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 and the related dodecanol derivatives ammonium lauryl sulfate and sodium laureth sulfate are all used in shampoos. Dodecanol is tasteless, colorless, and has a floral odor.[4]
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| Names | |
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| Preferred IUPAC name
Dodecan-1-ol | |
| Other names
Dodecanol
1-Dodecanol Dodecyl alcohol Lauryl alcohol | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.003.620 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C12H26O | |
| Molar mass | 186.339 g·mol−1 |
| 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 | |
| GHS labelling:[3] | |
 
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| Warning | |
| H319, H410 | |
| P273, P305+P351+P338 | |
| 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).
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Production and use
editIn 1993, the European demand of dodecanol was around 60,000 tonnes per year. It can be obtained from palm oil or coconut oil fatty acids and methyl esters by hydrogenation.[5] It may also be produced synthetically via the Ziegler process. A classic laboratory method involves Bouveault-Blanc reduction of ethyl laurate.[4]
Dodecanol is used to make surfactants, which are used in lubricating oils, and pharmaceuticals. Millions of tons of sodium dodecylsulfate (SDS) are produced annually by sulfation of dodecyl alcohol:[6]
- SO3 + CH3(CH2)10CH2OH → CH3(CH2)10CH2OSO3H
- CH3(CH2)10CH2OSO3H + NaOH→CH3(CH2)10CH2OSO3Na + H2O
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
editDodecanol can irritate the skin. It has about half the toxicity of ethanol, but it is very harmful to marine organisms.[7]
Mutual solubility with water
editThe mutual solubility of 1-dodecanol and water has been quantified as follows.[8]
Mutual solubility of water and 1-dodecanol (98%, melting point 24 °C), Weight % 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
edit- ^ Merck Index, 12th Edition, 3464.
- ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ GHS: GESTIS 035500
- ^ 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. ISBN 3527306730.
- ^ Holmberg, Krister (2019). "Surfactants". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–56. doi:10.1002/14356007.a25_747.pub2. ISBN 978-3-527-30673-2.
- ^ "MSDS Safety Sheet". Archived from the original on 2011-07-16. Retrieved 2009-06-14.
- ^ Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70.