Dodecanol

Dodecanol[1]
Skeletal formula
Space-filling model
Names
Preferred 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
  • InChI=1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3 checkY
    Key: LQZZUXJYWNFBMV-UHFFFAOYSA-N checkY
  • InChI=1/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3
    Key: LQZZUXJYWNFBMV-UHFFFAOYAU
  • OCCCCCCCCCCCC
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
Hazards
GHS labelling:[3]
GHS07: Exclamation markGHS09: Environmental hazard
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).
checkY verify (what is checkY☒N ?)

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]

Production and use

In 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

Dodecanol 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

The 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

  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. ^ a b 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. ISBN 3527306730.
  6. ^ 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.
  7. ^ "MSDS Safety Sheet". Archived from the original on 2011-07-16. Retrieved 2009-06-14.
  8. ^ Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70.