Allyl alcohol
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| Ball-and-stick model | |
| Names | |
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| IUPAC name
2-propen-1-ol, Allyl alcohol
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| Other names | |
| Identifiers | |
107-18-6  |
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| ChEBI | CHEBI:16605 |
| ChEMBL | ChEMBL234926 |
| ChemSpider | 13872989 |
| Jmol 3D model | Interactive image |
| KEGG | C02001 |
| PubChem | 7858 |
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| Properties | |
| C3H6O | |
| Molar mass | 58.08 g·mol−1 |
| Appearance | colorless liquid[1] |
| Odor | mustard-like[1] |
| Density | 0.854 g/ml |
| Melting point | −129 °C |
| Boiling point | 97 °C (207 °F; 370 K) |
| Miscible | |
| Vapor pressure | 17 mm Hg[1] |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Allyl alcohol (IUPAC name: 3-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.[2] Today allyl alcohol can be obtained by many methods. Allyl alcohol is the smallest representative of the allylic alcohols.
Contents
Production
Allyl alcohol was first prepared in 1856 by Auguste Cahours and August Hofmann by saponification of allyl iodide.[2] 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
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.[3][4] Allyl alcohols in general can be prepared by allylic oxidation of allyl compounds by selenium dioxide.
Applications
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.[2]
Safety
Allyl alcohol is more toxic than related alcohols. Its threshold limit value (TLV) is 2 ppm. It is a lacrymator.[2]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Cite error: Invalid
<ref>tag; no text was provided for refs namedNIOSH - ↑ 2.0 2.1 2.2 2.3 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
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External links
- International Chemical Safety Card 0095
- Lua error in package.lua at line 80: module 'strict' not found.
- 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
