Dodecanol

Dodecanol^[1]
Names
	Preferred IUPAC name Dodecan-1-ol
	Other names Dodecanol; 1-Dodecanol; Dodecyl alcohol; Lauryl alcohol
Identifiers
CAS Number	112-53-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28878 ;
ChEMBL	ChEMBL24722 ;
ChemSpider	7901 ;
DrugBank	DB06894 ;
ECHA InfoCard	100.003.620
KEGG	C02277 ;
PubChem CID	8193;
UNII	178A96NLP2 ;
CompTox Dashboard (EPA)	DTXSID5026918 ;
	InChI InChI=1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3 Key: LQZZUXJYWNFBMV-UHFFFAOYSA-N ; 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	186.339 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)
Solubility in water	0.004 g/L
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:
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). verify (what is ?) Infobox references

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.

Dodecanol can irritate the skin. It has about half the toxicity of ethanol, but it is very harmful to marine organisms.^[7]

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

^ 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.