Dodecanol , or lauryl alcohol, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

produced industrially from

palm kernel oil Palm kernel oil is an edible plant oil derived from the kernel of the oil palm tree ''Elaeis guineensis''. It is related to two other edible oils: ''palm oil'', extracted from the fruit pulp of the oil palm, and ''coconut oil'', extracted from ...

coconut oil Coconut oil (or coconut fat) is an edible oil derived from the kernels, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat below around , and a clear thin liquid oil at higher temperatures. Unrefined varieties have a disti ...

. It is a

fatty alcohol Fatty alcohols (or long-chain alcohols) are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length vari ...

Sulfate esters The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many a ...

of lauryl alcohol, especially

sodium lauryl sulfate Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an organic compound with the formula and structure . It is an anionic surfactant used in many cleaning and hygiene products. This compound ...

, are very widely used as

surfactants Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a blend of "surface-active agent", coined in 1950. As t ...

. Sodium lauryl sulfate and the related dodecanol derivatives ammonium lauryl sulfate and sodium laureth sulfate are all used in

shampoo Shampoo () is a hair care product, typically in the form of a viscous liquid, that is formulated to be used for cleaning (scalp) hair. Less commonly, it is available in solid bar format. (" Dry shampoo" is a separate product.) Shampoo is use ...

s. Dodecanol is tasteless, colorless, and has a floral odor.

Production and use

In 1993, the European demand of dodecanol was around 60,000

tonne The tonne ( or ; symbol: t) is a unit of mass equal to 1,000 kilograms. It is a non-SI unit accepted for use with SI. It is also referred to as a metric ton in the United States to distinguish it from the non-metric units of the s ...

s per year. It can be obtained from

palm oil Palm oil is an edible vegetable oil derived from the mesocarp (reddish pulp) of the fruit of oil palms. The oil is used in food manufacturing, in beauty products, and as biofuel. Palm oil accounted for about 36% of global oils produced from o ...

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

s and methyl esters by

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

. It may also be produced synthetically via the Ziegler process. A classic laboratory method involves Bouveault-Blanc reduction of ethyl laurate. Dodecanol is used to make

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

s, which are used in lubricating

oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) and lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturate ...

s, and

pharmaceutical Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...

s. Millions of tons of sodium dodecylsulfate (SDS) are produced annually by

sulfation Sulfation (sometimes spelled sulphation in British English) is the chemical reaction that entails the addition of SO3 group. In principle, many sulfations would involve reactions of sulfur trioxide (SO3). In practice, most sulfations are effected ...

of dodecyl alcohol: : : Dodecanol is used as an

emollient A moisturizer, or emollient, is a cosmetic preparation used for protecting, moisturizing, and lubricating the skin. These functions are normally performed by sebum produced by healthy skin. The word "emollient" is derived from the Latin verb ''mo ...

. It is also the precursor to dodecanal, an important fragrance, and 1-bromododecane, an

alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...

for improving the

lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are called lipophilic (translated ...

of organic molecules.

Toxicity

Dodecanol can irritate the skin. It has about half the toxicity of

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

, but it is very harmful to marine organisms.

Mutual solubility with water

The mutual

solubility In chemistry, solubility is the ability of a chemical substance, substance, the solute, to form a solution (chemistry), solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form su ...

of 1-dodecanol and water has been quantified as follows.Richard Stephenson and James Stuart, "Mutual Binary Solubilities: Water-Alcohols and Water-Esters", J. Chem. Eng. Data, 1986, 31, 56-70. :

References

External links

MSDS at Oxford

{{Authority control Fatty alcohols Primary alcohols Alkanols Dodecyl compounds