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| Names | |
|---|---|
| IUPAC name Dodecan-1-ol | |
| Other names Dodecanol 1-Dodecanol Dodecyl alcohol Lauryl alcohol | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.003.620  |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
Chemical formula | C12H26O |
| Molar mass | 186.34 |
| Appearance | Colorless solid |
| Density | 0.8309 |
| Melting point | 24 °C (75 °F; 297 K) |
| Boiling point | 259 °C (498 °F; 532 K) |
| 0.004 g/L[2] | |
| Solubility in ethanol and diethyl ether | Soluble |
| -147.70·10−6 cm3/mol | |
| Related compounds | |
Related |
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| Hazards | |
| R/S statement (outdated) | R36 |
| Flash point | 127 °C (261 °F; 400 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Dodecanol /ˈdoʊˈdɛkɑːnɒl/, or lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate, ammonium lauryl sulfate, and sodium laureth sulfate are all used in shampoos. Lauryl alcohol is tasteless and colorless with a floral odor.[3]
Production and use
In 1993, the European demand of dodecanol was around 60 thousand tons per year (Tt/a). It can be obtained from palm kernel or coconut oil fatty acids and methyl esters by hydrogenation.[4] It may also be produced synthetically via the Ziegler process. A classic laboratory method involves Bouveault-Blanc reduction of ethyl laurate.[3]
Dodecanol is used to make surfactants, lubricating oils, pharmaceuticals, in the formation of monolithic polymers and as a flavor enhancing food additive. In cosmetics, dodecanol is used as an emollient. It is also the precursor to dodecanal, an important fragrance, and 1-bromododecane, an alkylating agent for improving the lipophilicity of organic molecules.
Toxicity
Dodecanol can irritate the skin. It has about half the toxicity of ethanol, but it is very harmful to marine organisms.[5]
Mutual solubility with water
The mutual solubility of 1-dodecanol and water has been quantified as follows.[6]
| Temperature, °C | Solubility of Dodecanol in Water | Solubility of Water in Dodecanol |
|---|---|---|
| 29.5 | 0.04 | 2.87 |
| 40.0 | 0.05 | 2.85 |
| 50.2 | 0.09 | 2.69 |
| 60.5 | 0.15 | 2.96 |
| 70.5 | 0.09 | 2.70 |
| 80.3 | 0.14 | 2.89 |
| 90.8 | 0.18 | 2.96 |
| standard deviation | 0.02 | 0.01 |
References
- ^ Merck Index, 12th Edition, 3464.
- ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b Ford, S. G.; Marvel, C. S. (1930). "Lauryl Alcohol". Organic Syntheses. 10: 62. doi:10.15227/orgsyn.010.0062.
- ^ Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2.
- ^ MSDS Safety Sheet
- ^ Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70.