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Allylic alcohol

Allyl alcohol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Prop-2-en-1-ol
Other names
Allyl alcohol
1-Propen-3-ol
Vinyl carbinol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.156
KEGG
PubChem CID
UNII
Properties
C3H6O
Molar mass 58.08 g·mol−1
Appearance colorless liquid
Odor mustard-like
Density 0.854 g/ml
Melting point −129 °C
Boiling point 97 °C (207 °F; 370 K)
Miscible
Vapor pressure 17 mm Hg
-36.70·10−6 cm3/mol
Hazards
Safety data sheet External MSDS
Toxic (T)
Dangerous for
the environment (N)
R-phrases (outdated) R10, R23/24/25,
R36/37/38, R50
S-phrases (outdated) (S1/2), S36/37/39,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)
378 °C (712 °F; 651 K)
Explosive limits 2.5–18.0%
Lethal dose or concentration (LD, LC):
1000 ppm (mammal, 1 hr)
76 ppm (rat, 8 hr)
207 ppm (mouse, 2 hr)
1000 ppm (rabbit, 3.5 hr)
1000 ppm (monkey, 4 hr)
1060 ppm (rat, 1 hr)
165 ppm (rat, 4 hr)
76 ppm (rat, 8 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
2 ppm
REL (Recommended)
TWA 2 ppm (5 mg/m3) ST 4 ppm (10 mg/m3) [skin]
IDLH (Immediate danger)
20 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Allyl alcohol (IUPAC name: prop-2-en-1-ol) 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:

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:

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


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