| Allyl alcohol | |
|---|---|
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Prop-2-en-1-ol, Allyl alcohol |
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| Identifiers | |
| CAS number | 107-18-6 |
| ChemSpider | 13872989 |
| KEGG | C02001 |
| ChEBI | CHEBI:16605 |
| ChEMBL | CHEMBL234926 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3H6O |
| Molar mass | 58.08 g mol−1 |
| Density | 0.854 g/ml |
| Melting point |
−129 °C |
| Boiling point |
97 °C |
| 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 |
3
3
0
|
| Flash point | 21 °C |
| Autoignition temperature |
378 °C |
| Explosive limits | 2.5–18.0% |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 used as a precursor to many specialized compounds. Allyl alcohol is the smallest representative of the allylic alcohols.
Contents |
Allyl alcohol can be obtained by many methods.[1] The hydrolysis of allyl chloride is the traditional route:
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. Alternatively, propylene can be oxidized to acrolein, which upon hydrogenation gives the alcohol.
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.
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]
Allyl alcohol is more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lacrymator.[1]