Dodecanol

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.[4]

Dodecanol[1]
Names
Preferred IUPAC name
Dodecan-1-ol
Other names
Dodecanol
1-Dodecanol
Dodecyl alcohol
Lauryl alcohol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.620
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3 Y
    Key: LQZZUXJYWNFBMV-UHFFFAOYSA-N Y
  • InChI=1/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3
    Key: LQZZUXJYWNFBMV-UHFFFAOYAU
SMILES
  • OCCCCCCCCCCCC
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)
Solubility in water
 0.004 g/L[2]
Solubility in ethanol and diethyl ether Soluble
Magnetic susceptibility (χ)
 -147.70·10−6 cm3/mol
Related compounds
Related
  • Dodecanal
  • Dodecanoic acid
  • 1-Bromododecane
Hazards
GHS labelling:[3]
Pictograms
Signal word
 Warning
Hazard statements
 H319, H410
Precautionary statements
 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).
Y verify (what is YN ?)
Infobox references

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.[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, 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.[6]

Mutual solubility with water

The mutual solubility of 1-dodecanol and water has been quantified as follows.[7]

Mutual Solubility of Water and 1-Dodecanol (98%, Melting Point 24 °C), Weight %
Temperature, °CSolubility of Dodecanol in WaterSolubility of Water in Dodecanol
29.50.042.87
40.00.052.85
50.20.092.69
60.50.152.96
70.50.092.70
80.30.142.89
90.80.182.96
standard deviation0.020.01

References
  1. Merck Index, 12th Edition, 3464.
  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. GHS: GESTIS 035500
  4. Ford, S. G.; Marvel, C. S. (1930). "Lauryl Alcohol". Organic Syntheses. 10: 62. doi:10.15227/orgsyn.010.0062.
  5. Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2.
  6. "MSDS Safety Sheet". Archived from the original on 2011-07-16. Retrieved 2009-06-14.
  7. Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70.


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