Dodecanol

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Dodecanol[1]
Skeletal formula
Space-filling model
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 Edit this at Wikidata
KEGG
UNII
Properties
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
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R/S statement (outdated) R36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).
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Infobox references

Dodecanol /ˈdˈdɛkɑːnɒl/, 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[edit]

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[edit]

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[edit]

The mutual solubility of 1-dodecanol and water has been quantified as follows.[6]

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]

  1. ^ Merck Index, 12th Edition, 3464.
  2. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ a b Ford, S. G.; Marvel, C. S. (1930). "Lauryl Alcohol". Organic Syntheses. 10: 62. doi:10.15227/orgsyn.010.0062.
  4. ^ Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2.
  5. ^ MSDS Safety Sheet
  6. ^ Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70.

External links[edit]