1-Hexanol (IUPAC name hexan-1-ol) is an organic

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

with a six-

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

chain and a condensed structural formula of CH₃(CH₂)₅OH. This colorless liquid is slightly soluble in water, but

miscible Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). The term is most often applied to liquids but also applies ...

with

diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...

and

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

. Two additional straight chain isomers of 1-hexanol,

2-hexanol 2-Hexanol (or hexan-2-ol) is a six carbon Alcohol (chemistry), alcohol in which the Hydroxyl, OH group is located on the second carbon atom. Its chemical formula is C6H14O or C6H13OH. It is an isomer of the other hexanols. 2-Hexanol has a chiral ...

and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C₆H₁₃OH. It is used in the

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

industry.

Preparation

Hexanol is produced industrially by the oligomerization of

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...

using

triethylaluminium Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2( C2H5)6 (abbreviated as Al2Et6 or TEA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially ...

followed by oxidation of the alkylaluminium products.. An idealized synthesis is shown: :Al(C₂H₅)₃ + 6C₂H₄ → Al(C₆H₁₃)₃ :Al(C₆H₁₃)₃ + O₂ + 3H₂O → 3HOC₆H₁₃ + Al(OH)₃ The process generates a range of oligomers that are separated by

distillation Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...

Alternative methods

Another method of preparation entails

hydroformylation Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon d ...

of 1-pentene followed by

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

of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C₆-alcohols, which are precursors to

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

s. In principle, 1-hexene could be converted to 1-hexanol by

hydroboration In organic chemistry, hydroboration refers to the addition of a hydrogen-boron bond to certain double and triple bonds involving carbon (, , , and ). This chemical reaction is useful in the organic synthesis of organic compounds. Hydroboration p ...

(

diborane Diborane(6), generally known as diborane, is the chemical compound with the formula B2H6. It is a toxic, colorless, and pyrophoric gas with a repulsively sweet odor. Diborane is a key boron compound with a variety of applications. It has attracte ...

tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is ma ...

followed by treatment with

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%� ...

and

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from

Occurrence in nature

1-Hexanol is believed to be a component of the odour of freshly mown grass.

Alarm pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavi ...

s emitted by the

Koschevnikov gland The Koschevnikov gland is a gland of the honeybee located near the sting shaft. The gland produces an alarm pheromone that is released when a bee stings. The pheromone contains more than 40 different compounds, including pentylacetate, butyl ...

honey bee A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the current co ...

s contain 1-hexanol. It also is partly responsible for the fragrance of

strawberries The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown hybrid species of the genus '' Fragaria'', collectively known as the strawberries, which are cultivated worldwide for their fruit. The fruit is widely ap ...

References

External links

* {{DEFAULTSORT:Hexanol, 1- Flavors Hexanols Primary alcohols

Preparation

Alternative methods

Occurrence in nature

See also

References

External links