–18.0%
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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.[1] Today allyl alcohol can be obtained by many methods. Allyl alcohol is the smallest representative of the allylic alcohols.

Production[edit]

Allyl alcohol was first prepared in 1856 by Auguste Cahours and August Hofmann by saponification of allyl iodide.[1] 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

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

Other methods[edit]

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.[2][3] Allyl alcohols in general can be prepared by allylic oxidation of allyl compounds by selenium dioxide.

Applications[edit]

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.[1]

Safety[edit]

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

References[edit]

  1. ^ a b c d 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
  2. ^ Oliver Kamm and C. S. Marvel (1941), "Allyl alcohol", Org. Synth. ; Coll. Vol. 1: 42 
  3. ^ Cohen, Julius (1900). Practical Organic Chemistry 2nd Ed.. London: Macmillan and Co., Limited. p. 96. 

External links[edit]

See also[edit]